The Real Molly's Game: Actors and High Stakes Poker

In the world of high-stakes poker, the line between reality and Hollywood is often blurred. Most of the time, movies become exaggerated versions of the truth. Occasionally, it's the opposite. 

The 2018 movie Molly's Game, starring Jessica Chastain, is a perfect example. The film is based on the true story of Molly Bloom, a former Olympic-class skier who was badly injured, and then ran high-stakes poker games in Los Angeles. But what really happened behind the scenes and how was Toby Maguire involved? 

What really took place in Molly’s Game may surprise you more than the movie did. In this article, we'll delve into the fascinating story of Tobey Maguire, Molly Bloom, and the celebrity poker game that inspired the movie.

The Celebrity Poker Game Turned Movie Script

In 2005, Tobey Maguire, known for his role as Spider-Man, collaborated with card cheat-turned-TV producer Houston Curtis to create a regular poker game for themselves and their rich friends. The game, which took place at The Viper Room or Beverly Hills Four Seasons Hotel, attracted A-list celebrities like Ben Affleck, Matt Damon, and Leonardo DiCaprio. The stakes were incredibly high, with players often betting hundreds of thousands of dollars per hand.

But, this wasn’t a game you’d read about online or see in the news. It was the highest degree of private, with a hand-picked roster of wealthy players. 

Playing in these high-stakes games would be a dream for any poker player, but to be honest, those kinds of big wins can still happen online. There’s no need to know Spider-Man, Jason Bourne, The Wolf of Wall Street, or the actor from Gone Girl. One online poker site just held a $12.5 million tournament in 2024, far more than the actors probably played for all year. 

It’s quite easy to enter these tournaments. A few months after your first small deposit, you might be looking up the ACR withdraw steps to cash in your winnings.

In stark contrast to the security of online cashiers, Molly’s Game probably used cold hard cash or ran tabs for players. There was always someone watching the bottom line, perhaps a little too closely. 

Bloom and Maguire Clash

Molly Bloom, who was initially hired to serve drinks and manage the game, became a key figure in the operation. Especially in the movie, she’s portrayed as a vital asset to Maguire’s operation (played by Michael Cera in the movie). 

However, according to Curtis's book "Billion Dollar Hollywood Heist," Bloom was not the mastermind she claimed to be. Instead, she was primarily there to deflect attention from Maguire and Curtis, who were allegedly manipulating the game to win millions. Curtis claims that Maguire was "petty" and "hated seeing Molly taking home as much as $30,000 in tips per night."

As the game continued to grow, so did the tension between Bloom and Maguire. Curtis recounts a story where Maguire tried to humiliate Bloom by offering her a $1,000 chip to bark like a seal. 

Despite this, Bloom remained a crucial part of the game, and her charisma helped attract new players.

The game eventually imploded in 2009 when one of the players, hedge-fund manager Brad Ruderman, was busted for running a Ponzi scheme. The bankruptcy attorneys went after the players to recover Ruderman's ill-gotten gains, and the game came to an abrupt end.

In the Hollywood rendition of this story, Molly became the target of an FBI investigation. She was accused of collecting fees for the games, which is a huge no-no in the eyes of Uncle Sam. It was quite a mess, nothing like the clean, digital Americas Cardroom withdraw and deposit process. There was too much untraceable cash, undeclared income, unpaid taxes, and illegality. 

So, what can we learn from this fascinating story? For starters, the world of hosting high-stakes poker games is a dicey one. Playing in online poker rooms is the way to go, whether you want to play inexpensively or at higher stakes. Who knows, you might even run into Toby Maquire at your table.