4 of the Craziest Celebrities Gambling Tales

4 of the Craziest Celebrities Gambling Tales

Gambling involves risk, thrill, flashing lights, and the allure of money. How can anyone say no? Over the years, some of the most famous people in Hollywood have made headlines, not for their celebrity, but for their wild gambling escapades. In this post, we look at four names from this long list that stand out:

Michael Jordan

You could call Michael Jordan the king of NBA basketball and not be too far from the truth. Known as much for his prowess on the court as his trademark Nikeys, Jordan is also an avid gambler. Hollywood banter has him betting on everything from card games in online casinos to the outcome of golf games.

In 1983, Jordan lost a $1.3 million bet to businessman Richard Esquinas on a golf wager. In 1993, he was forced to testify in open court over a $57,000 check he made to a known gambler, alleged drug dealer, and now-convicted money launderer James “Slim” Boulder. Jordan testified under oath that the check was payment for gambling debts accrued over the years.   

Allen Iverson

Allen Iverson has had a well-documented struggle with gambling addiction. Once valued at over $200 million, the former NBA legend lost most of his fortune to his compulsive gambling streaks and lavish lifestyle. Iverson is banned from casinos in Atlantic City and Detroit and has fallen into debt severally. In 2004, he was kicked out of Bally’s Casino for relieving himself in the trash can to remain at the table during an exciting blackjack game.

Ben Affleck

It seems even Batman is not immune to the charms of the house. Renowned and award-winning actor Ben Affleck is also a stellar blackjack player, except his success at the table has little to do with luck and more to do with his card-counting abilities. In 2001, Affleck won a whopping $800,000 in a single night of betting on blackjack. Unfortunately for the Argo star, casinos would soon catch up to his not-exactly-legal-but-frowned-upon habit. Affleck is banned from playing in multiple Las Vegas locations.

50 Cent

If gambling were a business venture, 50 Cent would be a mogul. The famous rapper is known for making outlandishly large bets, which make for great social media content when they pay off. In 2012, Cent bet $1 million on the New York Giants to win a Super Bowl game. When they beat the New England Patriots, he walked away with an obscene payday of $500,000. But arguably, his most famous bet is the $1.6 million he placed on Floyd Mayweather to win a boxing match against Manny Pacquiao.

50 Cent has been very candid about his gambling problems, including referencing them in a 2017 song. 

Wrapping Up

From Ben Affleck’s prowess at the blackjack table to Michael Jordan’s woes on the golf course, these stories reveal that celebrities enjoy a good game like us. Logging into your Betway account and playing a few rounds of slots or poker is a great way to wind down after a long day. That said, these stories also expose the ugly underbelly of unchecked gambling. So, as you play your favorite online casino games, remember to set a budget, use a strategy, and walk away when you hit your target.