NEW YORK MAGAZINE: The Wolf of Wall Street Can't Sleep

By Geoffrey Gray

The courts at the tennis club in Manhattan Beach are full, and the pool is overflowing with bikinis. It’s a brilliant summer afternoon, and over at the juice bar, drenched in sweat after hitting for an hour or so, Jordan Belfort and I are parked on stools and talking about his Big Problem. It’s plagued him since he was a child. Even in prison, he couldn’t make it stop.

“I can’t sleep,” he tells me as the waitress arrives to take our order.

“Oh my God!” she says with a gasp. “You look just like Jordan Belfort!”

Belfort looks confused. He doesn’t know what to do. He’s never been recognized like this before.

“Actually,” the waitress goes on, “we just looked you up on the Internet. You are Jordan Belfort!”

Then the gushing starts. She tells him what big fans she and her friends are of his books, that she follows his motivational-speaking career on the web. Juice Bar Woman is a bona fide Jordan Belfort groupie.

“Can I get a picture?” she asks, and soon her smartphone camera is clicking.

The spotting is incredible for many reasons. The city of Los Angeles and its satellite communities like Manhattan Beach make up the celebrity mecca of the universe, and among all the hot stars and not-so-hot ones who can be spotted around here, the name does not quite register. Jordan Belfort? And Jordan Belfort is also a convict, one of a particularly loathed class—a white-collar crook who duped innocent investors to finance an insatiable greed. Belfort was convicted of scamming more than $100 million throughout the nineties to finance a hedonistic paradise. Stratton Oakmont, the firm he started, became a kind of cult. “It should have been Sodom and Gomorrah,” Belfort would later write. “After all, it wasn’t every firm that sported hookers in the basement, drug dealers in the parking lot, exotic animals in the boardroom, and midget-tossing competitions on Fridays.”

Belfort’s background in finance was limited. After dropping out of dental school, he sold frozen lobsters and steaks door-to-door; one of his first experiences in sales came from hawking ices as a kid. He proved to be a great talker and fearless mimic, modeling himself after his hero, Gordon Gekko, the ruthless corporate raider in Wall Street, a favorite film, and assumed what he called “a devilish alter ego.”

It was a truly epic scam, in which he used his powers of persuasion to screw investors and then train a small army to do the screwing for him. But eventually, Belfort sank his own empire. He spent some of his fortune on megamansions, only to have the government seize them. He purchased his own helicopter, only to almost crash it on his front lawn while flying it stoned. He owned a 166-foot yacht built for Coco Chanel, only to tell the captain to steer it into a storm and nearly kill himself, his friends, and his crew before the ship sank in the Mediterranean. Even with the hundreds of prostitutes he claimed to have hired, Belfort struggled to perform. He was taking so many drugs that his penis, as he writes, had taken the form of a “No. 2 pencil eraser.”

It was in prison that Belfort discovered his talents were transferable. His cube mate, or “cubie” (at his facility, there were no cells), was Tommy Chong of Cheech and Chong fame. Chong laughed so hard at Belfort’s stories he pushed Belfort to write them down and get them published. Employing the same zeal that made him a financial-industry tycoon, Belfort set out to become a writer. In prison, he studied Tom Wolfe’s Bonfire of the Vanities, taking notes on character development, dialogue, tone. He then applied the Wolfean techniques to his own tales, writing two memoirs that detail his quest for fortune and approval.

And, now as then, people cannot get enough of Jordan Belfort. He’s using the same skills, working the same stories, only this time, the gig is entirely legal. His ruthless rise and self-destructive fall was ripe for a big Hollywood production. Leonardo DiCaprio signed on to play Belfort, with Martin Scorsese directing. After many snags in production, The Wolf of Wall Street will finally be released next month and in time for Oscar season.

Back at the tennis-club juice bar, Belfort still can’t believe it: Leonardo DiCaprio playing him? During production, Belfort even coached DiCaprio personally on the stages of a ’lude high (“tingle,” “slur,” “drool,” “amnesia,” and on), with Belfort rolling around in DiCaprio’s living room. He laughs about it now, but before he went to prison, Belfort had become a kind of neurotic, Long Island version of Scarface. “I was in the midst of a cocaine-induced paranoia that was so deep I’d actually taken a few potshots at the milkman with a twelve-gauge shotgun,” he writes in his first book. After that, he nearly killed himself. “It looked beautiful, a purple pyramid,” he writes of morphine pills piled up in his hand. “I threw them back and started chewing.” The drugs. The greed. That always empty feeling. The Big Problem.

“From the time he was born, he never really slept,” Leah Belfort, Jordan’s mother, tells me in the kitchen of their two-bedroom apartment in Bayside.

“He can’t sit still,” Max Belfort, his father, says.

