(2017) Graduating summa cum laude from the University of Colorado with a BA in political science and plans to enter law school, Molly Bloom (Jessica Chastain) competed in mogul skiing with a digitally-remastered spinal cord - coming back against her doctor's recommendation to the sport after surgery for rapid-onset scoliosis at thirteen - at Deer Valley for the Winter Olympics only to suffer a freak accident. A dozen years later at 35 in West Hollywood, Molly's awakened in the middle of the night by the FBI; she's arrested for running an illegal gambling operation.
Adapting Molly Bloom's book, Molly's Game: From Hollywood's Elite to Wall Street's Billionaire Boys Club, My High-Stakes Adventure in the World of Underground Poker, into a dramatized biopic, Aaron Sorkin wrote and directed the story of the "Poker Princess," depicting something far worse than her injury and disappointment as an athlete. A book agent tells Molly of an offer from publishers willing to pay $1.5 million for her story, but she resists the terms: "Go big or go home and live with your mother for the rest of your life."
Postponing law school, ostensibly for a year, Molly goes to LA, sleeping on a friend's couch, where she becomes a cocktail waitress and an office assistant to Dean Keith (Jeremy Strong). Her boss requests her helping run a high-stakes poker game ($10,000 cash buy-in) with celebrities and wealthy clients at the Cobra Lounge: "Don't fuckin' tell anybody." She collects $3,000 in tips.
Raised by a demanding taskmaster in a competitive family with two brothers, Molly tried winning attention from her father, Larry Bloom (Kevin Costner), a therapist and psychology professor at CSU, away from her siblings' accomplishments by being cynically antagonistic - no heroes, distrustful of people, confrontational regarding his profession.
At the poker table, movie star Player X (Michael Cera) - Molly protects the true identities as much as possible from public exposure, not wanting to destroy careers and lives, turning down a lucrative offer from publishers to name real names - the dominant participant, asserting that money won is better than money earned, is the shark for whom Molly's expected to recruit fish. Following a heated disagreement with Dean - "You are unimportant," he declares, accusing her of sleeping with his clients: "You are fired" - she turns the tables on him, contacting the gambling addicts on the list to attend the next game at a new location with herself as hostess.
Strictly keeping her rules of no romance or sex with any of the players, no raking or direct payments for her service other than tips (though failure to tip would disqualify a player from being invited back), Molly runs her games legitimately on the fringes of acceptance, avoiding breaking the law. Two participants at opposite ends of the spectrum of skill, hedge-fund manager Brad (Brian D'Arcy James), a terrible card player, and Harlan Eustice (Bill Camp), the rare poker player among gamblers, collide in a bluff that blows circuits, resulting in one bleeding big money but determined to "get back to even."
Player X admits to Molly that his greatest pleasure in playing with these gamblers comes from destroying their lives. Leaving LA, she opens up shop in New York, employing Playboy playmates and a Yankees baseball player as a draw for clients willing to buy-in at $250,000. Running the world's most-exclusive, most-lucrative high-stakes poker games gave Molly an identity, respect, status, but also drove her into a dark hole of humiliation, depression, drugs; watching these powerful men conflicted with her sense of fairness and justice.
Eventually, addicted to drugs and greed, she couldn't stand herself, having become like Circe, turning men into swine; she gets careless at vetting the players. Warned by B, her dealer, against extending too much credit, Molly, shorted during a multimillion-dollar game, violates the criminal code.
Thinking she's Irish with the Joycean name Molly Bloom, Douglas Downey (Chris O'Dowd), "a victim of circumstance" who falls in love with her, agrees to bring her Russian Jewish players from Brooklyn, including art-gallery owner Shelly Habib, who presents an authentic Monet as security for his credit. After turning down a proposal from two men for a partnership with protection, Molly in her own hotel room becomes a victim of robbery and severe beating.
Seeking a criminal defense attorney without a shady reputation, Molly presents herself before Charlie Jaffey (Idris Elba), telling him that after running her gambling operation for a decade, eight years in LA and two in New York, she hasn't been involved for the past two years. At the same time as her arrest, 31 people were arrested by the FBI, including members of the Russian mob connected with her poker games to launder money.
In the office, Molly notices that Jaffey's daughter Stella (Whitney Peak) is reading The Crucible, which she says her father assigned her to read; she's also read Molly's book, taking the author's side. Unable to pay upfront Jaffey's $250,000 fee, but claiming she has ten times that amount owed to her, conflicted he declines to defend her, though he offers to guide her through the preliminary court appearance.
Partly under the spell of Stella's influence and intrigued by Molly's obstinate refusal to implicate anyone else - "I am going to figure you out" - Jaffey changes his mind and agrees to defend her. Presented with a generous offer from the FBI in exchange for her agreement to be a cooperative witness along with turning over her computer's hard-drive, containing all of her e-mails and names of clients, Molly in possession of all the dirt the government wants remains resolute against cooperating.
On her behalf, Jaffey doggedly contends with two FBI agents, appealing to their sense of justice under these circumstances, pointing out that she didn't employ muscle to collect on her debts and that she adamantly has refused to cash in her lottery ticket for a best seller, that Molly "doesn't deserve to be on a mob indictment." In federal court before Judge Foxman (Graham Greene), Molly, fully aware of the likely consequences, pleads guilty.
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