Jeffrey Epstein once told a billionaire that he’d invented the derivatives market—a claim that is totally false. But without question, he helped create one of the signal trades of the last few decades. He came to prominence in the 1990s, as the modern meritocracy was taking shape in the collision between the cult of technology and the burgeoning class of billionaires. Epstein played a role in this marriage. He was one of the people who figured out how to arbitrage the particular needs, desires, and vulnerabilities of these groups. He recognized, long before others, that Wall Street, Silicon Valley, Park Avenue, and the Academy were converging around a new salon culture embodied by TED Talks and “billionaires dinners.” Genius wanted to ride on a private plane—it deserved to travel by private plane. And billionaires wanted to certify their own genius by conversing with other geniuses. MIT and Harvard were brand names the superrich wanted to associate with, a fact that dropout Epstein understood innately. Science was sexy, a way to beat the markets. He once told an academic that he gamed the stock market by studying mating patterns of termites. Epstein grasped that, for the new meritocrats, genius and great wealth were two sides of the same coin, and that the health of capitalism inevitably required both. The girls—he always called them girls—were there too. For many in his glittery circle, they were decoration, seen but not heard or touched. None of them raised alarms about this situation—a person of means did not have to live by the rest of the world’s rules.

Epstein’s own Brooklyn accent and lack of a college degree, his idiosyncratic background, were no hindrance here but somehow a badge of his special gifts. He was mysterious, boundary pushing, living in that strange house, as big as an embassy, the former Birch Wathen school on 71st Street.

Then and now, no one knew exactly how he made his money. Beyond his having managed money for the apparel billionaire Les Wexner, Epstein’s only public client, who knew what to believe? The former Bear Stearns CEO Jimmy Cayne told people Epstein made a killing trading foreign currencies. Apollo Global Management cofounder Leon Black told colleagues Epstein was the smartest tax adviser he’d ever met. Epstein was said to run money for the Rockefellers and the Bronfmans, though both denied it.

A longtime Epstein employee confided in friends that she still has no idea what her boss actually did for a living. “He’d call the office and say he wanted her to find a $10,000 umbrella he saw in Paris and she’d have to buy it. He was very, very demanding. But you weren’t allowed to ask questions. It was not a normal coworker relationship,” a source, familiar with how Epstein’s office ran, recalled.

Epstein’s glib confidence was validating to a cohort that craves sure things. In this way, he had some resemblance to figures like Donald Trump, Bernie Madoff, Elizabeth Holmes. Jonathan Farkas, an heir to the Alexander’s department store fortune, recalled meeting Epstein in the Hamptons during the recession of 1982 and being buoyed by Epstein’s absolute certainty that he knew where the economy was going. “I’ll never forget this. The stock market had dropped to around 700 points from 1,000. And one day Jeffrey just said, ‘You’ll never see it below 1,000 for the rest of your life. It will never go down,’ ” Farkas told me. “He was right.”

And in those circles, he was clubbable. “He’s incredibly glib. He’s charming. He’s quick,” one acquaintance, a Wall Street player, recalled. His casualness—the sweatshirts, the jeans—were an aggression, keeping his people off-balance. “Epstein treated the fanciest people in the world with complete irreverence in a way they were unaccustomed to. He let it be known he called Prince Andrew ‘Andy,’ ” the Wall Streeter told me. He presented his interest in women as another noble eccentricity—he never hid it. Epstein reportedly once told an academic he only had two interests: “science and pussy.”