Tobey Maguire Is the Greatest Celebrity Poker Player Ever, and It's Not Close

As well as being the best Spider-Man (if you argue with this, go kick rocks), Tobey Maguire can almost certainly put himself down as the number one celebrity poker player of all time.

Is his competition tough? Not so much. A handful of celebrities have solid résumés, like former NFL great Richard Seymour, and we've seen retired soccer players hit the felt too, from Gerard Piqué and Sergio Agüero to Neymar, who's now a regular sight in both live and online poker. But none of them are operating on Maguire's level.

What's most staggering about Maguire is his alleged winnings, which reportedly range from around the $36 million mark into the hundreds of millions. Most of it came from insane nosebleed private cash games, the world immortalized in the book and movie Molly's Game.

He was reportedly a ruthless, crushing player, and just about every whale (a big-money losing player) wanted a seat next to him. It's a bizarre situation, but that's the pull you get when you're Spider-Man, I guess.

Maguire was an apparent top-tier game builder, too. Alongside card cheat-turned-TV producer Houston Curtis, he ran a weekly game that pulled in Leonardo DiCaprio, Ben Affleck, Matt Damon and other A-listers. He knew star power drew out the billionaires and big-action players, and reportedly used his best friend DiCaprio as bait, staking him in the game because Leo didn't want to risk his own money. According to Curtis, DiCaprio would sit there in headphones folding almost every hand, but having the star of Titanic at the table was enough to lure the whales.

Molly Bloom didn't exactly paint him in a good light. In her memoir she called Maguire the best of the famous players, but also "the absolute worst loser." She also recounts a hand where a badly-losing player held the second nut flush on the river, got check-raised all-in, and Maguire earnestly swore on his life he had the nut flush and told him to fold. The player folded… and Maguire tabled a stone-cold bluff. A bit of dirt in the eye, for sure.

But Maguire's biggest confirmed score didn't come from a curated Hollywood line-up.

In December 2019, Maguire sat down in a heads-up match against billionaire banker Andy Beal, whose legendary battles against a team of poker’s best are documented in the classic poker book The Professor, the Banker, and the Suicide King. Maguire beat him for a reported $15.6 million, of which his share was $7.8 million.

That's where the story crossed into mainstream news. To recover the debt, Maguire hired Tom Goldstein, a former top U.S. Supreme Court lawyer who moonlighted battling in heads-up games around the world for tens of millions before being charged with tax evasion. When Maguire testified at Goldstein's trial earlier this year, he told jurors he'd met the lawyer through "poker circles," and that Goldstein successfully clawed back his $7.8 million from Beal for a $500,000 fee. Not a bad day's work for Spider-Man.

And for anyone thinking Maguire only won because he was in super soft games, his tournament record says otherwise. In the early-to-mid 2000s he entered a handful of WSOP events and put together some genuinely solid deep runs, including a 292nd-place finish out of 6,358 entrants in the 2007 WSOP Main Event. This is proof he could switch up from the nosebleed cash games to the tournament scene.

Either way you look at it, Maguire is a cash game crusher with a fearsome reputation at the table. Greatest celebrity poker player ever? It's hard to argue with.