Stratton Oakmont racked up plenty of victims and fortunately its tenure was brief. The FBI, the National Association of Securities Dealers (NASD) and the U.S Securities and Exchange Commission were on Belfort’s scent for years and would eventually shut it down in 1996. Belfort made a fortune but would serve 22 months in prison, where he began writing his memoirs, later to be shaped into this 2007 book. Wolf was a bestseller and Belfort wrote a follow–up two years later, Catching the Wolf of Wall Street, in which he tells his origin story and how he formed his crew, and also serves a sequel to the events of the first book.
In 2013, director Martin Scorsese released the film The Wolf of Wall Street, combining elements of both books. Scorsese shaped the film like a white-collar version of his earlier masterpiece, Goodfellas, with Leonardo DiCaprio portraying Belfort as a 1990s version of Henry Hill. The movie was a financial and critical success, and garnered accolades not only for DiCaprio’s performance — he won Best Actor at the Golden Globes — but also for Margot Robbie as Belfort’s wife and Oscar–nominated Jonah Hill as his business partner (the names of the people upon which they were based were changed for the movie). Belfort himself has a bit part in the film.
A Jewish kid from middle–class Bayside, Queens, Belfort focuses Wolf on three areas: 1) his legal struggles 2) Stratton Oakmont and its excesses, and 3) his rampant drug use, physical ailments, and marital tensions — often weaving all three into the same scene.
In the first focus of the book, his legal struggles, one gets the impression that he enjoyed writing this part of the book the least, although that is understandable. Stratton Oakmont’s financial crimes broke a laundry list of federal and state regulations and before his arrest Belfort was forced to spend considerable time, money, and imagination in hiding them from the authorities.
Stratton Oakmont specialized in selling penny stocks, which are inexpensive stock shares from smaller companies. Although usually marketed to investors of more limited means, Stratton Oakmont marketed them to unsuspecting wealthier investors, making an insane amount of money in the process. A classic boiler room operation, brokers were trained to sell using slick, cutting–edge, high–pressure tactics. The firm thrived on manipulation and deception, with an intense focus on closing deals no matter the ethical cost.
A significant portion of the book is dedicated to explaining Stratton Oakmont’s approach to stock price manipulation. Belfort’s traders would artificially drive up the stock price of a company during its Initial Public Offering (IPO), while retaining more shares of that company than SEC regulations permitted. Belfort uses the example of Steve Madden Shoes, a company he helped take public, to demonstrate this practice.
Belfort outlines how stock manipulation during an IPO works: He would invest heavily in a new business, like Steve Madden Shoes, and then leverage his controlling stake to take the company public. Belfort’s brokers would use aggressive tactics to inflate the stock price when selling to investors. Once the price reached a certain level, Belfort would sell enough of his shares to recover the cost of his initial investment — meaning he paid nothing for the remaining shares, which were now worth significantly more.
However, under SEC rules, an investment firm sponsoring an IPO is only allowed to hold a limited amount of stock in the company they are offering, but Belfort and Stratton Oakmont held far more Madden shares than the law allowed.
Belfort was also involved in money laundering, a scheme that began when he secretly traveled to Switzerland, a nation notorious for hiding money. The Swiss bankers he met with openly explained how the Swiss banking system hides vast sums of money and how they avoid cooperating with foreign institutions, like the U.S. SEC. Since the practice of issuing “numbered” bank accounts without names ceased after World War II, Belfort’s first step was to open accounts under the names of proxies, similar to those who held his stock. These individuals were tasked with smuggling large amounts of cash across the border, so Belfort relied on people he trusted who wouldn’t raise suspicion — including his wife’s elderly British aunt and a member of one of his drug dealers’ Swiss relatives.
As a sidenote, Belfort comes across as cynical to the whole stockbroking profession. He argues that stockbrokers, including himself, don’t truly produce anything of value and lack any specialized stock market knowledge. At their core, he says, they’re essentially just slick salesmen, especially after Belfort taught his crew high–powered sales scripts that drew customers into opening their wallets. With this training, Belfort says, even a high school or college graduate can be taught to talk like a stock market expert, which leads into the second focus of the book, the atmosphere at Stratton Oakmont.
