6 Celebrities Who Love to Gamble—And Aren’t Afraid to Admit It

Gambling holds an allure that appeals to people from all walks of life, from grandparents who reminisce about days at the racetrack and sports fans backing their favourite teams on betting apps to celebrities who love to test their luck and spend their fortunes. Many celebrities have discussed their enjoyment of gambling, openly sharing their love and passion for sports betting, blackjack, or poker. 

Some, like the six below, are more vocal about this passion than others. Before we reveal who they are, let’s address a question you might be having—why do celebrities gamble? For most of us, part of the allure of gambling is the possibility of a cash prize. Since celebrities already have plenty of money, what draws them to gambling? Let’s take a look.

Why Do Celebrities Gamble?

For celebrities, gambling is less about winning money than the thrill, entertainment, socialisation, and escape from the pressures of public life that it come with it. Let’s also not forget that celebrities have already taken a significant gamble in life: they pursued notoriously difficult careers and succeeded. They have a natural inclination to take risks and a higher threshold for them, making gambling a natural fit.

Celebrities may be rich and famous, but they aren’t immune to natural human behaviours, such as the dopamine rush triggered by taking risks. Gambling is just as exciting and rewarding to their brains as it is to anyone else. Unlike most of us, however, celebrities are unlikely to seek out no-deposit options or a selection of the top 20 online slots. They’re far more likely to waltz into glamorous, high-stakes gambling venues like Casino de Monte-Carlo. They also place wagers with friends who can match their high-roller lifestyle at a private box at the Super Bowl or whatever other major event is on.

Now that we’ve established the appeal of gambling for celebrities, let’s reveal some of the A-listers with a love for gambling.

1. Michael Jordan

Michael Jordan, one of basketball’s greats, is widely known for his love for gambling. He’s long been a sports bettor and someone who makes casual wagers with teammates and friends, including while they’re playing his second favourite game, golf. His love for gambling has permeated his life; even before he became famous, he was placing bets. In college and high school, they were small. One college friend who Jordan lost a pool game to saved the cheque for the $5 they wagered on the game. The friend never cashed the cheque, believing that Jordan would make something of himself and that the paper with his signature would become more valuable. As Jordan found NBA success, his bets grew bigger, and so did his losses. He has gambled most of his life, yet the thrill never seems to wear off. To this day, it’s a part of his lifestyle and something he’s passionate about. 

2. Matt Damon

While Jordan had a passion for gambling early on, Matt Damon discovered his interest through his career. When Damon starred in the gambling-themed movie Rounders, he learned the ins and outs of poker and has remained a player since. Unlike others on this list, he’s said to be a more cautious player who doesn’t place high-stakes wagers. Though he plays with lower bets, he’s rumoured to still walk away with impressive sums by making several small bets and playing with skill and care.

3. Ben Affleck

It’s hard to talk about Damon without bringing up his friend and co-star Ben Affleck. Affleck is widely known for his love of gambling, particularly when it comes to the games of poker and blackjack. He won the California State Poker Championship in 2004 and has participated in quite a few World Series of Poker (WSOP) events. The actor was banned from the Hard Rock Casino in Las Vegas in 2014 for counting cards, generating numerous headlines speculating about Affleck and whether he has a gambling problem. While Affleck doesn’t specify one way or another, he still seems to be an active gambler who enjoys the thrill and escape it offers.

4. Tobey Maguire

Tobey Maguire may be best known for portraying the nerdy and affable Peter Parker in the Spider-Man movies. However, his love for poker and high-stakes wagers has gotten him into hot water. Maguire was among several celebrities caught up in an underground poker ring, which the FBI shut down in dramatic fashion. The story inspired the film Molly’s Game, and from these games, Maguire reportedly walked away with an extra $36 million to his name—and a lawsuit. Since the drama and scandal have blown over, Maguire continues to indulge in his passion for poker and has been found at the table elbow-to-elbow with other celebrities and incredibly wealthy players. 

5. Timothée Chalamet

One of those celebrities sitting alongside Maguire includes the Dune, Wonka, and A Complete Unknown actor Timothée Chalamet. Following his Oscar nomination for Best Actor for his portrayal of Bob Dylan in the latter film, Chalamet celebrated with a poker night at the Chateau Marmont. The event had celebrities like Kylie Jenner, Kevin Hart, Kid Cudi, and Rich Paul in attendance. While this event is the most notable of Chalamet’s poker ventures, it’s not the first time his love for the game has caught people’s attention. He openly talks about his passion for it and has been spotted at numerous poker venues.

6. Cristiano Ronaldo

Cristiano Ronaldo is known for his athletic prowess on the pitch, which has earned him a reputation for being one of the greatest footballers of all time. What you may not know about him, however, is that his skill and competitive nature extend to gambling, particularly and sports betting. His love for these activities has even led to him becoming an ambassador for the organisation PokerStars. Like many celebrities on this list, Ronaldo has participated in star-studded poker events. In 2016, he gained attention for beating Breaking Bad star Aaron Paul in a celebrity poker event.