During Donald Trump’s rise to the presidency, Americans became even more confused than usual over the meaning of wealth. Recall the moment when Trump descended that escalator at Trump Tower in June 2015 and announced his qualifications: political outsider, dealmaker, keeper of a net worth of more than ten billion dollars—which he had accumulated in the Horatio Alger way, rising from humble beginnings in the outer boroughs to leave his mark on the Manhattan skyline. “That’s the kind of thinking our country needs,” he said, and a lot of people believed him.

Trump’s opponents were quick to point out the gaping holes in his narrative. Anything but rags-to-riches, he had received millions of dollars and (just as valuable) New York City political connections from his father. If he had put his inheritance into a mutual fund, he would have earned more from plain old compound interest than he did with his investments in real estate. And whatever his success in creating wealth for himself, it had often come at the expense of others: workers, contractors, customers, lenders—many of whom he had stiffed, whether through one of his four corporate bankruptcies or (allegedly, but quite credibly) in sundry cases of outright fraud.

The problem with this line of attack was that it came up against a consensus that the Democratic Party itself had lately helped to build: that net worth is a measure not just of assets minus liabilities but of merit, and of one’s contributions to society. So rather than use the Trump candidacy as an occasion to confront the assumptions of wealth-based meritocracy, Democratic leaders hailed a solution that emerged from the very ranks of the Forbes 400. A slew of billionaires—Michael Bloomberg, Warren Buffett, Mark Cuban—would line up against Trump. Given the American veneration of the entrepreneur, what voice could be more credible, more impervious to accusations of class warfare? A few of the billionaires—Seth Klarman, Meg Whitman—were even Republicans: political gold for a Democratic nominee who perhaps best represented her party’s slow creep rightward.

Some anti-Trump billionaires cited his racial demagoguery (which is a pretty good reason) or his aversion to free trade (which is more complex). Others, though, took aim at Trump’s most important credential: his record as a businessman. And this is where things got interesting. At the Democratic National Convention in July, Bloomberg said, “Trump says he wants to run the nation like he’s run his business. God help us. I’m a New Yorker, and New Yorkers know a con when we see one!” Bloomberg spoke with the authority conferred by his personal fortune of $44 billion. What’s more, having spent a not-unsubstantial slice of that fortune to win three terms as New York City’s mayor, he was a much-richer iteration of Trump’s own self-image as the ultra-rich nonpolitician. Bloomberg actually agreed with the central premise of Trump’s candidacy—that America needs entrepreneurs to rattle the uncreative thinking of its public sector. On this point, the two differed only in their ideas about which billionaire was qualified.

But Bloomberg’s appeal against Trump, like so many others, proved fatefully mismatched to the anti-elite feeling among voters. And in the end, criticisms like his revealed less about their target than they do about the billionaire self-image. As Hillary Clinton put it in the final days of her campaign, “Donald gives a bad name to billionaires.” Bloomberg wanted to draw a line between Trump and the good rich—those who create jobs and give to charity. By framing Trump as an outlaw from capitalism, he and his fellow anti-Trump plutocrats also created a convenient diversion—pulling the debate away from the root problems of inequality in America, and locating the threat in one person.

The Muppet Show

When Bloomberg called Trump a con man, he had good reasons to do so. But who earns Bloomberg’s defense? Before he built his financial-information empire, Bloomberg made millions on Wall Street, and in his 1997 book, Bloomberg on Bloomberg, he praised his old bosses at the investment bank Salomon Brothers: “I owe a great debt to William Salomon and John Gutfreund. They were my mentors. They taught me ethics, philanthropy, hard work, and to take care of others.” This may come as a surprise to anyone who read Liar’s Poker, in which Michael Lewis described Gutfreund as one of the Big Swinging Dicks who ushered in the reckless greed culture that culminated in the financial crash of 2008. Bloomberg dissents: “Wall Street is a better place because of their efforts.”

Warren Buffett is the platonic ideal of the good billionaire, something like capitalism’s teddy bear.

