Celebrities Who Have Racked Up Casino Wins

It’s a well-known fact that a lot of celebrities like to gamble, but some do it better than others. On the list of the world’s top gambling winners and losers, we find celebrities from around the world known for their success in Hollywood, sports, music, politics and more. We tend to hold celebrities in high esteem, but they enjoy the same things in their ordinary life as most of us, including playing a game of poker. The only thing that makes them different from us is that they can afford to gamble with much higher stakes than the rest of us. That’s why some of them end up on the list of the worlds biggest gambling winners, or losers. Let’s take a look at some of the celebrities who seem to have a special talent for gambling. 

Jennifer Tilly

Jennifer Tilly happens to be a special case amongst Hollywood celebrities because she considered becoming a professional gambler as a serious career at one time. She has had a passion for poker for a very long time and has been involved in many tournaments landing around $900,000 in poker tournament winnings. Being the movie star she is, Tilly has been involved in many poker TV shows like GSN’s Poker Royale and Bravo’s Celebrity Poker Showdown.

In 2005, Tilly participated in the World Series of Poker Ladies’ No-Limit Texas Hold’Em competition, where she won the championship and took home $158,625 but Tilly is not the only celebrity woman in the World Series of Poker. Moroccan born Sarah Shafik (also spelled Chafak) won the title Miss Finland in 2012 but it’s the story of how she pulled off a bluff against WSP record-holder Ronnie Barda during the 2014 World Series of Poker that has made her a celebrity in the Poker Industry as one of the most successful Arabic casino and poker players of all times.

Ben Affleck

Ben Affleck is a well known Hollywood star, writer, and director, known for his role in many widely acclaimed blockbuster movies for many years now. Ben Affleck is not only good at movies, but he is also a proficient card-based casino game player, especially Poker and Blackjack. In 2004, Affleck participated in California State Championship, where he showed his prowess at the Poker Table and emerged as the winner. He walked away from the table as the champion and took home over $300,000. In 2014, Affleck also went on a winning streak playing Blackjack at Hard Rock Hotel in Las Vegas. It was reported that after playing two sessions of Blackjack, Affleck had already raked in about $1 million, which prompted the casino’s management to politely ask him to leave the table. Ben Affleck was even busted for participating in an underground Poker ring along with Matt Damon, Tobey Maguire, and other big Hollywood celebrities.

Matt Damon

The famous movie star Matt Damon was said to have found a love for casino games when he researched and prepared for his role in “Rounders.” In Rounders, Matt Damon played the role of a law student that also dabbles in Poker games. Obviously, Damon’s research into the Poker game wasn’t purely only for his role, but he became quite captivated with the famously appealing game. Damon and Ben Affleck are close friends, with the pair being seen at the grandest blackjack tables across different casinos. It was also reported that Damon was also involved in the Hard Rock Casino fiasco, where Ben Affleck raked in over a million dollars. Damon was also involved in the underground poker ring of 2011.

Tobey Maguire

Toby Maguire is a Hollywood actor that is famously known for his role, playing “Spiderman.” Maguire has been known to be involved in the casino scene with an affinity for poker games. In 2011, Maguire was also involved in the underground poker ring that included other celebrities and businessmen. During the investigation of this case, it was revealed that Maguire won somewhere between $30 and $40 million during this poker game. It means that Maguire may very well be one of the highest poker game winners of all time. The underground poker ring incident even inspired a 2017 movie titled “Molly’s Game.”

Derren Brown

Derren Brown, the world-famous master magician with regular television shows that dazzles audiences with feats of amazing `tricks and illusions, also dabbles in the casino scene. Even before his career as a magician kicked off, Derren was already well known at Blackjack tables. Many casinos don’t like when players win constantly, and even though Derren stakes small bets, it is said Derren is so good that he has never lost a hand, and he wins big. This led to Derren getting banned from many British casinos.

I can only mention a few, but many more celebrities occasionally or regularly grace casino halls to play their favorite casino games and have had pleasant experiences. Some of the other celebrities you might come across at a Poker game or Blackjack table include Paris Hilton, Dana White, Vitoria Coren Mitchel, etc. There are many celebrities that may not be the biggest fans of casino games but are very enthusiastic about sports betting. Some celebrities that are avid sports betting enthusiasts include Floyd Mayweather, Jr (the American boxer and businessman), Michael Jordan, Tiger Woods, and many more. 

About RJ Frometa

Head Honcho, Editor in Chief and writer here on VENTS. I don't like walking on the beach, but I love playing the guitar and geeking out about music. I am also a movie maniac and 6 hours sleeper.

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