Big Wins & Losses of Celebrity Gamblers

With so much money to burn, celebrities attract a lot of attention with their ridiculous gambling winnings (and losses). Walk through Caesars Palace in Las Vegas and you might run into big name celebs like Ben Affleck, Matt Damon, or Ashton Kutcher betting thousands of dollars on their favorite card game or sporting event. For them, throwing around a few hundred grand at the casino doesn’t even put a dent in the wallet. Celebrity gamblers know how to cash checks and stack the deck.

P-P-P-P-Poker Face

Imagine a smoky room with guys like Leonardo Dicaprio, Matt Damon, Ben Affleck, and Tobey Maguire sitting around a Poker table toking cigars and sipping Single Malt Scotch. No, this isn’t a scene out of a new movie, but what went down when a dozen of Hollywood’s biggest celebrities got busted for participating in an illegal underground Poker ring. The games took place in a multi-million dollar Beverly Hills mansion with a $100,000 buy in. Apparently, Tobey Maguire didn’t have enough spidey sense to avoid a law suit which he later faced for participating.

$100,000 Buy in for Poker? Yea. That's normal.

A $100,000 Buy in may seem like a lot to us po’ folks, but for gambling celebrities like Matt Damon and Ben Affleck, it’s hardly a dent in their 75 million dollar wallets. Both stars have a penchant for gambling large sums of money.During a trip to Las Vegas,the two old time buddies won $800,000 playing three $20,000 hands of Blackjack. According to the casino, a wicked drunk Ben Affleck also tipped about $150,000 to the staff. Bet we all wish we had been working the casino that day.

I won $800,000 at Blackjack. How about them apples?!

Read about famous celebrity gambler, Ben Affleck, who just starred alongside Justin Timberlake in a movie about online gambling called Runner, Runner.

Heeeeere’s Johnny!

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Who can forget the recent blunder made by Arizona State Senator, John McCain? On September 3, 2013, the former Republican Presidential Candidate must have gotten bored during an important hearing regarding US intervention in Syria when he got caught playing VIP Poker on his iPhone. Gee Senator, hope the hearing wasn’t about anything important like war in the Middle East or something…

Can’t get enough of Poker like Senator McCain? Find out about Online Poker now available in New Jersey.

Poker at a war hearing? Yes, Senator. That’s exactly why we pay you $174,000 each year.

Dude, Where’s My 700 Grand?

In between starring roles in hit movies and TV series, Ashton Kutcher got his hands in a pretty lucrative sports betting operation. In an interview with Esquire Magazine, the actor admitted, "I actually used to be a front for the largest national sports-betting syndicate in America." Basically, Kutcher placed bets on behalf of professional sports bettors who knew how to beat the system:

"So, generally these types of individuals aren't allowed to gamble, but they know how to handicap the house. So they sent me in. I basically just placed the bet…We were clearing, like, $750,000 in four weeks of college football. It was pretty fun. Then they caught on. The hypothesis had been that the house would just assume that I was a dumb actor with a lot of money who liked football."

Engaged to Mila Kunis and cashing in $750,000 on sports betting? Yea, I’d say Ashton Kutcher has a reason to smile.

The Queen of Poker

You may recognize Academy Award Nominee, Jennifer Tilly, from movies like The Fabulous Baker Boys and Bride of Chucky or more recently, as Shorty’s girlfriend on Modern Family. This sexy screen siren could be considered a professional gambler in her own right. She won the World Series of Poker Ladies bracelet in 2005 and took home $158,625 in a Ladies' No-Limit Texas Hold’em event against 600 other players. This famous celebrity gambler also appeared in the cover of Card Player Magazine.

Jennifer Tilly knows how to work it on screen and off screen at the Poker tables. Get it girl!

Listen to the Voices in Your Head!

Celebrity gambler, 50 Cent definitely lives by his credo, get rich or die trying. He has made millions on record sales, movie roles, endorsements, and business ventures like his very own flavor of vitamin water. The rapper also knows how to hustle in gambling, when he wound up with $1 million extra cash in his pocket betting a boxing match between Floyd Mayweather against Oscar de la Hoya. 50 cent also banked $500,000 when he bet on a NFC Championship Game between the 49ers and Giants in 2012. After the big win, 50 Cent tweeted:

Nice Grammar, “Fitty”.

Celebrity gamblers bet thousands of dollars without even batting an eye. Winning millions at a casino might seem absurd to the average person, but that kind of money is nothing but pocket change to the celebrity gambler.With so much money to throw around, it’s no surprise that celebrities make headlines with their outlandish gambling habits.

Movie stars and musicians aren’t the only ones with crazy gambling habits. From the field to the felt, check out these sports stars who win (and lose) millions at the casino.

About The Author

I made my entrance to online gambling in 2004 in an attempt to understand the psyche of the casino goer. I've spent prolonged periods delving into the industry and its inner functions and continue to do so at VegasMaster every day. My research and experience has given me insights into gambling that I hope you'll benefit from.

1 Comment

  1. Dolan

    I totally knew about Jennifer Tilly being a top celebrity poker player, but I had no idea that Ashton Kutcher actually placed bets on behalf of other pro sports bettors! Makes you wonder how much other celebrities gamble…

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