“We’d come into the room, and he’d be watching his fingers,” Leah says about Jordan’s infant years. “I’d say to Max, ‘He’s not sleeping. He must be dumb. What kind of dummy are we raising?’ ”

In the kitchen, the appliances look plucked from a fifties time capsule, and framed recipes for gefilte fish and matzo-ball soup hang above us on the wall. The product of Bronx tenements and night-school master’s programs, Belfort’s parents represent the immigrant dream of hard work and ambition. Max and Leah are both accountants, but Leah decided to choose another profession after retirement. She went to law school in her sixties, graduated from St. John’s University, and still does pro bono legal work. With a home that appears so steady, part of the Belfort mystery is how a nice Jewish boy like him could destroy himself with such gusto.

Consider the following list of ingredients he packed inside “a brown leather Louis Vuitton shower bag” on a trip to Czechoslovakia, according to his memoir: “a half-ounce of sinsemilla, 60 pharmaceutical Quaaludes, some bootleg uppers, some bootleg downers, a sandwich bag full of cocaine, a dozen hits of ecstasy, and then the safe stuff: a vial of Xanax, a vial of morphine, some Valiums and Restorils and Somas and Vicodins, and some Ambiens and Ativans and Klonopins, as well as a half-consumed pack of Heineken and a mostly consumed bottle of ­Macallan’s to wash things down.”

In his memoirs, Belfort describes his parents as pushy and overbearing. He calls his dad “Mad Max” and fears his chain-smoking, vodka-drinking fury; Leah appears as a Jewish mother on steroids, demanding he start studying for medical school from the cradle. Both Max and Leah have read most of their son’s memoirs. Max and Leah are at least proud that he didn’t let the misery go to waste: Teaching himself to write and turning his gonzo tales into page-turning books, they believe, are great accomplishments.

“It’s an enigma, really,” Max says about his son.

“I wanted to deny he was my child,” Leah says.

“That time we found him growing pot in the closet,” Max says. “Very, very entrepreneurial. He said it was a school project, right?”

“He said, ‘I’m going to get an A.’ He was trying to buy me off with the grade,” Leah says. “I said to him, ‘I’ve been manipulated by better than you!’ Then Max came home, and you gave it to him.”

“A lot of lectures,” Max says, shaking his head again.

Leah says, “He always wanted to be part of the older kids, and all the big boys were taller. Much taller than he. And all the girls were much taller. He tried to build himself up with a bodybuilder, but that didn’t make him taller!”

“Yeah, all those girls were taller than him.”

“Maybe that’s one of the reasons he tried to compensate,” Leah says.

“Like Mayor Bloomberg, right?” Max says.

“Or Napoleon!” Leah says.

“My chief insecurity is that I was a late bloomer,” Belfort tells me. “I didn’t go through puberty until later in the curve. I didn’t feel confident in high school. Ninety percent of my focus was hot girls. I thought if you got rich, you’d get the girls. A lot of guys think that. And it’s true—it worked for me. It worked really well. When I really hit it, I had all these gorgeous women throw themselves at me. But the problem with that stuff is, it doesn’t really change you.”

Belfort has the salesman’s look: a flash of white teeth, tan skin, all of which radiate a youthfulness that’s impressive considering his age (he turned 51 this summer) and former drug habit. “A testament to the regenerative qualities of the human liver,” he likes to say of himself, with a heavy Long Island brogue.

It’s another tennis morning for us, and this time we play at the private court of Jeff Tarango, his personal tennis guru. Tarango is not any tennis instructor. The former pro and commentator has been rated one of the top over-40 players in the world.

“Obsessive-compulsive talent,” Tarango says of Belfort. “He’s not autistic, but he could be. He just can go into that tunnel.” Belfort is so committed to improving his tennis strokes that he and Tarango play together every morning. Belfort wanted to play on weekends, too. His sessions are tutorials. Behind the baseline, Belfort props up his smartphone to videotape himself in action; later, at night, he’ll study his technique in bed with his fiancée, Anne Koppe. His intensity can be overwhelming, but it’s all part of his recipe for success, a life philosophy he’s now hit the road with in his new incarnation as motivational speaker for hire. “I believe in total immersion,” one of his creeds goes. “If you want to be rich, you have to program your mind to be rich. You have to unlearn all the thoughts that were making you poor and replace them with new thoughts—rich thoughts.”

After hitting balls, I trail him back to his home. He drives a Mercedes SL convertible and lives in an oceanfront mini-mansion on Manhattan Beach. I follow him through the garage and up the spiral steps into an expansive living room where the doors and windows are open to the view of the Pacific and the warm breeze comes and goes just so.

“Making money is so easy,” Belfort tells me. “It really is. It’s not hard to do.”

Belfort’s actual net worth is something of a mystery. He earned more than $2 million for the books and film rights (“I thought they were fucking crazy,” he says about actually getting published), five figures for speeches he gives, along with income from investments he’s made in Australia.

