Molly Bloom is a world-class mogul skier with Olympic aspirations, thanks to years of enforced training from her overbearing father. In a qualifying event for the 2002 Winter Olympics, she is severely injured, ending her career.
Instead of attending law school immediately, Molly takes a yearlong sabbatical and moves to Los Angeles. Becoming a bottle service waitress at a club, she soon meets Dean, an ostentatious but unsuccessful real estate developer. She becomes his office manager and is soon involved in running his underground poker games at "The Cobra Lounge". Many famous and wealthy individuals, including movie stars, investment bankers and sports players, are involved in Dean's game. Molly earns large sums of money in tips alone.
Initially unfamiliar with poker, Molly quickly learns how to appeal to the players for tips. In particular, she hopes to please the most successful player, a film star named Player X, by attracting new players to the game. Dean, upon seeing that Molly is becoming increasingly independent in running the games, attempts to control, and then fires her.
Molly, having contacts through years of running the game, creates her own poker games. She rents a hotel penthouse and hires a staff. Additionally, she contacts club and casino employees to spread the word about her games. Player X, along with many others, leaves Dean's games to play at Molly's. Increasingly successful, as Molly gains more money, she is pressured by Player X to raise the stakes. Harlan Eustice, a skilled, conservative and successful player, joins Molly's game.
One night, after accidentally losing a hand to the notoriously worst player, Brad Marion, Harlan becomes increasingly compulsive, suffering heavy losses; later, Molly finds out that Player X, who enjoys ruining people's lives more than the game itself, has been funding him to keep him playing. After Molly berates him for his unethicality, Player X decides to change venue for his games. Others join him, leaving Molly.
Molly moves to New York City to begin a new underground poker game. After reaching out to many wealthy New Yorkers, Molly finds enough players for several weekly games. Despite continuous success, she fears being unable to cover her losses when players cannot pay. Her dealer convinces her to begin taking a percentage of large pots, recouping her potential losses but making her game an illegal gambling operation.
Brad is indicted for running a Ponzi scheme; Molly is investigated and questioned as to who attended her games. At this time, she becomes increasingly addicted to drugs, as the games have taken their toll. Her players also begin to include wealthy individuals from the Russian mafia, among others.
Molly is approached by the Italian mafia, who offer their services to extort money from non-paying players. After she declines, she is attacked in her home, held at gunpoint and her mother's life is threatened. As she is about to return to her poker games, the FBI conducts a raid after Douglas Downey, a player infatuated with Molly, informs on her. Molly's assets are seized, and she returns home to live with her mother.
Two years later, Molly has published a book, naming only a few individuals that played in her games. Arrested by the FBI, she is indicted for involvement in illegal gambling with the mafia. She enlists the help of Charlie Jaffey, a high-profile lawyer in New York, who agrees to help after learning she has been protecting innocent people affected by her poker games. While she is in New York awaiting trial, her father, Larry, seeks her out and attempts to reconcile. He admits he was overbearing and that he treated Molly differently than her brothers, because she had known about his affairs.
Charlie reads Molly's book and becomes interested in helping her case, as he feels she has not committed serious enough wrongdoing to merit prison. He negotiates a deal for Molly to receive no sentence and for her money to be returned in exchange for her hard drives and digital gambling records. Molly declines this deal, fearing that the information about her players would be released, and she pleads guilty. The judge, deciding that she had committed no serious crimes, sentences her to 200 hours community service, one year probation and a $200,000 fine.
