Debbie and I watched The Invite this week. Seth Rogan and Olivia Wilde star in the movie as a forty-something couple, miserable with themselves and each other. Penelope Cruz and Ed Norton are their joyful upstairs neighbors who come visiting for cocktails.

On the surface The Invite is about sex. Seth and Olivia’s dead bedroom is contrasted with the very loud sex noises coming each night from the upstairs apartment of their amorous neighbors.

Seth and Olivia lie in bed listening to Penelope’s wild, spectacular orgasms, aspirational to Olivia and un-manning to Seth. They try to figure out which of Penelope or Ed Norton is the “groaner.” The truth about the noises is revealed when the two couples get together.

The sex, however, is downstream from status and self-esteem.

Seth and Olivia live in a very large apartment in San Francisco that belonged to Seth’s parents. Their dead bedroom is where Seth was conceived. It’s an apartment that Seth cannot afford as he’s an associate music professor at a small, non-elite college. Seth likely earns less than $100,000 a year. He’s ashamed for anyone to know he’s living off his parents.

When Olivia and Seth met in their twenties, Seth had a band. His band had one hit, but that was it. Now, Seth won’t play the piano in the apartment because it’s a painful reminder of his descent from promising young rock n’ roller to sad sack music teacher.

Olivia gave up her passion for photography to marry Seth and have a child. Olivia spends her days maniacally shopping for the apartment, which has become the epicenter of her life. She spends the entire movie on the edge of a nervous breakdown.

Seth admits to being a failure and just wants to be left alone to be miserable. His misery is perhaps the one thing he’s proud of.

Physically, Seth has become a schlub; he looks like an old man. But Olivia is still lithe and beautiful. Seth is keenly aware that he has married well above his range in looks, and that he’s failed to bring any other appealing aspect to the marriage. Except his parents’ apartment.

In contrast, the upstairs couple Penelope and Ed Norton are filled with confidence. Penelope is a talented therapist and Ed Norton is a retired, heroic Firefighter Captain, which in San Francisco means he has a pension that might be as high as $200,000 a year. Their apartment may be smaller but they are a superior version of Seth and Olivia.

My forties were not my best decade for self-esteem

When I was living my forty-something decade, I don’t recall being introspective or intentional about my life. Life just seemed to happen, and I was carried along by things bigger than myself, whether my children, my career, or my marriage. Those were well-defined roles that kept me occupied.

Unlike Seth in the movie, I was advancing in my career during my forties, meeting or exceeding my earlier expectations. Yet I was often plagued by self-doubts. I paid far too much attention to peers who had achieved greater success.

As well, I “weighted” my success against the advantages I’d inherited. I often told myself that relative to those advantages my career achievements were mediocre and deserved a grade of no better than a “C.” In diving competition terms, my degree of difficulty was low. 1

However, no matter how irrational and angst-ridden I could get about my career, I had my familial roles to fall back on to bolster my self-esteem. I knew I was a good husband and a good father. I loved my wife and believed I had “married up” compared to any expectations I might have ever had. And my children were an elixir to self-doubt.

A great memory at the end of my forties

At my 50^th birthday celebration in 2012, what I remember best are the toasts given by my three children. My daughter Lauren serenaded me in poetic rhyme, a tradition she inherited from me. My son Michael said that he loved when his friends told him that he and I were similar.

My son Andrew got a round of applause when he said I was home every night for dinner, which was basically true. He also drew a round of laughter when he noted that I attended his middle school basketball games to watch some of the worst basketball ever played on any basketball court anywhere. That also was basically true.

Expectations are the most potent source of status anxiety

Usually, we think of status as a way of assessing how we compare to other people. In The Invite, it’s true that Seth and Olivia feel worse about themselves after spending time with their status-superior neighbors, Penelope and Ed Norton, who have an air of casual elegance, an air of sprezzatura.

But by far the most painful comparison is between what Seth and Olivia expected their lives to be and how their lives have turned out. Comparison with “what I could have been” is the most pernicious form of envy because it is the most readily imagined “miss.” But if we meet or exceed expectations, then we’re happy.

For example, when I consider my tennis game, it would be ridiculous for me to be envious of the pro who gives me lessons. I’d be far more likely to envy the game of a slightly better “B” player. But I was terrible when I was younger and over the last ten years, my tennis game has steadily improved so that despite my many tennis defects, I never expected to play as well as I do now.

Expectation failure in a song

One of my favorite songs is “Taxi” by Harry Chapin. It’s a mournful ballad about the failure of a couple to live up to their expectations. It reminds me of the failure of Seth and Olivia in The Invite. Like the movie, the song is set in “Frisco.” 2

The singer Harry is a taxi driver who picks up a sad woman in a fancy gown. She asks him to take her to a ritzy address. She recognizes Harry from his name and picture on his taxi license. Turns out she is Sue, Harry’s long-lost young love. They catch up.

Toward the end of the song, Harry realizes that they’ve each achieved a twisted version of what they’d hoped to become. Sue had wanted to be an actress and now she’s “acting happy, inside her handsome home,” while Harry had wanted to be a pilot and now he’s “flying in [his] taxi, taking tips and getting stoned.”

Clip of this great song below.

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But while the memories abide, the grief has slowly seeped in. Grief for the loss of my friend, grief for the passage of time, grief for lost opportunities to see him.

I want my HBO

When the real world seems gray, a television world provides a more effective escape for me than books do. Reading takes more effort than watching. And unlike my earlier days of reading when I assumed that every writer was an infallible genius never to be questioned, now I read with a critical eye that I cannot turn off.

These past two weeks, I’ve been watching the television show Succession for the third time and finding comfort in a fictional world that’s familiar through repetition, that’s artistically excellent, and that’s sufficiently removed from the present time in that it takes place in the 2018-2023 time period.

Young children love to watch what’s familiar to them. At age 64, so do I. Plot twists are surprises. They can startle you and make you realize that what you’re reading or watching is something outside of yourself. Newness breaks the spell.

Rolling with Kendall Roy

When I re-watch Succession, I’m inside the show rolling along with my favorite character, Kendall Roy, the older son, the greatest screw-up of the screwed-up adult Roy children who shamelessly compete for the favor of their father Logan, the patriarch billionaire media mogul modeled mostly after Rupert Murdoch with a hint of Joseph Kennedy.

Kendall suffers from chronic substance abuse, he’s a divorced philanderer, and he speaks with an inarticulate patter that, in its supreme awkwardness, is a triumph of writing and acting. Kendall owns the most excruciatingly awkward moments in the show, especially when he tries to be cool. It’s hard to watch him sing his obsequious rap song for his dad without feeling a dreadful yet mesmerizing sense of embarrassment. The clip of the song is at the end of this post.

To revel in the embarrassments and misfortunes of a fictional character like Kendall Roy can be a temporary balm to my sorrows. It’s schadenfreude without feeling disreputable because to feel joy at the pain of real people is an ugly feeling.

Kendall Roy, the over-the-top rich boy, is especially fit for the purpose of making me feel better about myself. I was an often awkward and cosseted rich boy too, although unlike Kendall, I grew up.

“You’re not a killer”

My childhood feeling of inadequacy connects me to Kendall Roy, who is forever failing to live up to his father Logan’s expectations. Logan is constantly diminishing Kendall, telling him he’s “not a killer,” that he isn’t tough enough, that he backs away from doing the hard thing.

Kendall wants to be like Michael Corleone, the cold-blooded killer of The Godfather. I can relate.

Michael Corleone is perversely aspirational for me, embodying absolute power and the willingness to kill to protect himself and his family. I’ve never been in an actual physical fight. I still regret hitting a snake with a rock in 1998, the most violent act I can recall.

Michael Corleone represents the dark side of who I can never be. If we often despise people for flaws similar to our own, perhaps we also covet traits that we lack.

I love to re-watch the Godfather but there’s no schadenfreude in it for me. Because I know now just how inept I’d be as a mafia boss.

Make-believe was my “narcotic”

I suppose the key difference in my suspension of disbelief between now and when I was younger is the nature of the fictional worlds I can lose myself in.

As a child, I used my imagination to create worlds where I could be all powerful and where I was admired and even worshipped. In those worlds I could find happiness and self-esteem, a relief from the reality of the impotent, uncool, nerdy teenager that I was.

I didn’t have many friends when I was in my early teens so I used games to assume a heroic identity. I’d play Avalon Hill war games and become the leaders of countries and supreme commanders of armies.

Or, using a nerf basketball hoop in my room, I’d become a star player of the high school team, a canny guard who could shoot well from distance and feed great passes to my imaginary friend George the tall center who could dunk.

But those were fantasies. Like Kendall, I might have imagined myself a “killer” in executing my intentions. But like Kendall, my actual execution was often more like Spaulding the hapless teenage nerd from Caddyshack, the great country club comedy.

Spaulding’s Caddyshack scenes feature his inability to hit a golf ball. That brings me back to the trauma of my 13-year-old self whiffing repeatedly on the first tee of the Hollywood Golf Club in front of everyone after I heard the caddy master tell my father, a club champion, that I was going to be a great player, just like him.

My kind father pretended it didn’t happen and whisked me down the fairway out of sight to drop a ball.

In my current incarnation and at my current age, I’ve long lost my fantastical abilities to pretend to be another person. I cannot become Kendall Roy nor do I want to.

However, I can lose myself in his gloomy aspect and in his gloomy world when I’m faced with things that bother me.

The rich boy

In his short story The Rich Boy, Fitzgerald famously writes that “the rich are different from you and me.”

A theme of my Substack is that the rich are not quite so different as most might think. We have our moods, good and bad. Wealth does not eliminate life’s inevitable sorrows.

In the same story, Fitzgerald writes that those born into wealth believe

“…deep in their hearts, that they are better than we are because we had to discover the refuges and compensations of life for ourselves.”

I disagree. The born rich are softer, more fragile, because we’ve always had our considerable refuges and compensations. We take them as a given. We’d be utterly lost without them.

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In every rich boy lurks a bit of Kendall Roy. Here he is below in all his awkward glory.

A disaster such as a debt and interest rate spiral would hurt everyone, including my family and me. I’m motivated for taxes to rise by self-interest, but long-term self-interest, which is in line with the self-interest of the country.

Governments generally have two favored ways of dealing with unmanageable debt. Default or inflation. Let’s assume the United States will never default. Instead, we would inflate the debt away.

We know that inflation harms the middle class, the working class, and the working poor far more than it harms the affluent and the wealthy. The less privileged classes have far greater financial precarity and spend a far greater share of their income, often more than 100%, on basic items like food, shelter, medical expenses, child care, gas, and utilities.

So, for any leader serious about inequality, addressing the debt risk is an imperative.

Our “Locust Years”

The deficit and the associated record high national debt (as a % of GDP which is the right way to measure it) is a problem few want to face or discuss because the solutions are hard. Tax increases are unpopular both with politicians and voters.

This is the fault of both political parties. Neither has spent political capital to inform the country of the danger.

Winston Churchill memorably called the 1930s failure of Britain to re-arm and confront Germany the “Locust Years.” We are likely living through another such period with regard to our country’s finances. If we have another significant crisis, or even an ordinary recession, we are not prepared to handle it.

We need more revenue soon and that additional revenue can only come from the wealthy.

The gist

I make my case with charts and commentary—”my receipts”—in a long footnote (that I worked hard on). Check it out! Or at least scroll down to the picture of the sad fellow pushing a wheelbarrow of worthless cash. 1

Here’s the gist:

• Our national debt is now 100% of GDP, as high as it was during WW2, and is projected to be 175% in thirty years.

• The debt is projected to continue rising because even during this strong (aggregate) economic period, we are spending about $2 trillion dollars more in outlays than revenues, a deficit of about 6% of GDP.

• The debt burden—the interest rate paid by the government times the debt—is at an all time high as interest rates have risen from historic lows.

• A debt spiral happens when investors in government bonds see greater risk and thus demand higher interest rates causing the deficit to widen further.

• The overwhelming majority (75%) of our outlays are mandatory—Social Security, Medicare and Medicaid, pension payments to veterans, interest expense on our debt—so don’t believe the sad, old lies that we can solve our fiscal problems by “cutting waste” or by “not sending our money overseas.”

• The overwhelming majority of our revenues (75%) comes from individual income taxes and social security taxes.

• The wealthy and affluent account for most of our revenues; the top 25% in income pay 87% of income tax. That’s where the money is for more revenue.

The wealthy will not welcome an increase in their taxes

The question is not whether the wealthy as a class will oppose any increase in their taxes. Of course they will. To paraphrase James Madison, taxes are necessary because people are not angels.

The question is what approach is best suited to take the edge off of that opposition and convince some portion of the wealthy that reducing the risk of a fiscal disaster is in their long-term best interests.

This question is especially important in light of the Supreme Court ruling on Citizens United and subsequent related cases, which vitiated campaign contribution rules for corporate entities, including PACs. The effect has been to magnify the power of the wealthy to influence elections. 2

Clinton got the message right

Bill Clinton was the last president to make our fiscal health a national priority. He presented his plan in the language of shared sacrifice. He avoided demagoguery against the rich. We can learn a great deal from his success.

In 1993, newly elected President Clinton made raising taxes his top priority. He noted that from 1980 to 1992, during twelve years of Republican “trickle-down economics,” the national debt as a % of GDP doubled from 30% in 1980 to 60% in 1992 (compared to 100% today).

And in 1993, although the ten-year treasury interest rate had declined from the 15%+ heights of the early 1980s, it was still stuck at around 7%. Clinton viewed this combination of rising debt and stubbornly high interest rates as a threat to American prosperity.

The centerpiece of Clinton’s plan was to raise taxes on the top 2% of earners from 31% to 36%. Clinton sold his plan as a reversal of the Reagan policy of trickle-down economics.

“…by asking the most of those who benefited the most in the past, and by asking more Americans to contribute today so that all of us can prosper tomorrow.” 3

Absent from his “pitch” were any harsh words for the wealthy. There were no accusations of greed, no singling out of any individuals or any groups of individuals. No blame and no shame. No morality tale.

Clinton was realistic that there would be opposition. But he asked the country to face the plain facts.

“And nobody likes the tax increases, but let’s just face facts. For 20 years, through administrations of both parties, incomes have stalled and debt has exploded and productivity has not grown as it should. We cannot deny the reality of our condition. We have got to play the hand we were dealt and play it as best we can.” 4

In the end, Clinton got most of what he asked for. Crucial to passage was the support of conservative Democrats in Congress. It’s well documented that Clinton was able to convince a significant number of prominent CEOs to lobby their Democratic representatives to support the bill. 5

In a radio address just prior to the final vote, Clinton said:

“On Wednesday, I met with more than 60 corporate executives who support my economic growth plan. Many of them are Republicans who will have to pay higher taxes under the plan. But they made the hard-headed economic decision that their companies, their shareholders and their country will be better off with this economic plan because it means lower deficits, lower interest rates, and a more stable environment to grow.” 6

Bernie Sanders

Currently, Sanders is the most high-profile national leader of the left wing of the Democratic party. He is focused above all on attacking and taxing billionaires who he blames for all the country’s problems. In the past, his attacks were against “millionaires and billionaires” until it was pointed out that Bernie was himself a millionaire.

Sanders’ new favorite attack word is “oligarch.” Here’s what Sanders said from the Senate floor last year.

“And it is not just power that [the oligarchs] want. Despite the incredible wealth they have they want more, and more and more. Their greed has no end…Bottom line: The oligarchs, with their enormous resources, are waging a war on the working class of this country, and it is a war they are intent on winning.” 7

In his speech, Sanders rails against the rising wealth of Musk, Bezos, and Zuckerberg. He doesn’t mention that the increases in their wealth came from rising stock prices of their companies.

Instead, Sanders implicitly blames the increase in their wealth for the struggles of less wealthy Americans.

“Meanwhile, while the very rich become much richer, 60% of Americans live paycheck to paycheck, 85 million are uninsured or under-insured, 25% of seniors are trying to survive on $15,000 or less, 800,000 are homeless and we have the highest rate of childhood poverty of almost any major country on earth. Do you think the oligarchs give a damn about these people?” 8

Sanders believes that rich people cause poverty. He never says how. For good reason, because that cause and effect does not exist in the real world.

Below, fictional Senator Eavis from TV show Succession, next to his inspiration, real Senator Bernie Sanders. In the show, Senator Eavis has a lot in common with Bernie Sanders, including his monomaniacal and ill-tempered pursuit of Logan Roy, the Rupert Murdoch-inspired billionaire character. In the end, the hapless Eavis fails to lay a glove on Logan Roy.

We need a truth teller

It’s a matter of vital concern that our debt and deficit be addressed. It would be unrealistic to expect the Republican Party to propose a tax increase. George H.W. Bush (“read my lips, no new taxes”) was excoriated in 1990 for raising taxes by a little bit and then lost the 1992 election to Clinton.

