In the glittering world of fame and fortune, where the stakes are as high as the skyscrapers of Las Vegas, some celebrities and athletes find excitement not just in their work but in the adrenaline-pumping world of gambling.
From famous athletes to Hollywood stars, the allure of high-stakes gambling has attracted many, resulting in legendary wins as well as huge losses.
Whether it’s Michael Jordan’s infamous casino nights or Ben Affleck’s blackjack prowess, these stories reveal the dangerous and often costly side of the rich and famous.
So, in no particular order, OLBG took a closer look at the stories of 10 celebrities whose gambling habits made headlines for various reasons.
1. Michael Jordan’s high-stakes gambling
First off, the greatest player to ever step onto an NBA court is none other than Michael Jordan.
A man who dashed the basketball dreams of many rivals, he was also a notorious gambler, known for betting on everything from golf tournament outcomes to casino games, and once reportedly lost millions of dollars in a single night in Atlantic City.
His gambling habit has even led to rumors that his initial retirement from the NBA was linked to these actions, but this has never been confirmed. One thing is for sure, he has made millions thanks to his trademark Nike Air Jordan trainers.
2. Ben Affleck’s Blackjack Obsession
Actor Ben Affleck, who recently made headlines when Jennifer Lopez announced their divorce after two years of marriage, is also known for his blackjack skills and has reportedly been banned from the Hard Rock Casino in Las Vegas for being “too good” at the game.
There are rumors circulating in Hollywood that Affleck has won large sums of money by counting cards, which, while not an illegal strategy, is certainly frowned upon in casinos and a quick way to get banned from such establishments.
3. Charles Barkley’s Gambling Troubles
Back on the basketball court, Charles Barkley is another athlete known for gambling. The former Phoenix Suns star has admitted to losing over $25 million on various forms of gambling, including betting on sports outcomes and casino games.
As a TV commentator, Barkley has shelled out staggering amounts to sportsbooks and casinos, and while he says he has no regrets, the losses mean he’s putting less money on the table.
4. Floyd Mayweather’s huge sports gambling spree
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 lavish lifestyle, including betting huge amounts on sports.
He reportedly bet millions of dollars on single sporting events, primarily NFL and college football games, and in doing so, parlayed his winning qualities in the ring into winnings at the sportsbooks as well.
Mayweather claims big wins while also publicizing his losses, which raises the question: Are unbeaten fighters simply the best, or just better at hiding their losses?
5. Tiger Woods’ Big Gambling
One of the two golfers on this list is none other than Tiger Woods. Woods was reported to have had a penchant for high-stakes gambling, especially in Las Vegas, known as “Sin City.” Rumor has it that he was betting as much as $25,000 per hand on blackjack.
That may seem like a lot, but considering his lifetime earnings are approaching $2 billion, $25,000 is a pittance in comparison.
But the high profile that comes with being an accomplished sportsman also means that his daily life comes under intense scrutiny, with Woods’ gambling habits coming into the spotlight in recent years.
6. Dana White’s casino wins and losses
Enter the world of MMA, dominated by Boston’s Dana White. White, the president of UFC, has a soft spot for Las Vegas, home to many of the league’s fighting league events, but also the city’s many blackjack matches.
Like any good gambler, White is quick to tell the world when he wins. In fairness, the MMA mogul isn’t shy about losing either. In March of this year, the 55-year-old told Max Friedman he’d lost $3 million. White initially thought he’d lost $80,000.
It was a bitter defeat, but he’s also had his share of blows at the blackjack tables, winning $3.2 million at a Las Vegas casino that got him kicked out of the establishment shortly after, and his skill has led to him being blacklisted from several venues.
7. Tobey Maguire and the high stakes poker scene
Now, the story returns to Hollywood, but this time starring Tobey Maguire, who, along with other big-screen celebrities, was involved in illegal underground high-stakes poker games.
These games became infamous after being exposed in the memoir “Molly’s Game” (which was later made into a film), and involved high stakes and millions of dollars for those involved.
Maguire has reportedly won significant amounts of money in this series of underground card duels, with some reports claiming the Spider-Man star has won as much as $36 million in this high-risk/high-reward game.
However, $300,000 of that winnings was reportedly won from a hedge fund investor currently serving time in prison for running a Ponzi scheme. Maguire was subsequently sued and announced an out-of-court settlement of $80,000 in 2011.
8. Phil Mickelson’s sports betting
Of the two golfers on this list, the one who will be following Tiger Woods back onto the putting green is none other than Phil Mickelson. Mickelson is no stranger to sports betting, with his most famous bet being on the Super Bowl.
During the 2000-2001 NFL season, Mickelson bet that the Baltimore Ravens would win the Super Bowl. With odds of 22 to 1 at the start of the season, he confidently bet $20,000. When the Super Bowl ended with the Ravens winning, Mickelson walked away $440,000 richer.
But that figure is a fraction of what the golf star is said to have gambled over his career – as much as $1 billion, according to Billy Walters’ book “Gamblers: The Secrets of a Risky Life.”
9. Allen Iverson’s gambling problem
Former NBA star Allen Iverson struggled with gambling throughout his career, reportedly losing a lot of money at casinos and being banned from several casinos for disruptive behavior.
The basketball star was once worth a reported $200 million, but has reportedly blown through that sum. His lowest point in gambling was probably not the vast sums of money he’s lost over the years, but getting kicked out of Bally’s Casino in 2004.
During a trip to Atlantic City, Iverson was sitting at a blackjack table when he felt the need to go to the bathroom, but instead of leaving he relieved himself in a nearby trash can – not a behavior he’s likely to revisit.
10. 50 Cent’s Million-Dollar Bet
Last but not least, we cannot forget 50 Cent, one of the kings of rap. When it comes to betting acumen, 50 Cent is no less of a king. In 2012, 50 Cent made headlines when he bet $1 million on the Super Bowl game, betting that the New York Giants would win over the New England Patriots.
The Giants went on to win the championship and hoist the Vince Lombardi Trophy, and 50 Cent reportedly walked away with a lot of money as reward for what must have been a nerve-wracking game.
It hasn’t all been smooth sailing for the G-Unit frontman, however, as he’s rumored to have lost significant amounts on other bets as well, though his $40 million personal fortune would go a long way towards cushioning any big losses at the sportsbooks.
This story was produced by OLBG and reviewed and distributed by Stacker Media.
