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Hollywood’s Biggest Casino Wins: True Celebrity Gambling Stories (2025)

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Hollywood celebrities stay for the joys—whether or not it’s on-screen motion or high-stakes playing. A number of the largest names within the trade have examined their luck at casinos, with jaw-dropping wins and, typically, devastating losses. Right here’s a take a look at among the most legendary on line casino wins in Hollywood historical past.

Ben Affleck – The Blackjack King

Oscar-winning actor Ben Affleck isn’t only a gifted filmmaker; he’s additionally a talented blackjack participant. In 2014, he was reportedly banned from taking part in blackjack on the Arduous Rock On line casino in Las Vegas after profitable an excessive amount of. Affleck allegedly mastered card counting, a authorized however frowned-upon technique, and took house a whole bunch of hundreds in winnings earlier than the on line casino requested him to cease taking part in.

Charlie Sheen – The Huge Curler

Recognized for his extravagant life-style, Charlie Sheen was as soon as a high-stakes gambler, reportedly betting $200,000 per week on the peak of his profession. Whereas particular particulars of his wins stay unclear, Sheen admitted to dropping tens of millions in playing, proving that even celebrities aren’t proof against the dangers of the on line casino flooring.

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Dana White – On line casino Enemy No. 1

UFC president Dana White is likely one of the most profitable superstar gamblers. He has reportedly gained tens of millions at Las Vegas casinos, notably in blackjack. Nonetheless, his repeated wins led to a number of casinos banning him from taking part in at their tables. White has confirmed in interviews that some casinos even refused to let him place bets as a result of he was too good on the recreation.

Tobey Maguire – Underground Poker Champ

Spider-Man star Tobey Maguire was a significant participant within the high-stakes poker scene, collaborating in unique underground video games with different celebrities and rich businessmen. He was rumored to have gained tens of millions, however his identify turned notorious when his involvement in an unlawful poker ring was uncovered in 2011.

Paris Hilton – A Fortunate Evening in Vegas

Paris Hilton as soon as walked right into a Las Vegas on line casino and walked out with $30,000 in winnings—on her first strive. She credited her luck to carrying a fortunate costume, proving that typically, fortune favors the daring (and trendy).

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