Celebrities Who Love to Gamble on Sports

There's plenty of stories out there about celebrities, be them sports stars or otherwise, making big bets and spending much of their time gambling and making wagers.

Michael Jordan

His Airness is arguably the GOAT, not only in basketball but all sports. Though his record with betting can compete well with his on-court skill.

Jordan still had the same confidence and swagger, whether it included betting on himself or others. 

MJ's most famous bets:

  • Former best friend Charles Barkley said once Jordan bet $300k on a single golf putt! 
  • According to former golf partner Richard Esquinas, he and Jordan used to have a baseline wager of $1000 per hole.

Jordan is now a shareholder and ambassador for DraftKings Sportsbook.

MORE: Best Sports Betting Movies

Charles Barkley

Sir Charles may be the best thing to happen to our screens since color television. Chuck's guarantees have become infamous, winning as often as the Jacksonville Jaguars. Barkley has also made some, as he would say, turrible bets over time. 

The Round Mound of Rebound has lost over $30 million gaming, but has also said to have won a million dollars around 10 times. Chuck has since learned moderation and is now working with FanDuel Sportsbook as a brand ambassador. He can be seen placing basketball bets on TNT every week of the NBA season.

Chuck's famous bets:

  • Lost $100,000 betting on the Atlanta Falcons to conquer New England in Super Bowl LI. 
  • Bet $100,000 on the Portland Trailblazers winning the 2020-21 NBA Western Conference.
  • Bet $500,000 on New England against the spread (+14) and $50,000 on NE moneyline, against the St. Louis Rams in Super Bowl XXXVI – won a payout of $800,000.

MORE: Best Sports Betting Quotes Ever

50 Cent

Fiddy isn't shy about much, certainly not the sports and money he wagers on them either – which we don't mind at all! 

Like every bettor he's had varying success, perhaps he would have benefited from using Dimers' Bet Hub before wagering his millions. 

50's most famous bets:

  • Made a $500,000 profit on the New York Giants to defeat the San Francisco 49ers in the 2012 NFC Championship Game. 
  • Agreed to share a nude photo on Twitter if the NY Giants lost Super Bowl XLVI, thankfully for Fiddy they didn't.

MORE: How to Read Vegas Odds

Ashton Kutcher 

Ashton may be known as the poor man's Charlie Sheen on Two and a Half Men, but the actor certainly knows how to bet sports. Despite his own successful acting career, some may say he was an even greater bettor. 

Kutcher admitted he used to place bets for the largest syndicate in America and they "cleared $750,000 in four weeks of College Football."

Kutcher used data and analytics, rather than emotion to become a successful bettor. Be like Ashton, use Dimers' Bet Hub and Quick Picks to get the edge and make a winning play against the sportsbooks.

MORE: Top Sports Gambling Podcasts

Phil Mickelson 

One of the greatest golfers of this generation, Lefty is also a tremendous sports bettor. Mickelson formed a sports betting syndicate back in 2000 with fantastic results. 

Long before the NFL regular season began in 2000, Phil put $20,000 on the Baltimore Ravens (+2200) to win the Super Bowl. As we know, they pummeled the New York Giants 34-7 in Super Bowl XXXV, establishing their legacy as one of the greatest teams of the 20th century. To put the wager in context – Cam Newton's Patriots had virtually the same odds (+2300) of winning Super Bowl LV.

Phil's famous bets:

  • Lost a $1 mid-tournament bet with a spectator at Augusta for failing to get up-and-down in practice. Mickelson had to borrow the single from his caddy!
  • Won $1200 from patrons at Tin Cup after they thought he couldn't hit a ball over a tree. 

MORE: This Week's Golf Picks and Predictions


Drizzy is known for his love of sports. The world's most recognizable Toronto Raptors fan is notorious for wearing the jerseys of every team under the sun. It would only be logical that Drake's love for sports transferred into the betting arena. 

We're certain Drake has won his fair share of wagers, but from what's been publicized, he is Doing It Wrong. Drizzy seems like a pretty fun guy, hopefully his sports betting game isn't so much Laugh Now Cry Later. We'll see ourselves out. 

Drake's famous bets:

  • Lost $60,000 after betting Golden State would defeat the Cavs in 2016 NBA Finals. 
  • Lost $6,000 after he wagered Kentucky moneyline against Wisconsin in 2015 NCAA Basketball Final Four.

MORE: Latest NBA Betting News


If you don't know Birdman from his rapping career, you'll almost certainly have heard of him from his sports betting exploits. He hasn't been shy about his betting success and losses, of which there have been a few. 

Birdman wanted to bet $5 MILLION on the New England Patriots to beat the New York Giants in Super Bowl XLVI – the rematch – but it remains to be seen if the wager ever went through. 

Like his beloved New Orleans Saints, Birdman has had his fair share of big wins and crushing losses in recent decades.

Birdman's famous bets:

  • Lost $2 million wagering on LeBron James' Miami Heat to defeat the Dallas Mavericks in the 2010 NBA Finals. 
  • Bet $4 million – and won – on Floyd Mayweather Jr. to defeat Shane Mosley back in 2010. Birdman made a $1 million profit.

MORE: How to Bet on NFL Games

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