Winner Takes All: Michael Mechanic’s Deep Dive into the Super-Rich

August 6, 2021   •   By Lauren Sarazen

Jackpot: How the Super-Rich Really Live — And How Their Wealth Harms Us All

Michael Mechanic

PICTURE A GAME of Monopoly in which you start out with $500, and your opponent gets $2,000. They pass Go multiple times ahead of you because they’re rolling with two dice, and their payout is twice yours. They’re the one percent, and you’re middle class, and from the start, they’re winning. The game is rigged. Except there’s not enough money in the game set if you want to get the financial ratio right. Want to pit the middle class against the .001 percent? You’re going to need all the cash inside 163 Monopoly sets. Want to play against Jeff Bezos? That’s 17,973 banks.

The Monopoly metaphor, while a bit shopworn, is one of Michael Mechanic’s ways of describing the American wealth gap. In his new book, Jackpot, the senior editor for Mother Jones magazine peels back the layers of what it means to be mega-rich — from the windfalls that rocketed them into the one percent to what their mere existence says about inequality in the United States.

Following a year of reckoning with material and racial inequalities, Jackpot’s timing is ideal. If there were ever a moment to interrogate our collective attitude toward extreme wealth, it’s now. At the beginning of 2020, he writes, “Americans owed more than $14 trillion on home mortgages, auto and student loans, and credit cards, and that debt is a huge source of family stress.” No wonder we keep buying lotto tickets. Mechanic cites a study in Nature Human Behaviour, which revealed that in the United States and Canada, we “tend to hit peak satisfaction when all of our basic needs are met and we no longer live in fear of our credit card bills.” What does that look like? We get a satisfaction hit when our annual earnings rise, with our emotional well-being plateauing around $75,000 per year. Earning more affords you the ability to splurge, but as Mechanic points out, “You can only live in one house and wear one pair of Yeezys at a time.” Your first house might make you break out into a jig, but your third? Your fourth? Your sixth?

The wealthiest Americans are hopelessly addicted to this dragon-chasing, finding endless ways to fritter away millions. Mechanic lingers on quite a few: bespoke suits made of pure Vicuña, $300 shots of Louis Treize cognac, a Rolls the shade of your signature lipstick, a giga-mansion fitted with multiple panic rooms, nannies trained in countersurveillance, and an Amex black card that can send an agent to procure Dead Sea sand for your kid’s school project or track down Kevin Costner’s horse from Dances with Wolves. You name it, you’ve got it. The folks with the most money also seem to get the most freebies. Why pay for a private jet to Bermuda when one buddy can loan you his plane, and another can toss you the spare keys to their seafront mansion on a private island for free? It’s easy to see how wealth begins to accumulate.

While reading about all the absurd things vast amounts of money can buy sparks a certain voyeuristic hate-reading joy, it’s sobering to witness the way wealth erodes attitudes toward work, purpose, and integrity. Mechanic ponders whether your work ethic is irrevocably altered when you come into extreme wealth: “How prudent would it be to stay in a gig that pays you $40 an hour when your portfolio is seesawing $400,000 a week one way or the other?” It changes everything. How could it not?

An entrepreneur tells Mechanic that when luck brings a financial windfall, “you move from this mentality of creating wealth to preserving it. […] You put the walls up and you want to guard it and protect it and defend it and heaven forbid somebody should take it from you. […] You’re fear-based now.”

It’s this fear that prompts the super-rich to stick together against reforms that could even the economic playing field. Despite tending to be “more progressive than the broader public on social issues such as abortion, criminal justice reform, and marriage equality,” the super-rich — who often have direct lines of communication with our elected government representatives — are “significantly more conservative on economic issues such as taxation and entitlements and the government’s role in helping people who are down-and-out.”

