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.