The Real Story Behind Molly’s Game

Molly’s Game is a film adaptation of the book by the same name. The film is directed by Aaron Sorkin and tells the real story of Molly Bloom, the “poker princess” who ran Hollywood’s most elite underground games. Jessica Chastain plays Molly Bloom and presents a strong yet broken woman whose drive for success sees her make her fortunes among some of the most well-known celebrities on the planet. Here we explore the connection between Molly’s Game the film and Bloom’s real life.

The Real Molly Bloom

Molly Bloom was born in Colorado in 1978, and in her early career was a competitive skier, once ranked 3rd among women in North America. Bloom suffered an injury during qualification for the Olympics and after that, she could no longer pursue her dreams of making it as a sports star.

Still motivated and driven for success, Molly moved to Las Angeles in 2003 and worked many jobs, including as a cocktail waitress and an executive assistant to Darin Feinstein, co-owner of the Viper Room club. It was here that Molly Bloom was asked to host her first poker game.

Feinstein had been approached by Tobey Maguire, known for his role as Peter Parker in Spider-Man, to hold high-stakes poker games in the basement of his club. Feinstein accepted and asked Molly to cater to the players and host the games. Bloom earned $3,000 in tips during her first game, inspiring her to delve deeper into this world previously unknown to her.

Molly Bloom, Inc.

During her days working at the Viper Room, Molly had to deal with disrespect from her hotheaded boss, who eventually fired her from the club. It seemed like Bloom would be down and out, forced to take back work as a cocktail waitress, but this was never going to happen with a woman so ready to fight for her success.

In 2007, Molly registered an events and catering company, Molly Bloom, Inc., using her list of high-profile contacts to organize poker games. In 2008, the games moved to private homes and hotels, and hands were being played for as much as $4 million. It was nosebleed-stakes poker with a cast of A-list celebrities like Maguire, Leonardo DiCaprio — who will star in Tarantino’s 9th film — Matt Damon, Ben Affleck, the Olson twins as well as other rich and famous faces that have never been revealed.

As the games dried up, Bloom moved on to NYC in 2009. However, she was less connected in New York, and although she attracted Wall Street-types to her games, there were also degenerates and criminals (aside from the Wall Street investors, that is!). The stakes were smaller, and busts were more frequent.

It wasn’t until 2011 that one of Molly’s games was shut down. A Ponzi scheme by player Bradley Ruderman caught the attention of the feds, who busted him and others.

In 2013, Molly Bloom herself faced an arrest and a list of charges. At that time, she was facing a maximum of 10 years in prison, 6 years supervised release and a fine of up to $1.5 million. That’s quite steep for running poker games, but by this point, Molly’s life had degenerated, and her games involved everyone from bankers to Russian mobsters.

With the help of her lawyer, Molly pleaded guilty to lesser charges in 2014 and was given the slightly reduced sentence of 1 year of probation, 200 hours of community service and a $200,000 fine that she never had to pay due to her lawyer managing to convince the courts that she didn’t have the money.

The Accuracy of the Film Portrayal

For those of who have seen the film, you already know the real story of Molly Bloom. The film follows the real events quite closely. Sorkin draws on information from the book published from Bloom’s memoirs as well as spending a lot of time interviewing Bloom to unravel details and get her to open up about her days as the “poker princess.” During an interview with Vice, Bloom herself says that Sorkin’s adaptation is to her liking.

So, this means that Molly Bloom was a skier, did hold poker games with hands running into the millions and had a gun held to her head by the Russian mob. Even the bits in the film that you would think are sensationalized accounts follow details accurately — that’s how crazy and fascinating the real story of Molly Bloom is.

One particularly memorable scene shows an analysis of a poker hand in which player “Bad Brad” bluffs Harlan Eustice, and then reveals that he had nothing. Eustice is the only player at the table who doesn’t have millions of dollars to throw away, but even so, he makes a terrible fold with a full house, one of the best poker starting hands, derailing him from the game and leading him to $1 million in debt.

It’s rare to get a full house, and so it would be a tricky fold to make.

Harlan Eustice is an on-screen stand-in name for TV producer Houston Curtis, who did lose this money and ended up making an unfair deal with “Player X” to cover his losses. The events in the film and in real life are similar, if not identical.


The hand that led to Harlan Eustice getting in severe debt and making a bad deal with “Player X.”

Of course, Aaron Sorkin did chop and change parts of the film and exercised his artistic license to some extent. Molly Bloom’s lawyer Charlie Jaffey, played by Idris Elba, is a fictional character. Sorkin did not interview Molly’s real lawyer Jim Walden, instead of creating a character to help tell the story. However, actual events such as the lawyer vouching for $250,000 that Bloom didn’t have are true to real life.

Identities are protected in the film, and only celebrities who have already been linked to involvement with the games have been mentioned. Although it is made obvious that “Player X” is Tobey Maguire, who according to Bloom, treated her so badly that he once tried to offer her a $1,000 tip to bark like a seal.

Aside from minor changes to the details of the story such as the name of the Viper Room on the Sunset Strip, the real name of the club in which Molly hosted her first poker games, being changed to “Cobra Lounge,” the film is an accurate portrayal of the events that happened to Molly Bloom. The riveting story is all based on the life of one incredible woman driven for success. If you haven’t seen it, the film is worth a watching.