Celebrities Who Love to Bet on Sports

When you’ve got millions in the bank and an unhealthy appetite for risk, the thrill of just watching sports just doesn’t always scratch that itch.

From Hollywood A-listers to chart-topping musicians, some of the world’s biggest celebrities love putting serious money on the line when their favourite teams take the field. These are some of the highest-profile bettors who prove that sports gambling isn’t just for the average fan.

Hollywood Stars Who Love to Bet on Sports

Ben Affleck: Poker Champ and Sports Bettor

Ben Affleck isn’t just counting cards in the movies. The Oscar-winning actor is a serious poker player who’s been banned from the blackjack tables at the Hard Rock Casino in Las Vegas for card counting. However, while Affleck’s poker skills are pretty well-documented, he’s also known to enjoy sports betting, keeping some private wagers here and there that are rumoured to be worth quite a pretty penny. 

Charlie Sheen: High-Risk Sports Gambling History

Charlie Sheen is the poster boy for wild, high-stakes gambling. During his peak on “Two and a Half Men,” where he was earning $1.8 million per episode (≈ CA$2.5 million), Sheen was reportedly betting up to $200,000 per week (≈ CA$279,350) on sports. His most famous bet? He dropped $1 million (≈ CA$1.4 million) on Manny Pacquiao to beat Oscar De La Hoya, claiming he had a premonition. He won, but the victory felt hollow. As Sheen put it, “I felt nothing.” That moment led him to become what he now calls a “retired gambler.”

Musicians Who Wager on Games Off-Stage

Drake: Heavy NBA and NFL Bets, Public Slips

Drake might be the most public celebrity bettor in the world. The Canadian rapper regularly posts betting slips showing wagers worth hundreds of thousands, sometimes millions. 

One example of this happened in 2024, where Drake lost $500,000 (≈ CA$698,380) betting on the Dallas Mavericks to win the NBA championship before dropping $355,000 (≈ CA$495,850) on Mike Tyson to beat Jake Paul, and throwing away $300,000 (≈ CA$419,030) betting Canada would beat Argentina in the Copa América.

But when Drake wins, he wins big – claiming victories of over $1 million (≈ CA$1.4 million) on NFL accumulators and UFC fights. The problem? His losses are so frequent that the “Drake Curse” became an internet meme. 

50 Cent: Boxing Bets

Curtis “50 Cent” Jackson lives up to “Get Rich or Die Tryin” when it comes to betting. In 2015, he wagered $1.6 million (≈ CA$2.2 million) on Floyd Mayweather to beat Manny Pacquiao and won comfortably. He’s also had NFL success, winning over $500,000 (≈ CA$698,380) when the New York Giants beat the 49ers in the 2012 playoffs. As he once rapped, “I lost money when I bet on Roy, won money when I bet on Floyd.”

Snoop Dogg: NFL Picks

Snoop Dogg is as much a part of NFL culture as touchdown dances. The Long Beach legend regularly shares his picks on social media and has hosted NFL commentary shows. While Snoop bets more for entertainment than serious investment, he’s not shy about putting money on football games.

Athletes Who Bet After the Final Whistle

Michael Jordan: The Ultimate Competitor

Michael Jordan’s competitive streak didn’t end on the basketball court, as many of us probably know. The Bulls legend is notorious for his gambling habits that allegedly contributed to his first retirement. Jordan admitted to losing $165,000 (≈ CA$230,460) at Atlantic City in one night and dropped $1.25 million (≈ CA$1.75 million) to businessman Richard Esquinas over golf games, and those are just the losses we know about.

Charles Barkley: $30 Million in Losses

“Sir Charles” has openly admitted to losing approximately $30 million (≈ CA$41.9 million) through sports betting and blackjack. But for an ex-athlete, he is probably the worst bettor of all time. He consistently picks the underdog for no reason and bets against the favourite just to prove a point.