They won the golden ticket, but managing this level of wealth becomes a full-time job if they’re bent on preserving it. Enter “family offices.” These limited liability companies team up wealth managers, property managers, lawyers, and accountants to oversee their estates, paying their bills and finagling their tax chicanery. Want that super-yacht, but don’t want to pay the sales tax? Anchor just outside of state territorial waters, and helicopter the lawyers out to close the deal. Don’t forget to snap a pic of the GPS coordinates with both signers within the frame. How about a 1966 Ferrari worth around $2 million? Register the vehicle in a bordering state with lower taxes. Or better yet, have your shell company make the purchase.

But what about philanthropic initiatives? This is simply a way for some of the richest American families to legitimize their largesse in the eyes of society, argues Rob Reich, a Stanford political science professor who identifies the philanthropic gestures of the super-rich as a “reputation-laundering exercise to construct an aura of altruistic do-gooding and distracting people from attending to the source of the moneymaking.” According to tax law, United States donors can deduct charitable giving up to 60 percent of their taxable income, but in order to reap the rewards, you have to itemize. Yet only about 13 percent of taxpayers itemize, and most of them are within the top percent of earners. And it gets worse: the larger your tax bracket, the larger your subsidy. Though large donations look impressive, they ultimately cost the rest of us money while the rich keep more and more of theirs.

Near the end of Jackpot, Mechanic turns specifically to wealth held by minority players. While he restricts his analysis to Black Americans and women, the statistics are concerning. Middle-class assets tend to be centered on homeownership, but looking at census data, redlining has taken a toll, as “white homeownership today is about 76 percent vs. 47 percent for Black Americans, and that data doesn’t consider the value of those homes.” Moreover, research shows that in almost every state, Black and Latino neighborhoods are paying 10 percent to 13 percent more in property taxes for the same level of public services. Lastly, according to Wealth-X, “we should have at least 105 Black billionaires. We have seven,” Mechanic notes.

Shall we move on to women? “Not only are women more likely than men to be poor, they are far less likely to be very rich,” Mechanic writes. Looking particularly at the finance world, “a minuscule 3 percent of the total assets held by U.S. hedge funds launched from 2013 through 2017 were managed by women-led firms — there were more funds initiated by men named David than by women.” It’s not simply that the most lucrative industries, like tech, crypto, and blockchain, are dominated by bro culture. The bros claim that women are simply more risk-averse, but what about the fact that these industries typically make for challenging environments for women based on company culture?

As Jackpot progresses, amusement at the ridiculous ways people spend their money shifts into a deep dissatisfaction. Why do we let them get away with this? How do you compete with the allure of the unattainable that allows this system of inequality to continue mostly unchecked? Mechanic argues that our desire to strike it rich isn’t the problem — it’s the “peculiarly American notion that anyone can succeed via grit and smarts and hard work, [leading] us not only to tolerate mind-blowing economic unfairness, but to support the kinds of policies that produced this mess in the first place.” Our damning optimism is rooted in stories like Horatio Alger Jr.’s serial Ragged Dick, the tale of an impoverished shoeshine boy who becomes a member of the upper middle class thanks to his drive, and James Truslow Adams’s conception of the gilded American Dream. If we all secretly harbor the belief that if we run a little faster, work a little harder, play the stocks a little smarter, we’ll be living in the mansion by the sea, we’ll never bring the super-rich back down to earth.

Ultimately, Mechanic takes an optimistic stance, if only toward each individual’s best intentions: “No chief executive, investor or rich person wakes up in the morning, looks in the mirror, and says, ‘Today I want to go out and create more inequality in America.’ And yet, all too often, that is exactly what happens.” Mechanic acknowledges that our collective wealth fantasy has always been with us — from the first colonists of the Virginia Company to the post-grads who set out for Wall Street, finance degrees in hand — and we would be hard-pressed to shake it off. Nonetheless, there’s no better time than now to try.


Lauren Sarazen is a freelance writer who lives in Paris, France. Her words have appeared in The Washington Post, VICE, Elle, and Air Mail, among others.