Celebrities Who Love to Gamble: A Look at the Rich and Famous

person holding white and black playing cards
Photo by Michał Parzuchowski

Gambling has long been a favorite pastime among the rich and famous, with some of the most iconic celebrities known to have made quite a fortune at casinos across the globe. From Hollywood stars to professional athletes, the gambling world has seen it all. Although it can be risky business, it sure looks like lots of fun when you’re rich and famous!

Popular gambling activities among celebrities

Celebs enjoy a variety of gambling activities. One of the most popular is poker, as it requires skill and strategy to succeed. Another is blackjack, which offers players the chance to use their knowledge of probability and card counting to increase their chances of success. Other favorites include sports betting, baccarat, craps, roulette, slots, and keno. Celebs also relish playing at online casinos for real money or just for fun, taking advantage of bonuses and promotions – Grand Mondial casino rewards, to name but one – and many have been known to frequent Las Vegas casinos in order to take part in high-stakes games.

Famous celebrity gamblers

Some celebrities have become legendary for their gambling exploits, while others are known for their more notorious gambling habits. Here’s a look at 5 of the most famous:

  1.  Michael Jordan – The NBA legend is one of the most famous celebrity gamblers in history. He was known to bet large sums on golf and poker games, and even once lost $57 million in a single year!
  2. Charlie Sheen – The actor is another well-known gambler, who has been spotted playing high-stakes poker games around Los Angeles and Las Vegas casinos.
  3. Floyd Mayweather Jr – The boxing champion is no stranger to betting on sports events, having placed bets on himself during his fights, as well as other sporting events like basketball and football games.
  4.  Tiger Woods – Woods has reportedly wagered up to $25 million on a single round of golf!
  5.  Robert De Niro -The iconic actor may not be a professional gambler but he certainly knows how to enjoy himself when it comes to casino gaming! He’s been seen playing blackjack at some prestigious casinos across Europe , including Monte Carlo Casino in Monaco.

Big wins and losses in celebrity gambling

Celebrities are no exception to the highs and lows of gambling. At a Las Vegas blackjack table in 2001, actor Ben Affleck experienced a high when he reportedly won $800,000 at a Las Vegas blackjack table in 2001.

Also able to boast an impressive victory was poker player Phil Ivey, who bagged $20 million playing baccarat at Crockfords Casino in London back in 2012.

On the other hand, golfer John Daly has been known for his big losses over the years – he once blew $1.5 million in one night playing craps at Caesars Palace in Las Vegas.

Perhaps more devastating still was the misfortune of Tobey Maguire, who is said to have lost millions of dollars playing high-stakes poker games with Hollywood’s elite between 2006 and 2009.

From poker tournaments to luxurious casinos, many famous faces enjoy the thrill of the game and have been known to take big risks for even bigger rewards.


Richard Owens
Richard Owens
Richard is a Editor-in-Chief at DatingCelebs. He loves Hollywood gossip, entertainment, and celebrity dating news. Follow him at @rowens13.