Famous Sports Betting Athletes and Celebrities

There are numerous famous sports betting athletes and celebrities that have made some huge wagers. We all love betting on sports. It makes no difference if you’re the neighbor who bets a few bucks or if you’re an A-list celebrity betting a cool million. No matter how much money you already have, the thrill of winning big money is alluring. There have been a number of recognizable celebrities and athletes that have been known to partake in the gambling world.

Key Points

– There have been several well-known bets placed by athletes and celebrities. 

– Some of the largest wagers in sports betting have been placed by famous athletes.

Floyd Mayweather Jr. Loves Risk

Floyd Mayweather Jr., also known as “Money,” is a world champion boxer who has experienced success both inside and outside of the ring. His stellar gambling record matches his impressive boxing resume.

Mayweather randomly wagered $50,000 on a Colorado State football game. He won $45,000. That’s nothing. He went on a four-day bender betting on NBA games and boxing. He wagered a total of $350,000 and walked away with over $825,000!

It is said that Mayweather once won $4.7 million in a month betting on the NFL. Of course, he was betting ridiculous amounts, including $800K on a single bet. It’s also reported that Mayweather had gambling losses of $50 million in 2017 alone.

50 Cent on Famous Sports Betting

The rapper Curtis Jackson, aka 50 Cent, loves to show off his huge wagers. He once famously tweeted that he won $500,000 betting on the New York Giants to beat the San Francisco 49ers in Super Bowl XVI. 

Jackson loved the Giants so much he doubled down, wagering a cool million dollars on the G-Men in Super Bowl XLVI. It was one of the most thrilling Super Bowls in history as the Giants ended the New England Patriots’ perfect season with a 21-17 victory. 50 won a lot more than 50 cents. 


His Airness

He is arguably the greatest basketball player of all-time, possibly even one of the greatest athletes ever. It’s also well-known that Jordan loved to bet, especially on himself. Jordan’s gambling stories are absolutely legendary.

After winning $100K in a craps game, Jordan famously wagered all his winnings in a game of Rock, Paper, Scissors. There were numerous trips to casinos, including a night where Jordan lost $165,000.

Some of his biggest bets came on the golf course. Jordan would bet as much as $300K on a single hole! He once lost $1.25 million on a round of golf to San Diego businessman Richard Equinas. 

Jordan bet on anything. Watch the documentary “Last Dance” and you’ll find out about bets like this one. Jordan bet one of his Chicago Bulls teammates $900 that his luggage would come off the team plane first.

Famous Sports Betting Athletes – Sir Charles

Sir Charles Barkley claimed that before admitting he had a minor gambling problem, he had lost about $30 million on sports and blackjack wagers. He continues to maintain that he didn’t actually have a problem, just that he was betting excessively.

Barkley “probably” put $100,000 on this year’s Super Bowl. He once won big on a Super Bowl. Back in 2002, he put $500K on the New England Patriots and won $700K to walk away with a nice $1.2 million.

It is said that Barkley has tamed his sports betting and now only loses thousands instead of millions.

Two Full Men

Charlie Sheen played the lead role in the TV show Two and a Half Men. He was eventually replaced by Ashton Kutcher. Both actors are known to dabble in betting on sports. 

Sheen made a reported $1.8 million per episode. That’s a good thing because he typically bet around $200K per week on sports. His excessive partying is stuff of legend and led to his being ousted from the show. 

Kutcher then took over. He actually had a side business where he would place wagers for the biggest sports betting syndicate in the U.S. Kutcher’s group would routinely make $750K per month betting on college football.

Another Famous Sports Betting Athlete – Pete Rose

The only MLB athlete in history to appear in more than 500 games at five different positions was Rose, a former player and manager for the Cincinnati Reds. He also has another record, which is not particularly admirable.

Pete Rose was the first player to be permanently banned from baseball for sports betting in 1989. Rose initially denied the allegations, but finally did admit that he had bet on baseball games. 

Rose is MLB’s all-time hits leader with 4.258 hits. He won three World Series rings and numerous other awards but has been left off of every Hall of Fame ballot in which he has been eligible. 


Rapper Birdman, who is a Patriots fan, shared an Instagram post about a $100,000 wager he made against fellow rapper AR-Ab in 2018. The two wagered on that season’s Super Bowl matchup between the Patriots and Eagles’. 

The original bet was for $100K to the winner. Before the Instagram post disappeared, the bet was reportedly increased to $200K. New England lost to the Eagles.

Birdman wasn’t hurting. In 2010, he wagered $4 million on Mayweather to beat Shane Mosley. Mayweather’s win earned Birdman a nice $1 million.