As for the Democrats, I have heard no nationally prominent politician make addressing the deficit and the debt a priority. The truth is grim and it is the rare politician who is willing to tell the grim truth.

The truth teller we need must call for a shared sacrifice rather than engaging in performative rage politics. Because begrudging the wealthy their wealth is class war, is resented, and will lead to far fiercer opposition from the wealthy of both political parties.

That opposition would include me. I would oppose a Democratic candidate who took the Sanders/DSA approach to taxes and the wealthy. To paraphrase James Madison again, that is a cure that is worse than the disease. Attacking billionaires with wealth taxes because you think they’re greedy is not a serious approach. (NB: I am far, far, far away from being a billionaire).9

I’ll give Logan Roy of Succession the last word.

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1

“My receipts”

The charts below from the Congressional Budget Office and The Federal Reserve tell the tale of my concern.

First, the history and projection of national debt as a % of GDP if we keep on our current course.

The sharp peaks in the 1940s and early 1950s were caused by expenditures for World War Two and the Korean War. The debt then went down in part due to GDP growth but in part due to a series of very significant tax increases that had bipartisan support (1942, 1943, 1950, and 1951). U.S. Treasury Analysis

The increase in debt in the 1980s was reversed by economic growth and Bill Clinton’s budget bill that included both spending cuts and tax increases on the wealthy.

Now, in 2026, we have climbed to a precipitous peak of debt, not because of an existential crisis like a World War, hot or cold, but because of fiscal carelessness during generally good times for the aggregate economy.

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The chart below shows why our national debt keeps growing. We’re not collecting nearly enough money to match our expenditures.

The sad old lies that if we could “just cut waste” or “send less money overseas,” we could solve our deficit will always be sad old lies no matter how many times politicians repeat it. That’s because 75% of our expenditures are composed of mandatory outlays such as Social Security, Medicare, and Medicaid and interest expense on the debt. The remaining “discretionary outlays” are roughly half defense, half for everything else that the federal government does.

If we want to make a dent in the outlays, we would have to reform entitlements, perhaps even more of a political “third rail” than raising taxes.

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About 85% of the revenues to pay for our government comes from individual income taxes and social security taxes. So, if we’re going to increase taxes, that’s where the money is.

Note: the problem with increasing corporate taxes is that it is relatively far easier for corporations to relocate to more favorable tax regimes than it is for American citizens to give up their American citizenship. Also, there are countries like Malta that give corporations opportunities to profit-shift. See this NYT article from 8/5.

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The people who pay most of the taxes are the wealthy and affluent, so that’s where additional revenues need to come from. The top 5% of income earners pay almost 60% of federal income taxes, the top 25% pay 87%.

Note: the chart below is based on federal income taxes, not social security or local taxes which are far less progressive.

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To put the national debt in context, we need to recognize that there are two components of interest expense, the amount of debt and the interest rate paid. Debt can be very high but if interest rates stay low, it can seem like the debt is not a problem. And ever since the 2008 great financial crisis, we’ve had generally low interest rates.

The ten year treasury rate is a good proxy for the expected cost of government borrowing over the near term future. Note that the interest rate on the ten year Treasury was in the teens in the 1980s and fluctuated between 5% and 7.5% for most of the 1990s.

Now the ten year treasury is at 4.65%. It’s true that expectations of inflation are often the chief driver of interest rates. However, all other things being equal, the higher the national debt, the greater the risk perceived by investors, and hence the higher the interest rate demanded.

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The next chart takes the amount of debt and multiplies it by the ten-year treasury rate to arrive at an interest burden. It then calculates the interest burden as a % of GDP.

Sounds complicated but the bottom line is that as a country we are currently set to use about 5% of our total output to service our debt. That’s an all-time post-war high, matched only during periods when the interest rate was significantly higher.

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So, if buyers of treasuries demand higher rates because they see the Federal Government not doing anything about deficits, we will have to devote more money to interest expense and the deficit will widen and we will have more national debt and interest rates will rise further making deficits worse, and the awful spiral that has been the ruin of many a nation will take its deadly course.

I enjoyed writing this post last May, using current numbers to analyze the financial life of Sherman McCoy, “hero” of the ‘80s novel Bonfire of the Vanities.

In Tom Wolfe’s ‘80s novel Bonfire Of The Vanities, Wall Street WASP striver Sherman McCoy is “going broke earning a million dollars a year.”

My title’s not a typo. The equivalent of McCoy’s one million circa 1985 is five million in 2025. 1 Later in this post I imagine how Sherman McCoy, transported to 2025, might spend his way into insolvency, extravagant details included.

I loved Bonfire, especially the way Wolfe gives specific details on Sherman’s financial life––the crushing cost of servicing his ‘80’s high interest rate personal debt to buy his envy-inducing P ark Avenue apartment, the costs of keeping up his Southhampton home, private school tuition for his young daughter, his wife’s decorating obsession, and so on. 2

Bonfire was the last modern novel I know of that makes an attempt to capture the totality of a wealthy character’s financial life. I have theories on why that is, but that’s for a future essay.

“Master of the Universe”

That’s the nickname Tom Wolfe has Sherman McCoy give himself based on a line of toys, and it’s become immortal. Thirty-eight-year-old Sherman believes that a Master of the Universe like him, earning a million dollars a year, should get whatever he wants. Money should not be a constraint

Sherman and his equally striving wife spend stupendously to keep up with their social set who are mostly older and richer. Their spending more than exhausts Sherman’s entire million-dollar- income. Sherman has a lot of income but minimal savings.

A blank slate of risk

When people say a person is “wealthy,” they could be making a judgement based on what they observe of that person spending. Or they could mean a person has a big income. Or that the person has a lot of assets in excess of their debt, otherwise known as net worth.

Spending, income, and net worth are very different barometers.

Sherman has a big income but it’s not guaranteed. Worse, he has no special talent that would enable him to make that income in a different setting. He happens to be in the right place at the right time with the right connections. 3

People think Sherman is “wealthy” because of his lifestyle, but they have no idea that he’s spending all his income. For Sherman, each year is a blank slate of risk. He could be fired, he could get sick, get a massive pay cut because of poor performance, or, as in the novel, be involved in a hit and run fatality while driving with his mistress. A career ending event.

In polite society no one will ask “What’s your net worth?” Except if you want to buy a co-op apartment in Manhattan. Then the half dozen strangers on the co-op board, your future neighbors, will ask you to parade nude, financially, in front of them. 4

Translating Income into Net Worth

The five million dollars that Sherman-2025 earns can be translated into a net worth equivalent. A short hand way of doing this is to take the after-tax income available to Sherman-2025 of two and a half million dollars and divide by 3% (same as multiplying by 33), which produces a net worth of $83 million.

The 3% number is not plucked from the air; it assumes a 5% investment return on net worth and a 2% inflation rate. Given those assumptions, $83 million is the amount you’d need to have in order to support spending of two and half million, inflation adjusted, in perpetuity. 5

Net worth is much more reliable than income. If some or all of your income comes from net worth, there’s no blank slate of risk at the beginning of each year. Net worth can certainly fluctuate, particularly if it’s concentrated in a few correlated investments, but the level of risk is still far lower than Sherman’s. And in most cases, it’s not an either/or situation. Many, if not most, wealthy people will have both an income from what they do as well as income from the net worth they’ve built up.

The expense of appearances

If you’re a Bonfire fan, you might recall how Sherman and his wife find it necessary to hire a town car to take them to a party a few blocks away and then have the car wait for them for hours to take them home. It would have been an insupportable social disgrace to have fellow guests see them entering on foot or hailing a taxi upon leaving. That behavior seems anachronistic in 2025. Now there’s Uber!

I’ve made Sherman-2025 an investment banker who must preserve appearances in different ways. His clients are mostly hedge fund and private equity guys (the “buy side”) who are far wealthier than he is in terms of both income and assets.6 It’s important that Sherman fits in with them, be at the places they go to, have similar experiences, have his daughter play with their children. Not only does that help him get and retain clients, but also, one blessed day, he might be able to flip from the sell side of investment banking to the buy side of investing other people’s money and become net worth wealthy.

Warning: Wealth porn ahead

Below I’ve done my best to replicate the Sherman-1985 lifestyle in a 2025 context and in a detailed category by category format. I’m aware this could be seen as “wealth porn” and be frowned upon (or spat upon) at a time when many people are furious about economic inequality and the behavior of some of the wealthy.

But just as Sherman McCoy in Wolfe’s Bonfire is a fictional character so is his derivative, Sherman-2025. In fact, Sherman McCoy is an outstanding example of my contention that contemporary fictional wealthy characters must be awful and must be made to suffer. In McCoy, Wolfe created an entitled Wall Street jerk brought low by his hubris and moral failings.

First, after-tax income

Sherman’s $5 million a year is all ordinary income and is taxed at an all-in tax rate of 50% taking into account Federal, State, City, FICA, and Medicare tax. That leaves $2.5 million of disposable income.

Manhattan Apartment

Because Sherman is income rich but relatively net worth “poor,” he doesn’t have the money to buy a “prestige” apartment, and he’s certainly not a viable candidate to pass the Board of a Park Avenue co-op. Those co-op Boards require significant liquid net worth in excess of the price of the apartment you want to buy before they will accept you into their buildings. 7

Nevertheless, Sherman and his wife must have a drop-dead apartment like his 1985 doppelganger. As Wolfe described McCoy’s apartment in Bonfire,

“…the sort of apartment the mere thought of which will ignite flames of greed and covetousness under people all over New York.”

The solution is to rent rather than buy an envy inducing apartment. So Sherman lives in an apartment at 15 Central Park West, a new building designed successfully to look like an older, pre-war building. His apartment costs $60,000 a month, or $720,000 per year.

Picture below from StreetEasy. 8

The Hamptons

Sherman doesn’t have the savings to buy a house in the Hamptons. He has to rent there too. His image demands that he has to be South of the Highway in an estate area, where his clients own houses. He and his wife want a house large enough for house guests. They need at least five bedrooms.

They rent in East Hampton near The Maidstone Country Club. (Perhaps Sherman-2025 belongs.) The house rents for $425,000 for the “Season,” meaning Memorial Day Through Labor Day. 9

Children

In the Manhattan bubble, kids are super expensive. Tuition at private school is $70,000 for Sherman’s six-year-old daughter compared to about $7,000 in 1985.

They have to have a full-time nanny for their daughter: $75,000.

One of Sherman’s clients told him “It’s a crime” not to take advantage of annual tax-free giving to their daughter. In 2025, Sherman and his wife can give $36,000 annually to their daughter without any tax being paid.

Then there’s new clothing for their daughter, toys, after school and summer activities including equestrian lessons ––another $30,000.

Total cost is $211,000.

Vacations

Flying business yes, flying private no, unless invited on planes owned or chartered by Sherman’s wealthier clients/friends.

Two family trips:

Skiing at Beaver Creek for President’s Week requires two rooms at the Park Hyatt Beaver Creek (the nanny stays with the daughter) and a private ski instructor for their daughter. Cost: $50,000.

For Spring Break in March, two rooms at the Four Seasons in Hawaii. Another $50,000.

In the fall a week in Paris for Sherman and his wife. $25,000 not including shopping.

Total travel: $125,000.

Charitable Contributions

Sherman’s wife is on the Board of three not-for-profit organizations. She’s expected to give $100,000 a year to each. She asks her friends to attend the organizations’ annual galas and contribute smaller amounts––$10,000 here, $25,000 there.

In order to ask their friends for contributions, she and Sherman have to be prepared to reciprocate by giving to their friends’ favorite causes. Sherman also has to give to the favorite charities of his best clients. In addition, Sherman has to give at least $25,000 a year to their kids’ school’s annual fund.

On the gala invitations and in the annual giving report of the school, everyone can see who’s given how much based on which giving tier they’re placed in––Platinum, Diamond, Emerald, or Quartz. People scour the lineups of these tiers like baseball fanatics scour box scores.

Charitable contributions add up to about $500,000 a year, a neat tithe or tenth of Sherman’s pretax income. The contributions shield about $200,000 of tax so the after-tax cost is $300,000. 10

Health and Welfare

Sherman pays for his family’s health insurance through his bank’s plan. It costs about $5,000 a month or about $60,000 a year.

The insurance plan is top notch, and Sherman and his family are young and healthy so they bear only $10,000 a year in non-reimbursed medical expenses, mostly dental.

An investment banker must present a good physical image, and Sherman’s wife is a fanatic about exercise.11 Flab in their world might signal sloth. Sherman and his wife both work out with private trainers three times a week. Six sessions at $200 each=$1,200 a week=$60,000 a year.

Sherman’s wife is proactive about her beauty treatments and spends about $40,000 a year on facials, injections, skincare products, manicures, and pedicures.

Total is $170,000.

Clothing and accessories

The wife of a five-million-dollar husband assumes she should be able to buy whatever she wants. In the context of five million, why can’t she buy a $20,000 Chanel suit or a $3,000 Prada cashmere sweater?

Or a limited edition Hermes Birkin bag, which she buys for $30,000 on the secondary market because she doesn’t want to wait to be allowed to buy one from Hermes. (According to Sotheby’s, the secondary market price is 2.4x the price at Hermes.) 12

I have a good friend who is a personal shopper to a wide range of women. I gave her the profile of Sherman-2025’s wife. Her estimated range of spend was $150,000 to $250,000. Using the midpoint, that’s $200,000.

Household and Miscellaneous

Sherman and wife have a housekeeper who has the same cost as the nanny: $75,000

Two cars leased and garaged: $20,000

Insurance: renter’s, auto, collectible, and liability : $50,000

Food and restaurants: Three meals out per week at $350 each. Plus groceries, which in the city cost $300, and in the summer cost $600 because Round Swamp in the Hamptons is so expensive.13 Total: $70,000

Club Memberships- Dues at a New York private dining club at $10,000 plus a tennis club and lessons in the summer at $10,000. Total $20,000.

Total Household and Miscellaneous: $235,000

Total Identified Spending

The numbers above add up to $2.2 million compared to $2.5 million in disposable income so there’s about $300,000 left over.

But I’ve left out some important categories.

• Furniture, art, and jewelry.

• If Sherman-2025 is having an affair like his 1985 predecessor, there’s the cost of the affair, which might include rental of a “love nest” nearby or hotel rooms.

• Sherman would probably belong to a golf club although between his work and his affair he might not have time.

• Utilities would be paid by Sherman on his two rental properties.

• Various streaming (and Substack!) subscriptions, but more significantly, outrageous bills from the A/V company when their televisions and remote controls inevitably malfunction. (This one’s personal!)

• Various one-time expenses that occur every month.

The Real McCoy

If Sherman McCoy, either 1985 or 2025, is a realistic character, and I believe he is, what can we glean from his spendthrift ways?

Seeing what a person decides to spend their money on is often a poor guide to their financial situation. If Sherman-2025 loses his job, he has nothing to fall back on. His wife, grown accustomed to a certain standard of living, probably would leave him. She certainly will when she learns about the affair.

When Sherman’s whole life blows up, everyone will be surprised if not shocked. How could a Wall Street guy, given his facility with numbers, put himself in such a fragile position when he could have been saving a great deal of his income during his years of plenty?

We say that the past is not prologue to the future but we don’t really believe it. When prosperity has been the status quo for many years, it’s difficult to remember that fortune is fickle. Right now, as I write this, everyone I know inside the Manhattan bubble says they are worried about the future of the economy, among other things. But I have no evidence that the wealthy are changing their spending habits. I’ve looked for a tightening trend and it’s not there yet.

Those who experience a long stretch of good times can become soft, vulnerable, fragile to shocks. Joseph gave his Pharoah seven years of plenty. We in the privileged bubble have had seventeen.

Question for the comments: “Who is rich? He who is happy with his lot.” Is it possible for anyone today to truly feel that way?

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The comments from last week’s post on Beauty, Class, Wealth inspired me to post this one minute video note highlighting a few of the most interesting comments.

The rhetoric against the wealthy has grown more harsh, more bitter, more belligerent. Understandably.

The concentration of the wealth at the very top is historically high.

And according to Moody’s research, the aggregate spending of the top 20% is 50% more than the aggregate spending of the bottom 80%. That means the average household in the top 20% is spending six times more than the average household of the bottom 80%.1 As Mark Zandi, Moody’s chief economist writes:

“No wonder most Americans are upset with their financial situations and the broader economy.”

Initially, no one took Donald Trump seriously. I suggest we take Bernie Sanders and his DSA (Democratic Socialists of America) associates seriously. Having seen the political pendulum swing wildly one way, we should acknowledge the possibility that it can swing just as wildly the other way. 2

The leftmost faction of the Democratic Party has gained popularity and won elections. Their policy proposals are anti-capitalist and anti-wealth. Their rage at the wealthy for the sin of being wealthy is unrelenting.

Accordingly, I see an increased risk that anti-capitalism will take hold. Inequality might then be “solved” not by raising some people up but by tearing everyone down. That would be a terrible thing.

