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The Wolf of Wall Street Can’t Sleep

Jordan Belfort with his fiancée and an assistant in Manhattan Beach, California.  

“In a single word, it’s attention, a craving for attention,” Coleman says. “I think it’s the issues that cause the insomnia, not the insomnia that causes the issues.”

Coleman spent six years investigating Belfort. From the outset, what bothered Coleman most, he says, is that Belfort put so many of his friends and family members at criminal risk. When he started laundering money in Switzerland, for instance, Belfort cajoled his wife’s aunt, a retired schoolteacher in London, to be the front for bank accounts into which he illegally funneled millions to hide from other regulators chasing him. “There’s a difference between influence and manipulation,” Coleman says. “He’s a great motivational speaker, and he manipulated everyone around him with a Svengali-like trance.” After his arrest in the fall of 1998, Belfort, then 36, faced a sentence of more than two decades in prison. He did not protest the charges and take his case to trial. He did not keep his mouth shut and spare others.

“He cried like a baby,” Coleman says.

Wearing a wire, Belfort worked with Coleman and other federal officials to make cases against his partners and associates. By cutting a deal, Belfort hoped to persuade a judge to cut the lengthy sentence awaiting him and spare himself heavy prison time. Working with the government, Belfort also proved he’d mastered the art of being liked. Dan Alonso, a former federal prosecutor who handled Belfort’s case, was so impressed with Belfort’s speaking ability that he invited him to the Manhattan district attorney’s office, where Alonso is now a top official, to have Belfort give a speech to prosecutors. (“He’s a salesman,” Alonso tells me of Belfort’s performance, “and he sold himself well.”) Alonso and others lauded Belfort’s efforts during the investigation, and he only served two years and four months in prison. “A slap in the face,” Coleman says of Belfort’s punishment. Coleman was so upset with Belfort’s sentence he considered moving out of the unit that handles white-collar crime. “At the very least, he should have done a year for every year I investigated him,” Coleman says. That Belfort is now a celebrity, immortalized by his books and a performance from Leonardo DiCaprio, galls him.

“Crime pays,” Coleman says.

But Coleman can’t get enough of Belfort either. Agent and cooperating witness stay in touch, going out to dinner every so often when their schedules allow. “He tells a good story,” Coleman says of Belfort.

“He’d come back from playing tennis, and I’d crack up, man, because we’re in fucking jail,” Tommy Chong says.

“I was shocked,” Belfort says. “Everyone’s playing tennis and basketball. The Latins have their music blasting. I was like, Wow, this isn’t so bad.

We’re at Chaya, the Asian-fusion restaurant in Venice, for a prison reunion. The dining room is roaring, and under the chandeliers and stagelike lighting, waiters pass plates of shishito peppers and soy-glazed black cod. Chong, then jammed up for selling bongs over the web, and Belfort, serving out his white-collar sentence, got close in prison. They shared their meals and stories, like the prison chef who cooked, in a microwave, delicacies that included fresh squirrels he’d trapped. “The Quaalude stories are my favorite,” Chong says.

Belfort recalls a night where he spent $1,000 on a rare ­Quaalude pill and vowed to savor the high. “I stick my finger down my throat. I wanted to get all the frickin’ food out of my stomach. Then I take a fuckin’ enema, shove it up my ass. I want to be completely clean, from top to fucking bottom.”

Across the table, Chong’s wife, Shelby, is cackling with laughter.

“He has to do everything the best,” she says. “Perfect. Number one.”

And the story goes on, just as Belfort tells it in the book: about learning that the Feds are following him while completely stoned, then driving out to use a pay phone at the local country club, only to fall backward and crash on the floor in his ’lude binge.

“I’m lying on my back and see the ceiling has cracks in it,” Belfort says. “I’m like, Why are the Wasps not paying for their ceiling? What a troubling thought that they don’t fix the ceiling in this Wasp heaven—maybe they’re running out of money. I try to stand. I can’t stand! I curl myself into a little barrel and fucking roll myself down the steps. I do the prayer to Jesus. Even an old Jew. Jesus, please God, just get me home one last time.”

“I love this!” Shelby says. The more Belfort reveals, the more laughs he gets. Especially in the story’s dénouement: totaling seven cars at one mile an hour.