When actor Tobey Maguire took down Phil Hellmuth’s Poker Invitational at the Hollywood Park Casino in October of 2004 – parlaying his $2,000 buy-in into a $95,480 payout after defeating 122 other players – most poker people viewed the win as merely a “one-hit wonder.” After all, fellow Hollywood heartthrob Ben Affleck also won a major poker tournament earlier that year, but his victory at the California State Poker Championship remains Affleck’s lone career cash.
Maguire was different though, displaying a dedication to the game that many self-professed professionals have trouble keeping pace with. Maguire earned his first World Series of Poker cash the following summer, weaving through a stacked field of 1,403 entries to place 54th in the $2,000 buy-in No-Limit Hold’em event during the 2005 series. Just a month later, Maguire was at it again, reaching the final table of the $10,000 Bellagio Challenge Cup NLHE Main Event in July, where he wound up registering an eighth-place finish.
Maguire added two more WSOP cashes to his record in 2007 – including a 292nd place result in the WSOP Main Event – and while those results represent his final forays into the money of live poker tournament, his overall record remains quite impressive. Between July of 2004 and July of 2007, Maguire cashed a total of 12 times to push his career earnings over $218,000. Even more remarkable, 10 of those 12 cashes came in tournaments boasting a buy-in of $1,000 or higher, meaning Maguire was competing against top caliber players for the most of his four-year run.
Tobias Vincent “Tobey” Maguire was born in Santa Monica, California on June 27th, 1975, and at the age of 14 he was already a budding actor, appearing in films, television shows, and commercial spots throughout the 1990s. By 1998 Maguire was landing more substantive roles, including parts in hit films such as Fear and Loathing in Las Vegas and Pleasantville. During this time Maguire consistently found himself auditioning against another young actor destined for bigger things, and eventually, a strong friendship was forged between himself and Leonardo DiCaprio.
Maguire’s big breakthrough occurred in 2002 with the release of Spider-Man, in which he starred as the lead Peter Parker and provided a voice for the masked superhero. Two more entries in the Spider-Man trilogy soon followed in 2004 and 2007, and the subsequent combination of box office success and critical acclaim elevated Maguire to legitimate movie star status. Over the next few years, Maguire expanded his interests to include producing, and he is credited as a producer on hits like Rock of Ages (2012) and Z for Zachariah (2015).
First showing an interest in poker in 2004 – like millions of other American men did during the boom inspired by Chris Moneymaker’s momentous win at the 2003 WSOP Main Event – Maguire was shown conversing with Daniel Negreanu on the rail during ESPN’s broadcasts of the 2004 edition of poker’s premier tournament. He began playing in earnest that year, recording his first live cash at the $2,080 buy-in Mirage Poker Showdown on July 28th, where he finished in 15th place. The very next day Maguire entered the $10,200 buy-in World Poker Tour Main Event at the Mirage, and despite playing against an elite field comprised mostly of pros, Maguire went on to a 24th place finish.
Over the next few years, Maguire was highlighted by ESPN’s cameras while playing in the 2005, 2006, and 2007 WSOP Main Events – including his deep run to make the money in 2007. According to a Vanity Fair article published in February of 2005, Maguire ranked as one of the “five most avid poker players in Hollywood,” along with Affleck, Mimi Rogers, Gabe Kotter, and James Woods.
Along with his live tournament exploits, Maguire was also a fixture on the now infamous “Hollywood home game” circuit which thrived during the poker boom’s heyday. In fact, one of the most celebrated of these home games was called “Tobey’s Game” by those in the know, featuring blinds between $100/$200 and $500/$1,000, and standard buy-ins of $50,000. Playing alongside longtime friends and fellow A-listers Affleck and DiCaprio, and poker pros like Phil Ivey and Jamie Gold, Maguire typically hosted “Tobey’s Game” in the famed Viper Room on the Sunset Strip.
Some 10 years after “Tobey’s Game” took Hollywood by storm, former cocktail waitress and reputed Hollywood home game madam Molly Bloom penned a memoir of her experiences hosting the game in conjunction with Maguire. Titled Molly’s Game: From Hollywood’s Elite to Wall Street’s Billionaire Boys Club, My High-Stakes Adventure in the World of Underground Poker, the tell-all was published in 2014 – bringing to light many of the lurid details which must accompany any poker game believed to be private. According to Bloom’s recollection of the events, Maguire was always both “the best player and the worst tipper” at the table.
In a particularly detailed account excerpted from Bloom’s book by Vanity Fair, she recounts a particularly tense hand involving Maguire and Jamie Gold – winner of the 2006 WSOP Main Event:
“Tobey was losing, so he was back to disapproving of me, my tips, and the game in general. Now he was in for $250,000, down to his last $50,000, and trying to dig his way out. Jamie was once again playing like it was his last day on earth, and Tobey knew his best shot at getting out of the hole was Jamie. Pale and thin, Jamie had won $12 million in the World Series of Poker Main Event, the largest sum in the history of the tournament. Usually, I wouldn’t have considered allowing a World Series champion into the game, but Jamie was no pro; he had simply been running hot and playing fearlessly.
Jamie and Tobey were all in, and I wasn’t sure which one I was rooting for. Jamie had almost lost his bankroll, and once he did, I wouldn’t be able to let him play anymore. I liked Jamie – he was kind and generous. Tobey was the worst tipper, the best player, and the absolute worst loser, but I had to worry about my job security if he lost. I held my breath and watched Diego turn over the cards. Tobey won.”
There were many negative allegations to surface in the wake of Bloom’s book being published, but perhaps the most damning to Maguire’s reputation were insinuations that “Tobey’s Game” was not exactly on the level. According to Bloom, she and Maguire collaborated to set up a game which ostensibly featured a lineup of novice players like DiCaprio and Matt Damon, both of whom liked to play and had more than enough money to burn. An article published by British newspaper The Observer in 2014 detailed Bloom’s allegations of game-fixing by Maguire:
“Maguire is regarded as the single best player among the poker-playing actors. According to two sources, neither of whom would agree to be quoted by name because both continue to operate in the poker circles where Mr. Maguire plays, Ms. Bloom says that one of Mr. Maguire’s tricks is that he essentially staged the games in order to attract well-heeled players.
‘Tobey got Molly to concoct these games using friends like Leo DiCaprio to sit at the table. Tobey was basically paying their entry fee, and using Leo as a lure to get these billionaires like Alec Gores and Andy Beal to come to the games.’”
While claims such as this made by Bloom are as yet unproven, Maguire’s time hosting “Tobey’s Game” did result in tangible consequences for the actor in June of 2011. That year a lawsuit was filed by trustees of Ruderman Capital Partners, after the company’s CEO Bradley Ruderman regularly played in the game and lost six-figure sums.
According to the suit, which also included up to a dozen other Hollywood figures, including Nick Cassavetes and Gabe Kaplan, Ruderman’s bankroll at the time was comprised of illegally obtained funds resulting from his own participation in a massive Ponzi scheme. With Ruderman facing a 10-year prison sentence for his crimes, and Ruderman Capital Partners sunk into bankruptcy as a result, trustees representing his various creditors sued Maguire and the other home game participants, claiming that their winnings represented ill-gotten gains. In particular, the suit claimed that Maguire personally won $311,000 from Ruderman between 2007 and 2008.
In November of 2011, Maguire reached a settlement with Ruderman’s trustees, agreeing to pay them $80,000 to end the lawsuit. The legal proceedings cast a light on the phenomenon of Hollywood home games, leading many of the players to relocate the games to New York City, which is where Bloom was indicted for her role as a host, resulting in the release of her memoir the following year.