In staffing Stratton Oakmont, Belfort eschewed licensed brokers (those who passed the Series 7 exam) and instead brought in a more impressionable team, a hardscrabble gang of local kids fired up to make big bucks. The place was awash in money and to reward the brokers for their highly stressful — and aggressive — jobs, Belfort spared no expense in keeping them happy. He cultivated a bacchanalian, party–like atmosphere, a sort of adult frathouse full of sex, hookers and drugs.
During his tenure at Stratton Oakmont, Belfort became known for his loud and proud persona. He would routinely motivate his troops by giving thumping, over–the–top speeches (marvelously re–enacted by DiCaprio in the movie), preaching like an evangelist about the glory of earning big money.
The book’s final focus is his drug use, physical ailments, and marital tensions, three issues that are tragically intertwined.
Belfort suffered from intense back pain and sleep problems, the latter which plagued him since childhood. As an adult, the chaotic and party-fueled atmosphere at Stratton Oakmont enabled him to indulge easily, and he would use a powerful cocktail of drugs to cope. He was particularly known for his abuse of Quaaludes, a hypnotic sedative drug which he used recreationally and frequently, often mixing them with alcohol or other substances, but it became a full-blown addiction. Besides Quaaludes, he also used cocaine, morphine, and other prescription medications.
Belfort reported frequent blackouts and memory loss due to mixing drugs, especially Quaaludes and alcohol. He often had no recollection of things he said or did while under the influence, sometimes waking up to damage, arrests, or people furious at him. He had multiple close calls with overdoses, particularly from taking too many sedatives or mixing drugs dangerously. In one story, he recalls almost choking to death on his own vomit after passing out. Long–term drug use left him in a near–constant mental haze, affecting decision-making, mood, and impulse control.
Belfort describes in cringing details the most notorious effects of his Quaalude abuse, the loss of basic motor control. He described episodes where he was physically unable to walk, speak clearly, or even stand up — calling these “cerebral palsy phases.” There’s a wild (and comic) scene — later portrayed in the movie — where he attempts to crawl to his car while stoned out of his mind.
Belfort writes at length on his wives and family life, and herein lies the part which Belfort seems to have enjoyed writing the most.
Belfort met his first wife, a local Queens beauty, after college while working as a meat salesman. The business thrived for a while, thanks to Belfort’s silver-tongued persuasion abilities. But after overextending himself, the business went under, leaving him with a young wife and bills to pay. By all his accounts, his wife stuck by him through the lean times and he has not had (at least publicly) an unkind word to say about her. But Belfort ended up leaving her for a London–born and Brooklyn–raised model, Nadine Caridi, a stunning beauty whom he met at a party. His life with the Duchess — as he refers to her due to her birth country and British heritage — provides some of the most memorable scenes, and their life together became a bizarre mix of luxury, chaos, and toxicity (not to mention lust).
The two met when Belfort was already rich from Stratton Oakmont and their relationship quickly became intense. Marrying in the early 90’s, Belfort provided Caridi with a glam life of extreme wealth: yachts, mansions, exotic vacations, and nonstop partying. Belfort showered her with expensive gifts and built a lavish life for them and their children in one of the most expensive areas of Long Island. Their mega–mansion boasted a helicopter pad, a swimming pool, tennis courts, servants galore and a fleet of luxury cars.
But behind all the glamour, things became unstable. Belfort and Caridi had some intense, ugly shouting matches during their marriage, and they usually exploded over his drug use, infidelity, and parenting. Although Belfort loved his kids dearly, Caridi got especially furious when his reckless behavior endangered them. One of their biggest, most infamous fights was when Belfort, high on drugs, tried to kidnap their daughter and crashed his car into a pillar inside their property (also re–enacted in the movie). Their marriage eventually broke down under the weight of Jordan’s addictions and criminal behavior, and they divorced in the early 2000’s.
How did it all end for Belfort? After getting cornered by the FBI, who had a strong case against him, Belfort was given a choice: either go to prison for decades, or cooperate and help bring down the dozens of brokers, business partners, and shady investors he worked with. To get a lighter sentence, he agreed to become an informant, wearing a hidden wire during meetings and conversations to secretly record people he worked with. However, a lot of his old friends and colleagues ended up getting arrested and betrayed by him — and he was absolutely hated by many in that world after that.
