In 1999, Seth Davis (Ribisi) a 19-year-old college dropout who lives and runs an illegal but successful underground casino in his Queensapartment. Because of dropping out of college and running an illegal business to support himself, his father Marty (Rifkin), a New York Cityfederal judge disapproves of him and worries that Seth's criminal living may cost him his judgeship. In hopes to get on his father's good side, Seth joins J.T. Marlin, a brokerage firm based somewhere on the Long Island Expressway, after Greg Weinstein (Katt) comes to his home to check out Seth's business and offers him a job at the firm. Seth agrees and becomes a trainee under Weinstein.
Everything seems to work out for Seth in the early days of his job. Arriving at J.T. Marlin, he learns from Jim Young (Affleck), one of the heads of the company, what he needs to do to become a millionaire working at the firm. Seth learns the ways of the company and does very well at his new job. He also embarks on a romance with Abbie Halpert (Long), an ex-girlfriend of Greg's, which Greg shows disapproval of and who often worries about her effect on his friends and workers. Seth also becomes part of the crowd of successful stock brokers, including Chris Varick (Diesel) and Richie O'Flaherty (Caan), and lives a high-life type of lifestyle with them, usually going out to restaurants with them and seeing their fights with other people. He hits a few snags though, including fights and arguments he has with Greg when Greg becomes too worried about Seth's explosively good work at his job, and when Seth closes down his casino because his employees don't appreciate their significantly increased salaries.
Seth is unaware of the dark side of his quickly successful job, as the FBI have been tracking the firm for a period of time. The company is achop shop brokerage firm that runs a "pump and dump", using its brokers to create artificial demand in the stock of expired or fake companies by cold calling investors and selling them shares at prices set by the brokerage firm, which include a large commission to the brokers (up to three dollars a share for a penny stock). When the firm is done pumping the stock, the investors then have no one to sell their shares in the market, and the price of the stock plummets. This becomes a problem for one of Seth's clients, Harry Reynard (Nichols), a family man who is a purchasing manager of a gourmet foods company and is trying to buy a new house. After Seth sells him one hundred shares at eight dollars each, the stock market plummets and gets Harry into an excruciating financial situation. When Harry calls Seth back asking why the investment has done so poorly, Seth (under coercion from Greg) sells him even more worthless shares, convincing Harry to invest his $50,000 downpayment that he was saving for a family home. Seth promises a smooth process in the investment, however this promise does not live up and causes Harry to be abandoned by his family. Now well aware of the firm's fruadulent and unethical practices, Seth becomes deeply unerved by his work environment and how he has knowingly scammed Harry.
Seth is eventually arrested by the FBI for the violation of SEC regulations. He is taken into custody by the FBI along with his father, who was taken in for attempting to conceal his son from the federal law – a conversation that was of a taped phone call. Seth is given federal immunity, meaning he cannot be arrested for as long as he agrees to testify against J.T. Marlin once all the suspects are taken into court. He does this on the condition his father does not get involved with the case, as he exchanges that for information on the firm's techniques of selling, relocations if law enforcement gets too close, etc. Seth is released and instructed by the FBI to return to work the next day, only to gather evidence and leave shortly before the FBI raid the building by midday. To deliver evidence that can be used against the firm, he inserts files of investments onto a floppy disk and hides it away. Before leaving, Seth attempts to get Harry's money back by lying to J.T. Marlin the way they do with their clients. Michael Brantley (Scott), one of the company heads, agrees to go along with Seth's explanation, saying that in order to complete the process, Seth needs a ticket sale signed by a senior broker, something that his direct supervisor, Greg, has explicitly said that he would never do. On his way out of the building, Seth leaves Chris a note asking to meet in private, at which point he informs Chris about the raid and convinces him to sign the sale ticket. Chris then hastily gathers a few belongings from his desk and quickly leaves. Seth is then shown leaving the building deciding what to do with his life now that his job and ties with J.T. Marlin are finished. As he leaves, several cars including prison buses are seen speeding into the parking lot from which FBI agents emerge, ready to raid the building.
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