Remembering Occupy Wall Street

In 2011, there was populist outrage that the people who had helped to cause the Great Financial Crisis had been neither prosecuted nor properly punished. In the meantime, while Wall Street had been rescued, millions of Americans had lost their homes and jobs. The country was deep in a recession. Median real household income fell from $73,000 in 2007 to $67,000 in 2011. 3

The injustice of it was overwhelming to enough people that Occupy Wall Street was born. There were mass protests in cities all over the developed world, but the beginning and the epicenter of OWS was in the financial district of Manhattan in Zuccotti Park where there was an encampment of thousands of protesters.

There was a great deal of media coverage while Zuccotti Park continued to be occupied. But that encampment only lasted two months, from mid-September until mid-November when Mayor Bloomberg dismantled the encampment and OWS on Wall Street was no more.

From the point of view of Wall Street people, most of whom actually worked in midtown as I did, Occupy Wall Street seemed like a piece of downtown, avant-garde theater, critically panned, and thus deserving of its short run.

The wrong lesson of OWS

The lasting effect of OWS is debatable. Some might say the effect was merely the widespread currency and permanent place in the lexicon for the tagline “We Are The 99%.” Others might say OWS generally raised consciousness about wealth inequality even if nothing was done to combat it and it continued to get worse.

But what if the effect of OWS was something more subtle, more of an absence than a presence? The implicit takeaway of the wealthy may have been that the “99%” were completely ineffective at accomplishing anything.

OWS was famous for its lack of any specific demands as well as for its lack of any organization. If that was the best the 99% could do in conditions ripe for real reform, then maybe the wealthy had nothing to fear.

Another implicit takeaway by the wealthy may have been the Ayn Rand/Atlas Shrugged idea that it is the 1% that makes the world work. Without the 1%, nothing could or would get done.

There hasn’t been a repeat of anything that resembles OWS. Big protests have largely been along political lines, rather than wealth and income lines. No encore after fifteen years might lead the wealthy to think that inequality was something that people talked about, agreed had gone too far…and that was it.

Self-interest properly understood

I no longer see the quick unravelling of Occupy Wall Street as a permanent reprieve for the wealthy but rather as evidence of a potent and enraged force that has not gone away. In fact, the rage and the potency have increased, available for use by a charismatic leader.

I fear that our current gilded age will end not by reform but by ill-considered, radical policies that severely harm our economy. Even if I had no other reasons, my self-interest alone would lead me to favor policies that reform the excesses of capitalism, including our current, heightened inequality, before it’s too late.

So, what would I have the wealthy do? Use your resources to support political moderation and to shun extremists, whether MAGA or DSA. Do good works. Avoid spectacles.

But maybe it’s already too late.

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While I appreciate a good movie or show, few things make life better than falling in love with the world of a novel, the sort of book that while you’re reading it, you’re dimly aware that with every page you turn, you’re hastening the end of your love affair with the story. But you cannot stop.

Here are four novels Debbie and I loved and recommend strongly. They all have first-person narrative voices that captured us early on and never let us go.

They were welcome respites from the clamor of reality.

The Calamity Club by Katherine Stockett

Two caveats. First, The Calamity Club is a bestseller so it is far from an “undiscovered gem.” Second, I have a financial interest in the book’s publisher and thus a financial interest in the book continuing to do well. 1

The world of Calamity Club is 1933 Mississippi told through the two, alternating voices of a girl and a woman. It’s a big book at over 600 pages but I didn’t want it to end. The action keeps coming. The plot is intricate but not convoluted. It all made sense to me.

I found the two narrators on the page distinct and compelling. Debbie listened to the audio version and was so mesmerized by the voices that it led to a ridiculous fight between us (described in a recent post, link in the footnote). 2

The author Katherine Stockett (The Help) did a great deal of research and it shows. You get a good sense of the Deep South Depression status hierarchy, from destitute to former rich to still rich. I was transported (a cliché but it’s the right word) away from the real world, which was a delightful relief.

I didn’t find the novel overtly political. However, reading about some of the worst cruelties of that time and place made me angry for the suffering characters, glad that there’s been great progress since 1933, and regretful that some of that progress has been recently squandered.

Days Without End by Sebastian Barry

When I finished Calamity Club, having closed one escape route from current reality, I craved a “rebound novel” that would offer a similar escape. I asked Claude (Anthropic) for suggestions of other, high-quality historical novels, i.e., well reviewed. That’s how I found Days Without End.

The narrator is an immigrant from Ireland to the Western United States in the mid-19^th century. He’s looking back as an older man on all his adventures, starting in the frontier town of St. Louis in the 1840s when he’s a teenager.

For much of the story, he’s a soldier fighting Indian tribes, the Confederate Rebels, and various bandits. There’s a lot of violence and gore but it’s delivered in a narrative voice that manages to be rough, explicit, and eloquent all at once.

The narrator also carries on an unusual and magnificent love affair. To say more would risk spoiling the plot.

Like Calamity Club, the pace of Days Without End is quick.

Also, Sebastian Barry is a prolific novelist. I’m looking forward to reading his other books.

The Rest of Our Lives by Ben Markovits

In The Rest Of Our Lives, a fifty-five-year old man is trying to figure out his life as he’s driving his daughter, his only child, to drop her off at freshman year in college. We learn right away that a dozen years ago, his wife had an affair. As a consequence, he vowed that he would file for divorce once they were empty-nesters. That time has come.

The story takes place in modern day America, so no “transport,” but the writing is so good that it was easy to escape into the novel’s world. There’s a simple clarity to the narrative voice. It doesn’t show off. The skill is hidden by the skill itself.

The man’s journey through geographical space, through time, and in his head, had more than enough action and uncertainty to keep me deeply interested. There’s a great one-on-one pick-up basketball game scene, and I also liked the storyline of his wife’s travails as a teacher at Brearley, a quintessentially elite, all-girls private school in Manhattan.

I found myself more than once giving advice to the protagonist as if he were my friend pouring out his heart. He didn’t take all of my advice but nevertheless I rooted for him to the very end.

Medium Rare by Natasha Joukovsky

Medium Rare is historical in that much of the action takes place during the 2019 NCAA March Madness tournament. It’s a take on the myth of Icarus, played in the novel by a “mid-level” Washington lobbyist who achieves sudden and “stratospheric celebrity” when it looks as if he’s filled out a perfect bracket to win a billion-dollar prize.

The narrator Cassandra is a female friend of the bracket “genius.” Like her mythical namesake, Cassandra has the power of prophecy, although clouded enough to keep a reader guessing.

Cassandra is very status conscious and aware precisely of how far she stands above her mid-level lobbyist friend and his wife. The narrator’s snark and her ruthless snobbery were especially appealing to me, which may be a self-condemning statement! And waiting for the “lucky” bracket winner to fly too close to the sun played upon my sense of schadenfreude.

Also, the NCAA basketball scenes, true to the 2019 tournament’s history, are great.

Full attention and completing

My full attention standard for television is much lower than it is for reading a novel. There are some, rare TV shows and movies that grab my full attention, that eliminate the temptation to either multi-task or let my mind wander, e.g., The Pitt 3

For the rest, I’ll lazily follow along unless I think it’s really bad. Then I’ll cut it off.

However, if a book is not grabbing my full attention, I’ll stop reading. I probably have a book completion rate of about a third.

In this regard, Debbie and I are very different. As I’ve mentioned elsewhere, she’s a “completist” and considers it a moral failure to begin anything without finishing it. I’ve decided to be grateful for this quirk of her character as it could be an important reason why the project of our marriage has endured.

Comments appreciated about the books above and your reading (or TV/movie) suggestions

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Below is a link to our full year 2025 books and shows recommendations. We picked too many!

The marriage of Taylor Swift poses a question of whether it’s possible to remain at the peak of any endeavor and still have a balanced life. Can a superstar like Taylor Swift shift priorities as her situation shifts or will she always prioritize her work no matter what.

I come at this question from a position of being far from the peak of any single endeavor. Instead, I stand on various hills (husband and father) and look up from many valleys, too numerous to name.

So, as a “balancer” who never went all-in on any one endeavor, I have a selfish interest in believing that the answer to my question is no, you rarely if ever can be number one at anything and still lead a balanced life. The requirements to stay at the top are too intense and the seduction of being at the top is so strong that your life and your ambition become the same.

I admire Taylor Swift without being a fan of her music. From what I can tell, she’s a terrific role model for girls and young women. She’s philanthropic, having shared the wealth of her Eras tour with her crew. Coincident with her recent wedding, she donated to many charities, including NYC food banks. Perhaps as penance for shutting down the area around Madison Square Garden. 1

Taylor Swift is top of my mind not only because of her wedding, but also because of my recent literary encounter with Charles Dickens, a different celebrity in a different century in a different field. In his time Dickens was as famous and feted and observed as Swift is today.2

Taking into account the volume of their creative output, including performances, one can say with some confidence that Dickens and Swift share the trait of being obsessive about their work. Like most superstars, Dickens failed to balance his dominant artistic fame with a happy domestic life. I wish Taylor Swift better success in achieving a happy balance if that’s what she wants.

Gloomy Charles Dickens in middle age

I just finished reading Francine Prose’s new novel Five Weeks In The Country in which she creates a version of the historical Charles Dickens from fact, conjecture, and her imagination. This compelling version of Dickens by Prose (what a Dickensian name!) is for now the “true” version imprinted upon my brain.3

Five Weeks in the Country takes place during the disastrous five-weeks-long visit to Dickens’ country home by fellow writer Hans Christian Andersen, a Dane with almost no proficiency in English.

The outstanding feature of Five Weeks in the Country is Prose’s novelistic portrait of Charles Dickens at age 45 in mid-life crisis. By then, Dickens had already been famous for twenty years after his serialized novel The Pickwick Papers went viral internationally. When Prose introduces us to him in 1857, his fame and reputation are at a zenith, yet he is deeply unhappy.

“He had a beautiful house, professional success, a loving family, but he was as morose and distracted as he’d been as a boy…No one expected happiness in a blacking factory, but now with such an enviable life, it was unseemly to be gloomy.” 4

One source of Dickens’ gloom is the fear that the secret of his shabby, impoverished origins will be uncovered––his father’s stint in debtor’s prison, his childhood humiliation working in the blacking factory, his grandparents “working in service.” He worries that he will be discovered as an imposter by the upper-class society whose approval and adoration he craves. 5

Prose’s writing is so skillful you can forget you’re reading a book. It’s also funny. The humor—mocking and often Nabokovian cruel—is centered on an unintended contest to see who makes the visit of Hans Christian Andersen more terrible, the ungainly and inappropriate Andersen as houseguest or Dickens as the imperious, impatient, and bleak-minded host.

Andersen’s visit begins with him collapsing on the parlor floor, exhausted.

“Watching [Andersen] open his eyes and try to stand was like watching a giant wounded cricket trying to right itself. He used his elbows and knees like crutches to hoist himself onto his feet.”

Over the next five weeks, the visit never gets better.

A family unhappy in its own way

Dickens is a self-admitted failure as a father. He’s dissatisfied with his nine children, ages five to twenty. Dickens’ children must compete not only with Dickens’ expectations, not only with the public whose love Dickens prefers, but also with the many children and young characters who inhabit the world of their father’s beloved novels. Characters who he seems to prefer over his real life kids.

Dickens suffers from the typical invidious comparisons of the self-made man who, in providing his children with the comfort and ease he never had, resents them precisely for what he has provided them. Dickens thinks his children lack “initiative, drive, persistence—-all the qualities that made [Dickens] who he was.” 6

The children feel their father’s displeasure and his distance. When he’s at home with them, he’s often in a “writing trance,” never present in a way that he was when they were much younger and he was less famous.

In Prose’s novel, the children speak in a communal voice:

“Why did someone who writes so feelingly about the powerlessness of children not realize how helpless we felt?”

Much of the gloom of the Dickens household extends from the terrible state of Dickens’ marriage. To the extent Dickens pays attention to his wife Catherine, it’s to show his annoyance when she interferes with his work.

By 1857, Catherine had gone through ten births (one baby died), and Dickens has decided that she is stupid, dull, and fat. Dickens never got over his platonic love for Catherine’s younger sister Mary who died at the age of seventeen in 1837. Twenty years later, around the time of the novel, Dickens decides “to save his life” by leaving Catherine for an eighteen year old actress, Ellen Ternan.

Dickens the workaholic

When we meet Prose’s 1857 version of Dickens, he considers himself a “sad old man.” He’s unwell from working too hard. He suffers from sharp, recurring pains in his side and on his face. As well, his eyesight is shot.

“Black spiders crawled across his visual field, his punishment for writing for so many hours in flickering, feeble light.”

Dickens’ memory of past happiness pains him and the only way he can stop the pain is by working so hard he can think of nothing else. But even his work threatens him. He’s jealous of his own characters whose lives he makes so eventful while his own life seems like a prison he can’t escape.

His envious wish is to make the characters who spring from his mind unhappy at the end of his stories. “Happy endings sicken him,” because his own happiness is elusive. But he knows what his public demands. 7

”Denying [his]readers a satisfactory ending was like refusing a child a slice of birthday cake.”

His prodigious writing is bad enough in terms of obsessive work. But Dickens also has a grueling schedule of live performances, reading his novels and acting in the plays he’s written. During the time of the novel, Dickens is trying to lose himself rehearsing an acting role he created of a jealous lover. 8

“He would practice his soliloquy until he was no longer himself…until he was no longer an overworked writer and the father of so many children, until he no longer fell in love with every young woman he met, until he forgot that he was a dissatisfied husband and father and now the host of an eccentric houseguest who spoke no English.”

That sums up Dickens’ misery nicely. He continued his mad schedule of writing and performing until he succumbed to his illnesses thirteen years later at the age of 58.

Who benefits from great talent

A similarity between Charles Dickens and Taylor Swift is that the information generated about each of them is so voluminous that it’s difficult to pick this letter of Dickens or this song of Swift’s and say this is the true Charles Dickens or this is the true Taylor Swift. Perhaps every fan has their own “true” version.

We do know, however, that Dickens worked himself to death. His readers were impatient for the next installment of his serialized novels. His performances in England and America were sold out. And when he performed, he usually acted out the most dramatic scenes of his novels, the ones that exhausted him physically, e.g., the murder of Nancy by Bill Sikes in Oliver Twist.9

Dickens sacrificed himself and perhaps sacrificed much of his happiness to his work. Hundreds of millions of us are the beneficiaries of that sacrifice.

Creators are naturally envious creatures. But it’s hard if not impossible to think of any creator envying Prose’s version of Dickens.

Instead, we envy the carefully curated images of celebrities without knowing what their true lives are like to them. And even if we could know the truth, would we really want to? We need our myths and role models.

Because beneath the curated images, when the reality is revealed, so often we find pain and insecurity and distress. Perhaps those are the natural accompaniments of successful creative obsessiveness.

Great talent is more a gift to the public than it is to the artist.

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The title of this essay, High Flying Adored, is a song I love from Evita, one of my favorite plays. It’s about the life of Eva Peron who in the 1940s rose from an undistinguished background to become the First Lady of Argentina at age 26 beside her dictator husband Juan Peron. Eva died at age 33.

High Flying Adored are words that could describe Charles Dickens or Taylor Swift.

“So famous so easily so soon is not the wisest thing to be.”

This past Sunday evening, a sharp and mysterious pain presented itself on my face. On Monday, I saw my regular dentist. He got me an immediate appointment with a fellow dentist, a Park Avenue endodontist (a root canal specialist). When you have undiagnosed facial pain, needing a root canal is a hope, not a fear. Assuming that paying for it is not an issue.

In the waiting room, I sat across from a beefy, sandy-haired man in shorts and a tee-shirt. We nodded to each other. He had a kind face and was about my age. After a few minutes he went up to the reception desk.

He spoke softly but I was near the desk so I could hear what he was saying. He was going to put off the procedure he had come for because he couldn’t figure out how to pay for it. Plus, he owed money for a past procedure.

The man left the office, his shoulders sagging. My immediate thought was “why do I deserve to be seen and treated and this man does not?” There was nothing I could do. I leaned back into the chair. Then, inside my head, I shouted at myself, F**k this!

I stood up and went to the desk. I told the two receptionists that I wanted to pay for the man’s procedure, whatever it cost. I wanted to remain anonymous to him. I asked them to let the dentist know.

In the end, the dentist discovered I had a badly infected tooth. An hour later, he performed a root canal that quelled my pain. Before I left the office, the office manager told me that the dentist was going to work something out with the man. My offer to pay was appreciated but unnecessary.

Who is deserving

The day after my root canal, I read an excellent essay on the concept of “deserving.” The essay, written by Christine Tan, an expert on Chinese philosophy, was linked by fellow Substack writer who writes superbly about many things. 1

Tan’s essay begins by pointing out how natural it is for us to want to see people get what they deserve. We want people to be rewarded for their good behavior and punished for their bad behavior. Both vice and virtue should have consequences. Otherwise, there’s no sense of moral justice in the world. Instead, there’s chaos.

