Hollywood Flashback: In 2008, Molly Bloom Was Tinseltown's Poker Queen

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Molly Bloom exited New York federal court with her attorney Jim Walden on Dec. 12, 2013.

Aaron Sorkin brings Bloom's story to the big screen in his directorial debut, 'Molly's Game,' an adaptation of her 2014 memoir which details the rise and fall of underground poker games she hosted for celeb attendees ranging from Ben Affleck to Tobey Maguire.

For a while, Molly Bloom really had a good thing going. The Colorado-born cocktail waitress turned Hollywood poker queen was raking in $4 million a year to stage manage high-stakes games attended by stars like Tobey Maguire (who once demanded she “bark like a seal” for a $1,000 chip; she refused) and Ben Affleck (“nice, polite”), among various pro athletes, business tycoons and Russian underworld types. The first games where held in 2004 behind The Viper Room, where Bloom served cocktails and collected $3,000 a night in tips.

By 2008, the games had graduated to private homes and hotels like the Peninsula Beverly Hills, with hands going as high as $4 million. The affable Bloom, then 28, was put in charge of setting up the suites; sending the invites; hiring dealers; ordering food, drinks, massages and bodyguards; and keeping track of all wins and losses. And so it went until March 2011, when the FBI got a whiff of something fishy and sent 20 agents to raid a game. (Bloom was out of town.) Her assets were seized and she was grilled about her connections to the mob, but ultimately got off.

Her luck ran out two years later, however, when she was arrested and charged with profiting from illegal poker games. She plead guilty in December 2013, resulting in a fine of $125,000 and a year’s probation. A movie based on her 2014 book about her experiences, Molly’s Game, premiered at TIFF on Sept. 8. It stars Jessica Chastain as Bloom and marks the directorial debut of Aaron Sorkin, who also wrote the screenplay, which delves into Bloom’s hard drug use — something she doesn’t address in the book.

“But,” says Sorkin, “she wasn’t apprehensive at all about putting that in. What was more difficult was talking about her relationship to her father. But that kind of thing makes this story much deeper.”

This story first appeared in The Hollywood Reporter's Sept. 10 daily issue at the Toronto Film Festival.