To be fair, when Bloomberg wrote that, he was just the owner of a financial-information service. And yet his esteem for Wall Street survived unscathed by his time as a public servant—and even survived the near-collapse of the global economy that began less than ten blocks from Bloomberg’s office in City Hall. In 2012 a Goldman Sachs executive named Greg Smith explained his decision to resign from the firm by saying its culture had grown “toxic.” Even amid evidence that Goldman had knowingly pawned off financial time bombs on its customers, Bloomberg, despite his New York roots, still didn’t see the con. In a radio interview, asked about Smith’s revelation that Goldman execs referred to their own clients as “Muppets,” Bloomberg deployed the bad-apple defense: “Even if it was said, it’s a few people. And you know, Goldman Sachs is a firm that’s been around for well over a hundred years, and it’s a great firm.”

Bloomberg went on to justify his support for Goldman as part of a larger, civic-minded campaign to shore up the public good in a time of crisis: “It’s my job to stand up and support companies that are here in the city that bring us a tax base, that employ our people.” Indeed, this faith in the public magic of unlicensed pelf had already prompted Bloomberg to help secure $1.65 billion in subsidies for Goldman to build its new headquarters near Ground Zero. In the days before they became political enemies, Bloomberg could even fit Trump into this view of civic uplift. In 2013, after New York City spent $127 million in municipal funds to revamp a golf course in the Bronx, the then-mayor handed the nearly completed golf-course project to Trump, despite his by-then well-known history of shady deals.

And why not, in the cloistered world of the very rich? Bloomberg’s was the same logic voiced by a past patrician leader, John F. Kennedy, who popularized the phrase “a rising tide lifts all boats” in part to justify a package of tax cuts for his own social class. As usual, though, not all boats enjoy the same buoyancy. Given that Goldman is one of the largest customers for his financial-information terminals, the firm’s prosperity weighs directly in Bloomberg’s personal fortune. (I should disclose here, by the way, that my own judgment is likely colored by the four years I spent as a reporter at Bloomberg News.)

This is not to say that Bloomberg acted out of cynical self-interest. He seems to truly believe in the mythical win-win arrangement by which vast inequality is shrugged off as a small price to pay for a growing economy. This may explain why, in his book, he names two of history’s greatest monopolists as his personal heroes: “From John D. Rockefeller to Sam Walton (and ultimately to Mike Bloomberg, I hope), great financial success comes from starting businesses with concrete products in the real world, building jobs, creating value, and helping people.”

The confusion of money with moral virtue is, of course, about as old as America, land of the Protestant ethic. But it probably reached its apotheosis in the 1980s, when Bloomberg was building the company that bears his name, and our policy makers were converting en masse to the notion that peeling back the regulatory state and lowering taxes on the rich would free business to bring about a new era of untold prosperity. Even the legendary Chicago School economist Milton Friedman, though, made an exception to his declaration that the “one and only one social responsibility of business” is to increase its profits—the caveat being, “so long as it stays within the rules of the game, which is to say, engages in open and free competition without deception or fraud.” For free marketeers such as Bloomberg, Trump’s gleeful abuse of the rules clouds an otherwise sunny picture of benevolent plutocracy. And yet this raises a question: Is it the abuse itself, or the gleefulness, that does the most damage?

The Billionaire’s Dilemma

Donald Trump’s antithesis is Warren Buffett, the bespectacled and ever-smiling investor who oversees the Berkshire Hathaway conglomerate, cautious steward of wholesome American brands like Coca-Cola and Geico. Buffett is the platonic ideal of the good billionaire, something like capitalism’s teddy bear. At a Clinton rally in August in Omaha, where he lives in the same five-bedroom home he bought back in 1957, he laid into Trump with all the statesmanlike authority that the American republic can bestow on the world’s third-richest person—and from the moral high ground claimed by a billionaire who calls for the rich to pay higher taxes. Buffett said Trump refused to release his tax returns because he was “afraid” of what they would reveal. He took aim at Trump’s business record, recounting how anyone who put a dollar into the IPO of Trump Hotels and Casino Resorts in 1995 ended up losing ninety cents, even as Trump himself extracted $44 million in compensation. “One time after another, he went into bankruptcy,” Buffett said. “I’ve really never known another businessman that brags about his bankruptcies.”

It’s true that throughout his campaign Trump liked to boast about manipulating the rules of the game to his advantage. He exulted in skirting taxes and using campaign donations to win favors from politicians. Among his rank-and-file supporters, Trump’s appeal derived in no small part from his contradictory status as exemplar of pure meritocracy and low crony capitalist, whose mastery of a rigged system made him (he claimed) uniquely qualified to clean it up. This idea clashes with the American business establishment’s wholesome picture of itself. In his book The Making of Donald Trump, investigative journalist David Cay Johnston even details the tycoon’s connections to New York City mobsters.