Tan brings in Confucius from 2,500-years ago to give us a solution, a prescription for a morally just society. Leaders of a society should be those who attain the highest degree of “worthiness (xian).” Tan defines xian as “compassion, righteous judgment, and moral restraint.”

Confucius held that xian should dictate a society’s status hierarchy. The more xian one has attained, the greater one’s leadership role ought to be.

What follows is the greater the leadership role, the greater the responsibility. With greater responsibility comes greater power. Greater power requires greater material resources. A night watchman of a gate needs only himself, but an emperor in his magnificent palace might need thousands in his retinue to support his work.

A key assumption of the Confucian solution is that all people are capable of attaining xian, so there’s a fairness to rewarding those who excel at it. And who can argue against “compassion, righteous judgment, and moral restraint” as being the proper measures for awarding status, responsibility, and resources?

Enter Zhuangzi the contrarian

Tan tells us that Zhuangzi, a Daoist philosopher writing about 100 years after Confucius, thought the Confucius solution was fatally wrong in a few major respects. 2

Pursuing xian is actually antithetical to human flourishing, because you’re pursuing titles and credentials, things that are outside yourself. Tan writes:

“This leads one to treat their own life as raw material for that abstract identity. One’s material body becomes an instrument for something immaterial.”

Zhuangzi tells the story of being summoned to a palace and offered a prestigious position. He points to an exquisite bowl made from a turtle’s shell and asks whether the turtle would rather be alive or have his body used for an ornament. Point made; Zhuangzi turns the position down.

Zhuangzi thought that Confucius had the order of operation reversed. The titles, the power, and the resources, come first. The attainment of xian was then used to justify the spoils. And who, after all, was the arbiter of xian except the powerful and the rich? What say would the night watchman have about who had xian compared to the word of the emperor?

Tan writes:

“Power, therefore, often does not reflect virtue, but instead has the ability to produce the appearance of virtue. This is how hierarchy manufactures its own moral narrative. Those who rule come to be called righteous.”

Zhuangzi’s most powerful point, however, is to demolish the Confucian point about equality of opportunity to attain xian. Zhuangzi thought this was a complete fantasy. One’s circumstances have a great deal to do in determining the course of one’s life. What we now call meritocracy is both a myth and a scam. Tan writes:

“[Meritocracy] offers a narrative in which suffering is temporary, sacrifice is rational, and the future will vindicate the present.”

If you’re a “loser” in the game of meritocracy, it becomes difficult to admit that you’ve sacrificed for nothing or admit that you were just not good enough. And if you’re a “winner” in this game of meritocratic striving, how irresistible it can be to believe that you are the primary author of your own success.

Zhuangzi argues that these are false beliefs used by the people in power to justify themselves and to effectively imprison everyone else in a Confucian competition that most people are bound to lose. Because there can only be one emperor but thousands of night watchmen.

Finally, to underscore that no one is self-made, Zhuangzi uses the example of a mythical god who glides gracefully in the air. Even this deity, however, depends on something else to appear effortless, in this case, the wind.

From deserving to acceptance

I have wrestled with my own good fortune and whether I “deserved” it. To bolster my claim of deserving, I could point to many decisions I’ve made that have led to the life I have now. But that’s a trap. 3

Because I cannot ignore Tan’s list of relative advantages:

“upbringing, pedagogy, institutional pathways, emotional and material support, health, luck and the ordinary labour of others,”

all of which played a significant role in shaping my life. There’s room for my personal agency but personal agency takes place within the context of all the advantages above. The winds have been at my back.

The entire concept of deserving is flawed. A while ago I disabused myself of the myth that I was the chief agent responsible for my successes in life. So if the question of whether I deserve my life is irrelevant, then so is the concept of guilt. How can I be guilty about advantages over which I had little to no control?

This is not a cop-out or an amoral concept. Instead, I can use the agency I do have to love and help others––family, friends, and strangers––because it makes me feel good in the moment. My actions do not have to serve as the raw material for some future credential or recognition.

Accepting inequality

We know that contingencies play a huge role in our life, whether it’s where we’re born, who our parents are, who, or if, we marry, or whether we happen to pick a career that suits our skills and fills our bank account.

Once you accept the contingencies that underlie inequality, then the moral infrastructure of meritocracy is demolished. We are not the prime agents of our success or failure. We are all fated to be unequal in many ways.

But some aspects of inequality are choices made by society. They are not fate.

The inequality of my access to dentistry compared to that man in the waiting room is one such choice. It’s a barbaric one. His pain and my pain are the same. A wealthy society like ours should not be organized so something as universal as pain is treated unequally.

A truth, a proposition, or a myth

We know that no society has ever made everyone equal or given everyone equal opportunity. But on July 4^th, we read aloud the Declaration of Independence and the famous “self-evident” truth that all [people] are created equal. In his Gettysburg Address, Lincoln called it a proposition, rather than a truth. And in his I Have a Dream speech, MLK called it a promissory note that America had defaulted on.

Pretending that we are all created equal leads the privileged to narcissism and the non-privileged to despair. It divides us into winners and losers, as if we all start off life at the exact same starting line, like runners in a race.

Christine Tan writes in her essay that if we can rid ourselves of the myth of meritocracy:

“We would be rid of the cruel fantasy that a person’s place in the world is a reliable valuation of their worth as a human being.”

It is morally correct that all people ought to be endowed with certain rights by virtue of simply being alive. One such inalienable right should be healthcare, including dentistry.

Ideally, no one should have to wait for or defer a root canal. One day, I hope, we’ll have true universal healthcare. But we have a long way to go.4

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We were charmed by the staircase, which was from an actual stage set. Or so we were told. The charm faded once we experienced the reality of endless trips up and down the many steep stairs to fetch the endless material needs of our baby.

The apartment had good light from the west. We looked out from a distance upon an ABC studio building. However, known to everyone but us, ABC had decided to expand and was poised to begin constructing a brick building up to the property line, just a few feet away from all our windows. There would be many months of noisy work and construction workers who could peer in at us. When it was done, our light would be extinguished.

Before we closed on the apartment, we asked our four NYC-based parents to come see it. We don’t remember whether they came, but now we look back in wonder that not one of them asked us any questions or asked us if we had done our due diligence. They let us learn our own lessons.

When a stray brick crashed through one of our windows and soon thereafter all of Debbie’s jewelry was stolen by one of the workmen, the lessons hit home very hard. And when we sold the apartment, we took a loss despite a boom in NYC co-op prices during our ownership.

As for our missing in action parents, they were living their lives and we were living ours.

Under Parenting

Throughout the decades, I complained at great length to many therapists about my parents. Mostly, about their hands-off approach. Their selfishness, their aloofness. One bored male therapist, couldn’t take my kvetching anymore and yelled at me “to just grow up.” 1

My perspective today is that my parents’ hands-off approach was just fine. After all, I’m happy with the person I am, including my relationships with my own children. These are dispositive points.

My parents were definitely more interested in themselves than in their children. They frequently traveled, mostly to weeklong national bridge tournaments, and we had governesses when we were young.

Ideally, we didn’t bother them with any troubles and instead were sources of fun and amusement. Watching sports and playing ping-pong with my father, a shared fanatical love of the New York Islanders with my mother.

My father valued having a stock of funny stories to tell. On one parent-teacher day, he delighted in telling my biology teacher one of his favorites. That at Cornell in the 1950s he’d blown up the chemistry lab, which, together with his terrible grades, had gotten him expelled. 2

At another school gathering, my father accused my headmaster of running a school that lacked academic rigor. My father never saw me doing any homework, yet I was getting straight “A’s.” This turned into a good “story” for my father when the headmaster told him that he’d never heard such a peculiar and astonishing complaint from any other parent.

As for my mother, she was always searching for her purpose beyond being a wife and mother, and that search absorbed most of her attention and made her often unhappy until she found her calling. 3

My mother’s interventions when I was growing up were infrequent, but when she felt strongly about my going off course, she was fierce, as when she sabotaged my relationship with a girl she decided was unsuitable for me. She was right in the end but her means were cruel.

Over Parenting

I’m glad I had parents who were mostly self-centered rather than parents who lived their lives through me or considered me some sort of status symbol. Of course I’m not suggesting those are the only two parenting choices, but parental self-centeredness seems far healthier for a parent-child relationship than the burden of making a child the center of a parent’s life.

Trophy children

In Ann Patchett’s new novel Whistler, Patchett’s fifty-something heroine Daphne is a child of divorce with a difficult mother but a wonderful sister Leda. The two sisters have turned out fine. They are (annoyingly) self-satisfied with their resilience and grit.

Daphne teaches literature at an elite all-girls private school in Manhattan (think Brearley or Spence or Gossip Girl/NYC Prep). The two sisters dish out contempt for these teenage girls and their wealthy parents in contrast to their own upbringing.

Daphne’s sister Leda observes that Daphne’s students are the kids to worry about today.

“…the ones who are the singular light of their parents’ lives, the ones who hit thirty and are still calling their mom five times a day.” 4

Daphne piles on. Her students’ parents “might as well have carried them to school on golden plinths.”

And then Leda says it’s not too much love, but

“too much crippling dependency…which masquerades as love.”

Novelists and essay writers often take a point of view that casts their own life as the best of all possible worlds. Patchett does it in Whistler–––Daphne is an autobiographical character––– and I’m wary of committing the same Panglossian sin in this essay.5

Vicarious parenting

My son Michael and I recently saw the latest (and wonderful) production of Death of a Salesman. The play is not usually considered a commentary on parent-child relationships. But that’s the theme that stood out to me when I saw it this time. Maybe because I was with my son Michael, who’s the same age as the play’s adult children.

The play is the tragic tale of a faltering salesman Willy Loman, a father who invests all his hopes and dreams in his son Biff. The tragedy can be traced to Willy’s own moral failure––teenage Biff catches his father cheating on Biff’s mother. That incident throws the lives of both father and son horribly off course.

But even before the revelation of Willy’s cheating, the doom of both father and son was already sealed by Willy’s monomaniacal obsession with a peculiar type of success for Biff, an adolescent football hero with no academic talent. Willy is constantly telling Biff that all Biff needs for phenomenal business success is to be “well-liked” by the right people.

Willy compares Biff to a demi-god––an “Adonis” or a “Hercules.” Both Willy and his wife note Biff’s golden football uniform and helmet. Willy tells Biff that his charisma and good looks will always win out. He’ll be “five times” as successful as his neighbor and classmate Bernard, a studious academic star who helps Biff cheat on his exams.

Willy is a travelling salesman, and his own success is based on how much people like him and how impressive he looks. But when we meet Willy at the start of the play, he’s no longer “well-liked” or even merely “liked.” He’s a sad old man, and buyers aren’t buying from him. This puts him in financial peril.

Worse, Biff has turned out to be a monumental failure. Biff is back at home as a thirty-four year-old, having drifted around for fifteen years as a “dollar a day” worker. Willy is sixty-three (I can’t believe I’m older now than Willy Loman!). Willy and Biff can’t be in the same room without inflicting great pain on each other.

In one of the cathartic moments near the play’s end, Biff tries to explain to Willy exactly how and why Biff’s life went awry:

“And I never got anywhere because you blew me so full of hot air I could never stand taking orders from anybody! That’s whose fault it is!”

And even at the bitter end (spoiler alert), Willy is still clinging to a desperate, foolish hope that Biff can have a glorious future that will redeem Willy’s own failures. Willy’s scheme, “approved” by Willy’s hallucination of his sinister older brother Ben, is to stake Biff in business with the $20,000 his family will soon collect on Willy’s life insurance.

But that too will be a failure, because the insurance won’t pay out for suicide.

Children are the ultimate judges

My own children have allowed us to believe that we are okay as parents. We’ve always been involved in their lives and we did step in when we thought we could help. Undoubtedly, not always in a way that was welcomed.

We see and speak and text with our children frequently. I don’t keep score but I think they contact us as often as we contact them. And now that our very young grandchildren are in the mix, we are available as babysitters so our status has risen.

Whether we’ve been over-involved is not our call. Ultimately, it’s up to children to pass judgment on their parents.

And a child’s judgment that contains the full sweep of right and wrong and the complete record of unanticipated and permanent memories of their parents––vagrant, capricious moments, some loving, some painful––is a judgment that parents may not care ever to hear.

Rather, a judgment of such radical transparency is a custom more honored in the breach. 6

Question for the comments: On the continuum between under parenting and over parenting, where do you stand?

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Carly Simon’s Legend In Your Own Time, a beautiful and haunting song with relevant lyrics.

“Well I have known you
Since you were a small boy
And your momma used to say
"Well my boy's gonna grow up
And be some kind of leader someday"
Then you turn on the radio
And sing with the singer in the band
Your momma would say to you
"This isn't exactly what she had planned"

Below, from a while ago, my father and his three sons. According to my wife Debbie, I (far left) look possessed.1

I know it was the summer of 1978, because my father had taken my younger brothers and me to see the movie Grease at the theater nearest to our home on the Jersey Shore. Long Branch, to be specific, remarkable to us for its iconic Windmill restaurant serving hot dogs and hamburgers beneath its giant blades. My father, now 89, was 41 at the time, I was sixteen and my brothers would have been ten and eight.

I obviously ate candy at the movie. But as well, pre-movie, my father had taken us to a store where I had bought additional candy to bring home for later feasting. The store-bought candy was in a white bag that I placed at my feet during the movie.

I was absorbed by the movie and fascinated by it in a wistful way. The high school experienced by Danny Zuko (John Travolta), Kenicki, and their friends at Rydell High seemed so vastly superior compared to my experience at my high school. While the movie was running, I could forget for a while the real life of my own adolescence and in the darkness of the theater pretend that the movie was somehow my real life.

Of course, I fell hard in love with Sandy (Olivia Newton John).

My sixteen year old self preferred the Sandy on the right. The one on the left scared me.

When the movie ended, so did my fantasy high school life, and my father, my brothers and I went to our car, parked between the Windmill and the theater. I remember my father looking around at all the teenagers––girls and boys––outside the Windmill and saying, “Look at all these youngsters hanging out. It’s kind of like the movie.”

It was an accurate and innocent observation, but it cut at me, because I knew I’d never be like those kids in Long Branch, scarcely older than I was if not sixteen themselves. And here I was being taken to the movies by my father with my two little brothers. The divide between being me and being cool never seemed greater.

When we got to the car, I realized I’d left my bag of store-bought candy in the movie theater. I believe there was a suggestion I should just leave it, but I needed that candy more than ever to sustain me through the night. I went back to get the bag, found it quickly, and walked back, swinging the bag to and fro, which turned out to be unwise in a packed parking lot.

On one of my swings my bag hit a car, hard enough to make a noise but not hard enough to cause damage. A girl sat cross-legged on the hood of the car, just like in a Springsteen song. “Hey, watch the car,” she shouted at me.

The indignity was too much for me, so I shouted back, “Oh, why don’t you just shut up.”

My words must have been indistinct, because she screamed, “This kid just told me to fuck off.”

I had a split second to wonder who she was screaming at before her boyfriend was on me, one hand firmly around my neck, telling me to get down on my knees and apologize. I started to protest that the girl had misheard me, but he squeezed a bit harder and repeated his command for me to kneel.

Suddenly my father appeared, and his presence changed the dynamic. My father was taller than the boyfriend and, more importantly, had about him an air of quiet confidence and reasonableness. An air of getting his way in things.

He asked the boyfriend to release me so “we could work this out.” I was released and repeated my protest at being misheard. Still standing, I apologized for hitting the car with the bag of candy. (As bags of candy go, this one was on the softer side; I’m guessing from memory of my tastes back then that the bag’s contents were mostly black Twizzlers and red Swedish fish.) 2

The boyfriend inspected the car and saw it was undamaged. He seemed annoyed at the girl for causing this disruption and maybe even felt a little foolish for his own hasty reaction. He must have sensed that I was not the type of kid, with that type of father, to go around telling strangers to “fuck off.”

The boy turned his back to us, and my father said something to the effect of “alrighty,” and, with his arm around my shoulder, led me back to the car.

I was still very embarrassed. I was sixteen after all and in my interaction with the local Grease kids, I’d acquitted myself as a loser and a dork.

But thanks to my father, I never had to suffer the humiliation of getting down on my knees or endure any physical assault. My father had saved me with the speed of his coming to my aid and then had defused the confrontation with his reasonableness and the confident ease with which he carried himself.

It’s only in retrospect, as a father myself, that I can fully appreciate how my father was a hero that night. Quiet but firm. The best kind of hero.

Question for the comments: Who are your quiet heroes?

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In the parable that opens Wallace’s speech, an older fish asks two younger fish, “How’s the water today?”

