10 Personalities Known for Their Passion for Gambling
For some celebrities, the thrill of competition doesn’t stop with their careers—it extends to the casino floor. Whether they’re high-rolling at blackjack tables, making strategic poker moves, or placing jaw-dropping sports bets, these famous personalities have embraced gambling as a serious pastime. Here’s a look at ten well-known figures whose love for the game is as legendary as their main professions.
1. Floyd Mayweather Jr.
Known for his extravagant lifestyle, boxing champion Floyd Mayweather Jr. is just as fearless at the casino as he is in the ring. His love for high-stakes gambling is well-documented, with reports of him placing massive bets on sports events and casino games.
Once, Mayweather allegedly placed a staggering $400,000 bet on a college football game and frequently shares his winning tickets on social media, showcasing his confidence in both the ring and at the tables.
- Game of choice: Sports betting & blackjack
- Amount wagered: Often six to seven figures per bet
- Active in gambling: Throughout his career, particularly in the 2010s
2. Drake
The Canadian rap superstar Drake is not only passionate about music but also about casino gambling, particularly online. He has been seen streaming his high-stakes bets on platforms like Stake, where he plays roulette with millions at stake.
In 2022, he famously placed a $1 million bet on Argentina to win the World Cup final against France, an event that had millions of fans on edge.
- Game of choice: Online roulette
- Amount wagered: Frequently over $1 million per bet
- Active in gambling: 2020s
3. Tiger Woods
One of the greatest golfers of all time, Tiger Woods is also known for his competitive nature off the green, especially at blackjack tables in Las Vegas. He was reportedly a VIP at the MGM Grand, where he was known to play high-stakes games.
At one point, Woods had a special $1 million betting limit arranged for him at MGM, demonstrating both his love for the game and the casino's confidence in his loyalty.
- Game of choice: Blackjack
- Amount wagered: Up to $25,000 per hand
- Active in gambling: 2000s–2010s
4. Charlie Sheen
Charlie Sheen’s larger-than-life personality extends beyond Hollywood, as he has been an avid gambler for years. His fondness for betting reportedly played a role in his extravagant lifestyle and financial troubles.
In a 2006 divorce filing, his ex-wife Denise Richards claimed that Sheen spent over $200,000 a week on gambling, particularly sports betting.
- Game of choice: Sports betting
- Amount wagered: $200,000 per week at peak
- Active in gambling: 1990s–2010s
5. George Clooney
Unlike others on this list, George Clooney’s connection to gambling isn’t just about playing—it’s also about business. The Hollywood star once tried to launch his own casino in Las Vegas but the project never materialized.
While filming Ocean’s Eleven, Clooney developed a love for poker and was often seen playing with co-stars off-set. His attempt to open a casino showed his deep fascination with the industry beyond just playing.
- Game of choice: Poker
- Amount wagered: Unknown, but invested millions in casino plans
- Active in gambling: 2000s
6. Wayne Rooney
Football star Wayne Rooney has never shied away from his love of gambling, particularly in casinos and on sports. His high-stakes betting habits have made headlines multiple times.
At one point, Rooney reportedly lost £500,000 in just two hours at a Manchester casino, a testament to the risks he was willing to take.
- Game of choice: Roulette & blackjack
- Amount wagered: Lost £500,000 in one night
- Active in gambling: 2010s
7. Dana White
UFC president Dana White is known for his love of high-stakes blackjack, and unlike many celebrities, he’s actually a consistent winner. His skills at the table have even led to some Las Vegas casinos banning him or reducing his betting limits.
White once won over $7 million in a single night at the Palms Casino, prompting the establishment to cut off his privileges.
- Game of choice: Blackjack
- Amount wagered: Up to $50,000 per hand
- Active in gambling: 2000s–present
8. Charles Barkley
NBA legend Charles Barkley has never hidden his love for gambling, though he admits it hasn't always been in his favor. He’s spoken openly about losing millions in casinos.
Barkley estimated that he lost about $10 million through gambling, with one single-night loss of $2.5 million. Despite this, he remains a frequent visitor to casinos.
- Game of choice: Blackjack & sports betting
- Amount wagered: Lost over $10 million in total
- Active in gambling: 1990s–present
9. Ben Affleck
A known poker and blackjack enthusiast, Ben Affleck has taken gambling seriously, even studying card counting. His skills became so sharp that he was famously banned from playing blackjack at the Hard Rock Casino in Las Vegas.
Affleck once won $800,000 in one night using card counting, proving his ability to outplay the casino.
- Game of choice: Blackjack & poker
- Amount wagered: Frequently plays high-stakes games
- Active in gambling: 2000s–present
10. 50 Cent
Rapper 50 Cent is known for placing bold, high-stakes sports bets, often making headlines for his confident wagers. His fearless attitude in gambling mirrors his persona in the music industry.
He once won $500,000 on a bet that the New York Giants would win the NFC Championship, showing his willingness to put his money where his mouth is.
- Game of choice: Sports betting
- Amount wagered: Frequently over six figures per bet
- Active in gambling: 2000s–present
From the calculated risks of Ben Affleck’s blackjack strategy to Floyd Mayweather’s fearless sports betting, these personalities bring the same confidence and intensity to gambling as they do to their careers. Whether winning millions or taking massive losses, their passion for the game remains unwavering—proving that, for some, the stakes are always high.