What is lost in the denunciations of Donald Trump’s conduct in business is that, for the most part, he built his fortune through legal—and in fact disturbingly commonplace—means.

But Trump is hardly alone in his tolerance of sketchy partners, or in his bending of the rules. In more recent years, banks like Wachovia and HSBC have paid massive settlements after the U.S. government accused them of laundering money for Mexican drug cartels. And of course, even the most virtuous billionaires can find space in their hearts for Goldman Sachs. In September 2008, after years warning that derivative securities such as those created by Goldman were “financial weapons of mass destruction,” Buffett put $5 billion into the firm to help it ride out the financial crash. And he went further. Two years later, asked about allegations that Goldman had duped the Royal Bank of Scotland in a subprime-mortgage deal, Buffett said, “It’s a little hard for me to get terribly sympathetic with the fact that a bank made a dumb credit deal.” Asked whom he would like to see as CEO if Lloyd Blankfein were to leave, he replied, “If Lloyd had a twin brother, I would vote for him. I have never given that a thought.”

In other words, when Buffett’s own money is on the line, he’s willing to set aside his role as scold of bad business practices. In 2015, after the Center for Public Integrity reported that Berkshire Hathaway’s mobile-homes company had systematically snookered working-class families into exorbitantly high-interest loans, Buffett said he would make “no apologies whatsoever” and described the company’s lending practices as “exemplary.” Meanwhile, behind the scenes, lobbyists tried to pass a law protecting the company against predatory lending lawsuits.

Buffett’s moralism is similarly flexible when it comes to taxes. Though he’s definitely right to say that billionaires like himself should pay the same rate as their secretaries, he also refuses to chip in more until the law changes for all. And in recent years, he has engineered deals to avoid hundreds of millions of dollars in taxes—whether through a loophole known as the “cash-rich split off” or through “inversions” like the one he financed to move Burger King’s corporate nameplate to Canada. Legal tax maneuvering is actually a pillar of Buffett’s investment philosophy. Berkshire Hathaway now carries more than $60 billion in deferred tax liabilities, much of which will come due only when the companies he has acquired are finally sold—a benefit Buffett calls an “interest-free loan” from the government, allowing him to compound his returns in the meantime. This benefit is not unlike the one that allows real estate developers such as Trump to deduct imaginary depreciation expenses even as their properties rise in value.

Called out for his tax dodging at the second presidential debate, Trump delivered a self-serving deflection, noting that Democratic mega-donors such as Buffett use the same sort of loopholes. Buffett evidently sensed a danger to his reputation, for he quickly publicized his latest personal income tax return, which showed a few banal deductions of less than $6 million. But Trump was incorrect only in that Buffett’s tax feints took place at Berkshire. And according to the consensus among today’s investing class, shielding corporate profits from the government is merely one’s “fiduciary duty” (a nobler-sounding way to refer to brazen self-interest). The real scandal, then, is not in Trump’s abuse of the tax code, but in a tax code that lends itself to abuse by Trump. By the same token, the difference between Trump and other businesspeople is not that they magnanimously spurn their legal edge in bankruptcy proceedings, but that they refrain from (as Buffett protested in Trump’s case) bragging about it. To name one example, American Airlines went into bankruptcy a few years ago basically as a strategy to shred its labor agreements. Its managers were just polite enough to pretend it was for the good of all, even as they extracted full compensation for themselves, shareholders, and creditors.

It would be impossible to list all of Trump’s transgressions and their parallels, but one of the most odious took place in the seventies, when he settled accusations by the federal government that he had discriminated against blacks in his family’s Brooklyn properties. Comforting as it may be to see Trump as an outlier, banks across America would continue redlining black neighborhoods, denying them credit based solely on race, for years to come. What is lost in the denunciations of Trump’s conduct in business is that, for the most part, he has built his fortune through legal—and in fact disturbingly commonplace—means. Even where he broke the law (allegedly, allegedly), it was in the friendly penumbra where lax enforcement amounts to the decriminalization of most white-collar malfeasance. The point here is not to let Trump off the hook for his cronyism and racist grift. It’s to emphasize that these indictments of Trump ought to double as indictments of an economic system whose rules routinely skew toward the rich and powerful.