The two young fish are puzzled. They swim away, and Wallace has one young fish say to the other, “What the hell is water?” 1

Wallace goes on to say that for humans the equivalent of a fish’s water is our default setting to make every moment of our lives, especially the mundane, trivial, and boring moments, all about ourselves, i.e., “me-centered.”

For instance, you’re in traffic and you see every other driver in every other car as just an obstacle in the way of your getting home. These “others” are the equivalent of non-player characters in the unfolding game of your life.

Wallace urges us to recognize that these other drivers actually have lives and needs just as complex as our own. For some of them, the traffic may be far more burdensome than our mild annoyance. For example, a husband may be trying to get his wife to the hospital to give birth.

Wallace advises us to resist that me-centered default setting and instead be intentional about choosing what to pay attention to.

This is water in 2026

Reading Wallace’s speech made me wonder what an equivalent of “This Is Water” might be in 2026. I went back to read again an excellent and thorough essay by from April titled, If America’s So Rich, Why Did it Get So Sad? 2

Derek identifies the “news” as one of the chief culprits of the disconnect between prosperity and unhappiness.

“Today’s news is more surprisingly negative than at any period of news on record.” 3

Derek is referring specifically to economic news. But let’s consider how much of our attention is dominated by negative news of all sorts.

I’m not suggesting the world has gotten so much worse, although it may feel like it has. What I am suggesting is that we’ve become hyper-aware of all the negativity. Within hours or minutes we become aware of a disaster, a violent crime, an incendiary speech or a scandal. The odious flow is always there. It never stops. The ceaseless availability is what’s new.

Back in 2005, when Wallace gave his speech, there were no iPhones, no Instagram, no Tik-Tok, no Youtube, no Twitter, no AI chatbots, no video-on- demand streaming services.

So, Wallace’s exhortation below had more of a fighting chance in 2005:

“The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day.”

Now in 2026, the competition for our attention and awareness includes our always available screens, which by their nature are solipsistic as they involve only one person-–ourselves.

And what’s on those screens inevitably discourages us through the natural negativity of news and, as well, through invidious comparisons with others, which inflames our envy. (I wrote about my own irrational envy of Haley Bieber last year.)4

This is the 2026 water we swim in.

One way to recognize the stink of what we’re swimming in is to turn it all off. To detox, as it’s fittingly called. But I never do that for more than a few hours, which tend to coincide with the hours I’m asleep. No one I know consistently turns it all off.

A good news story

Absent ignoring the world or somehow curating our information flow so it’s all lollipops, sunshine, and butterflies, one way to mitigate the negativity is by paying attention to some positive news. With that in mind, I wanted to highlight the inspiring work done by one of the organizations my wife and I support.

The Hebrew Free Loan Society provides an array of interest-free loans to low and moderate-income people facing financial challenges or needing a helping hand, both within and beyond the Jewish community. They are the only not-for-profit providing a full array of zero interest loans in NYC and its surrounding area.

HFLS makes zero interest loans to address everything from education to housing to debt consolidation and unexpected expenses. Their best known type of loan is “general needs” to borrowers who need to get over a financial rough patch. Every story for every borrower is different. But one thing borrowers have in common is they almost never fail to pay back their loans. HFLS has a 99.9% repayment rate.

I think the HFLS secret sauce is that they require all borrowers to have a guarantor. The guarantor is typically a relative, a friend, or a neighbor. No borrower likes to default. But when someone you know has put themselves on the line for you, the desire to repay that kindness by not calling on your guarantor becomes magnified. I see this as a testament to the fundamental goodness of human nature.

What qualifies as lower and moderate income

The cost of living in the NYC area is very high. So an income that would be considered comfortably middle class or upper middle class in the heartland of America is a very different story in NYC.

A household of four, perhaps a married couple with two kids for example, can be eligible for an HFLS loan even if their family pre-tax income exceeds $100,000 or even $150,000. In NYC, that type of income for a family of four does not make you rich and can leave you vulnerable to all sorts of financial vicissitudes.

A zero interest loan of $5,000 or $7,500 to that family, repayable monthly over a two year period, can make the difference between stabilizing a family’s finances or that family falling into a predatory debt trap with ultimately disastrous consequences.

Impact and history

One of the great aspects of the HFLS model is that with its near perfect repayment rate, any money it receives in support of its mission can be recycled again and again to many borrowers. I love that type of impact.

Another thing I love about HFLS is its long history. It was founded in 1892 by ten leaders of the Jewish immigrant community on Manhattan’s Lower East Side. These friends pooled $95 to create an interest-free loan fund, non-denominational from the start, and made loans starting at 50 cents. 5

Currently, HFLS makes many tens of millions of dollars of loans every year. But it still only serves a small proportion of its ”addressable market,” to use a venture capital-ish term. There are plans to grow.6

Tetiana’s Story

There are many individual stories on the HFLS site. I picked Tetiana’s story, below in italics, because of the tremendous impact HFLS has had on her family. Plus, Debbie supports an organization that helps people in Ukraine where Tatiana’s family is from.7 Plus, cute babies!

“When my husband and I first heard about the Hebrew Free Loan Society (HFLS), we were at a breaking point.

For eight years we had been trying to get pregnant and had exhausted every option available to us. When the doctor told us that our last hope would be extremely costly In Vitro Fertilization treatments, we didn’t know where to turn. That’s when we heard about HFLS’s 0%-interest Fertility Treatment Loan. We applied and quickly received the support we needed to continue pursuing our dream of having a child. Now, one year later, we are blessed to announce that we are the parents of two healthy twins.”

“Our family was happy and at peace, until the crisis in Ukraine began. My father, mother, sister, and my two nieces are all in Ukraine and have found themselves in an impossible situation. Because no one is able to work, they are now lacking the means to afford basic necessities such as food and water.

My husband and I have tried to do everything in our power to help, but with two young children to care for, money is stretched thin; we can’t afford to send the funds that they need. When we received an email from HFLS about the availability of interest-free loans for those with families affected by this devastating situation, we felt as if a weight had been lifted off of our shoulders.

Once again we were able to quickly acquire the funds we needed to help my family, without placing added stress on our own finances. Now we can breathe more easily, knowing that our loved ones have access to the resources they need.

We are incredibly grateful for the help HFLS has provided in both of our times of need and want to send a heartfelt thank you to everyone who contributed to the organization that made these life changing loans possible.”

Unwavering optimism?

I’m told the TV character Ted Lasso represents unwavering optimism. 8

Unwavering optimism is not my default setting. I try to be realistic.

There are many terrible things happening in the world, mostly to people who are without one or more of FDR’s Four Freedoms:

• Freedom of Speech

• Freedom of Worship

• Freedom from Want

• Freedom from Fear

But there are many organizations whose mission is to help these people. Sometimes at scale and sometimes one person or one family at a time. That’s good news. So is the fact that most people are decent and want to do the right thing. Consider HFLS and its 99.9% repayment rate.

We can’t dismiss things like this or we’ll lose ourselves to hopelessness, and then the foul waters really will close in over our collective heads.

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Belle Burden is the author of the best-selling memoir Strangers about her husband’s sudden and brutal abandonment of her and their children after twenty plus years of what Belle thought was a happy marriage. 1

Belle was born into a prominent family that had been wealthy for many generations. Part of the book’s appeal is an authentic look inside that world.

The greater appeal, however, is Belle’s effort to come to grips with her self-blame, as in how could I have been so stupid and careless to miss all the signs? And how could I have squandered my financial security?

Strangers debuted in January. I read it that month and admired Belle’s authentic voice. As well, I could relate to Belle’s being born into generational wealth. I wrote a post about the book, focusing on the very relatable torture of hindsight bias.2

A few weeks ago, The New Yorker published an attempted “gotcha” article by Jessica Winter on Belle’s book.3

Winter obtained some of the sealed legal documents4 surrounding Belle’s divorce and concludes that Belle misled her readers when she claimed to have felt financial precarity.

To bolster her accusation, Winter uses selective items from the court documents without sufficient context. The most pertinent example is Belle’s listing in a 1999 document of her interests in various trusts totaling $63 million, the majority of which was and is highly contingent. Winter does not sufficiently caveat the $63 million number, a sum that she must have known would stick in her readers’ minds. More on this later.

Winter also uses excerpts from Belle’s various post-publication interviews to “catch” Belle in exaggerating her financial desperation. But in those excerpts Winter mostly quotes Belle’s interviewers, not Belle. 5

There’s a clear thru-line of disdain in Winter’s article for Belle and for Belle’s distress over her finances. But since this is an article in The New Yorker, there are enough equivocations for plausible deniability. 6

Toward the end of her article, Winter throws in a quote from acclaimed memoirist Mary Karr about memoir being “not an act of history but an act of memory, which is innately corrupt.”

I’m unsure if Winter is condemning or excusing Belle for writing a “corrupt memoir,” but either way she’s hiding behind Mary Karr’s quote to insinuate that Belle’s memoir is corrupt.

Then there are the last lines of Winter’s article:

“[Belle’s] long-term financial security, as opposed to her emotional security, was never at risk. It might be difficult for anyone in her position to separate one from the other.”

When Winter refers to “[Belle’s] position,” does she mean her generational wealth, her distress over her divorce, or the combination of the two? Is Winter suggesting that Belle as a wealthy person could not separate her anguish over her husband’s betrayal from her financial fears?

Winter’s ending is the type of writing that seems clever; but its very cleverness obscures its clarity.

Correcting the record

Belle Burden does not need me to defend her from her critics. Her book speaks for itself and so does its phenomenal and deserved popularity.

That said, Winter, as well as writers in other publications that are less equivocal and less editorially careful (more on them later), seem to lack an understanding that money matters can be emotionally painful even to those with generational wealth. They also do not seem to understand how to write about someone’s contingent interest in a trust.

Since I understand both these issues, I feel compelled to correct the record.

Fear of squandering

Those of us born with tremendous privilege feel some measure of guilt. We know some people will resent us for it, although we had no agency in choosing our parents. We also feel that whatever we may accomplish in life has an asterisk attached to it.

We’ve had advantages that few have had and it’s impossible to separate ourselves from those advantages. It’s who we are.

But the biggest fear is to squander our advantages and in doing so disrespect the people who gave them to us. We fear that those alive and somehow even those who are dead will be bitterly disappointed in us if we waste their gifts.

As an inheritor, I’ve wrestled with all these feelings and know them quite well. You know them well too if you’ve been reading my essays for some time!

Belle felt she had squandered

In Strangers, Belle indicts herself severely for failing to protect her fortune from her husband. She had signed a prenup against her lawyer’s advice. It held that she had no rights to her husband’s earnings.

After they were married, she exhausted the two trusts she had access to in order to buy their two homes. Even though she’d paid 100% of the cost, she shared ownership of the two homes with her husband 50/50.

Belle entrusted her husband to handle their financial affairs. So, when the divorce came, her ignorance exacerbated her uncertainty, distress, and fear about what would happen to her and her children financially.

As the divorce proceedings unfolded and her husband played “hardball,” Belle realized she did not have the money to buy out her husband’s 50% share in their homes. She’d have to sell both.

She “fell into a deep well of despair and shame.”

She writes:

“I was going to lose what my grandparents and my father had given me, betraying them…I was going to lose my financial security.”

From the POV of people unfamiliar with the built-in fears of generational wealth-holders, Belle’s comment about losing her financial security will seem odd. No matter what, she was going to net many millions of dollars from her 50% share in the two homes. 7

But everything is relative, and so a sudden negative change in fortune, or just the threat of one, can seem like a financial earthquake. Even to someone very wealthy.

My mother as a case study

Like Belle Burden, my mother never had a good handle on her own finances. They were overseen by her father or her husband (my dad). Large sums in the millions were ethereal to my mother. She could only relate to smaller, everyday sums.

In late 2008, when oil prices plunged, my mother was told by our wealth management firm that her income from her oil and gas interests would also plunge. My mother objectively had nothing to worry about financially as she had many other assets and no debt. Yet she gathered up her jewelry, intending to sell it for a pittance to a store on Madison Avenue.

I tried to reassure my mother about her finances and convince her not to go through with the sale. I knew she was getting ripped off, and that the money she’d receive was not going to make a difference to her. 8

She didn’t care. If her oil and gas income could suddenly be disrupted, how could she depend on her other assets? The money from the jewelry was real to her. So was her panic.

My mother’s feelings were similar to Belle Burden’s who writes of her own financial panic:

“But my fear had made me myopic again, only able to see what I would lose.”

Show me the person who has always acted with perfect rationality about their financial situation, and who, having reached a certain level of financial security and a certain standard of living, has never feared a status decline. You can’t, and Jessica Winter of The New Yorker can’t, because that person does not exist.

Belle’s trust

In 1996, Belle’s father Carter died. The great shock of his death at age 54 was followed by the shock of discovering that his estate had $40 million of debt collateralized by all his assets. As Belle describes it, her father spent money like “he had an endless supply,” and so her father and her stepmother were living “a life on the edge of potential ruin.” If their debts were called in, they’d lose everything.

In her article, Jessica Winter does not mention the perilous state of Belle’s father’s financial situation at the time of his death in 1996. Instead, Winter makes a huge deal of Belle’s disclosure a few years later, in 1999, of her interest in a trust that her father set up for the lifetime benefit of her stepmother.

Winter reports that in 1999 the value of Belle’s share of that trust was listed as $45 million, the majority of her “net worth” of $63 million in 1999. There’s not much that’s clear about this trust. We don’t know what the assets were in 1999, how they were valued, or how they related to her father Carter Burden’s finances at the time. We also don’t know what’s in the trust today, 25 years later. 9

In fact, in 2019, Belle’s lawyer told Belle that her stepmother “could no longer pay the kids’ school tuition; her assets were too depleted.”

That’s a quote from Strangers.

It seems likely that the stepmother’s depleted assets would include the trust. That seems like a crucial piece of information in assessing the current value of a trust valued at $45 million twenty years earlier. But Winter omits this from her article.

Winter admits that the trust “was, and remains, inaccessible to Burden” and that Belle will only have access to her share of the trust after her stepmother dies. We don’t know the terms governing Belle’s future access to the trust, what’s in it today, or whether the terms of the trust can be changed.

Nor should it be any of our business.

It seems irresponsible for Winter to highlight the 1999 listing of Belle’s share in the trust as a key item proving that Belle misrepresented her financial situation at the time of her divorce in 2022. Or as proof that Belle exaggerated her feelings of distress over her finances at that time.

The Belle-bashing bandwagon

After Winter’s article appeared, other writers for publications like the Washington Post seized the opportunity to jump on the Belle-bashing bandwagon, further distorting the $63 million number used by Winter. 10

I came across quite a few writers on Substack doing exactly that, including , writing for The Free Press. Her first article about Strangers was titled Belle Burden’s Fans Don’t Care If She Lied.

If Jessica Winter’s weapon was an icepick, then Kat Rosenfield happily wielded a hatchet.

When I challenged Kat about whether Belle had a $63 million net worth as Kat claimed, Kat responded by saying that she was “just reporting the news!” as if The New Yorker article was dispositive. My full exchange with Kat is in the footnote. 11

It’s like the children’s game of telephone. The New Yorker publishes a long and insidiously critical piece on Strangers with much of the information sourced from sealed documents that may have been selectively used to make an anti-Belle case. Then, less prominent publications quote selectively from and distort what The New Yorker published to make foolish assertions. Then, some readers of these less prominent publications end up thinking that Belle is a rich, lying grifter.

Wealth Derangement Syndrome

I wrote a post in April 2025 called Wealth Derangement Syndrome, available below, in which I noted how convenient and widespread it is to think that anyone who is wealthy must be awful. To have Wealth Derangement Syndrome is to judge someone’s character solely by the quantity of their bank account.

This syndrome is glaringly apparent in modern storytelling about the wealthy. Rich people must be portrayed with one or more of the following tropes: wicked, miserable in their marriages, awful parents, or shamefully outlandish spenders.

I’m still searching for modern exceptions in the fictional realm. In most non-fiction stories the wealthy are usually portrayed negatively. Sometimes that’s deserved because it’s based on their behavior; sometimes it’s undeserved because they’re targeted and criticized only because they’re rich.

Such is the case with The New Yorker’s deceptive article about Belle Burden and her memoir. Jessica Winter’s attempted takedown is squarely, and sadly, part of Wealth Derangement Syndrome, which has entered the current mainstream of our culture.

Belle Burden was born rich and now she continues to be rich. What right does she have to complain about anything? She’s not a person. She’s a rich person.

Question for the comments: Hating on the rich seems to me to be an ineffective, if not self-defeating, strategy for addressing the problem of extreme inequality. What say you?

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The TV marriage in Scenes is between beautiful Jessica Chastain and handsome Oscar Isaac (albeit disguised as a Jewish professor under loads of facial hair and glasses). They talk a great deal about their relationship, treating it as something separate, as a third partner in their marriage. 1

I wondered if Debbie and I had done much talking and analysis about our relationship.

