The Story Behind Tobey Maguire’s High-Stakes Underground Poker Ring
The Wild Truth Behind ‘Molly’s Game’ and Tobey Maguire’s Poker Empire
Celeb Poker Ring
How did a twentysomething LA cocktail waitress end up running an exclusive weekly poker game for Hollywood’s biggest high rollers—think Leo, Ben, and Tobey? We’ll get into that. But as someone who was also a cocktail waitress in LA during college, I have to admit, I’m a little jealous.
The venue was the infamous Viper Room on the Sunset Strip—a nightclub legendary for all the right (and wrong) reasons. And this isn’t just the kind of story movies are made from—this one actually became a movie. So what’s the real deal behind Molly’s Game? Let’s dive into the salacious (and highly illegal) celebrity rumors.
Molly Bloom was in charge of the world’s most exclusive high-stakes poker game … then she was targeted by the FBI.
Jessica Chastain stars in the truly excellent true story Molly’s Game. Now on Netflix. pic.twitter.com/8pbdjQdArE
— Netflix (@netflix) April 13, 2022
Molly’s Game
Back in the late ‘90s and early 2000s, the Viper Room was a hotbed of illegal activity, from drug use to high-stakes gambling. By the early ‘00s, it became home to one of Hollywood’s most exclusive poker games, where a $50,000 buy-in was considered casual.
In 2014, Molly Bloom—a former waitress turned underground poker queen—was all over casino news headlines when she detailed the high-stakes games in an interview on 20/20. According to Bloom, she regularly hosted illegal poker nights featuring some of Hollywood’s biggest names, including Leonardo DiCaprio, Ben Affleck, and Tobey Maguire. (Yes, that Tobey Maguire, aka Spider-Man, aka one of the biggest sore losers at the table.)
At one point, he allegedly made Molly “bark like a seal who wants a fish” in exchange for a tip. After reading this, if I saw him on the street, I’m not sure I could be civil. Oh, and other notable guests? A-Rod, Matt Damon, the Olsen twins (who once brought a billionaire with them), and a rotating door of other ultra-rich gamblers.
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
These games saw players winning and losing six-figure sums in a single night, while Bloom herself was raking in a reported $4 million a year by 2008. As an LA native who spent plenty of nights at the Viper Room, it’s wild to think all this went down there.
playing poker w tobey maguire… it’s over pic.twitter.com/8oQFk035dC
— guilherme (@gayparanoidpark) February 25, 2025
Tobey Was Problematic…
Out of everyone who sat at her table, Bloom admitted that Tobey Maguire was both the biggest sore loser and one of her most frequent players. (At least at his most recent poker event with Timothée Chalamet, there were no reports of him being an absolute menace.) She estimated he made millions and even used his buddy DiCaprio to lure in bigger fish. Oh, and he wasn’t just playing—he was controlling the game (it’s giving psychopath, tbh).
Case in point: Maguire once insisted on using his personal $17,000 card-shuffling machine—then had the audacity to charge Molly $200 every time it was used. He was also notoriously stingy with tips and threw tantrums when he lost. In a Vanity Fair article, Bloom wrote, “Tobey, despite being the biggest winner, gave me the smallest tip.” Again—this man is worth tens of millions of dollars.
Oh shit, Molly’s Game Tobey showed up to the party. Chalamet’s laughing but this is no joke https://t.co/oRp8xJtHoZ pic.twitter.com/tedmSgXYTs
— Brandon Streussnig (@BrndnStrssng) February 25, 2025
One particularly insane night featured a game with Ben Affleck, where the buy-in was $50,000, and at one point, there was $2 million on the table. Maguire wasn’t having a good run, but after knocking out a player named Jamie (wasn’t me guys, I swear), he decided to flex his power over Bloom—who, let’s remember, was a 26-year-old cocktail waitress before she started running these games.
A Scandal Unlike Any Other
Of course, things eventually spiraled. When Bloom started taking a percentage from every pot, she crossed into organized crime territory. The mob came knocking (literally—she was assaulted for refusing to cut them in), and the FBI wasn’t far behind. Eventually, the feds raided one of her games and froze her assets. She pleaded guilty to illegal gambling and was sentenced to 12 months probation.
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While Molly became the face of the operation, not everyone agrees with her version of events. New York Post reported that Houston Curtis, a former player, claims he and Tobey Maguire were the true masterminds—downplaying Molly’s role. (Not sure why anyone would want to take credit for what happened to her, but okay.)
So, was this an underground empire built by a cocktail waitress-turned-poker queen? Or was she just a pawn in a game controlled by Hollywood’s elite? Either way, Molly’s Game is one of the juiciest scandals to ever hit the Sunset Strip. Just remember, there may not be a Molly’s Game-esque poker game on every corner, but the online casino is a much more reasonable way to go. You can play for real money and it’s completely safe and legal (unlike this wild celebrity poker ring).
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