Biggest Celebrities That Loves Being in the Casino

It is no secret that a lot of A-list celebrities, from professional athletes and musicians to Hollywood actors, are drawn to the thrill of gambling. Whether that is on the casino floors in Las Vegas or other popular establishments worldwide, some have no problem with their stories being public or sharing personal thoughts about gambling. Top10DesCasinos listed the biggest high rollers among celebrities, but we decided to keep the focus on the most popular names in the word. In this article, we will present 7 celebrities with a history of gambling, their preferred casino games, their biggest high-stakes wins, and even some unfortunate losses.

NBA Superstar Michael Jordan Net Worth

Michael Jordan

We start things off with the six-time NBA Champion, six-time Finals MVP, and 13-time All-Star Michael Jordan, who has a well-documented history of gambling. Back in his heyday, a lot of controversy went around Jordan about his gambling, with some claiming that he was a gambling addict.

Back in 1993, Jordan even did an interview where he talked openly about his gambling, saying that it doesn’t and will not ever affect his love and passion for basketball. Whether betting on personal golf games, big sports events, or even playing high-stakes poker, he described all of that as a hobby and that he could stop whenever he liked.

One of MJ’s biggest losses was in Las Vegas at a craps table. It is said that in one night, Jordan played a high-stakes craps game and lost close to $5 million. Whether he is a billionaire or not, it still puts a dent in his bank account.

Phil Hellmuth, a seasoned pro poker player, once participated in a charity poker game alongside Jordan. He recalls that Jordan showed pro-like skills and ended up winning the entire thing, getting $25,000, which he later donated to the Trent Tucker Charity.

NBA Star Charles Barkley Net Worth

Charles Barkley

Another NBA superstar, today known for his commentary in the Inside the NBA show on TNT, Charles Barkley is another well-known gambler. While Barkley has had some success on the casino floor, winning $750,000 on blackjack tables, he has also recorded some huge losses.

Over the years, Barkley has shared many stories of him and Michael Jordan betting and gambling on pretty much anything. Even during the 1992 Olympics, Barkley would play card games in their rooms with teammates such as Jordan, Pippen, and Johnson.

He has always been open about his gambling issues, and he knows he has a problem. He has also openly admitted to losing tens of millions of dollars in the past two decades, with the biggest loss in one night being $2.5 million.

Over a decade ago, Barkley was in trouble being sued by one major Las Vegas Casino for not paying his $400,000 debt. He made sure he paid off the debt and admitted to taking some time off gambling.

Businessman and Blackjack Player Dana White Net Worth

Dana White

Businessman and current CEO of the UFC, Dana White, is a well-known blackjack player. Over the last decade, Dana White has had some impressive stats when it comes to playing blackjack at some of the biggest casinos in Las Vegas.

It is reported that White’s biggest-ever night was around $7 million on blackjack. In his own words, while he has fun playing, he goes to casinos to win. There are plenty of instances where he has placed large bets, even up to $75,000 on one hand. The one strategy he always sticks to is collecting and leaving the table when he wins a big sum.

Over the years, White has been banned from several Las Vegas casinos, including twice from the Palms Casino. In 2012 and 2014, the owners and manager of the Palms had to ban him because on both occasions, he left the floor with more than $2 million in his pocket.

Rapper Drake Net Worth

Drake

Global superstar and rapper Drake is another big celebrity who has no problem showcasing his love for gambling. In 2021, he even became the global ambassador for Stake Casino, one of the biggest online gambling platforms.

Even though he is the ambassador of a crypto-online casino, and all of his wagers and bets could be prop money given by the operator, it is still interesting to see how much he has gambled. Over 3 years, Drake has wagered over $1 billion on Stake.com. One of his biggest wins was caught on a live stream he did back in 2022, where he won $17 million on a single hand in live roulette.

While most losses have been from betting on sports events, it is said that Drake has lost more than $34.2 million on Stake. On the other hand, he has allegedly accumulated more than $79.1 million in wins, mainly from sports betting.

Actor Ben Affleck Net Worth

Ben Affleck

The actor, director, and producer is one of the biggest Hollywood stars who have openly spoken about their gambling problems. Despite admitting he has a problem, Affleck has been part of some huge wins and striking losses over the years.

Back in 2004, Affleck participated in a No-Limit Hold’em Championship event hosted at the 2004 California State Poker Championship. Despite high-ranked pros attending the tournament with a prize pool of $891,000, Affleck emerged victorious, taking home $356,400.

Over the years, it has become public knowledge that Affleck hosted private high-stakes poker tournaments. It is said that Affleck has lost $400,000 on a single hand, playing against Ron Mayer, the president of Universal Studios.

In 2014, Affleck was banned from the Hard Rock Hotel and Casino. He openly shared the story in an interview, saying that he was banned because the casino thought he was counting cards at a blackjack table. He denied the claims, insisting they were just angry because he couldn’t stop winning.

Actor Matt Damon Net Worth

Matt Damon

We cannot include a story about Ben Affleck without mentioning his close friend Matt Damon. Besides starring in and producing various movies together, Damon and Affleck share a love of poker as well.

Damon has a long history in poker games, and that all became even more apparent once he starred in the 1998 poker movie “Rounders’. To prepare for the role, Damon accrued Johnny Chan, a famous poker pro, to teach and coach him.

After the movie, Damon started playing more, even appearing in various televised poker tournaments. Together with Affleck, in 2020, they hosted a charity poker tournament to raise money for Feeding America.

Alongside Affleck and Damon, various other celebrities entered the tournament, including:

Toby Meguire
Kevin Smith
Adam Sandler
Tom Brady
Adam Lavine
Brian Cranston
Jason Bateman

To grab a spot in the tournament, everyone had to donate $10,000.

One of Damon’s biggest losses was recorded at the 1998 World Series of Poker tournament. In his final hand, Damon lost $25,000 to former WSOP champion Doyle Brunson.

Olympian Michael Phelps Net Worth

Michael Phelps

Over the years, one of the most decorated Olympians of all time, Michael Phelps, has shown his love for poker, participating in countless online and land-based tournaments. In an interview in 2008, he admitted to playing poker from a young age and that the game gives him excitement, whether playing with friends, online, or at a tournament.

However, several of his close friends say that after retiring, Phelps has increased his wagering and that today, he is playing $25,000 per hand. In the past few years, we saw Phelps attending various tournaments, including the 2017 World Series of Poker, the 2018 Rio Daily Deepstacks, and the 2023 South Point Recurring Tournaments.

His most recent appearance was with Global Poker, where he had a personalized challenge where players could enter eight Sweeps Coin Qualifiers and get a chance to play with Phelps. Besides a winning prize pool and playing with Phelps, participants could also win $10,000 to donate to a charity of their choice.

Final Thoughts

While you and I are staking $1 and $2 bets on poker, it is always interesting to see how high-roller celebrities play. As we’ve seen, for some, it is a problem, and while they have the bank account to cover their losses, it is never smart to chase your losses.

While poker and other casino games can be fun and thrilling, it is always wise to stay within your budget and practice responsible gambling, otherwise you risk losing more than you can afford.