Top Casino Wins By Celebrities

The glitz and glamour around celebrities sometimes make people think of celebrities as superhumans in a world of their own. Yes, in some respects, celebrities could be in a world of their own. And in other respects, celebrities are in the same world as everyone else.   

When it comes to gambling, many celebrities are either casual gamblers or deep gamblers who are even fighting gambling problems. They just play different games like everyone else, and also either lose or win their bets. It is worthy of note that some have won huge amounts of money playing some interesting casino games. We take a look at such record-making wins made by celebrities:

Dana White

Aside from being a fantastic manager and president of the Ultimate Fighting Championship, Dana White is a potential GamStop customer. He hasn’t tried casinos not on GamStop via portal but there’s still time. He’s reputed to be a voracious blackjack player, staking expensive amounts for each blackjack hand he plays. In his first-ever tournament in July 2010, Dana White won the available prize of $250,000.

Going forward, he became a nightmare to Palms Casino in Las Vegas, where he won $1.6 million on multiple occasions. As a result, the different successive Managements of Palms Casino had to ban him from the casino multiple times also. Upon his re-invitation to play at Palms Casino, he landed his most remarkable single win of $5 million. This earned him a belt as the Undisputed Blackjack Champion at the casino.

Tobey Maguire

Tobey Maguire had learned poker strategies and skills from Daniel Negreanu, who has six world series of poker titles. Tobey Maguire has added huge poker wins to his big earnings as an actor in Hollywood. In 2011, he was linked to some illicit untaxed poker rendezvous which had a series of other celebrities like Matt Damon.

Other celebrities involved include Leonardo DiCaprio, Alex Rodriguez, Ben Affleck and Dan Bilzerian, as well as other businessmen. It was revealed that Tobey had won an average of $30 million through the illicit poker rendezvous.

Floyd Mayweather

Floyd Mayweather is not only a multi-millionaire boxer with a very outstanding career, but he’s also a proud gambler. His forte is sports betting, ranging from NBA matches to other matches outside of the US. In 2013, Mayweather placed a bet of $5.6 million on the NBA playoffs between Miami Heat and Indiana Pacers.

His bet was in favour of the Miami Heat and they emerged the winner of the match. As a result, Mayweather walked home with over $5 million. In 2017, he also won $1.4 million when Indianapolis Colts and Jacksonville Jaguars played a match and Indianapolis Colts won.

50 Cent

In addition to having an impressively successful music career, 50 Cent has also ventured into producing and acting movies. But what fascinates us is the fact that he has been gambling, and to our knowledge, also winning big. 50 Cent wagered on the New York Giants beating the San Francisco 49ers in 2012 and scooped a whopping $500,000.

In May 2015, he had wagered $2 million in favour of Floyd Mayweather Jr. winning the match between Mayweather and Manny Pacquiao. The outcome of the match was in line with his wager and he walked home with over $5 million.  

Ben Affleck

An accomplished and successful actor, screenwriter, director and producer, Ben Affleck has risen to the peak of his Hollywood career. But what surprises everyone is how the prolific celebrity has managed both his Hollywood career and gambling career. Yes, Affleck is also a wonderful poker player, having made his mark in the game of poker in the US.

In 2004, Affleck participated in the California State Poker Championship and won the competition, walking home with $356,400. Winning the competition secured his subsequent participation in the World Poker Tour final games. In 2014, Affleck reportedly won over $1 million in 2 blackjack sessions from counting cards at the Las Vegas-based Hard Rock Hotel. Sensing he was counting cards, the casino management at Hard Rock Hotel had to excuse him from the blackjack table.

Michael Jordan

Michael Jordan is known all over the world for his super-successful basketball career that has earned him great fortunes. Apart from being the first billionaire athlete in the world, Michael Jordan isn’t left out on gambling. He ensures to make the best of gambling, just like he did basketball, and currently doing business.     

He won the Dream Team poker competition in 1992, facing other basketballers such as Charles Barkley, Scott Pippen and Earvin Johnson.


Celebrities can afford to gamble on different casino games and win very huge amounts of money because of their status. This does not mean that some of them are not battling with gambling issues, many of them are.

However, the fun part remains common amongst them all. So, as much as they can afford to gamble, gambling is simply a side activity meant to offer some fun to them.  

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