However, Barkley eventually recognized he had a problem and took a two-year break before returning to gambling in “moderation” – though his moderation probably looks different than most people’s.

Phil Mickelson: Golf’s High-Stakes Bettor

A 2022 federal audit revealed Mickelson racked up $40 million (≈ CA$55.8 million) in gambling losses between 2010 and 2014, putting a dent in his overall legacy. Many didn’t see him as a gambler, but his most famous win came in 2001 when he backed the Baltimore Ravens to win the Super Bowl at 28-1 odds, netting $560,000 (≈ CA$782,180). He was once even reprimanded by the PGA for betting with fellow pros during tournament rounds.

Floyd Mayweather: Money Mayweather Lives Up to His Name

Floyd Mayweather regularly posts betting slips showing six and seven-figure wagers. In 2014, he reportedly won $4.7 million (≈ CA$6.56 million) in one month betting on NFL games. While less forthcoming about losses, rumours suggest he’s been down as much as $50 million (≈ CA$69.8 million) at various points.

Pete Rose: Banned for Life

Pete Rose holds the unfortunate distinction of receiving a lifetime ban from Major League Baseball for betting on the sport. The Reds legend denied allegations for 14 years before admitting in his 2004 autobiography that he bet on his own team every game he managed. Rose’s gambling destroyed what should have been a Hall of Fame career.

Big Wins and Even Bigger Losses

Celebrity sports betting is filled with so many cautionary tales that it’s almost laughable, but again and again people fall into the trap. For example, Czech hockey star Jaromir Jagr accumulated $500,000 (≈ CA$698,380) in losses with an online sportsbook despite being the highest-paid NHL player in the 1990s. While guys like Paul Hornung were suspended for the entire 1963 NFL season for betting just $100-$500 (≈ CA$140-CA$698) on games.

On the winning side, British golfer Lee Westwood did manage to win £48,000 (≈ CA$90,180) in 2019 at the Cheltenham Festival, turning £240 (≈ CA$451) into a massive payday.

The Influence of Celebrities on Betting Trends

When Drake posts a million-dollar betting slip, it doesn’t just get likes – it influences betting behaviour. Celebrity betting has become a powerful marketing tool, with Drake’s partnership with Stake normalizing high-stakes betting for millions of followers. 

However, it’s not always changing things in the way sportsbooks would hope. The “Drake Curse” phenomenon shows how celebrity bets can actually move betting lines, with some bettors actively betting against teams Drake backs.

Is Celebrity Betting Glamorous or Risky?

The glamorous image of celebrity sports betting – private boxes, million-dollar wagers, Instagram posts – masks a darker reality. For every Floyd Mayweather posting about wins, there’s a Charles Barkley admitting to $30 million (≈ CA$41.9 million) in losses or Phil Mickelson facing a $40 million (≈ CA$55.8 million) hole.

Celebrity betting glamorizes something that can be genuinely harmful. When fans see their favourite rapper dropping $500,000 (≈ CA$698,380) on a game like it’s nothing, it creates unrealistic expectations. Most people can’t afford those losses, and social media promotion normalizes risky behaviour.

Responsible Gambling

While it’s fun to laugh and read about celebrities winning and losing millions, gambling should always be done responsibly. Stories of massive losses aren’t just in the news or on your feed – they’re cautionary tales about what happens when betting spirals out of control.

If you bet on sports, set strict limits on what you can afford to lose. Treat it as entertainment, not a way to make money. If you find yourself chasing losses or betting more than you can afford, seek help. Many jurisdictions offer resources for problem gambling, including hotlines, counselling services, and self-exclusion programs.

If you’re experiencing problems with gambling, help is available through these Canadian resources:

• Problem Gambling Helpline: 1-888-230-3505 (24/7, free, confidential)
• Responsible Gambling Council (Ontario): responsiblegambling.org
• Centre for Addiction and Mental Health: camh.ca
• Gambling Therapy: gamblingtherapy.org (online support)