Debbie said we hadn’t. We were too busy. Ten years in, we had three young children and a built-in schedule of activities and a social life revolving around our kids’ school. What we talked about far more than anything else was our three children.

On the weekends we all retreated to a house in South Salem where we had minimal obligations and very few scheduled activities. Doing nothing together as a family was heaven.

During the week, Debbie woke up with the kids. I usually took them to school and then went off to work. Debbie was in charge of the household, and when I returned from work, we’d all hang out, and then I’d put the kids to bed, often performing ridiculous comedic set pieces to a uniquely enthusiastic audience.

I asked Debbie if we’d always been amorous. She said we had. When? Whenever the opportunity struck. She reminded me how we used to take “staycations” in downtown hotels. We were early guests of the Mercer Hotel when it opened in 1997.

The picture below is from 1999, 14 years into marriage when we were thirty-seven-years old. Yes, it was taken by a professional photographer, but the laughter is real.

Stresses

Of course we had conflicts and stresses. I had peaks and valleys at work that affected my mood, sometimes severely. I’d worry that I wasn’t succeeding as fast as some peers. Alternatively, I’d worry that by working in finance I was missing out on an intellectual career where my work would have more purpose.

Debbie questioned whether she had lost a part of herself by choosing to be a stay-at-home mother. When we met, we both were working on Wall Street. After we were engaged, Debbie decided that two people with finance careers wasn’t a good set-up for a family so she went to Parsons to study design.

But I don’t recall our stresses being a direct cause of fighting. Certainly when either of us was down, it could affect our moods and make us snap at each other. But the snapping never led to personal insults.

Snapping and bickering were about specific actions. There was my messiness and my legitimate incompetence at most chores. There was Debbie’s insistence on staying to the end of galas and other events when I desperately wanted to go home. 2

Many fights took place during our annual vacation every winter to The Breakers in Palm Beach. It was my family’s tradition and I loved it. Debbie hated it. My post about the most memorable of our many Breakers fights is in the footnote. 3

But we always made up quickly, and fights never stopped us from being each other’s biggest fans and cheerleaders. Debbie would listen to my complaints about work and reassure me that I was doing a great job balancing career and family. I was able to manage my work-life so I could be home almost every night at around six. And she appreciated that we were able to enjoy a lifestyle she’d never expected.

I’d tell Debbie in spoken words and many letters how wonderful she was as a wife and mother. How her skill at organizing our lives was invaluable and could be applied to anything she wanted. I encouraged her to take on a variety of what we’d now call side-hustles.

Both of us were insecure about our appearance. I’d grown up thinking I was ugly. Inexplicably to me, Debbie didn’t think she was pretty. She once asked me the brilliantly unanswerable question, “Have I always been this ugly?”

But I thought she was beautiful and she thought I was handsome. That may be shallow but it was important to us and it took decades of compliments to convince each other our compliments were sincere.

It also took decades for us to believe each other about our strengths. Without that mutual support, I’m convinced we’d be far less secure in ourselves today and far less happier.

A recent fight between Debbie and me

At the start of this month, Debbie and I were in our house, just the two of us, with no plans for the weekend, an ideal state of affairs and so an odd time for a fight to break out.

For most of the afternoon, Debbie was listening to an audio book on her AirPods as she munched on popcorn. The crunching was extremely loud––infernal to me, soundless to her. We were in the same room but she had her back to me.

When Debbie and I are in separate locations, I miss her but look forward to her return. And I’m perfectly happy when we’re at home together doing our own separate things. I still sense her presence and feel we’re connected and available to one another.

But that afternoon, self-secluded by her AirPods and the earthquakes of her crunching, Debbie had made herself unreachable. I felt intense loneliness. Perhaps it’s true that the most hellish loneliness is not when you are alone by yourself but being with someone and still feeling alone.

The audio book Debbie was listening to was The Calamity Club, a book I’d read, loved, and recommended. Debbie loved the Southern dialects of the book’s narrator. The fact that I’d suggested the book made me angrier. I’d been the architect of my own perceived isolation. 4

I went upstairs for a while both to escape the crunching and in the hope that Debbie might miss me and come looking for me. But she didn’t. Only Sophie padded upstairs to keep me company.

Sophie and I went back downstairs. The popcorn explosions had ceased but now Debbie was assembling shelves as she continued to listen to the book. I was invisible to her. I was way down on her list of priorities. My anger grew.

Debbie is a completist, and she loves puzzles. When she is assembling something, she is in a zone of absolute concentration and contentment. She hates to be taken out of that zone. These facts, which are well known to me, ought to have figured into what I did next. But they did not.

Debbie sat next to me on the sofa and put her arm around me. She was still listening to the audio.

In the fantastical life lived within my mind, we’d had a titanic fight. I was the aggrieved party, and by offering me casual affection, Debbie was twisting the knife in. So I detached her arm and looked away. Two could play at this game.

At that, Debbie finally removed her AirPods and asked me what was wrong. I told her that by listening to her audio, she had become a “ghost” to me. That it was awful to be in the same place as her and have her make me feel so alone. I gave her a look she calls the “Bad David.”

In our current state of marriage, if I express anger with words, a look, or both, Debbie will feel that she’s disappointed me. Then, she becomes incredibly sad. She will tell me that I have shattered her world and her heart. It’s worse when she’s surprised by my disappointment. And even worse when she has no chance to reverse what she’s done.

So when I called her a ghost, her face registered first shock, then pain. Then many hours of sadness followed until my apologies were accepted.

I have this to say for myself. At the age of 64, my capacity for acting like a child remains undiminished.

Codependency?

Codependency is supposed to be bad. You should be your own independent person and not rely on any one person for approval and self-esteem.

But Debbie and I are both codependent in our mutual reliance on each other’s approval. Our rare fights are generally triggered either by Debbie thinking she’s done something to disappoint me or by my being jealous of Debbie’s attention. The AirPods fight contained both elements.

Perhaps someone will tell me that I’m using the term codependent incorrectly. If it means holding each other down, then Debbie and I have done the opposite. We’ve built each other up.

Great love, great risk

As for the AirPod fight, I can’t recall why I was so vulnerable that day, why I interpreted Debbie’s actions as a brutal rejection of me. Of course it was irrational. And I’m sure I was projecting some external angst onto Debbie who was innocently enjoying her popcorn, her book, and her furniture assembly.

Over 42 years, our love has compounded, “as if increase of appetite grew by what it fed on.”5 Perhaps it was inevitable that we’ve made each other’s love a foundation, a condition precedent, for our self-esteem.

With great love comes great power over the other person for good or ill. To love as deeply as I love Debbie is to surrender myself to her. I’m usually absolutely secure in her love but every now and then I’m still a bundle of nerves. Even after all this time. Especially after all this time.

Here we are today, older and sometimes wiser.

Question for the comments: Tolstoy famously begins Anna Karenina: “All happy families are alike; each unhappy family is unhappy in its own way.”

However, it seems to me that families and marriages can be happy in an infinite variety of ways. What say you?

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My original essay on this topic in March 2025 began with the personal confession below in italics:

My older son Andrew is my Devil’s Advocate. He challenges me to keep an open mind. After he read my last post, People On TV Can’t Hear Me Scream, he was concerned about my state of mind regarding the current political situation. He and I had a long conversation about why I had been “triggered” to lose my temper as well as my inabiliy to find anything good about Trump’s second term. Andrew is by no means a MAGA advocate but he’s an independent thinker suspicious of anything that smacks of absolutist thought.

Near the end of the conversation, I told Andrew that “if things got too bad,” I would consider, for the first time in my life, leaving the United States. Andrew was alarmed. He said, “Don’t leave us, we’re building a family for you.”

That was poignant and loving. I assured him that I was far from the point of seriously considering leaving.

Andrew probed me more about why I was fearful. I could point to many specific actions taken by Trump 2.0 but I found myself at a loss to fit those actions into a narrative, other than just Trump’s grab for more power.

After that conversation, I realized that if I was unable to articulate the intellectual underpinnings of Trumpism to myself, I couldn’t adequately express why I was scared. And to dismiss the importance of intellectual influences places our comprehension at great peril. 1

Here begin my current thoughts:

N.S. Lyons and his Strong Gods

Back in March 2025, the most cogent argument for Trumpism I could find was made by Substack writer . Lyons had made a good effort to fit Trump into a larger intellectual framework. This was at and before the beginning of Trump’s second term. 2

Lyons saw Trumpism as a return of the Strong Gods, by which he meant the values of family, nation, moral truths, and religion, values that have a deep and primary appeal to many if not most. 3

The Strong Gods are in contrast to globalism, which, quoting Lyons, is “animated by peaceable weak gods of tolerance, doubt, dialogue, equality, and consumer comfort.”

The Strong Gods are unmistakably masculine.

Lyons’ warnings

One of the strengths of Lyons’s argument was that he did a “pre-mortem” of how the Trumpian project might fail. The root of Lyons’ worries was money, or, as Jesus expressed it":

“You cannot serve [both] God and mammon [greed for riches].” 4

Lyons warned in December 2024:

“The most difficult challenge is likely…resisting Donald Trump’s inexplicable but persistent urge to suck up to the East Coast financial elite (a core part of the regime opposing him) and waste political capital showering them with tax cuts and other goodies at the expense of the working class.” 5

In my March 2025 essay, I wrote these two paragraphs in response:

I agree with Lyons that it is money that could trip up Trumpism. The god of money is Mammon, and it’s very hard to dismiss that fallen angel from what drives our modern society.

In fact, I find it extraordinarily difficult to untangle the pursuit of money from the Trumpian project. Trump’s lifelong schtick has rested on his prowess as a businessman. The identity of his right-hand man Musk is as the richest man in the world. Trump’s most fervent supporters are some of the wealthiest men in the world, including the East Coast financial elite who according to Lyons Trump “sucks up to.”

Trumpism has in fact become all about money and corruption––enriching the Trump family and his allies at the expense of all other Americans. Financial markets have acted as perhaps the only effective check on policy.

The latest corrupt act, Trump’s self-negotiated '“settlement” with the IRS, is breathtaking in its audacity, its cynicism, and its contempt for this country.6

As for the working class, Trumpism has repeatedly kicked them in the teeth. While the bi-coastal financial elites have benefited the most from Trumpism. Exactly as Lyons warned.

Where I am

I was at a lunch in my hometown of NYC the other week with a political candidate. Before she left, she asked our small group what was giving us hope.

I said that on my way to the lunch I’d walked through Central Park where everyone looks happy on a sunny spring day. Emerging from the park onto the street, I went past a seemingly endless line of families and friends waiting for doors to open for a college graduation ceremony. Eager, dressed in their best, carrying bouquets to toss to their loved ones on a day of celebration.

Away from the “news,” it’s not hard to find countless moments of individual joy and love. Hope endures, hope prevails. I’m not going anywhere.

Below is my essay from March 2025.

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4

Matthew 6:24-25.

“No one can serve two masters; for either he will hate the one and love the other, or else he will be loyal to the one and despise the other. You cannot serve God and mammon.”

In the summer of 1984, I was 22, working in NYC and living at my parents’ apartment. At a bar one evening, I met a 27-year-old woman named Debby (not my wife). We had a mutual attraction, we kissed, and in the course of that evening I lied about my age and claimed that I, too, was 27. Five years older than I actually was, a big difference of almost 25%.

We went on a handful of dates. I’d pick Debby up at her apartment where I met her five-year-old son. He was very cute. He was learning to be fluent in French at the Fleming School on East 62^nd Street.

I didn’t have the courage to confess my true age to Debby. My answers to her questions about my past were vague and false. I’m pretty sure she knew I was lying. For one thing, she never allowed the romantic side of our relationship to advance.

After about a month, she said she wanted to see where I lived, a matter I had tried to cloud in mystery. I was in luck. My parents’ apartment was under renovation and my mother and father had just moved out for the summer to their house in New Jersey to avoid the racket and dust.

This, perhaps, was my opportunity to advance the relationship. But when I gave Debby a tour of “my bachelor pad” six bedroom Park Avenue apartment, I did not make the impression I’d aimed for.

She said something like, “David, tell me the truth, where are your parents?” I doubled down on my lie and said something like “It’s a very sad story and it upsets me to talk about it.” I was trying to convey, without success, the plight of an orphan, a sole survivor of some tragic peril.

That was the end of Debby and me. I still feel guilty about misleading her, a sweet woman with a young child. In recalling my unfortunate behavior I recall how my initial lie grew and grew.

London Falling

Lying is on my mind as I’ve just read Patrick Radden Keefe’s new book London Falling.

It’s a true story about the 2019 death of a 19-year-old named Zac who assumed an elaborate false identity and pretended to be the son of a billionaire Russian oligarch. Zac came from an ordinarily affluent family. But from an early age, he became obsessed with the extravagant flash of the lifestyles of the new Russian oligarch money and the associated “glitzy, aspirational culture of modern London.” 1

Zac was a talented and detail-oriented liar and his lies were mostly believed. As Keefe puts it:

“[Zac] came to understand something about the essential gullibility of human nature. Most of us have a default setting to believe other people.” 2

Zac’s fake persona and his obsession with the outward glitter of wealth led him to fall in with the dark side of London––gangsters and fraudsters. In particular, two older men who stole and cheated and extorted in order to grasp some of the Russian oligarch money that was flowing into the London economy.

These oligarchs and their money were of shady provenance but they were welcomed by a “morally elastic” British establishment that was willing to look the other way when it came to criminal behavior associated with wealthy Russians.

Zac was attracted to that dark side. As one of Keefe’s mobster interviewees put it, many people have a temptation to “flirt with a little bit of criminality.” To be “Saturday Night Gangsters.” 3

Eventually, Zac’s lies caught up with him. At the apartment of his London mobster “friend,” one late, winter night in 2019, Zac jumped off a fifth-floor balcony and fell to his death in the Thames River. Zac’s mobster friend was at home in the apartment. He was never apprehended and may have been a police informant.

Keefe does a masterful job of investigating all the threads, all the personal histories and stories that led to that tragic night. We get to know the gangsters and the fraudsters as well as Zac’s grieving and guilt-wracked parents. As a reader, you’re left to judge for yourself the what and why of Zac’s death. Suicide or desperate attempt to escape?

Hindsight bias strikes again

As a parent, when your teenager or young adult child seems to be headed off course, you want to intervene. But you also fear that your interference might trigger your child to shut off all communications or perhaps go into self-exile, thereby eliminating your remaining parental influence. It’s why countries at war keep channels of communication open to keep alive the prospect of peace.

While I was reading London Falling, however, I felt my parental hindsight bias at work. I judged Zac’s parents harshly. It was similar to my initial harsh judgment of Belle Burden in reading her memoir Strangers, which starts with the sudden destruction of her marriage and then goes back to the beginning of that relationship. Couldn’t she see the obvious red flags? 4

Similarly, as I read London Falling, I was harshly judging Zac’s parents. They seemed willfully ignorant, obtuse, and over the top, gentle-permissive in their parenting. Clearly, their son was lying to them. Clearly, he had an unhealthy relationship with the flash of wealth––the cars and the apartments and the members’ clubs. Clearly, he was involved in activities inappropriate for a nineteen-year-old.

But just like with Strangers, I knew the tragic ending. So, of course everything seemed clear. That’s how hindsight bias clouds our judgment.

A little humility is in order

I was fooled by a false identity.

Around 2006 I was introduced by my good friend Irwin to a father who had kids in the private school where Irwin was the headmaster. That man was Josef von Habsburg, a descendant of the royal von Habsburg family. I was starstruck. Irwin knew what a history nerd I was, and the von Hapsburgs were hugely important figures in the European history I’d always loved to read about.

Josef von Habsburg spoke with a wistful, polished, and faintly Germanic accent. He dropped names with great finesse. Apparently. the Shah of Iran’s family and the von Hapsburgs were very tight, hanging out together wherever former royals gathered to talk about the good old days.

I learned from Irwin that Josef had made generous charitable donations to Irwin’s school in addition to his children’s tuitions.

Josef was very strange but his strangeness only added to my belief in him. He came to a party at our apartment wearing an oversized gun holster loaded with a portable hairdryer. Only an eccentric royal could get away with that.

My wife Debbie and I went to Josef’s apartment for dinner one night. His pregnant wife was a designer, and the apartment, a vast loft in Soho, was crammed with colorful chandeliers and expensive looking furniture. You could get lost in the alleyways. It was part fairyland, part flea market, part showroom.

That night, we met Josef’s children who were dressed in a bizarre blend of lederhosen and tuxedos. We met his two greyhounds. I wish I could remember the names of the kids and the pets. Wolfie? Fritz? We saw pictures of Josef’s family castle where he and the family were headed when school let out for the summer. They served us food that was inedible. Gristly meat, I recall.

The penny drops

In 2009, Josef came to see me at my office. He was in tears because all his money had been held at Lehman International in London. Lehman went bankrupt in ’08, and Josef had been told his London money was irretrievable. All of it lost. I remember thinking that here in front of me was a “broken man.”

