Molly's Game (Molly Bloom Story)
Last updated: May 23, 2026
Molly Bloom (born 1978) ran underground high-stakes poker games from 2004 to 2013 — first in Los Angeles, then New York — attracting Hollywood A-listers, hedge fund managers, and unwittingly the Russian mob. A former Olympic-level mogul skier, she started as an assistant before taking over a Hollywood game at the Viper Room. The LA game (2004-2008) hosted Tobey Maguire, Leonardo DiCaprio, Ben Affleck, Matt Damon, and Alex Rodriguez at $10K-$50K buy-ins. After splitting with the LA crew she rebuilt at the Plaza Hotel in NYC (2010-2013), where buy-ins reached $250K-$500K. An April 2013 FBI raid (Operation Heavyweight) arrested 33 people connected to the Taiwanchik-Trincher organized crime network; Molly was indicted, pleaded guilty in 2014, and received one year of probation, a $200K fine, and $125K forfeiture. Her 2014 memoir became the basis for Aaron Sorkin's 2017 directorial debut starring Jessica Chastain (Oscar-nominated screenplay, $59M box office).
Definitions
Frequently Asked Questions
Who is Molly Bloom?
Molly Bloom (born 1978) is an American author and entrepreneur, former Olympic-level mogul skier. From 2004 to 2013 she ran underground high-stakes poker games in Los Angeles and later New York, attracting Hollywood A-listers, hedge fund managers, and (unwittingly) Russian organized crime. After a 2013 FBI raid she pleaded guilty in 2014 to operating an illegal gambling business; sentenced to one year probation, a $200K fine, and $125K forfeiture. Her 2014 memoir was adapted by Aaron Sorkin into the 2017 film 'Molly's Game,' starring Jessica Chastain.
Who played in Molly Bloom's poker games?
Publicly identified LA participants include Tobey Maguire (who reportedly recruited Molly initially and served as informal host), Leonardo DiCaprio, Ben Affleck, Matt Damon, and Alex Rodriguez, plus a rotating cast of producers, real-estate developers, and finance figures (most unnamed in her book due to legal threats). The NYC games attracted Wall Street traders, hedge fund managers, and — without her knowledge — Russian mob members linked to the Taiwanchik-Trincher organization, which ultimately drew federal attention.
How much money was at stake in Molly's Game?
The LA game began with modest buy-ins of $10K-$50K but grew. By the NYC era (2010-2013) buy-ins reached $250K-$500K, with individual pots occasionally exceeding $1M. Molly earned mostly from tips — at peak years she reported earning over $4M annually (reported income; actual figures debated). Notably, her memoir alleges Tobey Maguire was repeatedly stingy with dealer tipping despite winning huge sums, a detail that became famous after the book's release.
What happened in the 2013 FBI raid?
On April 16, 2013, the FBI conducted Operation Heavyweight, arresting 33 people connected to the Taiwanchik-Trincher Russian-American organized crime network. Molly Bloom was among those indicted, charged with operating an illegal gambling business. She had no knowledge of the mob connection to several NYC game participants. In 2014 she pleaded guilty to a single charge, received one year of probation, a $200K fine, and $125K forfeiture — far lighter than the maximum penalty, reflecting her cooperation and lack of violent or organized criminal intent.
Is the 2017 Molly's Game film accurate?
Mostly accurate in broad strokes, with key dramatic compressions. Aaron Sorkin (his directorial debut) collaborated closely with Molly Bloom. Jessica Chastain plays Molly; Idris Elba plays her defense attorney (a composite character based on Jim Walden). The film won acclaim for Sorkin's screenplay (Oscar nomination) but compresses timeline, simplifies the legal proceedings, and uses composite characters for certain players to avoid defamation suits. Tobey Maguire is widely identified as 'Player X' in the film, though never explicitly named. Box office: $59M worldwide on a $30M budget.
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