Belfort did easy time at Taft Correctional Institution in California, a low–security federal prison of the type that is called “Club Fed” in popular culture because it is so relaxed and safe compared to the tough penitentiaries that house hardened convicts. While there, he had the odd coincidence of sharing a cell with Tommy Chong, of the classic Cheech & Chong stoner comedy duo. Chong was there for selling bongs online, and the two became friends. It was Chong who encouraged Belfort to write his memoirs. Interestingly enough, his writing style was influenced heavily by Tom Wolfe’s The Bonfire of the Vanities, which he read while there.
Belfort’s New York humor shines through the book and is the saving grace throughout the scenes where the crime and sleaze bubble through, although the vulgarity might not appeal to all readers. His antics, though tragic and costly, often come off as comedic, with a rhythm similar to stand-up comedy or a raunchy sitcom. It makes for enjoyable reading but one has to question his motives for portraying the incidents in such a manner.
For example, the infamous yacht story — one of the highlights of both the book and the movie and one which Belfort has retold ad nauseum in interviews and personal appearances —involved a hair–raising incident where he ordered the captain of his yacht to sail through a 70–knot storm, instead of avoiding it, off the coast of Sardinia.
The yacht was battered by massive waves that smashed its windows and hatches, flooding it. Despite the dire conditions, all 27 people on board were rescued by the Italian Navy, but the yacht was lost at sea. Belfort — and unfortunately later Scorsese — play it up as bumbling dark comedy, something that would fit in the first season of Breaking Bad or Michael Bay’s 2014 crime caper Pain and Gain. But after the movie was released, two of the men who were on board the yacht — friends of Belfort since childhood — were interviewed on a local Long Island radio show and told their side of the story. The real events, as they stated, were a horrific, PTSD–inducing nightmare in which all aboard — crew included — thought they were about to die.
Another problem with the book is that it never actually defines itself. Is it a business book? A morality tale? A success story? A crime story? Is it fratire, the genre popularized by Tucker Max in I Hope They Serve Beer in Hell? It has elements of all of those, but they never truly come together into a cohesive whole. The business and legal sections are hard to follow for the average reader and Belfort didn’t seem interested — or patient enough — in describing the concepts in simpler terms. In fact, like a true salesman, at times he seems more interested in a carefully crafted portrayal of himself where even the self-deprecation — and there are loads of that — contain hints of braggadocio. One can hear him saying as he wrote the book, I had balls. I went for the brass ring. I did things that you didn’t dare to do.
After the movie was released in 2013, Jordan Belfort experienced a resurgence in public attention and became a media favorite, interviewing endlessly in his thick, fast–talking Queens accent while regaling a new generation of fans with the stories behind the movie. In time, he eased into the role of elder statesman, becoming an in–demand commentator on current financial affairs such as crypto and Wall Street. Belfort also rebranded himself as a motivational speaker and sales trainer, touring internationally and giving seminars on sales techniques, goal–setting, and entrepreneurship. His signature sales methodology, now marketed as the “Straight Line Persuasion” system, has become a core part of his training programs. He also created a podcast, The Wolf’s Den, where he interviews entrepreneurs, influencers, businessmen and others (although it is unclear as of this writing if the podcast is still active).
To his credit, he has shown remorse for his misdeeds and the effect his lifestyle had on his family and has repeatedly stressed the importance of ethics in business and sales. His speeches, as shown on YouTube, are enjoyable and engaging.
Unfortunately, the issue of restitution remains a sticky issue. Currently living in California, he was ordered some years ago to pay $110.4 million in restitution to victims of his stock fraud. However, critics and prosecutors accused him of not paying enough back, particularly in light of earnings from the film, books, and speaking engagements. Belfort has claimed he’s been steadily paying.
Despite the glamorized portrayal in the movie, many people — especially his victims — still view him with suspicion. He remains a controversial figure. Some see him as a charismatic redemption story, while others view him as an unrepentant fraudster profiting off his crimes. Read the book and decide for yourself.
