Notable Celebrities Who Gamble on Different Sports and Casino Games

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Celebrities do more than feature in your favorite TV shows, movies, music, and sporting events.  During their free time, some like to hit the casinos for some gambling action. As do many other people, they enjoy the high-adrenaline, charged experience that comes with risking your money. Below, we look at some notable celebrities who love to gamble as well as their favorite games.

 

Dana White: Blackjack

Dana White is famously known for being UFC president but is also an exceptional blackjack player. White is known in casinos across Las Vegas for making high-stake bets and winning large pots on blackjack. In fact, multiple casinos have banned him from playing the game. This is understandable considering White once won $7 million in a single night. At the Palms in 2014, White won $2 million playing $25,000 hands.

 

Ben Affleck: Blackjack

The former Batman actor is no stranger to the online casino scene and the thrills it offers. Ben Affleck is reportedly an impressive Blackjack player and has even been banned from several casinos for counting cards. His technique saw him win $140,000 at the Hard Rock Las Vegas in a game with friend and fellow star Matt Damon – money he used to tip casino staffers. A year later, Affleck put $20,000 each on three hands which he played simultaneously, netting a $800,000 win. The actor has also reportedly lost a whopping $400,000 on one hand of poker.

 

Pete Rose: Baseball Betting

Pete Rose was a remarkable player for the Reds. After becoming the team manager in 1984, Rose started betting on his own team. His 2007 confessions and findings by the IRS show that he bet between $8,000 and $10,000 every day on baseball. Among other things, this led to him serving a 5-month prison sentence for falsified tax returns in 1990. The realization that Rose was betting on the Reds while actively serving as team manager also got him banned from consideration for the Baseball Hall of Fame.

Charlie Sheen: MMA Betting

Charlie Sheen was once the highest paid man on TV and it seems he put his earnings to use at the casino. His most notable win came in 2012 when he bet on Manny Pacquiao to beat [Oscar] De La Hoya. When his wager panned out, Sheen was reportedly unfazed by his $1 million win, claiming he did not feel anything. He also claimed that this was when he decided to stop gambling. Before that, however, Sheen had an impressive gambling repertoire.

 

50 Cent: Super Bowl Betting

50 Cent enjoys sports betting. When he won his $1 million wager in 2012, he was quick to rush to social media to show his followers what “holding $1 million in cash” looks like. He had won the pot after betting that the New York Giants, his home team, would win their Super Bowl XLVI game against the New England Patriots. The giants won by 4 points. Cent had also won big the previous year by wagering $500,000 on the Giants.

 

Michael Jordan: Golf Betting

When he was no longer setting records in his favorite sport, Michael Jordan was playing and betting on golf. Unfortunately for Jordan, his prowess on the basketball court did not follow him to the gambling arena. A 1993 book by Richard Esquinas, a San Diego businessman, claims that the iconic player lost a $1.25 million wager at Aviara Golf Course. Esquinas says he agreed to settle the bet for $300,000.

 

Jennifer Tilly: Poker

In recent years, sighting of Tilly have been confined to the gambling arena. But before she became an active poker player – a game she loves – the talented actress starred in multiple A-list films. These include The Haunted Mansion, Liar Liar. and a voice acting role on Family Guy. Away from the screens, Tilly has had remarkable success at the poker table. The enchanting beauty is the proud winner of a WSOP bracelet, WPT title, and up to $1 million in pots.

 

Charles Barkley: Blackjack

Former basketball star Charles Barkley has a gambling problem that he has described as “not a problem” because he can afford it. Barkley enjoys gambling and has repeatedly said that he will not quit, despite multiple big losses. In a 2006 interview, the Hall of Famer explained how he lost $2.5 million on blackjack within 6 hours on one night in 2005. Barkley also mentioned that he has lost a million dollars’ multiple times in his gambling career, bringing his losses to about $10 million. His gambling expeditions have even landed him in legal trouble, having once been sued for a casino for unpaid debts.

 

Wrapping Up

The high-stakes world of gambling is highly attractive to celebrities, some because they have enough money to burn and others because they like the high-risk stakes. Whatever the case, it is entertaining – most of the time – to see your favorite athletes, actors, and musicians break the monotony of Hollywood crowds and hit the casinos for a change.