“I did really well with the mining industry,” he says. “I made some hits. Iron. Ore. Stuff like that.”

But he can’t keep it all. According to a judge’s order, half of everything Belfort earns must go to the $110 million he is obligated to pay back to the more than 1,500 investors he fleeced. It’s a hefty order to fill, and according to the government Belfort has been negligent in his payments. Belfort denies he’s hiding money from the government—a skill he once perfected on Wall Street—and currently the parties are working toward a resolution. Belfort says he’s not making a nickel off his story and has signed over all proceeds and profits to the government.

“I wanted to be above reproach with the whole thing,” he tells me. “I didn’t want people to think, Oh, he’s making money on the movie, on his crime. Like, ‘I don’t want the fucking money! Keep the fricking money!’ ”

“They never even call me,” he says, sounding insulted.

Waiting for Belfort in his living room are two assistants, both of whom seem to possess his requirements for employment.

“Let’s just say Jordan has a type,” one says.

Belfort’s lair here is like a high temple of the Shiksa Goddess. He laughs off his propensity for long blonde hair, blue eyes, and buoyant bosoms.

“I’m not going to lie,” he says as we make our way onto the deck. The water is sparkling on the crashing surf in front of us, and errant sounds of a volleyball game pass in the breeze. One assistant brings out a pair of cold beers, sandwiches, and chips.

Belfort spreads out on a lounger, his sunglasses shielding his eyes.

“I always felt if I had more, then I’d feel good,” he says. “I think the more I had, the worse I felt. We all have these holes, right? The problem is, there’s some ways we plug those holes that are sustainable. Going out and fucking twenty whores every night—it was fun when I did it, but that’s not really sustainable.”

Toward the end of his first book, Belfort describes his need for validation: how he and a friend are swimming in a pool, but the friend never comes up for air. Belfort pulls the friend out of the pool and proceeds to perform mouth-to-mouth resuscitation. Finally, the friend shows signs of life—by vomiting the hamburgers they were eating into Belfort’s mouth. When the medics arrive, one tells Belfort, “You’re a hero.”

“What a delicious ring those three words had,” Belfort writes. “I desperately needed to hear them again, so I said, ‘I’m sorry, I missed what you said. Could you please repeat that?’” Belfort then approaches his second wife (“with her loamy loins and brand-new breasts”) and “tried to find just the right words that would inspire her to call me a hero.”

No dice.

“Unfucking believable!” he writes. “She didn’t call me a hero!”

Belfort’s business model itself seemed based around ego-boosting. Instead of hiring seasoned stockbrokers or anyone with experience, he recruited naïve twentysomethings who would adhere to his ruthless sales creed: Buy or die. To motivate these young and wealth-hungry aspirants, Belfort would arrive to work in the same white Ferrari Testarossa that Don Johnson used to drive in Miami Vice and deliver not one but two boardroom speeches to them each day.

“From a moral perspective, he was a reprehensible human being,” says Greg Coleman, the FBI special agent who made the case against Belfort. A specialist in financial frauds and money laundering, Coleman has been an agent with the Bureau for more than twenty years. “Admiration would be the wrong word, but from the perspective of manipulating the market, he’s one of the best there is,” Coleman says of Belfort. Coleman also specializes in the behavioral sciences, giving talks inside the FBI on the psychology and interior motives of criminals.

“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.

“Banging into a car! Banging into a car!” Shelby howls. “Oh my God! Oh my God!”

“Was he the gold mine?” Tommy Chong asks. “Was he the gold-mine writer?”

“You do such a good setup,” Shelby says.

“You learned that from the early selling,” Chong says. “How to sell.”

Finally the conversation lands on his lack of sleep. Belfort tells us he’s seeing a psychologist now, trying to come up with a cure for his insomnia.

“Why can’t you sleep?” Shelby asks him.

“I hated going to sleep as a kid,” Belfort says. “I almost trained myself to fight sleep, and it eventually became a pattern.”

Shelby is confused.

“You make your real life so scary,” she says. “How could sleep be scary?”

The night is warm and clear. After dinner, I drive with Belfort back toward Manhattan Beach in the Mercedes. Top down, we pass the tattoo and taco shops on Lincoln Boulevard in silence. Finally, he breaks it.

“Did you like the stories?” he asks.

The stories were great, I tell him. He’d told them so well. It was the truth. Once he got rolling, all the laughing was infectious. He truly was a talent.

Belfort smiles to himself. For a minute, the compliment has perked him up, but the feeling soon fades. As the stoplights on Lincoln Boulevard pass by, I look back at him. He looks pale and deflated.

“Honestly, it’s just so exhausting,” he says.

Contact Us

A: 13-15 Little Burton St, Darlinghurst NSW 2010
P: +61 2 9332 9111

Scroll to Top
Scroll to Top