Timothée Chalamet’s Oscar nomination for Best Actor was a big deal, so big that Cartier threw him a lavish party to celebrate. But what started as a star-studded affair took an interesting turn when poker entered the chat.
Among the A-listers in attendance was none other than Tobey Maguire, who casually showed up to Chalamet’s game night. And if you know anything about Hollywood, you know that Tobey Maguire + poker is practically a genre of its own, books have been written, and movies have been made. So, what happened when the Spider-Man star sat down at the table? Here’s how it all played out.
How Tobey Maguire made Timothée Chalamet’s big night ever more legendary!
Timothée Chalamet‘s Oscar nomination called for a grand celebration, and Cartier delivered! But instead of the usual buttoned-up black-tie dinner, Chalamet had something much livelier in mind. Game night! (but for big boys)
Hosted on a rooftop with a cigar station and a DJ spinning everything from Sinatra to Let the Beat Build, the event was packed with famous faces. Among the A-list crowd were Kevin Hart, Rich Paul, Nathan Fielder, Theo Von, Kid Cudi, and Kylie Jenner. But one name stood out for a very particular reason, Tobey Maguire.
For those who know their Hollywood lore, Maguire’s reputation at the poker table is the stuff of legend. His high-stakes, behind-the-scenes poker history has been chronicled in books and even inspired a movie (remember Molly’s Game? Well more on that later). So when he walked into Chalamet’s game night, expectations were high. The night was so iconic, that fans can’t shut up about it, here is what they have to say,
Tobey Maguire showing up just so he can take Timothee Chalamet’s money at a poker table is a God-tier degenerate gambler move. https://t.co/NysVrsMrnC
— Sonny Bunch (@SonnyBunch) February 25, 2025
Tobey doesn’t have spider sense, but he does have poker sense. He can detect any legal or illegal table within a 5M radius
— Jonathan Riding S-Curves to Mars 🚀🚘⚡🔋 (@JonathanGuito) February 26, 2025
Tobey Maguire being a degen gambler continues to be my favorite long-arc for any Hollywood talent. Based on my limited exposure to him in Spider-Man/Great Gatsby it is so bizarre.
— Arthur Augustyn (@ArthurAugustyn) February 27, 2025
Never beating the Molly’s game allegations
— Gigi (@jordandefenses) February 27, 2025
Chalamet is so happy to be getting his ass kicked by Tobey, it’s basically a sacred right of passage in Hollywood at this point.
— Jonathan Riding S-Curves to Mars 🚀🚘⚡🔋 (@JonathanGuito) February 26, 2025
According to GQ editor Frazier Tharpe, who was at the event, there was even a showdown between Chalamet and Jenner, with Chalamet taking the loss in stride.
But in a surprising twist, it wasn’t Maguire who dominated the table, despite his reputation, he wasn’t the big, intimidating shark many expected in fact he was “among the first casualties to go all in and lose”.
Tobey Maguire’s secret life as a Hollywood poker king!!
Long before poker movies were inspired by him, Tobey Maguire wasn’t just playing in Hollywood’s high-stakes games, he was running them. In fact, from 2005 to 2009, the Spider-Man star secretly organized some of the most exclusive private poker nights the city of Los Angeles has ever seen, featuring a who’s who of A-list actors, billionaires, and business moguls.
These weren’t your average game nights. Hosted at hotspots like the Beverly Hills Four Seasons and the Viper Room, Maguire’s weekly games attracted stars like Leonardo DiCaprio, Matt Damon, Ben Affleck, and many many more. The stakes were sky-high, players routinely put down $200/$400 per hand, with some losing millions in a single session.
According to television producer Houston Curtis, who co-ran the operation, Maguire designed the games to maximize his own winnings, using strategy, intimidation, and a bit of psychological warfare to outplay his well-funded but less experienced competitors.
Maguire’s poker persona became so infamous that it made its way into Molly’s Game, the 2017 film based on poker host Molly Bloom’s memoir. The movie’s character Player X (played by Michael Cera) is widely believed to be inspired by Maguire, portraying a ruthless poker shark who manipulated weaker players and gloated over their losses. In the book, Bloom even described Maguire pressuring her to do humiliating tasks for tips, further cementing his cutthroat reputation.
But Maguire’s poker empire came crashing down when one of his regulars, hedge fund manager Bradley Ruderman, was exposed for running a $44 million Ponzi scheme. Ruderman had used stolen investor funds to buy into the games, and when the scheme unraveled, lawsuits followed.
Maguire, along with Dan Bilzerian, Nick Cassavetes, and other poker regulars, was forced to return some of his winnings to settle legal claims. Though the underground poker scene eventually moved on, Maguire’s name still remains legendary in Hollywood gambling circles.
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