In 1987, Jordan Belfort (Leonardo DiCaprio) loses his job as a Wall Street stockbroker employed by a man named Mark Hanna (Matthew McConaughey) due to Black Monday. He takes a job at a boiler room brokerage firm on Long Island that specializes in penny stocks. Thanks to his aggressive pitching style and the high commissions, Belfort makes a small fortune.
Jordan befriends his apartment neighbor Donnie Azoff (Jonah Hill), and the two found their own company. They recruit Jordan’s accountant parents as well as several of Jordan’s friends, whom Jordan trains in the art of the “hard sell”. The basic method of the firm is a pump and dump scam. To cloak this, Belfort gives the firm the respectable name of “Stratton Oakmont”. After an exposé in Forbes, hundreds of ambitious young financiers flock to his company.
As Jordan becomes immensely successful, he slides into a decadent lifestyle of prostitutes and Quaaludes. He has an affair with a woman named Naomi Lapaglia (Margot Robbie). When his wife Teresa finds out, they divorce and he marries Naomi, soon having a daughter. Meanwhile, the U.S. Securities and Exchange Commission and the FBI begin investigating Stratton Oakmont.
Jordan illegally makes $22 million in three hours upon securing the IPO of Steve Madden This brings him and his firm to the attention of the FBI, mainly agent Patrick Denham (Kyle Chandler). To hide his illegitimate money, Jordan opens a Swiss bank account with corrupt banker Jean-Jacques Saurel (Jean Dujardin) in the name of Naomi’s aunt Emma (Joanna Lumley), who is a British citizen and outside the reach of American authorities. He uses the wife and in-laws of his friend Brad Bodnick (Jon Bernthal), who have European passports, to smuggle cash to Switzerland.
Donnie gets into a public fight with Brad, and while Donnie escapes, Brad is arrested. Jordan also learns from his private investigator that the FBI is wiretapping his phones. Fearing for his son, Jordan’s father pressures him to leave Stratton Oakmont and lay low while Jordan’s lawyer orchestrates a deal to keep him out of prison. Jordan, however, cannot bear to quit, and decides to stay in the middle of his farewell speech.
Jordan, Donnie and their wives are on a yacht trip to Italy when they learn that Aunt Emma has died of a heart attack. Over the objections of his grieving wife and his yacht captain, Jordan decides to sail to Monaco so they can drive to Switzerland without getting their passports stamped at the border and settle the bank account, but a violent storm capsizes their yacht. After their rescue by Italians, the plane sent to take them to Geneva is destroyed when a seagull flies into the engine. Jordan considers this a sign from God and decides to sober up.
Two years later, the FBI arrests Jordan. Saurel, arrested in Florida over an unrelated charge, has told the FBI everything. Since the evidence against him is overwhelming, Jordan agrees to gather evidence on his colleagues in exchange for leniency.
Disgusted with Jordan’s lifestyle, Naomi tells Jordan she will divorce him and wants full custody of their daughter and their unborn child. Enraged, Jordan assaults his wife, takes cocaine, and ends up crashing his car in his driveway during an attempt to abscond with their daughter. Naomi takes her daughter off him and leaves him defeated in the car.
The next morning, Jordan wears a wire to work. Jordan slips Donnie a note warning him about the wire. Donnie gives it to the FBI, and Jordan is arrested for breaching his cooperation deal. The FBI raids and shuts down Stratton Oakmont.
Despite this one breach, Jordan receives a reduced sentence for his testimony and is sentenced to 36 months in a minimum security prison in Nevada. After his 2006 release, Jordan makes a living hosting seminars on sales technique.