Sweet Charity

Perhaps the most effective way to hush concerns over plutocratic privilege is to make the conversation one about philanthropy. Part of Buffett’s benevolent persona grows from his commitment to donate almost his entire fortune to charity. He and his friend Bill Gates even created the Giving Pledge to convince their fellow billionaires to do likewise. Gates, the world’s richest man, has been more circumspect about Trump but subtly put him down when a reporter asked if he had signed the pledge. “Donald hasn’t been known for his philanthropy,” Gates said. “He’s been known for other things.” And indeed, despite his claims to the contrary, Trump has given very little, in billionaire terms, to the foundation that carries his name. Worse, much of the foundation’s money went to distinctly uncharitable ends—like man-sized Trump portraits, to be hung at Trump golf resorts. Or even more scandalously, to a campaign group tied to Florida’s attorney general, who was considering whether to pursue a fraud case against Trump University and, by sheer coincidence, decided not to.

Philanthropy is the ultimate mark of billionaire virtue. This explains why Trump feels he must at least pretend to engage in it, and also why the deceit is so galling. But this commonly accepted standard for ruling-class behavior institutionalizes a confused notion about philanthropy’s social value. In his book, in a moment of almost Trumpian sincerity, Bloomberg acknowledges the pragmatic side to charity: “One’s success in business and society is often influenced by the contacts, respect, and satisfaction one’s largesse generates. Giving something away often leads to receiving back much more later.” Even when the intentions are more altruistic, philanthropy doubles as the ultimate PR campaign. Gates demonstrates this well. Not even two decades ago, the popular imagination held him as the ruthless monopolist he was, deploying Microsoft’s vast market power to crush any incipient competitors. Now that he leads the world’s largest private foundation, he has become, like Buffett, a symbol of ethical capitalism.

This is misguided, and not just because of Gates’s own questionable business practices. Some of Gates’s charitable causes truly are noble, like eradicating malaria in Africa, but some in the aid world worry about the consequences of what is becoming a monopoly in malaria research and policy. Similarly, no one disagrees that America needs better public education, but Gates has spent much of his foundation money to undermine teachers’ unions—hardly a neutral solution. At stake here is whether one person should have the right to impose decisions that, in a democracy, otherwise emerge from public deliberation.

The idea that it is the imperative of the lone entrepreneur to mold society as he sees fit is not new. While both Gates and Buffett mulled over what to do with fortunes vast enough to pay off the foreign debt of several developing countries, Buffett gave his friend a copy of The Gospel of Wealth, the 1889 essay in which the steel tycoon Andrew Carnegie declared it the duty of his fellow captains of industry to give away their money. Endorsing a kind of upside-down socialism, Carnegie even argued that wealth was “not chiefly the product of the individual, but largely the joint product of the community,” and that one’s accumulated profits should be considered “trust funds” to be redistributed to society. The catch was that, because successful businessmen had been gifted with “talent for organization and management,” it was they who should choose how to divvy up the surplus.

Carnegie funded libraries, church organs, and music halls: great causes all. In so doing, he also buried the infamy of his wealth—built first with kickbacks he took as a railroad executive, and later by wangling tariffs to protect his steel empire, colluding with fellow tycoons to fix prices, and brutally crushing strikes to keep wages low and work hours long. The reputational benefits, though, may have been unintentional. According to the biography by David Nasaw, Carnegie truly believed that his high-minded ends justified the means, no matter how base. He took comfort in the social Darwinism of Herbert Spencer, who argued that, on the road to progress, “harsh fatalities”—such as those suffered by Carnegie’s workers—“are seen to be full of the highest beneficence.” Other robber barons found this idea convenient, too. John D. Rockefeller expressed it in religious terms, frequently claiming that his fortune was a literal expression of divine will: “God gave me my money.” Today, this worldview remains common among those who see inequality as the result of neutral market forces, rather than of choices about how we arrange the rules—bankruptcy laws, tax codes, prosecution (or the lack of it) of financial crimes.

