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

Posted by: CasinosOnline in Articles
Yes, celebrities love to gamble too. Perhaps a bit too much at times. But they seem to afford it.

Yes, celebrities love to gamble too. Perhaps a bit too much at times. But they seem to afford it.

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

Dana White is the president of the UFC, and a person that loves to gamble. 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, 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.


A serious looking Ben Affleck at the poker table.#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.


#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 having won a total of $10 million so far in poker games. However, this is all due to his addiction to the game. He has also struggled with alcohol in the past.


Floyd Mayweather showing off his bling#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.


#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 vice was when he admitted that he lost $165,000 in Atlantic City in 1993. He is also known to actively play poker, although not that successfully. 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.


Charles Barkley with a big smile.

Charles Barkley with a big grin. “Life’s good!”

#4 Charles Barkley

Barkley is another famous athlete fully devoted to gambling, and losing in the meantime. 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 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.


#3 Ray Romano

The actor known for “Everybody Loves Raymond” is actually a former Gamblers Anonymous “patient”. He was admitted into the program at his own will, and has succeeded to put his bad habit under control. He is still gambling as part of the World Series of Poker, although not that successfully, and still makes bets when playing golf, but not with real money.


#2 Charlie Sheen

Charlie Sheen 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. He regularly plays poker and loves 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. Allegedly he doesn’t gamble anymore.


Allan Iverson#1 Allen Iverson

Average sports fans think of Allen Iverson as a successful basketball player, one of the very best, but 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 has been caught urinating in a trash can in front of a casino. Iverson has been banned by many casinos in Atlantic City and Detroit.