It was one of the worst kept secrets in not only the poker community but also in the realm of Hollywood. That does not mean that the court system would not get involved, however. Rather than litigate the case in the public domain and to save court costs, actor Tobey Maguire has settled a lawsuit brought against him regarding his time playing high stakes poker in Hollywood during the Aughts.

Maguire to Pay $80K, Makes the Case Go Away

The case dates to high stakes cash games that included the former Chief Executive Officer of Ruderman Capital Partners, Brad Ruderman. Ruderman was charged with running a Ponzi scheme that used the money of investors into his company. The money, which came from his relatives and other investors, was allegedly used by Ruderman to fund an outrageously luxurious Hollywood lifestyle. Some of that lifestyle included poker. In 2010, Ruderman was convicted of embezzlement and was sentenced to eight years in prison; upon his release in 2018, Ruderman said he was going to write a book about what happened, which has not, to this date, come to fruition.

Those who were bilked by Ruderman have taken the approach of suing those players in the game that Ruderman played. 23 people were sued for winning money in the poker game, with Maguire taking the route of settlement. Others that were sued in the case, which was worth $25 million, are director Nick Cassavetes, actors Leonardo DiCaprio and Ben Affleck, and poker commentator/comedian Gabe Kaplan. In court documents, Maguire was said to have won over $300,000 in those poker games; if the judge in the case approves the settlement come December 21, then Maguire will pay $80,000 and the case will go away against him.

Back in the Days of “Molly’s Game”

The supposed setting for these events came in what became known as “Molly’s Game.” In Hollywood in the 2000s, host Molly Bloom was noted for providing the locations for high stakes poker games. In these games, buy-ins of $50,000 and higher were the norm. Bloom, for her part, accepted tips from the players in the game for her organizational activities.

Bloom’s acceptance of the tips, along with the conviction of Ruderman, would eventually draw the attention of law enforcement. Bloom was arrested after departing Hollywood for New York in 2010, allegedly to set up a new operation there. In 2013, Bloom plea bargained to a single charge of illegal gambling, receiving a rather light sentence of a year of probation, 200 hours of community service and a sizeable forfeiture of money the next year.

Bloom would make up for that loss, however. She would author a book, Molly’s Game, which became a movie of the same name. The screenplay, written by Academy Award winner Aaron Sorkin, also garnered an Oscar nomination for Best Adapted Screenplay in 2017.

But nowhere in the book, nor in the movie, was the situation with Ruderman mentioned. Sorkin chose not to “name names” in the movie, but Bloom spilt a bit of tea regarding things that occurred during these high stakes games. Bloom pointed out how Maguire was one of the more aggressive players in the game, often getting Bloom to set up tables where he would be favored to win.

There have been no details on whether anyone else has settled in the case. Suffice it to say, we will keep an eye on the legal docket in California around Christmas this year to see if the settlement is approved for Maguire.

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