Without Merit

Trump did have his billionaire supporters: corporate raider Carl Icahn, hedge-fund manager John Paulson, Facebook investor Peter Thiel. Mark Cuban, the owner of the Dallas Mavericks, initially called Trump “probably the best thing to happen to politics in a long long time” in large part because “he was a businessperson.” This was a logical leap of faith for a man like Cuban, whose favorite book is The Fountainhead by Ayn Rand, Herbert Spencer’s twentieth-century pop successor. But Cuban later reversed himself. Explaining his change of heart, he cited Trump’s apparent aversion to studying policy issues, but he also betrayed concern that Trump would taint the image of his class. Stephen Colbert asked him, “In the billionaire world, what’s the take on Donald Trump?” And Cuban replied, “Well, in the meeting we voted him out. . . . We literally changed the secret handshake.” Cuban delivered this line as a joke, but in another, more serious interview, he conveyed the same idea: “I don’t see him as a reflection of . . . an entrepreneur.”

Andrew Carnegie funded libraries, church organs, and music halls: great causes all. In so doing, he also buried the infamy of his wealth.

Trump and Cuban weren’t business rivals, but they did compete as apostles of meritocracy. Both have written self-help books for aspiring entrepreneurs, and both have starred in reality TV shows: The Apprentice, where Trump selects a would-be corporate manager, and Shark Tank, where Cuban and a few other venture capitalists decide whether to invest in actual startups pitched by their founders. Suggesting that Trump lacked true talent, Cuban said in June, “He’d get kicked out of Shark Tank so fast it’d make your head spin.” By maligning Trump’s business acumen, rather than his ethics, Cuban’s line of attack was different from Bloomberg’s or Buffett’s. Smelling desperation in Trump’s deals to license his name to steaks and bottled water, he even suggested that Trump isn’t a billionaire at all. At the very least, Cuban boasted, Trump has less cash in the bank than he does.

Of course, implicit in this criticism is the same idea that guides Trump—that net worth is a measure of merit. Cuban is deeply committed to a vision of business where only the best rise to the top. Of Shark Tank, Cuban has said, “The show has become a reinforcement of the American Dream.” This faith in social mobility, despite all the data showing its decline, clarifies Cuban’s stance on Trump’s inherited wealth: “You don’t ask Daddy for a small loan of a million dollars. That’s not what entrepreneurs do.” The problem with this taunt is that, actually, that is what they do, albeit on a lesser scale. It’s privilege, not merit, that explains why Silicon Valley startups are founded overwhelmingly by white men.

If Cuban seems resistant to the impression that, in America, people very often luck into great wealth, it may be because he more or less lucked into his. Cuban is rich because he sold a video-streaming startup called Broadcast.com for $5.7 billion worth of Yahoo stock at the peak of the dotcom bubble in 1999. Broadcast.com never turned a profit and soon faded into oblivion, but Cuban sold his stock before the bubble popped, so he’s seen as a genius. Some on the Forbes list rely more on luck than others, but as Carnegie recognized, none among the so-called self-made can credit their own genius for everything. Even Bloomberg, who built his company from zero and still owns it, owes most of his fortune to factors beyond his control—namely, the swelling of the financial industry as a piece of the global economy.

The myth of meritocracy is one of the most enduring justifications for the plutocratic status quo. According to this myth, even when structural inequalities are acknowledged, they can always be overcome by individual effort. Cuban’s book is titled How to Win at the Sport of Business: If I Can Do It, You Can Do It. “If you have bills you have to pay, and it means taking a night job in order to keep looking for the day job or to keep a job you want, do it,” Cuban writes. “Be a waiter, a night janitor, wash clothes, sell vacuum cleaners door-to-door—whatever you need to do, all the while reminding yourself that it opens the door to your future.” Bloomberg likewise subscribes to the bootstraps theory of success. He writes: “If you’re not content . . . Change it!”

Like many of us, these tycoons had good reason to fear Trump’s rise to power. Still, it’s impossible to separate their opposition to him from their instinct to preserve the common wisdom about their proper place in society. As the limit case for the contradictions of plutocracy, Trump threatened the credibility of the cartel of good billionaires. Examining their business record, what emerges is a picture in which Trump is not an outlier, but instead the essence of unrestrained capitalism. For all the claims that he’s bad at business, he has clearly mastered the self-dealing rules that govern it. And while he left a trail of devastation in his path, he is a clear success according to the narrow terms of rational self-interest. Ultimately, thanks to this same logic, we may yet see our billionaires come around to President Trump.