It wasn’t just about the money for Glass—or if it was, the money was simply a means to an end. He had always wanted to be a player on Wall Street. And why shouldn’t it be possible? Hedge-fund managers like Steve Cohen and Ken Griffin used the same trading skills he had to transform themselves into billionaires with 32,000-square-foot mansions and $500 million art collections. Even his older brother was moving up in the world of hedge funds. At a recent Knicks game, David introduced him to friends as “the Mayor” because he seemed to know so many Wall Street bigs in the stands. But Glass himself had never managed to rise in Wall Street’s pecking order.
Growing up in the working-class suburb of Willowbrook, on Staten Island, Glass was always in the shadow of his brother, the “good son” who continued the family’s immigrant success story. His father was an IRS arbitration lawyer, his mother a schoolteacher. They were Orthodox Jews raising four kids in a sleepy Jewish enclave, their lives centered on Young Israel, the largest synagogue in the borough. Glass’s brother was a slow-and-steady sort who played by the book. He studied finance at Queens College and started his career as an accountant. Closer to his parents than his younger brother, he wore a yarmulke and always came home for Jewish holidays.
David Glass had different talents. When he was 9 years old, he bought a bag of five-cent candies and sold them to friends for 25 cents apiece. By his sophomore year at Queens College, he had established his first business enterprise: He ran two blackjack tables out of his apartment on 72nd Avenue in Queens, making $15,000 to $20,000 a week, according to a close childhood friend who attended the gambling nights. “He was a smart guy, and if there was a way he could make the odds in his favor, he would,” says the friend. “There was always a sucker in the room. He would never be that sucker.”
The money must have seemed like a vindication of sorts: His older brother was then an entry-level accountant making less than $30,000 a year.
After a summer internship at PaineWebber, Glass decided to leapfrog to Wall Street by dropping out of school a year early to work for Sterling Foster, a brokerage in Long Island. Sterling Foster was a classic “pump and dump” scam, in which phone salesmen would sell unsuspecting investors on stock in obscure tech companies, bidding up the share price so Sterling Foster’s owners could quickly cash out when the stock peaked, leaving their clients holding the bag.
While Glass was working there, his brother introduced him to Ben Younger, a fellow Queens College alum and an aspiring filmmaker from the neighborhood. Younger needed work, so Glass got him an interview at Sterling Foster. “He was my friend’s younger brother, and he was driving a new sports car,” Younger told New York Magazine in 2000. “This guy tells me, ‘Look, you work here for a year, you make your million bucks, go to the Bahamas, then you can write.’ I was like, ‘Um, I’ll check my book, but I’m pretty sure this fits into the game plan.’ ”
Younger decided instead that he’d found his movie idea. “I walked in and immediately realized, This is my movie. I mean, you see these kids and you know something is going on. I was expecting guys who went to Dartmouth, but they were all barely out of high school, sitting in a room playing Game Boys.”
The film that resulted was Boiler Room. A morality tale about working-class strivers involved in a stock scam during the dot-com era, it starred Giovanni Ribisi as Seth Davis, a streetwise Jewish kid from the outer boroughs who runs an illegal casino out of his apartment before dropping out of college to work at a shady Long Island brokerage called J.T. Marlin. Based in part on Glass’s detailed descriptions of Sterling Foster, Boiler Room showed bullying salesmen recruiting fresh-faced twentysomethings in ill-fitting suits with promises of millions. The boy-men aped Gordon Gekko’s speeches about greed. The top salesmen used their money to buy gigantic unfurnished houses and expensive sports cars, spending wildly on weekend bacchanals of liquor, drugs, and women.
Although he enjoyed the mythic status the movie conferred on him, Glass complained about not receiving royalties from Younger, who had Glass sign a waiver relinquishing his rights to the film. “He sat down with the guy and pretty much gave the guy the whole movie,” says Glass’s childhood friend. “He thought he was going to get some money, and they didn’t give him anything.” (“That makes two of us,” says Younger, who says he got only $15,000 for the script.)