Celebrity Gamblers: 10 Wild Wins and Jaw-Dropping Losses

Explore the high-octane world of celebrity gambling, where the stakes are sky-high. From Michael Jordan's legendary casino gambling to Ben Affleck's poker prowess, discover how iconic athletes and Hollywood stars have navigated the scary world of high-stakes casino and sports betting. Find out who came out on top, who faced colossal losses, and what these tales reveal about the price of fame and fortune.

10 of the biggest celebrity gamblers

In the glittering world of fame and fortune, where the stakes are as high as the skyscrapers in Las Vegas, some celebrities and sporting icons find thrill not just in their careers but in the adrenaline-pumping world of gambling.  

Therefore, in no particular order, we have delved into the tales of 10 celebrities whose gambling habits have made headlines for differing reasons. 

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1. Michael Jordan's High-Stakes Gambling

First up, arguably the greatest player to ever step foot on the NBA court—none other than Michael Jordan.

A man who shattered the hoop dreams of many a rival and a man who is infamous for his love of gambling. He has been known to bet on everything from the outcome of golf tournaments to casino games, with some reports suggesting he lost millions in a single night in Atlantic City.  

Such are his gambling habits, it even led to rumors that his first retirement from the NBA was related to these activities, though this was never confirmed. One thing that is confirmed? The millions he has made thanks to his trademark Nike Air Jordan trainers.  

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2. Ben Affleck's Blackjack Obsession 

Recently in the news after Jennifer Lopez announced their divorce after two years of marriage, actor Ben Affleck is also known for his skill at live blackjack, to the point where he was reportedly banned from the Hard Rock Casino in Las Vegas for being "too good."  

The whispers around Hollywood suggest that Affleck won large sums of money by counting cards—not a strategy that is not illegal but certainly frowned upon by casinos and a quick way to get banned from such establishments. 

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3. Charles Barkley's Gambling Woes

Back to the basketball court, Charles Barkley is another sports figure known for his love of gambling. The former Phoenix Suns star has admitted to losing over $25 million through various forms of gambling, including betting on sporting outcomes and playing casino games.  

The television analyst has handed over an eye-watering sum of money to the sportsbooks and casinos. Although Barkley is quoted as saying he has no regrets, such losses have meant a slowing down in betting volume. 

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 4. Floyd Mayweather's Massive Sports Bets

Moving from the basketball court to the boxing ring, Floyd Mayweather is the fourth entry on OLBG's list of those who have dabbled in the sport known as the sweet science. Floyd "Money" Mayweather is known for his extravagant lifestyle, which includes making massive sports bets. 

He has reportedly placed millions on single sporting events, particularly on NFL and college football games and when doing so, his winning attributes in the ring have also transferred to getting the better of the sportsbooks.

Mayweather has claimed to win big, but at the same time his losses are less publicized. This begs the question: Is the undefeated fighter simply the best or simply better at keeping any losing bets hidden?

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5. Tiger Woods' High-Stakes Gambling

One of two golfers to make this list is none other than Tiger Woods. Woods has reportedly indulged in high-stakes gambling, particularly within the "Sin City" known as Las Vegas. Rumors suggest that he is said to have placed bets as high as $25,000 per hand in blackjack. 

That hand may sound a lot, but considering his career earnings are approaching a rather cool $2 billion, $25,000 can be considered small change by comparison. 

 However, a high profile due to his sporting talent also means a higher level of scrutiny when it comes to his daily affairs, with Woods' gambling habits coming under the spotlight in the last few years. 

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6. Dana White's Casino Wins and Losses

Heading to the world of MMA—a world that is largely ruled by Boston's Dana White. UFC President White has an affinity for Las Vegas, not only because it hosts many of the fighting league's events, but also because it has hosted many of his blackjack hands.

Like any good gambler, White is quick to tell the world when he comes out on top. In fairness to the MMA mogul, he is not shy regarding his losses. In March of this year, the 55-year-old told Max Friedman of a $3 million loss, which White thought was $80,000 at first. 

A punishing loss, but he has also punished the blackjack tables to the point where a $3.2 million win at a Las Vegas casino would soon see him kicked out of the establishment. And because of his skill, he is also blacklisted from several venues. 

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7. Tobey Maguire and the High-Stakes Poker Scene 

We return to Hollywood now, and this time, Tobey Maguire takes center stage. Maguire was involved in illicit underground high-stakes poker games with other celebrities who have appeared on the big screen. 

These games became infamous after they were revealed in the memoir Molly's Game (which was later made into a movie). They involved millions of dollars and had nosebleed stakes for those involved. 

Maguire reportedly won substantial sums of money during this run of underground card duels—some reports suggest that the Spider-Man star won as much as $36 million in this high-risk/high-reward setup.

However, $300,000 of those winnings were reportedly won off a hedge fund investor who is now in prison for operating a Ponzi scheme. After Maguire was then sued, he announced an out-of-court settlement worth $80,000 in 2011.  

8. Phil Mickelson's Sports Betting

Returning to the putting green for the second of two golfers on this list and joining Tiger Woods is Phil Mickelson. Mickelson is no stranger to a sporting wager, with his most famous bet being connected to the Superbowl. 

During the 2000-2001 NFL season, Mickelson placed a bet that the Baltimore Ravens would win the Super Bowl. With 22-1 odds at the start of the season, he confidently wagered $20,000. When the Super Bowl concluded with the Ravens as champions, Mickelson walked away $440,000 richer.

However, this would be small change compared to the reported amount of money that the golfing star has bet across his career. A figure as high as $1 billion as quoted within Billy Walters' book "Gambler: Secrets from a Life of Risk."

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9. Allen Iverson's Gambling Troubles

Former NBA star Allen Iverson struggled with gambling throughout his career. He reportedly lost large sums of money in casinos and had been banned from several casinos for disruptive behavior. 

For a basketball icon who at one stage had a reported personal wealth of $200 million—a figure that he also reportedly blew through—his gambling nadir was arguably not the sums of money that may have been lost over the years but his ejection from Bally's casino in 2004.

A trip to Atlantic City saw Iverson at the blackjack table and with the urge to go to the toilet, he decided against leaving his current vicinity and instead relieved himself in a nearby trash can—not the kind of behavior that is going to get you a return visit. 

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10. 50 Cent's Million-Dollar Bet

Last but certainly not least is one of the kings of the rap game. When it comes to betting acumen, it seems as if 50 Cent is just as regal. 50 Cent made headlines when he bet $1 million on a Super Bowl game—backing the New York Giants to win at the expense of the New England Patriots in 2012. 

The Giants would subsequently go on to win and lift the Vince Lombardi Trophy. In doing so, 50 Cent reportedly walked away with a bumper payday as reward for what would have been shredded nerves throughout. 

However, he's also rumored to have lost substantial amounts on other bets, so it has not all been plain sailing for the man at the head of G-Unit. Then again, a personal wealth of $40 million will go a long way to softening any substantial losses with the sportsbooks.