Many celebrities are known for spending ridiculous amounts of money on flashy sports cars, luxury holiday homes, designer clothing and, in the case of Mike Tyson, Bengal tigers. One of the most costly (and profitable) activities pursued by superstars from all walks of life is high stakes betting. We take a look at some of the largest bets that have been placed by celebrities, the celebrities who excel at gambling, and which casino games celebrities seem to prefer.
Ben Affleck
The star of Gone Girl, Argo and Good Will Hunting, is a very accomplished blackjack and poker player, who has reportedly wagered as much as $60 000 a hand on a blackjack game. In fact, Affleck has shown such skill at blackjack that casino owners in Las Vegas have asked him to refrain from playing the game at their casinos, after realising that the actor is able to count cards and so increase his chances of winning.
Charlie Sheen
One of Hollywood’s most notorious bad boys, Charlie Sheen has apparently been struggling with problematic gambling habits since his teenage years. According to Denise Richards, Sheen’s ex-wife, the star of hit TV series such as Two and a Half Men and Anger Management enjoys wagering large amounts of money at both casinos and sports bookies. In a funny twist, you can also place bets on Charlie Sheen: the actor is so well-known for behaving badly (and getting caught doing it) that you can now place wagers online on what his next public misdemeanour will be.
Michael Jordan
The legendary basketball player Michael Jordan apparently enjoys betting on golf and card games. A close friend of Jordan’s, Richard Esquinas, revealed that the sports star has lost near $1.25 million betting on friendly golf games. Some even believe that Jordan’s retirement in 1993 was really just for public show and that the athlete faced forced suspension as a result of his problematic gambling lifestyle.
Pamela Anderson
Baywatch babe Pamela Anderson enjoys playing slot machines and poker. Anderson met her current husband Rick Salomon at a casino where she had accrued a considerable gambling debt. Apparently Salomon offered to pay off her debt and in return all he asked was that the former Playboy darling “make out with him”. Speaking to Ellen DeGeneres about the unusual start to their relationship, Pamela said “It worked out … I paid off a poker debt with sexual favours and fell in love. It’s so romantic”. And people say chivalry is dead.
Matt Damon
In preparation for his leading role in Rounders, a film that portrays the lives of high stakes poker players, Matt Damon reportedly spent $25 000 getting to know the game of poker and familiarising himself with the gambler’s environment. Subsequent to the film, Damon still enjoys the occasional round of poker and even participates in poker leagues.
Floyd Mayweather
The boxing sensation Floyd Mayweather is known for his lavish lifestyle and exorbitant spending: the athlete’s preferred boxer shorts cost $6500, but he only wears a pair once, plus he owns 1000 pairs of shoes, 17 high-priced cars and 10 luxury homes. But where he perhaps spends the largest portion of his fortune is on gambling. In 2012, Mayweather wagered $1.1 million on a college football match and more recently he bet $720 000 on the Colts, earning him a winning of $1.405.714 on a single bet – a fact publicised on his Twitter account, which boasts 5.3 million followers.
Originally published December 3, 2014. Updated November 29, 2022.
