Now, Maguire, who frequently came out on top, is being sued for some of his winnings, to the tune of $311,000, plus interest.
A bankruptcy trustee is suing Maguire and 22 others who participated in the unlicensed poker matches to try to recoup $4 million for investors who were duped in a Ponzi scheme.
According to The Associated Press, the legal actions claim that the underground Texas Hold 'em matches, held between 2006 and 2009, were played with some of the money taken in the Ponzi scheme by its architect, Bradley Ruderman.
Ruderman, who is now serving 10 years in prison for operating a wire fraud and investment advisor fraud scheme, stated in court records obtained by ABCNews.com that from 2002 to 2009 he lost about $5.2 million in investors' money in a "clandestine high-stakes poker game held on a regular basis in a suite at a luxury Beverly Hills hotel."
According to one of the lawsuits, obtained by the website Radar.com, the games were played at the Four Seasons and the Beverly Hills Hotel and, occasionally, private residences of the poker players.
TMZ reported that one of the residences was the Hollywood Hills home of Rick Salomon, Paris Hilton's sex tape partner in "One Night in Paris."
The upscale, high-stakes affairs included hired dealers, professional-type poker tables and massages.
In an attempt to recover Ruderman's losses, the trustee maintains in the lawsuit that Maguire is "not entitled to receive the transfers from the Debtor, which transfers were compromised of improperly-diverted investor funds."
Maguire's attorney, Robert Barta, as well as his publicist, Kelly Bush, were both unavailable for comment to ABCNews.com.
Nick Cassavettes, director of "The Notebook," is among those being sued. The trustee is trying to recover nearly $73,000 plus interest from the actor-director.
Billionaire businessman Alec Gores, who along with his brother attempted to buy Miramax Films last year, is another target of the lawsuits. Gores is being sued for $445,500.
A-listers DiCaprio, Affleck and Damon are not being sued, though according to records they were at some of the matches. Damon was said to be an infrequent player. And TMZ reported that DiCaprio pulled out of the games after he started dating Bar Refaeli.
None compare to Maguire, however, who is considered a heavy hitter in Hollywood. On his website, poker pro Phil Hellmuth estimated that Maguire has won more than $10 million in Hollywood home games, adding that the matches are often referred to as "Tobey's Game."
"This kid could be a legitimate pro," wrote Hellmuth, who has played with Maguire.
Here are a few other Hollywood's high rollers:
Kaplan may be remembered as the gentle, slightly befuddled teacher on "Welcome Back, Kotter," but at the poker table he's no joke.
With his "Kotter" earnings, he began playing poker professionally in the late '70s and reportedly has earned over $1million in earnings. He also hosted a popular television show, "High-Stakes Poker."
According to The Associated Press, Kaplan is among those being sued by the bankruptcy trustee and is being asked to return $62,000.
On the screen, Tilly excels at playing the bubbleheaded girlfriend. At the poker table, however, she gets to show just how smart she is.
Perhaps she picked up some tips from boyfriend and poker pro Phil Laak. In 2005, Tilly outlasted 600 other players in the $1,000 Ladies' No-Limit Texas Hold 'em event and won $158,625. Enamored of the game, she announced her retirement from acting to pursue poker.
But in 2008, she reversed herself, writing in Bluff magazine: "I love poker, but greatness in poker is an elusive dream. There are too many variants. Trying to find validation in poker is like trying to find a virgin in a whorehouse. I'm not giving up poker entirely -- gambling is an addiction after all. I'm just going to treat it more like a hobby and less like a career."
By 2010, she was back at the table, with winnings exceeding $660,000.
Affleck was the first celebrity to win a major open poker tournament.
Last year, he outlasted 90 players to capture the California State Poker Championship and pick up $356,400.
Elizabeth, best known for her role in "American Pie," turned heads at the 2007 NBC National Heads-Up Championship, when she came in fourth and beat some of the best players in the world.
Elizabeth has described poker as her "second career," visiting Las Vegas up to three times a month to play against some of the top poker players in the country.
As with his acting career, Woods has had mixed success with poker.
In 2006, the actor finished in 24th place out of 692 at the L.A. Poker Classic, taking home $40,000. He also plays for charity for the American Stroke Association.
Woods has a contract with a poker website, Hollywood Poker, where he's known as "The Shark" and hosts online poker games, along with actor Vince Van Patten.
According to the site, "You'll never know which Hollywood Celebrity you might find yourself playing with at Hollywood Poker because James Woods and Vince Van Patten have both invited their entourage of celebrity poker friends to play online poker with you!"