10 Most Famous Celebs with a Serious Gambling Addiction (Past and Present)

10 Most Famous Celebs with a Serious Gambling Addiction (Past and Present)

June 9, 2014
Staff Writer
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Celebrities with a Gambling Problem

Celebs are loaded with money, and many of them use that money to gamble.

Some are successful in it, some are just pure losers. Check out our list of 10 most famous real life celebrities that were reported to have an addiction to gambling.

#10 Dana White

The president of the UFC Dana White is very famous for his gambling habits. He is actually very good at gambling, and has reported that some nights he walks away with up to $5 million just from playing blackjack. He is known to bet $50,000 per hand and has been asked by many casino officials to stop playing at their grounds.

Obviously, his skills are hurting the casinos’ profits. He is notorious for not paying the UFC fighters enough for their fights, but he doesn’t mind making extremely high stakes at each hand. And just recently, Palms Casino in Las Vegas apparently banned Dana White for a second time from playing at their casinos. More information can be found at the Las Vegas Review Journal here.

#9 Tiger Woods

Besides being the most famous and probably the best golf player ever, Tiger Woods is known for his vices too, like sexual affairs and gambling.

One of his mistresses confirmed the rumor that Tiger bets $25,000 per hand when playing blackjack. He is known to be a high roller player and has even received a $1 million betting limit by the MGM Grand in Las Vegas, where he always requests for the table to be filled with beautiful girls. His gambling addiction has become public when he became good friends with Michael Jordan and Charles Barkley who are also on this list for their gambling addiction.

#8 Ben Affleck

Ben Affleck is a passionate card player, be it poker or blackjack. Once he lost a $400,000 poker hand and in 2001 and checked himself in rehab to solve his gambling problem. He is known to spend hours of playing cards in casinos, and many times under the influence of alcohol.

One time he wagered $60,000 on a blackjack hand while being drunk but managed to win $800,000. He even left a generous tip to the casino employees of $150,000. Perhaps the biggest incident for Affleck was when he was banned from a certain Las Vegas casino due to card counting. Oh, and that’s not a rumor – he admitted that he counted cards during rounds of Blackjack.

#7 Tobey Maguire

Toby is most famous for his leading role in the Spider-Man movies, but he is also famous for his addiction to playing poker. He is so addicted to this game that he was even sued for participating in an illegal poker ring. He is also active in the World Series of Poker and has had much success there.

Tobey is actually a very good poker player. So far, he has allegedly won a total of $10 million by playing poker games in casinos. However, this only serves to emphasize his gripping addiction to the game. He has also struggled with alcohol in the past.

#6 Floyd Mayweather Jr.

Floyd Mayweather Jr. is currently the undefeated professional boxer that has knack for betting on sports. His recent winning was reported to be a $3 million win from a wager on college football. He is also known to regularly bet up to $400,000 per sporting event.

His ex-wife even has said that one time she had to drop off $700,000 for him to cover his casino bet, and earlier in January 2014 media reported that Floyd Mayweather may have placed a $10 million bet that the Broncos will win the Super Bowl. In 2017, Conor McGregor mentioned Mayweather’s gambling addiction during their face-off before their fight in Las Vegas.

#5 Michael Jordan

Michael Jordan hasn’t had much success in gambling as he had in playing basketball. He is possibly the best basketball player there ever was, but his gambling skills might need improving. The first case where he displayed his gambling addiction was when he admitted that he lost $165,000 in Atlantic City in 1993.

He is also an avid poker player, with a track record that is less than impeccable. He even gambles when he plays golf with celebs like Tiger Woods and Charles Barkley. At one time Jordan lost $1.25 million in golf to Richard Esquinas, a businessman from San Diego. It is rumored that his gambling was the cause for his retirement from basketball.

#4 Charles Barkley

Barkley is another famous athlete fully devoted to gambling. However, it seems that his gambling career hasn’t been as successful as his athletic one – losing has been a major part of the story. In an interview back in 2006 he said that he lost nearly $10 million and incredible $2.5 million in just one night of Blackjack.

He has admitted that gambling is a serious problem for him when he said that he lost $700,000 in one weekend by betting on the Super Bowl. In 2008 he stated that he will not gamble anymore when a casino sued him for owing $400,000. After a 2-year break, he returned to his old habits. Since his return to casinos, Barkley has been practicing “moderation”. When he was asked how much money he had lost in the past, he responded by giving an estimation of $30 million.

#3 Ray Romano

The actor known for “Everybody Loves Raymond” is actually a former Gamblers Anonymous  “patient”. The funny and lovable guy we all watched in the popular sitcom was battling addiction while the show was still on. A couple of years after the end of the show he was admitted into the program.

He went there by his own will and thankfully, he has succeeded to put his bad habit under control. However, old habits do die hard – he is still gambling as part of the World Series of Poker, although not that successfully. These past few years, he placed bets when playing golf, and virtual bets, but not with real money.

#2 Charlie Sheen

Everybody knows Charlie Sheen! Charlie has always been in the spotlight for his many vices, and gambling is one of them. His ex-wife and actress Denise Richards claimed that Charlie has been spending over $200,000 each week just to satisfy his gambling lust.

According to her, he squandered millions of dollars on his bad habits, all the while forgetting to pay child support. He regularly played poker and loved to bet on sports. He was so addicted to gambling that he even placed a sports bet over his phone while rushing to the hospital for his daughter’s birth. However, after a couple of hard years, it seems that he learned his lesson. Allegedly he doesn’t gamble anymore.

#1 Allen Iverson

Average sports fans think of Allen Iverson as a successful basketball player, one of the very best.

However, little do they know that Allen Iverson went broke because of his gambling debts. His NBA career has earned him $200 million, only for him to throw them away on gambling and drinking. Despite being broke, he is also in debt. His wife left him because of this, and he lost much of the sponsorship deals, such as the $50 million lifetime collaboration with Rebook.

He has even had many unpleasant situations while playing in casinos, resulting in feuds with casino employees and being caught urinating in a trash can in front of a casino. Iverson has been banned by many casinos in Atlantic City and Detroit.

 

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