Plot
In 1999, Seth Davis (Giovanni Ribisi), a 19-year-old college dropout, runs an illegal but successful underground casino in his Queens apartment. His father Marty (Ron Rifkin) is a New York Federal District judge. Seth joins J.T. Marlin, a brokerage firm based in a non-descript office building in or near Commack, NY.
Arriving at J.T. Marlin, he learns from Jim Young (Ben Affleck) what he needs to do to become a millionaire working at the firm. He also embarks on a romance with Abbie Halpert (Nia Long), an ex-girlfriend of Greg's. Seth also becomes part of the crowd of successful stock brokers, including Chris Varick (Vin Diesel) and Richie O'Flaherty (Scott Caan). Seth closes down his casino.
Meanwhile, the FBI have been tracking the firm for a period of time. The company is actually a chop shop brokerage firm that runs a "pump and dump", using its brokers to create artificial demand in the stock of expired or fake companies. 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. 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. 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 fraudulent and unethical practices, Seth becomes deeply unnerved by his work environment and how he has knowingly scammed Harry.
Seth's father confronts and disowns him. Seth later shows up at his office offering to get his father to go along on a scam that would rob J.T. Marlin out of a lot of money, and that he would leave the firm soon after. His father angrily refuses, and orders him to leave. Before he is escorted out, Seth emotionally explains that he closed the casino, and joined the firm not only to gain his father's approval, but also to turn his life around. Upon learning this, but knowing he can't help due to the risk to his job, his father sadly declines, and Seth walks out.
Seth is set up by Abbie (who was working with the police), and is 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 between the two the day after Seth confessed everything. 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. Before he is taken into custody overnight, Seth and his father sit alone in the room. Seth's father explains that he has regretted every day that he has been a harsh father to him. He tearfully says 'I am more sorry than you will ever know', and the two tearfully embrace.
Seth is released and instructed by the FBI to return to work the next day. To deliver evidence that can be used against the firm, he copies 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 (Tom Everett 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 walking past Abbie in the reception area, ignoring her, and then 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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