Nowadays, gambling is marked by online casino games and mobile sports betting apps. However, when you turn the clock back 20 years to the 2000s, there was a dramatic shift in how society viewed brick-and-mortar casinos, and celebrities were at the heart of this transformation.

From athletes and film stars to music sensations, celebrities from different realms indulged in casino games, seeking to unwind or challenge their luck. While many stories of gambling losses made headlines, several celebrities also struck gold during their ventures. This article delves into the top ten biggest casino wins by celebrities from 2000 to 2010.

Ben Affleck’s Poker Triumphs

In the early 2000s, Ben Affleck displayed his prowess not just on the silver screen but also at the poker table. Affleck’s most notable win came in 2004 when he won the California State Poker Championship, pocketing a hefty sum of $356,400. His consistent streak in the game also earned him a reputation as a proficient poker player, showcasing the actor’s flair beyond acting.

50 Cent’s Astonishing Sports Wager

In 2007, the rap superstar 50 Cent, born Curtis Jackson, took a break from his musical pursuits to place an astonishing wager. He bet on Floyd Mayweather Jr. to win the boxing match against Oscar De La Hoya. When Mayweather emerged victorious, 50 Cent reportedly walked away with an impressive $500,000.

Matt Damon’s World Series of Poker Run

Best known for his roles in Hollywood blockbusters, Matt Damon made a significant impact at the World Series of Poker (WSOP) in the 2000s. Despite not making it to the final table, Damon’s performance was commendable, and he managed to rake in significant earnings throughout his run.

Damon’s poker success is attributed to his intense preparation for the role of Mike McDermott in the 1998 film “Rounders.” To get into character, Damon spent hours mastering poker, which later proved beneficial during his WSOP runs.

Although he didn’t clinch the top spot, his wins were noteworthy, demonstrating that even without securing the ultimate victory, significant winnings can still be achieved through dedication and strategy.

Pamela Anderson’s Slot Machine Success

Pamela Anderson, the “Baywatch” star, became a regular face in Las Vegas casinos in the 2000s. She particularly favored slot machines, and her preference led her to an unexpected win of $250,000. This victory underscored the potential for massive earnings even in seemingly straightforward casino games.

Michael Jordan’s Blackjack Winnings

Basketball legend Michael Jordan is well-known for his competitive spirit, a trait that extended to his ventures at the blackjack table. Jordan had several notable wins throughout the 2000s, with one remarkable run reportedly earning him over $500,000.

Charles Barkley’s Craps Wins

Former NBA player Charles Barkley also found success in the world of gambling. His game of choice was craps, and he had an impressive run in the 2000s. He reportedly bagged over $700,000 in a single night.

Bruce Willis’ Baccarat Victories

Known for his action-packed roles in Hollywood, Bruce Willis also made a mark in the world of baccarat during the 2000s. Willis reportedly won a significant sum of $500,000 in a single baccarat game.

Tobey Maguire’s Poker Streak

Tobey Maguire, most recognized as Spiderman, wove a web of victories in high-stake poker games in the 2000s. His consistent wins over the decade reportedly accumulated to a staggering $10 million.

Phil Ivey’s Poker Accomplishments

While primarily a professional poker player, Phil Ivey also made waves in the celebrity circuit thanks to his appearances in various TV shows and endorsement deals. During the 2000s, he bagged several WSOP bracelets, amassing millions in winnings.

Ivey’s poker victories are a testament to his mastery of the game’s complexities. His strategic approach, coupled with his ability to read opponents, contributed significantly to his success.

Derren Brown’s Roulette Feat

British mentalist and illusionist Derren Brown made headlines in 2009 when he seemingly predicted the outcome of a roulette wheel on live television, earning him a significant sum. While the validity of this feat remains a topic of debate, it certainly brought him attention.

Conclusion

These extraordinary wins from 2000 to 2010 serve as a testament to the thrills and surprises that casino games can offer. While luck often plays a vital role, the importance of strategy, knowledge, and calculated risk-taking cannot be overstated. These stories of celebrity casino victories remind us that whether it’s the roll of the dice, the turn of a card, or the spin of a wheel, the allure of the casino is the blend of skill and chance that keeps the players coming back for more.

The next big win could be just a game away. Each of these celebrities, from actors and athletes to musicians, has left their mark on the casino world, providing us with exciting tales of triumph, strategy, and sometimes, simply good fortune.