The Big Picture

• Molly Bloom was a competitive skier turned poker entrepreneur who rubbed elbows with A-list stars and mobsters.
• Bloom's lavish lifestyle led to addiction, encounters with Russian mobsters, and eventual legal trouble.
• After being arrested and charged with running an illegal poker empire, she published a memoir that eventually became the basis for the film Molly's Game, directed by Aaron Sorkin.

Having deployed his trademark brand of verbal fireworks via stage plays, screenplays, and teleplays for decades, it was only a matter of time before renowned wordsmith Aaron Sorkin would try his hand at directing films. In 2017, he did just that when he stepped behind the camera to helm Molly's Game. Based on the 2014 novel of the same name, Sorkin's directorial debut follows the story of Molly Bloom (Jessica Chastain), a budding Olympian hopeful who segued to a world of ruthless entrepreneurship in which she managed an underground poker empire.

Rubbing elbows with the rich and famous, Bloom was wildly successful in her business endeavors, though everything came to a screeching halt when, while battling personal demons, she attracted the attention of the FBI and Russian mobsters. Featuring one of Jessica Chastain's best performances alongside stellar supporting turns by Idris Elba and Kevin Costner, Molly's Game recounts Bloom's stranger-than-fiction tale of ambition, self-discovery, and redemption with Aaron Sorkin's signature writing and assured direction. But how faithful is the film to the story that inspired it?

Molly Bloom Was a Competitive Skier and Bartender Before Overseeing a Poker Empire

Years before she managed lucrative poker games, Molly Bloom grew up among overachievers and was a skilled skier with hopes of competing in the Olympics. "Literally if you weren’t the best in the world in my family, it wasn’t impressive," she remembers. "I was looking for this thing that was going to make me feel fulfilled inside." Having trained under the tutelage of her loving but domineering father and competed at a high level, she excelled at the sport and ranked third in the nation while in college, but abandoned her aspirations to compete further in favor of other endeavors.

With skiing behind her, Bloom relocated to Los Angeles. Having worked as a waitress, she nearly-and fortuitously-was almost struck by a man in his car who, upon recognizing her work uniform, offered her a position at a restaurant and employment as his assistant. The man, whom Bloom refers to as Reardon Green in her book, also co-owned the Viper Room, a local club where he hosted poker games with tinsel town elites. After working for and alongside Green, and becoming familiar with the world of high-stakes underground gambling, Bloom was fired, but not before amassing enough knowledge, experience, and personal contacts to lay the foundation of what would become her poker empire.

Molly Bloom Rubbed Elbows With A-List Hollywood Stars and Mobsters

While the identities of high-profile celebrities who played in Molly Bloom's games are obscured in Aaron Sorkin's film, the entrepreneur didn't hesitate to name names in her book. According to Bloom, A-listers including Tobey Maguire, Leonardo DiCaprio, and Ben Affleck frequented her games. Referred to as Player X (Michael Cera) in Molly's Game, Maguire made quite an impression, though not in the most charming of ways, allegedly behaving in demeaning and borderline abusive ways. Per TIME, one occasion saw the actor offer Bloom $1,000 to "bark like a seal," and he later taunted her over the phone after she lost control of her lucrative Los Angeles-based game. In 2017, when asked by Vice if she could ever look at Tobey Maguire as Spider-Man in the same way again, she responded, "I haven't even tried."

As Molly Bloom's profile was on the rise, so too was her indulgence in alcohol, drugs, and financial gain. She told Vulture, "I think I thought it was a hard period in my life, that that was just contextual, and I came to realize that really wasn’t the case at all: that I really was an addict." Holed up in New York City's Plaza Hotel, Bloom was managing poker games that, according to People, demanded buy-ins as high as $250,000 and hosted players whose losses often amounted to millions. Eventually, and perhaps inevitably, she attracted the attention of Russian mobsters, whose offer of security in exchange for profits she declined. In response, she was assaulted and robbed weeks later by an associate of the men she rejected. "That was a really dark thing that happened during the darkest time of my life," Bloom told Vice.

"I was bankrolling the games, vetting the players, extending the credit," she recalls. As the stakes surrounding her poker empire got higher and higher, Bloom made a crucial blunder. Wholly responsible for millions of dollars, and desperate to remain in control of the enterprise that had taken her to the top, she began skimming from the pot. "That's where I crossed that little gray line," Bloom told People. While it may have been greed or a momentary lapse in good judgment, the move would soon attract the attention of federal authorities and upend her lucrative endeavor.

Molly Bloom Was Arrested and Charged With Illegal Profiteering

In March 2011, the FBI raided one of Molly Bloom's poker games, though she wasn't present at the time. But according to The Hollywood Reporter, she was arrested two years later and charged with "profiting from illegal poker games." Facing years in prison and hefty fines, she pleaded guilty in December 2013 and was fined $125,000 in addition to a year of probation. In hindsight, having dodged a lengthy prison sentence and complete financial ruin, Bloom seemingly regarded her run-in with the authorities as a blessing in disguise. "I'd spent life so terrified of failure that when it happened, it was very liberating," she acknowledged.

Her poker empire may have been shattered to pieces, but from its deconstruction came an opportunity for Molly Bloom to tell her story. Before she was arrested and charged, she was already writing a book detailing her experiences as an entrepreneur rubbing elbows with the rich and famous. Thanks to HarperCollins, Molly's Game was published in 2014, and while Bloom wasted no time in trying to get her book in the hands of powerful Hollywood players, getting her memoir from page to screen was no easy feat. "Everyone wanted to take a meeting, but no one wanted to make the movie," she remembers. But she found an ally in Aaron Sorkin, who said of Bloom and her story, "Molly was an honest-to-God, real-life movie heroine found in an unlikely place. This was a morality tale of doing the right thing when the wrong thing is easier."

How Faithful is 'Molly's Game' to Its Source Material?

Considering the larger-than-life nature of Molly Bloom's story, one may be surprised to discover that Aaron Sorkin's film is mostly faithful to the truth. While Bloom's career in skiing didn't end due to an injury and the character of Charlie (Idris Elba) is a fictionalized version of her legal defense, many of the film's key players and events are depicted with an eye for accuracy. According to Sorkin, he dedicated "hundreds of hours" to chatting with Bloom during the research process of adapting her memoir for the screen. Per ESPN, Sorkin and Bloom worked together for five days a week over the course of months to develop the project. "It was intense," she recalls. "I should probably pay him for therapy."

While he was concerned with facts and reality, Sorkin, ultimately a dramatist, did add some creative flair to boost the film's narrative, characters, and themes of self-discovery and redemption. Among the events in Molly's Game that presumably never took place was Molly's final conversation with her father (Kevin Costner) near the film's end. "Very little about her father is in the book," Sorkin told Indiewire. "What is there is very much in praise of the strange relationship she had with her father." The interaction on that New York City park bench may not have happened, but it remains one of Molly's Game most powerful and cathartic scenes, linking Bloom's independent ambition and fraught personal trajectory to a history of complex familial relations. Truth is often stranger than fiction, and Molly's Game deftly balances reality and drama with compelling believability, thanks in large part to Sorkin's assured storytelling and Jessica Chastain's turn as the film's titular character.

Molly's Game is available to watch on Netflix in the U.S.

WATCH ON NETFLIX