He didn’t ask me for money but he did ask if I could help him with a venture in China that he hoped would restore his fortune. I referred him to someone I knew who did business in China.

Sometime soon after, it was revealed that Josef von Hapsburg was really Josef Meyers from Michigan. Josef was wanted for failure to pay child support to another family he had in Michigan. Also, Josef was a confidential informant, a CI, for the FBI.

Josef’s “job” as a CI was to hunt for people on the margins of Wall Street, strivers who might be easily susceptible to the lure of a fast buck via white-collar crime. Josef worked with an undercover FBI agent to set up his targets. Usually, the sting involved laundering briefcases of cash.5

In the meantime, the FBI was paying for Josef to maintain the lifestyle and thus the identity of a fabulously wealthy royal. Plus, whenever Josef himself was arrested for his own white-collar crimes, the FBI would step in to make the charges go away.

A Detroit newspaper broke the news that Josef was an imposter. He was extradited to Michigan from New York and sentenced to three and a half years in prison for failing to pay child support.

Our default setting

By the time I met Josef, I was likely too much in the mainstream of finance to be a typical victim of his. But given more time, he might have tried to turn me into one of his marks. Certainly, without his unmasking, I would have gone on believing and enjoying the fact that I was becoming friends with a genuine von Hapsburg.

As Keefe writes in London Falling, my “default setting” is to believe people when they tell me who they are. Especially if it seems that they have nothing to gain by lying. Perhaps that’s naive.

Part of me admires von Hapsburg for his elaborate con. Getting the FBI to pay him a lot of money, living a princely life, fooling everyone. A seeming mastermind of the world of the “nether shadowland,” just like the world that Zac entered in London Falling. A “shadowland” that can seem enticing precisely because it is illicit, forbidden.6

So, reading London Falling, I understood Zac’s attraction to the world of flash and gangsters. And with a few days’ perspective, I understand the unfairness of my initial, harsh judgments of Zac’s parents.

As I like to remind myself, the past carries an aspect of immutable inevitability. We tend to believe that things could have only turned out as they did because that’s the only way they turned out.

But every event in the past used to be in the future, subject to infinite different outcomes. It takes mental effort to remember this. It’s worth the effort because it allows us to understand the past far better.

And with that understanding comes compassion for those who are deceived, like the parents in London Falling who lost their son Zac.

Question for the comments: Have you ever been bamboozled by a fake as I was and have you ever lied as I did about your age or backstory?

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In this clip from Catch Me If You Can, con man Frank (Leonardo DiCaprio ) evades FBI agent Hanratty (Tom Hanks) by pretending to be a pilot and using a phalanx of beautiful stewardesses to surround him and divert attention.

6

There is something in many of us that attracts us to the dark side of things. Gangsters can seem glamorous. As a sixth grader, after I watched The Sting, I wanted to be a con man.

I told him I thought the way he was scrutinizing and questioning his Jewish identity was a quintessentially Jewish thing to do.

Being Jewish is an indelible identity, not just a religion. Even those who seek to mask their Judaism or to renounce it or to avoid Jewish rituals and traditions are acting in response to their Jewish identity.

In 1940 my paternal grandfather Alfred changed his last name from Rottenberg to Roberts. In December of that same year, Alfred decided to celebrate Christmas for the benefit of his three-year-old son Billy, my father.

In the 1930s, Alfred had graduated from Harvard Law School, a place where that era’s antisemitism would have been obvious––most law firms would not hire any Jewish lawyers.

Alfred then married a Jewish heiress Betty Block whose original family name had been changed to Block from Bialoblotcky. I suspect there was pressure from Alfred’s Block in-laws to change his name and to assimilate.

Alfred’s father, my great-grandfather Samuel Rottenberg, was not happy with his son Alfred’s name change and move toward assimilation. I have three beautiful letters Samuel wrote to Alfred expressing Samuel’s displeasure. In one letter, Samuel wrote, “you have no right to deprive [Billy, my father] of his birthright.”

A Rottenberg by any other name

Shakespeare claims that a rose by any other name would smell as sweet, i.e., would still be a rose. I disagree. Names have great power. I think of Moses at the burning bush asking God for His name. God refuses and replies “I Am Who I Am.”

I think that’s the all-time greatest name-flex. Second place in the footnote.1

I wonder how different my life might have been as David Rottenberg vs. David Roberts. Rottenberg is a name that even my most dull-witted classmates could have used to tease me. But as a Rottenberg I might have felt a deeper affinity early on to my Jewish heritage because my Jewishness would have appeared more obvious, at least to myself.

Escape vs. embrace

I’ve been thinking about the Rottenberg-Roberts name change and the tension between escape and embrace of Judaism ever since I devoured Nicholas Lemann’s terrific new book Returning, which tells the two-hundred -year story of how Lemann’s Jewish American family wrestled with their Jewish identity. 2

Reading Lemann’s book had a huge impact on me. It made me feel closer to my own ancestors, like Samuel Rottenberg, who had to struggle to establish themselves, something I never had to do thanks to their efforts.3

Lemann’s prosperous and accomplished family came from early German-Jewish immigrants who first settled in New Orleans around 1840. Eastern European Jews like Samuel Rottenberg came later and in far greater numbers, from the 1880s until the immigration restrictions of the 1920s.

The German Jews in America were desperate to differentiate themselves from the later Jewish arrivals who were generally poor, less healthy, less clean, and devout (clinging, perhaps) to their Jewish rituals and traditions, thus a people apart. The German Jews in America considered the mass arrival of Eastern European Jews to be a problem, a threat to how they’d be perceived.

The solution for the earlier immigrants was to conform as much as possible to Christian norms. Lemann’s family, along with the rest of the tightly-knit New Orleans Jewish community, celebrated Christmas enthusiastically. Lemann recounts how at his parents’ wedding his father hid away baskets of kippot (traditional head coverings) and then did the same at Lemann’s own wedding.

Kippot were too Jewish. 4

But as Lemann writes, the distinction between the two Jewish groups, which was obvious to the more established American German Jews, was not dispositive to Christians. A Jew, no matter how cultured, how handsome or beautiful, or how rich, was still a Jew.

Lemann quotes from New Orleans novelist Walker Percey whose protagonist Binx in the novel The Moviegoer has this to say:

“Whenever I approach a Jew, the Geiger counter in my head starts rattling away like a machine gun, and as I go past with the utmost circumspection and with every sense alert––the Geiger counter subsides.”

Quintessential Immigrant

My great-grandfather Samuel Rottenberg left his family and his small town in what’s now the Czech Republic in 1888 and arrived penniless and alone in New York City at the age of sixteen.

In that time and place, helicopter parenting was not a thing!

Samuel was part of the poor Eastern European wave that the German Jews looked down upon. He spent the first period of his American life as a peddler on the Lower East Side sleeping in a storeroom and earning $5 a month.

Samuel built a good life as a small business owner. He had seven children and a lifelong marriage. He became a pillar of his community, a key founder and first president of The Brooklyn Jewish Center, built in 1920 for a million dollars––really big bucks back then. It was the largest Jewish institution of its kind, combining a school, a shul, and all sorts of community activities.

As Samuel put it himself, accurately, if not modestly, “If ever some historian should write a history of the Jews in Brooklyn, I am sure my name will get some space.” It has.

Samuel’s Three Letters

Samuel wrote three letters to his son Alfred about Alfred’s name change to Roberts and his assimilation. The letters have an increasingly desperate tone. They remind me of the struggles of the father Tevye in Fiddler On The Roof as he contends with the increasingly non-traditional marriages of his three daughters. 5

In his first letter, Samuel writes that “a name to me is like a flag that a nation adopts at the beginning of its career.” And “I had hoped that my children would be proud to bear that name.”

When I first read those lines many decades ago, I felt angry at Alfred for rejecting his father’s name. I also felt shame that I was helplessly complicit in carrying on that rejection. No one had asked my permission or opinion about changing my name.

I briefly considered returning my name to Rottenberg in solidarity with Samuel (who died before I was born). But that would have been a rejection of my father’s name. And a pain in the neck. And I preferred the name Roberts to Rottenberg.

Samuel’s second letter was sent on December 20^th 1940 after Samuel learned that Alfred planned to celebrate Christmas, including the traditional tree. In that letter, Samuel writes “I do not think it does us any good to ape our Christian brethren.”

Samuel understood that the Geiger counters of the Christian majority were always turned on.

Finally, the third and harshest letter comes three and a half years later in 1944. Samuel criticizes Alfred for celebrating only Christmas and excluding the Jewish holidays. Samuel has given up trying to persuade Alfred not to celebrate Christmas. Now he just wants equal time for the Jewish holidays.

Samuel blames himself for not doing a better job as Alfred’s father showing Alfred the “beauties” of the Jewish tradition. Samuel wishes that “what I am writing you today could have been written to [myself] twenty-five years ago.”

I found that especially heartbreaking. I sense in that last letter a sad and weary surrender to his son’s drifting away from tradition. All five of Alfred’s brothers eventually followed Alfred in changing their last name to Roberts. Samuel lived to witness the abandonment of the banner of his name.

He likely worried that that the final abandonment would end with complete assimilation. Conversion.

Nicholas Lemann wrote about the conversion to Christianity of the children of Moses Mendelsshon, famed father of the German Reform movement:

“The possibility of acceptance, it turns out, turned Jews into Christians far more effectively than the more brutal methods of medieval Crusades and Inquisitions did.”

Challah as dense as a brick

My parents celebrated Christmas when I was growing up. But my parents also celebrated Hannukah and I celebrated my Bar Mitzvah in a temple, all for the benefit of my mother’s father (the oilman from Tulsa) who, like Sam Rottenberg, was unabashedly Jewish.

For about a decade in the 1990s, my mother, searching for a set of guidelines to give her life greater purpose and order, became Orthodox. When she stopped her strict observances and pivoted to medical philanthropy, she retained her Jewish faith and wore a prominent Star of David until she died in 2020.

My wife and I re-entered Judaism through our three children who we sent to the Rodeph Sholom Nursery School simply because it was the one school that waitlisted our two-and-a-half-year-old daughter.

(I wrote about our zany parental behavior in my post The Manhattan Nursery School Gods, linked in the footnote below.6 )

We loved the community of the Rodeph Sholom School, part of a large Reform Congregation. We kept our three children enrolled at the school for most of their pre-high school years.

In our family home, my wife and I never had a Christmas tree. We celebrated the Jewish holidays and had Friday night dinners with our children. Every Friday, the kids brought home challah from Rodeph Sholom, crushed at the bottom of their backpacks to a brick-like consistency. The challah could have been used as a bludgeon but, still, it was delicious!

Narrow escape

We might easily have become part of the large Jewish population that is unaffiliated and Jewishly uneducated. That’s easy to do in New York, especially in the Manhattan secular private school world, and especially for someone like me who had a career in New York finance, an industry dominated by Jews.

Inside my bubble, I could have been like the fish in David Foster Wallace’s famous graduation speech This is Water. The fish can’t understand water as a separate reality from itself. Similarly, I could have been oblivious to the Jewish waters I swam in. I could have taken my Judaism for granted.

As Nicholas Lemann puts it:

“New York might be the best place to be a Jew, the most comfortable…That means being Jewish doesn’t require much of you.”

Some of that laziness is in me. I give myself good marks in my ethical and intellectual Judaism but my lackluster observance of rituals and traditions is something that troubles me.

Because without ritual, Judaism would not thrive or even survive. That’s a fact I have to face.

In the meantime, below is some comedy from Larry David about his perspective on Judaism.

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Over the past few years, my wife Debbie and I have increased the time and resources we devote to not-for-profit organizations that help people who have urgent material needs.

My motivations for giving are complex.

I have family role models of community involvement going back generations with my mother Jill Roberts and a paternal great-grandfather Sam Rottenberg standing out. They would be proud of what we’re doing, which makes me happy.

When I’m engaged in philanthropy, I feel most deeply connected to my Jewish identity. I’m far more motivated to fulfill the commandments of ethical acts––doing our part to “repair the world”––rather than to observe the commandments of prayer, faith, and ritual. 1

Ideally, I would embrace both the ethical and the spiritual aspects but that’s not how I’m constituted.

Giving makes me feel good because it gives me agency to change lives for the better. I can read the news and curse the darkness––and I often do––but I can also light candles that make the darkness a little less dark.

All that said, my wife and I are not saints. We’re very far from renouncing worldly goods and material comforts and pleasures. Our spending on ourselves and our family creates limits to our giving, which I discuss below.

This Monday at 4 pm EST, I will be interviewed by about my approach to philanthropy and related topics. Jeremy writes the Substack , which is a tremendous source of information on the topic and a pleasure to read if the substance doesn’t make you too angry.

The invitation to our Live! interview is here.

The breach

America’s wealth has never been greater while inequality has never been greater. At the same time, our social safety net is being weakened in exchange for lower taxes and record national debt.

Philanthropy has not stepped into this breach. Jeremy Ney’s latest article Why Philanthropy Is Silent In The Golden Age Of Wealth contains the fascinating chart below comparing the giving of the big three plutocrats of the first Gilded Age––Carnegie, Rockefeller, and Mellon––with the giving of our current crop of plutocrats.

I wrote about Carnegie’s Gospel of Wealth a few years ago. My post was titled Would Andrew Carnegie Have Flown Economy, linked in the footnote below. 2

On the scale of this chart, I would be an imperceptible blue dot, somewhere beneath Bloomberg’s bubble, planning to march my little dot eastward past Mellon’s bubble.

My calculations

For every two and a half dollars we spend on ourselves and our family, we donate around a dollar. That ratio came about organically rather than as some grand plan. Over time we’ve added not-for-profit organizations to our portfolio of giving. And our spending has also increased.

Every week I keep track of our spending and keep track of our financial assets. I’m a spreadsheet guy.

I keep a long-term projection of what happens to our financial assets given an assumed rate of after-tax investment return and an assumed inflation of both our spending and our giving.

There’s an infinite number of “what if” games to play but my base case, meant to be conservative, although far from a disaster, is a 4% after tax rate of investment return and a 2.5% inflation rate. With those assumptions, after thirty years, at the age of 94, we still have some financial assets left, although greatly diminished in real, inflation adjusted, terms.

That makes me comfortable with our current rate of giving and increasing it with inflation.

The calculation for billionaires is far different. Their spending is likely to be a rounding error.

But for the less exceptionally wealthy––and there are far more of us––I think my methodology is useful. As long as you realize that a spreadsheet is a tool you control and not the other way around.

Solutions

In our upcoming interview, Jeremy Ney will ask me about solutions to address the insufficiency of philanthropy to make up for the gaps in our social safety net.

There are a few straightforward changes to the tax code that can indirectly tax wealth and encourage more charitable giving. They both have to do with capital gains taxes. I think direct wealth taxes are a poor way of addressing inequality as I discussed in a prior post. 3

Currently, long term capital gains (long term defined as a year and a day of holding period) and most dividends are taxed at a maximum federal rate of 20% vs. a maximum rate of 37% for ordinary income, including wages. As well, when someone dies, all their assets are “stepped up” for tax purposes to the asset values at death so that all the unrealized value up to that point in time remains forever untaxed. 4

I suggest that both of these provisions be changed so that all income, including capital gains, be taxed at ordinary rates and the step-up at death be eliminated and the estate be required to pay the capital gains tax.

These changes would increase the taxes paid by the holders of wealth. The changes would also discourage the strategy of “spend, borrow, die” wherein a wealthy holder borrows against their assets to support their spending and avoids paying gains taxes when they die and their assets are “stepped up.” 5

From a philanthropy point of view, I believe these changes would incentivize more giving of appreciated assets since there would otherwise be no escaping eventual taxes on gains.

Of course, the more charitable giving there is, the less paid in taxes since charitable giving creates a tax deduction.6 But if the gap we’re solving for is between government tax revenues and philanthropy, then more giving is not a bad thing.

Objections to my solutions

One objection is that the wealthy might “park” their assets in foundations and donor advised funds where most of the assets could grow without being given away. But the rate of giving (donations as a % of assets) from donor advised funds is above 20%. Foundations must give away 5% of their money annually. So eventually those assets will find their way into philanthropy. 7

The larger objection to my solutions is that they are far too modest. To provide the federal government with enough money to keep our national debt at reasonable historical levels (see alarming chart below) and provide the government enough funding to repair the social safety net, far more tax revenue is needed.

That means higher income tax rates at brackets that reach deep down into the ranks of the wealthy and the affluent. Certainly, a higher rate than 37% at the top.

We may eventually have no choice but to radically change the tax code and introduce a national sales, or value-add, tax as nearly every other developed nation has done.

Illegal loopholes

With all the current legal loopholes available, many wealthy American taxpayers still push their luck in trying to abuse the tax code through evasion rather than avoidance.

