Do bankers have imagination? That statement felt both like a challenge and like a lodestar for my work. I would find hedge funders worth writing about or invent my own. More than a few reminded me of Novogratz’s wrestling friends—scrappy lower-middle-class kids from the peripheries of New York or Naples or Moscow. As a hungry, insecure kid growing up in eastern Queens, I remember watching the movie “Wall Street” and fantasizing about how I would look in suspenders and a contrasting collar. The men on the big screen did not have to understand themselves; the money made them understood. Although my greed had been expunged at Oberlin, and the financial crisis of 2007-08 had left me with a more or less permanent view of finance as an industry built on fraud, I found it hard to dislike some of my new acquaintances. The more intellectually vibrant ones came with backgrounds in advanced math and physics; they approached their trades like a puzzle, albeit one they were increasingly unable to solve. Others seemed to be flirting with the edges of sociopathy, or, at least, an inability to pass “Blade Runner” ’s Voight-Kampff empathy test.

In the popular imagination, “hedge funder” has become shorthand for a special breed of super-rich, super-intelligent scoundrel. Hedge funds raise money from so-called accredited individuals (a minimum of a million dollars in investable assets is required) and institutions such as university endowments or pension and sovereign wealth funds, and then deploy it in any way they see fit. It may help to think of hedge-fund managers as an army of men—and they are mostly men—walking down the street with dustbusters, trying to suck up cash and assets from every nook and cranny in the universe. In theory, at least, hedge funds are supposed to generate returns in bear as well as bull markets, because the contents of their dustbusters are hedged, by the managers taking long positions on assets that are expected to increase in value and shorting those they expect will decrease.

The rise of this less regulated “buy” side of finance has put to shame the income of the “sell” side. Around Manhattan, “investment banker” now carries the same sad also-ran cachet as “doctor” or “lawyer.” An older managing director at a large bank complained of the struggles of the middle class. When I asked him to define “middle class,” he spoke of people like him, earning between two and four million dollars a year. Young analysts told me they were being priced out of Brooklyn, much less Manhattan, by rising hedge-fund plutocrats and their ilk.

Part of this may be ascribed to a strategy involving two numbers—“the two and twenty.” Traditionally, many hedge-fund managers have collected twenty per cent of a fund’s profits, and they have also kept two per cent of the assets committed to a fund, regardless of the outcome of their bets. Huge losses for clients could still mean a payday for managers. Wall Street has long been a place of outsized compensation for the few who can master its rules, or at least pretend to. (There is a book that handily explains the investor-manager relationship in its title alone: “Where Are the Customers’ Yachts?”) Hedge funds seemed to offer the best and the brightest the quickest road to riches yet. As one hedge-fund manager told me, “There’s money sloshing around and chunks falling off, and people get compensated for standing there.”

These people could be divided into many categories, but the two most useful I’ve found are the rainmakers—the polished, fraternal, athletically built avatars of the Princeton-Colgate-Duke axis—and the Dockers-wearing, kielbasa-munching math whizzes. Some funds seemed to make an art form out of how many brilliant physicists from the former Soviet Union can be squeezed into a small, overlit room. There was no question which of these two groups the socially brilliant but algorithmically challenged Novogratz belonged to.

What struck me about both sets was their desire to live their lives as a competitive sport. “Money has nothing to do with it,” Turney Duff, a former partner at a health-care hedge fund, told me. “It’s literally about winning.” I began to think of the financial world as a tax on the rest of us, a way to transfer wealth into the hands of a select few through their own considerable cleverness and also through the way their income was taxed versus our own.

And yet the majority of the hedge funders I befriended were not living happier or more interesting lives than my friends who had been exiled from the city. They had devoted their intellects and energies to winning a game that seemed only to diminish the players. One book I was often told to read was “Reminiscences of a Stock Operator,” first published in 1923. Written by Edwin Lefèvre, the novel follows a stockbroker named Lawrence Livingston, widely believed to be based on Jesse Livermore, a colorful speculator who rose from the era of street-corner bucket shops. I was astounded by how little had changed between the days of ticker tape and our own world of derivatives and flash trading, but a facet that none of the book’s Wall Street fans had mentioned was the miserableness of its protagonist. Livingston dreams of fishing off the Florida coast, preferably in his new yacht, but he keeps tacking back up to New York for one more trade. “Trading is addictive,” Novogratz told me at the Princeton reunion. “All these guys get addicted.” Livermore fatally shot himself in New York’s Sherry-Netherland Hotel in 1940.

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By 2016, I started drinking more heavily than is usual for me (I was born in Russia). For the second year in a row, there were more shuttered hedge funds than new ones, investors having been turned off by a mixture of high fees and subpar returns, owing in part to a crowded field of funds executing similar strategies and also to an unusual absence of volatility in the markets. Even the legendary traders, like Paul Tudor Jones II, of Tudor Investment, were being walloped. The “two and twenty” model was turning into more of a “1.5 and fifteen” one. The secret-sauce bottles containing trading algorithms and the like had run empty, and to fill the void my new friends and I turned to Scotch—thirty-year-old Balvenie and twenty-one-year-old Hibiki. After a particularly rough night, my wife found me at 4 A.M., sitting in the corner of our bedroom, trying, and failing, to unbutton my shirt. The stress and the consequent loss of control felt familiar. The fund managers’ ambition was like a drug whose potency I had forgotten. At Stuyvesant High School, a competitive math-and-science school in Manhattan with a high proportion of first-generation immigrants, my classmates and I would get up every morning to wage battle over a hundredth of a percentile on our grade-point average; my new friends were fighting over so many basis points on their Bloomberg monitors. When we failed, we failed in front of our families, our ancestors, our future and our past.

Novogratz ran his first quasi hedge fund when he was barely four years old. The Novogratzes were a military family; in the late nineteen-sixties, they found themselves in Torrance, California. Novogratz and his older brother, Robert, went door-to-door in their neighborhood selling leaves, a useless commodity, to neighbors, five cents for yellow ones, ten for red ones. Robert was shy and hung back, but Michael would run up and ring the doorbell. The neighbors would ask him why the red ones were ten cents, and, according to his mother, Barbara, he would answer, “Look around—there are hardly any red leaves.” He had mastered the concept of supply and demand, not to mention the difference between two asset classes. When I mentioned this incident to Novogratz, he laughed, quickly seeing the parallel between his childhood enterprise and his current bet on cryptocurrency, which, like red leaves, relies on a tricky—some would say, imaginary—valuation. “It could be bitcoins,” he said.