Hollywood’s Biggest High Stakes Poker Players: Where Are They Now

Back in 2011, Toby Maguire was all the rage in the world of celebrity high stakes poker while taking on the lucrative role of Spider Man in film.  Maguire played a prominent role in the underground games that would go on to hit the big screen later on as "Molly's Game".

Molly Bloom, the subject of the film, played host of the games on bahalf of Maguire and his friends like Ben Affleck, Matt Damon, Leonardo DiCaprio and “The Notebook” director Nick Cassavetes.

She would later go on to claim the Spider Man actor started organizing the underground high stakes poker games in his home until he grew suspicious of the attendees.  One just happened to be a gentleman known for scamming high stakes games.

Maguire would ultimately be named in a lawsuit filed by duped investors claiming jailed hedge fund manager Brad Ruderman used their monies to amass huge debt in the illegal underground high stakes poker games.

Poker pro and Instagram sensation Dan Bilzerian objected to the idea that Maguire was any type of “high roller” at the time.

“He's cheap as f**k and plays like a cheap b*tch... a guy who's worth all that money playing as if he's broke. Come on, dude."

Bloom seemed to support that notion in her recalling of the underground games.

Over a decade later, we hardly hear about Maguire. 

Hot for Teacher

We do still love our Gabe Kotter.  He was the teacher in "Welcome Back Kotter" and still one of the most successful celebrity poker players on the circuit today.

Welcome Back Kotter’s Gabe Kaplan was named in the aforementioned suit.  All parties reached a settlement later in 2011, months after the dreaded Black Friday indictments that would go on to cripple internet poker and, to a lesser degree, the online casino sector.

On the live poker circuit Kaplan is listed as having won just shy of $2 million.  He also featured prominently on the earlier year premier of High Stakes Poker along side one time Gambling911.com writer and Hollywood fixture AJ Benza.

Killer Bride

“Bride of Chucky” star Jennifer Tilly has long been regularly featured on the pages of Gambling911.com.  She is by far one of the most well known of the celebrity poker players and is the girlfriend of  big name pro Phil “The Unabomber” Laak. 

Tilly this month was just inducted into the Women In Poker Hall Of Fame (2022).

Her dad was the one who got Tilly playing poker at a very early age.  She would go on to win the Ladies' no-limit Texas Hold ‘Em event at the World Series of Poker one year later.  She also walked away with a bracelet and $158,625.

“After that, I was like, ‘Wow, I won a gold bracelet, I should switch careers, I’ve really got a knack of this poker thing,’” she said at a BUILD Series event in 2017. “Then it’s been really hard going after that. I’m like that child actress that at 13 years old wins an Oscar and then realizes after that that acting is really, really hard.”

American Pie

Shannon Elizabeth of American Pie fame is another of the Hollywood poker princesses and a 2007 NBC National Heads-Up Championship 4th place finisher. She beat out some of the best players in the world.

She was a frequent guest at parties held by the billionaire founder of CoinGeek, Calvin Ayre.

Still a Rebel Rouser and Back on Twitter

James Woods  also ranks among the biggest poker players in Hollywood.   The actor was at one time associated with the online poker site Hollywood Poker prior to the dreaded Black Friday. 

In recent years, Woods is an outspoken conservative and staunch supporter of the Make America Great Against (MAGA) movement.  He's also back on Twitter "owning the Libs" now that Elon Musk has taken control of the social media platform. 

Woods tweeted his praise for Musk.

Thank you, @elonmusk, for shining a light on who the true “fascists” are in America.

— James Woods (@RealJamesWoods) November 29, 2022

Brad Garrett

He's appeared on Poker Night in America and got into a fight with poker brat Phil Hellmuth.

More memorable for us, Garrett roasted poker icon Doyle Brunson back in 2008. 

We were there when the Everybody Loves Raymond star told Pam Anderson to "get out from under the tables".

Our tablemate was the fake Randy Meisner.

- Ace King, Gambling911.com