Rounders
Young hotshot poker player Mike McDermott (Matt Damon) loses his entire bankroll of $30,000 in a hand of Texas hold'em against Teddy "KGB" (John Malkovich), a Russian Mobster, who runs an illegal underground poker room Mike frequents. Stunned by the loss he decides to concentrate on his law school studies, and makes a promise to his girlfriend and fellow law student Jo (Gretchen Mol) not to play cards anymore. Fellow rounder Knish (John Turturro) offers to bankroll Mike, after watching his utter defeat at the table; depressed, Mike instead takes a part-time job driving a delivery truck for Knish to make ends meet.
Mike stops off on his way home to deliver papers to his law professor, Petrovsky (Martin Landau), who is playing poker with colleagues and several judges. Watching the other judges' reactions to the cards they are dealt, Mike pushes in a big raise for Petrovsky. Upset by the kibitzer, the other judges ask how Mike can raise without seeing the entire hand. Mike offers to tell each player what they're holding in exchange for a clerkship for Judge Marinacci (Tom Aldredge). Bewildered when Mike guesses correctly each hand, they fold only to learn that Petrovsky held a busted straight. Judge Marinacci is impressed and says that he will put Mike on the short list for the clerkship. And Mike keeps his promise not to play and departs.
After arriving home late the next morning, he explains to Jo that he was at a judges' card game, but didn't actually play, much to her skepticism. He asks to borrow her car to pick up his best friend and the rounder who taught him to play, Les "Worm" Murphy (Edward Norton), from his release from prison. On the trip back to the city, Worm asks Mike to take him to a game and tries to convince him to play. Mike declines and gives Worm what money he can spare, only $220. Driving away, Mike stops and contemplates the game. He remembers a quote from Jack King's book Confessions of a Winning Poker Player about how poker players don't recall big wins they have, but remember accurately their big defeats. He turns the car around and walks into the fraternity game as the boyfriend of the host and stranger to Worm. They clean out the trust fund students with card tricks and acting.
Mike again arrives home late. Jo quizzes him about what the two did last night and wants assurance that Mike didn't play cards with Worm. Mike lies and says he was nowhere near a card game. While in the shower, Jo walks in and finds a "gangster roll" of bills in his pants pocket. She places it in front of the bathroom mirror and leaves for school without him. When she confronts him about breaking his promise and lying to her, Mike admits that he feels alive at the game. Jo walks away, knowing that Mike will never stop gambling.
Mike's studies and punctuality suffer as he helps Worm get money to pay down the debt accrued before prison. While at a strip club one night, Worm is confronted by an old partner of his, Grama (Michael Rispoli). They end up in a fight when Worm smarts off about how Grama got money to buy Worm's debts. Worm learns that he is not only in debt to Grama, but to Grama's bankroller, Teddy KGB. With interest, Grama says Worm owes $25,000. He takes the money Worm cheated out of a couple of Russians at a local private club.
Meanwhile, Mike meets Petrovsky at a bar to discuss the situation with his studies. Petrovsky has an affinity and respect surrounding Mike's passion for cards. The judge shares with Mike a story of his experience as a young man when his family disowned him after choosing to study law rather than become a rabbi, against his family's wishes. Mike returns home to find Worm standing outside his front door, bruised up from Grama. When they get to his apartment, Jo has taken her items and left Mike. Worm suggests the two go to the Taj Mahal to play poker against tourists. At the noodle bar during a break from poker, Worm informs Mike of his debt with Grama, but leaves out Teddy KGB.
The next day, Mike shows up late and unprepared for his role as lead counsel in a moot court hearing. His classmates, including Jo, are aggravated by his inability to focus and lead their side. The two have a conversation which results in Jo leaving Mike for good. Alone in his apartment that night, Mike watches the final hand from the 1988 World Series of Poker, where Johnny Chan checks and traps Erik Seidel into going all-in against a better hand. Petra (Famke Janssen), Mike's friend from the local club, stops over to let Mike know that the debt he owes due to the money Worm's been borrowing under his name is due. He pays her what he can, tells her to put Worm on his own and thanks her for coming to him. She tries to kiss him, but Mike pulls away and lets her know he'll be by later to pay off the rest. When she leaves, Mike throws the glass of whiskey he was drinking into the wall, and leaves to confront Worm about the debt.
Mike finds Worm hiding at the church he hid at as a kid when he got into trouble. He demands to know how Worm could have put him into so much debt when Mike was trying to help Worm get into the black. Mike insists they go see Grama about getting the debt paid off, against Worm's wishes. Grama says Worm has five days to pay off the other $15,000, but Worm smart mouths again and nearly causes a second fight. Mike vouches for Worm and promises the money will be paid on time, and the two leave.
Mike and Worm find games they can round where Mike plays and Worm watches. After sixty-four hours of playing, and only $7,000 earned, Worm says he knows a "municipal workers" game in Binghamton (which turn out to be state police officers) that would earn them the rest of the money. Worm offers to play as well, but Mike says only one of them should play so no one realizes they are professionals. Worm drops Mike off and goes to find a bowling alley, promising only to return in the morning. Mike wins pots legitimately and his stack grows with each passing hour. During the session, another officer who meets Worm at the bowling alley brings him in to play. Mike acts as though the two are strangers when Worm sits at their table. Another officer notices Worm dealing off the bottom of the deck and the two are accused as cheaters, even though Mike was trying to play straight. The officers beat them both, steal all their money and toss them out. Worm is astounded that someone caught his trick and informs Mike that he has only few hundred dollars he hid in his boot. Mike says the two need to ask Grama for more time, but Worm suggests they go on the run until they have the money. Worm then admits that it's not Grama to whom he owes the money but Teddy KGB. With Worm refusing to go back to town now with the deadline near, Mike drives back alone, saying he'll see Worm when he sees him.
Grama refuses to grant Mike more time and reminds Mike that he backed the wrong person. Mike realizes that sticking up for Worm was noble, but that it has put him in a worse position in life than when he lost the initial $30,000. He tries to get a loan from Knish, who refuses to give him any money because Mike did not listen to Knish about Worm. Mike then explains the situation to Judge Petrovsky, who understands that Mike can't give up his life as a card player, much like Petrovsky could not give up his life as a legal professional. Petrovsky loans Mike the only money he can, $10,000. Mike uses the money to play against Teddy KGB before the deadline. In a quick heads-up match, Mike doubles his money and is able to pay off Worm's debt with $5,000 left to use to earn what he owes Petrovsky. Teddy KGB goads Mike into playing more by reminding Mike he only earned back some of the money KGB took off him in the movie's first game.
Mike takes the challenge. On the final hand, Mike is dealt a 9 and an 8, and the flop is a 6, a 7, and a 10, giving Mike a straight. Remembering the final hand of the 1988 World Series, Mike checks to Teddy and calls Teddy's bets. Teddy KGB bets all of his money over the course of the hand before Mike calls his final all-in bet and shows him the straight. Grama urges Teddy to take Mike out, but Teddy tells his men: "He beat me... Straight up... Pay him... Pay that man his money." Mike leaves with enough money to pay his debts to Grama and Petrovsky, and gives him the same $30,000 he started with. He comes across Jo whom he asks to give Petrovsky his money, and the two part amicably. The final scene shows Mike in a taxicab to catch a flight to Las Vegas to play in the World Series of Poker.
