In both real life and the realm of fiction, Hollywood actor Tobey Maguire moonlights as a high-stakes poker hustler. Maguire acted as the guiding force that brought together some of the world’s highest-stakes private poker games in the mid-to-late 2000s.
The roster of celebrities and other affluent figures that attended the Tobey Maguire poker games reads like an A-list of the rich and famous. The memoir Molly’s Game, and later the movie of the same name, tell the story of Molly Bloom organizing some of the richest nosebleed stakes games in the world.
Maguire, however, was actually the lead organizer of these games, which he put together in an effort to win millions from his inexperienced competitors. Here’s a look at the Tobey Maguire poker saga, which turned into the subject of multiple books, a hit movie, and multiple six-figure lawsuits.
The private L.A. games portrayed in the Molly’s Game book and movie were actually the brainchild of Maguire. The first of these games took place in 2005, organized by Maguire and television producer Houston Curtis.
Curtis forged a reputation as a regular in the underground L.A. poker games of the early 2000s. Maguire wanted to create a regular weekly game that invited some of Hollywood’s biggest stars and richest business figures to the table and collaborated with Curtis to make that happen.
According to Curtis’ book, Billion Dollar Hollywood Heist, the game was designed to hustle the well-bankrolled competition from the start. The book contends that it was Curtis’ job to dump chips to the Hollywood whales at the table, giving Maguire the opportunity to use his poker skill to win huge sums.
The games ran every Tuesday at L.A. locales like the Beverly Hills Four Seasons Hotel and the Viper Room nightclub. From 2005 to 2009, the lineup at these secret poker games included Matt Damon, Ben Affleck, Cirque du Soleil founder Guy Laliberte, Leonardo DiCaprio, Rick Salomon, Dan Bilzerian, and billionaire businessman Kevin Washington, among others.
Some of the stories coming out of these games make up the stuff of legend if Curtis’ book is to be believed. Included in Billion Dollar Hollywood Heist are tales that see DiCaprio get staked for a $5,000 buy-in because he didn’t want to risk his own money, and Affleck writing a check for Damon’s $50,000 loss in a game.
The games would sometimes go up to $200/$400 cash game stakes. Laliberte allegedly lost more than $2 million in one session, and Curtis claims he won upwards of $15 million in the game over a four-year period.
According to Curtis, the L.A.-based high-stakes private games that set the scene for the Molly’s Game book and movie would be more accurately referred to as Tobey’s game.
The 2017 film Molly’s Game takes a place among the most popular poker movies of all time. An on-screen adaptation of the book of the same name, the movie depicts high-stakes Hollywood poker games ran by host Molly Bloom.
The book version of Molly’s Game uses the real names and stories (according to Bloom) of the celebrities that played in the games. The movie doesn’t use real names, however, with a cast of characters that includes “Player X,” played by actor Michael Cera.
“Player X” is the fictional movie version of Maguire, and a character that pulls off many of the same moves as Maguire does in the Molly’s Game book. This includes Player X inducing a fold by convincing a baffled opponent that he held the best hand, only to show the bluff with a “f*** you” thrown in after getting the fold.
The Molly’s Game book and movie are inspired by the private poker games organized by Tobey Maguire in the late 2000s.
Another storyline from the movie sees Player X make a deal with Harlan Eustice, a character who goes into seven-figure debt after a horrendous losing session. Player X makes a deal with Eustice that gives Player X half of Eustice’s winning until the debt is paid off, but Player X takes none of Eustice’s losses.
According to Bloom in the book, the deal was real, and it involved Maguire and Curtis. Harlan Eustice plays as the on-screen version of Curtis, and the terms of that deal prompted Maguire to boast about his prediction to “make ten million this year on poker” according to the book.
That $10 million projection came with the deal, in mind, which was extremely unfavorable to Curtis, in mind.
“If what Houston told me was true, Tobey owned Houston now, and they must have both known it,” Bloom writes in the book. “He owned 100 percent of his downside and was only realizing 50 percent of his wins, and he was the only one at the table who was playing for his mortgage.”
Player X starts to resent the five-figure tips Bloom regularly earned at the games, and tells Bloom he wants to put a cap on how much Bloom could take home in a session. Bloom’s book backs this up with real-life anecdotes about Maguire’s criticism of Bloom’s gratuity-earning prowess.
Maguire and other players in the private games ended up as the defendants in a series of massive civil lawsuits. A group of investors targeted the game after losing money in a Ponzi scheme orchestrated by Bradley Ruderman, who allegedly took the group of investors for over $44 million.
Ruderman then used some of that money to play in the Tobey Maguire poker games, which in turn brought in several of the game’s regulars as defendants in the lawsuit. Gabe Kaplan, Bilzerian, actor Nick Cassavetes, and Maguire himself were among the list of defendants targeted in the lawsuit.
Ruderman ended up with a ten-year prison sentence for his involvement in the Ponzi scheme. Maguire settled his part of the lawsuit by paying $80,000 to Ruderman’s estate, as part of a deal in which Ruderman then had to pay $1.5 million in restitution to the bilked investors.
Kaplan settled by paying off $27,000 to Ruderman. Bilzerian was sued for $100,000, while Bloom was the biggest target and sued for $473,200.
Bloom eventually was arrested for her part in organizing the games, sentenced to one year of probation, and ordered to forfeit $125,000 in proceeds from the games.
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