There is a reason why sports betting has exploded in popularity over the last century. From humble beginnings, the game has completely changed over time. Whether it’s the casual sports bettor that wants to throw a few dollars on a game in an effort to add to the entertainment of an event or the professional handicapper that is completely invested in making some serious money by betting on sports, there are all kinds of different people that want to play. With so many different types of people looking to get in on the action, it’s no surprise that sporting heroes and some of Hollywood’s biggest stars are also famous gamblers. Here is a look at the top 10 biggest celebrity sports bettors.
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“Jeopardy” James Holzhauer
One of the newest additions to the list is James Holzhauer, a professional bettor who grew to fame through the show Jeopardy. He always dreamed of being on the show and when he finally got the chance, he put his sharp analytical skills to work. Using a keen sports betting strategy – often wagering his full amount in Final Jeopardy – Holzhauer would go on to win 32 shoes in a row and $2.462 million. He came close to beating Ken Jenning’s all-time record of $2.52 million in winnings but Jennings also won that over 74 episodes. Holzhauer’s performance showed that there is definitely skill related to sports betting and it’s not just a guessing game.
Sticking with another celebrity that loves to brag about the big bets that he places on sporting events, 50 Cent takes the second spot on our list of the biggest celebrity sports bettors. From his famous $500K tweet when the New York Giants beat the San Francisco 49ers in the NFC Championship game to countless other big time wagers over the years, it’s clear that 50 Cent loves to flex his sports betting muscle just as much as he loves to actually win money betting on the events.
It’s no secret that M.J. has earned a reputation over the years. One of the most famous athletes of our time, Jordan’s gambling record didn’t match his court success but he was a big time bettor and probably still is. The former Chicago Bulls star and current Washington Wizards owner admitted to losing millions at an Atlantic City casino. While he still has plenty of money to spare, those betting numbers combined with his incredible athletic legend earn him a top spot on this list.
Sheen is another example of a big name celebrity that loves to bet on sports. The infamous actor is rumored to have a slight gambling addition, with his ex-wife Denise Richards claiming that he regularly bet around $200K on sports each week when they were together. Sheen was also rumored to be partnered with a sports betting website back in the day. While he has had his share of issues with drinking and drugs over the years, it’s pretty notable that he is also one of the biggest celebrity sports bettors based on his fame and willingness to put down large sums of money on sporting events.
The second basketball legend to appear on this list, Sir Charles once admitted to losing about $30 million in sports and blackjack bets before he actually admitted that he has a problem. After taking a couple of years off to get his life back on track, Barkley got right back in to the action placing some big time bets on sports. While he doesn’t wager as much as he used to, there is no doubt that Barkley is still active enough to earn a spot in the top-five for our list.
Kutcher once told Esquire magazine that he was clearing $750K betting on college football over a month of work. While the celebrity actor isn’t as big as the man he replaced on Two and a Half Men, Kutcher’s penchant for betting large sums of money on sporting events ensured him a spot on this list.
The former Cincinnati Reds player and manager was destined for the Hall of Fame after playing more than 500 games in five different positions. However, Rose received a lifetime ban from baseball for betting on the sport, even though he never admitted it. Rose denied the charges for 14 years until the release of his autobiography titled “My Prison Without Bars”, in which he admitted to betting on his team every single game. Since it cost him a trip to the Hall of Fame and some harsh years under scrutiny, there is no doubt Rose deserves a spot on this list.
Floyd Mayweather Jr.
It should be no surprise that “Money” Mayweather tops our list of the biggest celebrity sports bettors. After all, the world champion boxing star is no stranger to putting big money on sporting events. From a $45K win after backing Colorado State with a $50K bet to a willingness to post pictures with seven-figure bets attached to them, Mayweather stands out as the biggest celebrity sports bettor in large part because of his fame and willingness to put a lot of money on the line. Considering he is worth more than $400 million and has such a passion for sports, it’s obvious why he is the biggest celebrity sports bettor in the world.
One of the highest paid NHL superstars of the 1990’s, Jagr was no stranger to betting on sports. However, the sports betting would bite him in the butt when he piled up $500K in losses with one online sportsbook, which was leaked to the press. While his hardcore gambling days seem to be behind him at this point, the fact that Jagr got himself in so much trouble while still in the prime of his NHL career landed him a spot on this list.
‘Birdman’ Bryan Williams
“The Birdman” recently posted on Instagram a $100,000 bet against fellow rapper Ar-Ab about the 2018 Super Bowl between the New England Patriots and Philadelphia Eagles. That same wager then grew to $200K before the posts mysteriously disappeared. The Eagles went on to win the Super Bowl and Williams posted an Instagram photo of himself covered in cash. Nobody knows for sure whether Birdman paid the $200,000 loss but AR-Ab definitely would want to collect on that kind of money. That bet alone earned Williams a spot on our list of the top 10 celebrity sports bettors.
One of the most famous actors of a generation, Ben Affleck has been a big fan of gambling for quite some time. As a matter of fact, his passion for it teetered over into addiction, which is never a good thing. He loved to play poker too, getting into $100,000 buy-in events. The A-list actor was forced to join rehab in 2001 for his addiction to gambling (as well as alcohol).
“The Golden Boy” was a professional American football player and a member of four world champion Green Bay Packers teams that included the first Super Bowl win. Despite his incredible fame at the time, he was suspended for the entire 1963 season for betting large sums of money on the NFL and NCAA games. While he might not be as well known as some of the other names on this list, there is no doubt that The Golden Boy earned his spot on our top 10 celebrity bettors based on his track record.
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