Recently I read about one such scheme. If you become a legal resident of Puerto Rico and you sell an asset for a gain, you do not have to pay capital gains taxes on the portion of the gain that occurred while you were a legal resident of Puerto Rico. 8

But apparently the rule has been sorely abused. People who knew they were about to realize a huge gain moved to Puerto Rico shortly before realizing their gain and then claimed falsely that all of the gain was realized while they were a resident of Puerto Rico. When, on the contrary, it was evident that much of the gain took place before they left the mainland United States and so on that portion of the gain, taxes are owed.

These accused tax evaders received legal opinion letters from lawyers, now under criminal investigation, so they could claim they were just following advice, which is the same morally obtuse excuse as “just following orders.”

Question for the comments: In which ways does our current tax, social safety net, philanthropy situation bother you, if at all?

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On the one hand, I like being without goals, without any new grand project pushing me forward. Because at 64, I’m in a “preserve, protect, and defend” mode. And with the notable exceptions of new grandchildren, any big news is likely to be negative. Just like the “news” of the wider world. 1

On the other hand, I wonder whether trying to keep the status quo and only making small changes around the edges is a game plan for a dull and dreary life. I have the outward frame of activity–– social, physical, and mental–– but inwardly am I rusting?

The world is changed by people pursuing their goals with great ambition. Behind most great feats of the arts or of science or of business is a single-mindedness that is ruthless and relentless.

But single-mindedness is not for me.

Ambitions of my youth

When I was very young, there were moments in my life when I was filled with great confidence, perhaps arrogance, even hubris. I felt there was nothing I couldn’t do or accomplish. I dreamed childishly big. At a minimum, President. Then at age six I found out we’d never had a President who was Jewish and that was unlikely to change.

My substitute dream a few years later was to become rich beyond my wildest dreams of avarice. Rich enough to buy the Frick Museum, around the corner from where I lived. I’d learned that The Frick had once been a private residence, and I dreamed of reclaiming it as my home and one day standing on the front lawn waving through the iron fence at the passers-by.

I took the picture below this week.

Some thirty years later, my firm shared an elevator bank with a Xerox sales and marketing unit. I often saw a white-haired Xerox sales executive, the lines on his face etched deeply. He always looked harried and rumpled, a perpetual cup of coffee in one hand, an invisible cigarette in the other. But he had a certain presence that commanded attention from his Xerox colleagues.

Once, I heard him declare to a younger colleague, “If I have a decent crap in the morning, that’s enough to make my day a success.”

There must be a reason that his comment has stayed with me all these years. It’s not just the ineffable mysteries of our digestive systems. It’s the realization that there are many things that can make us happy. And that much of happiness depends on how reasonable our expectations are.

Multiverses

This past week, my wife and I binge-watched the sci-fi-TV show Dark Matter. We don’t typically like sci-fi that includes multiple worlds because we get confused. But binge-watching helps. So does the pause button to confirm our mutual understanding of what’s going on.

Our son Andrew recommended Dark Matter and called it a love story, which it is. Mild spoiler ahead.

Joel Edgerton (“Joel-1”) plays a brilliant scientist who 16 years ago sacrificed his career in favor of his pregnant girlfriend, his great love, now his wife. They have a 16-year-old son. Joel-1 has some regrets but he’s mostly happy being a family man.

But there’s another Joel Edgerton (“Joel-2”) in a parallel universe who in a “Sliding Doors” moment chose his career over his pregnant girlfriend. He advised an abortion, they broke up, and then he dedicated his life to the single-minded pursuit of his scientific career.

Joel-2 became wealthy and insufferably arrogant, a “player.” Think of Steve Jobs, but in quantum physics. As the show opens, Joel-2 has been able to perfect the tools necessary to travel among infinite universes, i.e., the multiverse.

Now, 16 years after the two Joels went their separate ways, creating their separate universes, Joel-2 decides that wealth and fame are no longer enough. He wants Joel-1’s family, too. So, he travels to Joel-1’s universe and switches universes with Joel-1 in a violent way.

But having devoted himself to his lab to the exclusion of everything else, Joel-2 has become a world-class dick. He’s identical in many ways with Joel-1, but he’s hopeless at being a good husband to Joel-1’s wife and a good dad to Joel-1’s son. He makes grand, cliched, and suspicious gestures like buying his son a new car or by helicopter-husbanding his wife’s artistic career.

The message is that if you want to go all-in to just one thing, then that one thing is all you get. And if your one thing is the relentless pursuit of work success, you’ll end up a world-class dick.

At one point, I paused the show and told Debbie that of all the infinite universes in the multiverse, I would always choose the universe I had with her. I meant it.

Debbie looked at me with her lovely eyes and said, “What about a different universe where tonight you ordered the right sandwich for me?”

Sandwich-gate happened like this. Debbie wanted a chicken club, my usual. I thought she wanted her go-to, the Greek Salad wrap. I ordered her a chicken and mozzarella sandwich. Why? Because we argued about a side order of bacon. If you want more details, they’re in the footnote. 2

To rust at home or strive with gods

Odysseus, or Ulysses, was not an ideal husband. He left home for twenty years and had long affairs with Circe and Calypso.

Alfred Tennyson imagines a sequel to The Odyssey in his famous poem, “Ulysses.” It’s three years after Ulysses has returned home to Ithaka from ten years of war against Troy followed by another ten years on his boat, battling gods, sirens, and a one-eyed monster (Cyclops, not his penis! Although he did have those two long love affairs).

In Tennyson’s poem, Ulysses stews in his old age, impatient, kvetching that he’s stuck as a king ruling over a “savage race” and matched as a husband to an “aged wife.” That wife, Penelope, had been beset by raucous suitors until Ulysses returned home to kill them all.

Tennyson imagines Ulysses still itching to accomplish great feats. His adventures have ruined him for a domestic life. His ambition has not been sated. So he dreams of getting his sailing crew back together to recommence “roaming with a hungry heart.” 3

The poem’s most ringing lines:

“Some work of noble note, may yet be done,

Not unbecoming men that strove with Gods.”

Up close to my adolescent gods, the New York Islanders

The closest I ever came to striving with gods was as an 18-year-old in the New York Islanders dressing room. It was May 3rd, 1980, a Saturday afternoon playoff game against the Buffalo Sabres. It was the semi-finals, one step away from the Stanley Cup finals.

I was with my mother, my best friend Steve, and my two younger brothers. We were all Islanders fanatics.

Before the game, my 12-year-old brother Samuel’s braces had sprung a loose wire. The wire was scraping painfully against his inner cheek. Pre-game, Samuel and I approached a security guard who called down to the dressing room. Miraculously, the trainer Ron Waske said bring the kid down and I’ll take care of him. 4

Ron Waske went to work adjusting and clipping Samuel’s wire. And there I was in the locker room, in the midst of the Islander players who were like gods to me. I saw my favorite player, my hero Clark Gillies stomping about in his long underwear.

The Islanders won the game, the series, and the Stanley Cup that year. I was there for the final victory. 5

Sometimes, especially when we’re young, we can fuse ourselves with the ambitions and exploits of our heroes. I remember times in high school when I was down on myself. But when Clark Gillies had success, I felt it was my success too.

Binary choices

The idea of being president now horrifies me. As for the Frick, I’m happy to visit the museum and remember that Henry Clay Frick only had five short years of residence before his death in 1919. I remain somewhat fused with the ups and downs of the New York Islanders

I prefer to keep the status quo vs. grand ambitions. That preference has been formed by experience, knowledge of my limitations, and my age. I prefer contentment to pushing myself too hard. For example, I may never write a book. When I’ve tried, it’s consumed too much of my attention.

But I’m happy to benefit from the single-minded ambitions of others, whether they’re entrepreneurs or artists. Politics, we’ll leave to the side for now.

Below is a clip of one of my favorite writers, Aaron Sorkin, recreating a brutal argument between Apple co-founders Steve Wozniak and Steve Jobs. Jobs was a single-minded genius whose products I use and love. He was, however, like Jason-2 in Dark Matter, a world-class dick.

At the end of the clip, Wozniak calls Jobs “an asshole,” and then says, “Your products are better than you.”

Jobs says, “That’s the idea.”

Wozniak says, “It’s not a binary choice. You can be decent and gifted at the same time.”

Question for the comments: Is it a binary choice between being gifted in the Steve Jobs sense and being decent?

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Following are the three topics that have survived a few rounds of my mental Squid Games. 1

The beauty wars come for men

A year ago, I published Beauty, Class, Wealth, one of my most popular posts thanks to the insights of on how beauty is an ever changing status game where at the top of the hierarchy the bar is always rising.

For example, when visually obvious cosmetic surgeries like lip fillers and Brazilian Butt Lifts became mainstream, they were rejected by the elite in favor of “traceless transformations.” As Laura put it:

“There’s been a bunch of famous female faces of late that have turned up to events suddenly looking the way they looked 20 years ago, but better. And it’s not clear what’s been done here, but it’s so clear that many things have been done here.

This is the new level of aesthetic aspiration, which is traceless transformation and change. That is something you only have access to through exorbitant sums of money – in the hundreds of thousands of dollars – and social access, because you need to know who can do this for you.”

At the end of that post, I wondered to what extent men would be increasingly engaged in the male version of the “beauty wars.” I caught up with Laura first on Zoom and then this week over dinner in NYC and asked her what she was observing.

Both men and women vying for beauty status, Laura said, have always been able to be thin by simply not eating. And now GLPs have aided that effort. But acquiring muscle is an expensive pursuit in terms of time. So the toned look is not as readily accessible as the thin look.

Specifically, in terms of the male beauty wars, Laura thinks that the stigma of men having “work done” has declined a great deal. And that perhaps the popularity of Clavicular, the original “looksmaxxer,” caring only about his looks, is a sign that young men will increasingly pay more attention to their appearance.

That makes sense to me given the increase in high status women who have good life alternatives to marriage. Accordingly, young men need to increase their attractiveness as mates and while a lot of that can come from behavior, men would be foolish not to focus as well on their grooming and attractiveness.

Dr. Imber

I also spoke to leading Manhattan plastic surgeon Dr. Jerry Imber. He’s been doing procedures for more than four decades. He gave further perspectives on the current state of men and plastic surgery.

Dr. Imber’s clientele is now 35% men. A few decades ago, his male patients were people whose appearance directly affected their income. Actors, salesmen, and even airline pilots!

Now, his male clients are “the same type of guy you’d go to a Knicks game with.” Cosmetic procedures for men have become more mainstream and more socially accepted.

Most of Dr. Imber’s male clients are there to remove bags under their eyes, eliminate double chins, or for liposuction to remove fat around the middle. And yes, I inspected myself in the mirror immediately after speaking with him. 2

Dr. Imber said many of his male patients work out seriously at the gym, treat their bodies as “temples,” and get liposuction because they find no amount of workouts will get rid of their middle fat to their satisfaction.

In terms of the few plastic surgeons who have achieved public notoriety for their work on celebrities and their $250,000 plus prices, Dr. Imber said there are just a few of these “bold-faced” names, and they are the exception rather than the rule. He said he would be “embarrassed” to quote those prices.

He said the idea that you need some sort of special status to get access to a good plastic surgeon was simply not true. He gets his patients through word of mouth.

Last year’s post and discussion with below.

Is AI a bubble

This week I read an essay by (pay-walled) on recent developments on AI. Previously, Derek had believed that the AI buildout mapped closely to the 19th century railroad boom in which an excess of rail capacity ahead of demand caused financial panics, crashes, etc.

Derek’s latest essay describes how he’s now changed his mind.

“In the last few months, three big things have pushed me toward thinking that AI might be the opposite of a bubble.”

Derek points to Anthropic (Claude) growing its annual recurring revenues from $10 billion a few months ago to $30 billion today, “older” chips increasing rather than declining in value, and a scarcity rather than an excess of computing supply.

Derek now thinks the better analogy to the business of AI is electricity, not railroads.

Derek’s an extremely thoughtful writer and I always learn something from reading his work. And I give him great credit for shifting his views as the facts change.

But he’s not a finance guy.

I’m afraid I was snarky in my comment when I wrote:

What is most remarkable about this article is the absence of two words: Valuation and Profit.

This is akin to Sherlock Holmes’ the dog that didn’t bark in the night or, in this case, the writer writing about the possibility of a bubble who didn’t mention the defining characteristics of a bubble, which, after all, is a financial concept.

To Derek’s further credit he responded by saying that he ought to have focused more on the financial aspects of a bubble in his essay.

I think the analogy to electricity is interesting. However, the companies that generated and distributed electricity soon became geographical monopolies and then utilities. AI has no natural geographical boundaries, and it’s hard to see government allowing a monopoly to emerge.

That still leaves the question of how the aspirational trillion dollar valuations of the independent AI companies, OpenAI and Anthropic, can be justified by net cash flow in such a capital intensive business.

Or, looking at McKinsey’s estimate of $3.7 to $7.9 trillion required by 2030 to build data centers to meet demand, what sort of cash flow would justify that investment? Note that the wide range is based in different demand scenarios.

I wonder for the companies that already have great cash flowing businesses and huge market valuations ––Google, Microsoft, Meta, Amazon, and Apple––whether their investments in AI are a necessary evil. They have to protect their franchises and cannot be left behind.

Does that mean that the independents are doomed to lose because they don’t have the same access to cashflow and financing?

It will be fascinating to find out.

Michigan Democrats and Israel

Last week I wrote about how Israel hatred seems to lead inevitably to antisemitism. I used James Baldwin as an example of a brilliant man who “crossed over.” This week my wife Debbie saw the play Giant about Roald Dahl’s similar journey from Israel foe to antisemite.

In Michigan there’s a three-way race for the Democratic nomination for an open U.S. Senate seat. Israel has become a flashpoint in the race. That’s unfortunate because there are far more pressing issues for Michigan and America than Israel.

I am supporting Michigan State Senator Mallory McMorrow who has impressed me from when I first met her early last year as a smart, grounded, tough politician with good values.

However, the nomination race illustrates what last week I called a wicked problem for American Jews. 3

Stevens

On the “right” is Representative Haley Stevens who is backed by AIPAC, the well-funded pro-Israel lobby that imposes unconditional support for Israel as a purist test. Stevens has fallen to a distant third place in recent polling.

AIPAC recently campaigned against a moderate Democratic New Jersey candidate who was not pro-Israel enough. The effect was to elect the anti-Israel candidate who just won her special election. Great job, AIPAC! 4

El-Sayed

On the left is Abdul-El-Sayed who has recently campaigned with antisemite provocateur Hasan Piker. Piker recently doubled down on his preference for Hamas over Israel “a thousand times over.” If you want to know who Hasan Piker really is, see the clip in this footnote. 5

There is context to El-Sayed’s disastrous decision to invite Hasan Piker to campaign with him. Piker appeared on stage with El-Sayed just a few weeks after a heavily armed Hezbollah-inspired terrorist attacked a Michigan synagogue with 140 children inside the synagogue’s early childhood center. Luckily, the terrorist was stopped by security and ended up killing himself before he could murder any children or staff.

El-Sayed is hoping to follow Zohran Mamdani’s successful strategy in getting elected as Mayor of NYC. Mamdani was elected for many reasons but foremost among them was the appeal of his anti-Israel stance among young progressives, including many young Jews.

A key difference, however, is Mamdani ran against a very weak candidate, Andrew Cuomo. The winner of the Michigan Democratic primary will face a tough Republican opponent in Mike Rogers.

Mallory McMorrow

I support the “centrist” candidate Mallory McMorrow. She has been critical of the Netanyahu government, which I think is appropriate, but has never questioned the right of Israel to exist as a Jewish state.

McMorrow has refused to take any money from AIPAC. And she has justifiably criticized her opponent El-Sayed for campaigning with the hate-filled Hasan Piker.

McMorrow and El-Sayed are effectively tied in the polls. The primary election is not until August so there is still m much time remaining.

I believe that if nominated, McMorrow would defeat the likely Republican candidate Mike Rogers in the November general election. I don’t think El-Sayed would stand a chance.

I caught up with the always energetic Mallory via phone yesterday. She was recently endorsed by Senator Elizabeth Warren, and her enthusiasm for all the people of Michigan comes through clearly. She told me a story about a volunteer stuck in a snowstorm at the northern top of the state who was a happy warrior collecting signatures for Mallory’s campaign.

Plus, she has a Substack I didn’t know about!

On the question of the divisiveness over Israel, Mallory pointed me to a quote she recently gave to The Jewish Insider.

“[Piker] is not somebody that you should be campaigning with at a moment when there is clearly a lot of pain and trauma across our state,” said McMorrow. “How do you bring everybody together, especially when there are difficult conversations, where there aren’t easy answers? You don’t fan the flames and stoke division just to get attention.”

McMorrow first came to national attention in 2022 with the fiery and inspiring speech below on the floor of the Michigan State Senate. It’s well worth watching!

Question for the comments: Three topics to choose from. Comment on any or all, especially if you have a different take than those I have.

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