Top 7 Celebrity Gamblers

Jan 8, 2023 | Articles, Gambling

Celebrities love to spend their money, that’s no secret. Some of them, spend their money more recklessly than others, which often ends up in bankruptcy. From luxury cars to real estate, celebrities can spend several millions in one night, yet alone in one month. But one of the biggest addictions for celebrities is gambling, be it online, or in casinos. And while some celebrities end up being broke, others end up being “pros”, as they learn how to wager, how to bet, when to bet, and what to bet on. As mentioned, most celebrities play in live casinos, but few of them are fond of betting sites like, where they usually use aliases and other names to fuel their addiction, but stay unnoticed. Some 15 years ago, online gambling was not as developed as it is today. Best betting is just one website, but there are countless others, like for example. Let’s take a look at few famous people with a gambling addiction.

Ray Romano

The actor became popular with the sitcom “Everybody loves Raymond”, a TV show in which Raymond showed all the challenges and benefits of a middle class family living in the suburban area in the United States. The fame and fortune that Raymond brought to Romano was off the charts.

The actor became one of the most popular faces in TV, and one of the first to receive huge paychecks from a TV show. Raymond was almost as popular as Friends, and Romano was reaping the benefits. But few people know that when the show ended, Ray Romano battled with a huge gambling addiction that almost cost him everything.

In 2009, Ray produced and started in a new TV show, called “Men of a Certain Age”, in which he plays Joe Tranelli, middle-aged man who has gambling addiction. The show focuses on three middle-aged men that are staying friends after graduation. But at the time, few people knew that the character of Joe was actually based on Ray Romano. Few years after the show ended in 2011, Ray admitted that he was actually Joe, and that at one point, he asked for help from Gambler’s Anonymous.

Nowadays, the actor gambles on virtual bets, but doesn’t visit casinos or live betting sites as he used to. He does compete in World Series of Poker, but Romano is realistic he doesn’t stand a chance.

Tiger Woods

Tiger’s interest in gambling started when he became good friends with the likes of Michael Jordan and Charles Barkley, two extremely popular high rollers. The more Woods hanged out with Barkley and Jordan, the more he gambled.

But the golf player had his own version of what gambling should look like. It is a known fact nowadays that Woods has a $1 million limit in every casino in Vegas, and he bets as much as $25,000 per hand. His favorite casino though is the Mansion at the MGM Grand.

Going deeper into his gambling habits, according to some casino sources through the years, Woods always request a table for himself, filled with party girls. Those party girls are the reason he and his wife divorced, and she took huge part of his fortune. Several sources have confirmed that the divorce was worth $750 million.

Michael Phelps

Michael Phelps doesn’t only have a gambling problem, he has a competitiveness problem. The same driving force behind his competitiveness that netted him 22 Olympic medals brought Phelps to the gambling table.

According to his friends, Phelps reached culmination of the problem in 2012, after the Olympics in London, when he gambled more and more. His competitive mindset and his attitude “don’t quit until you win” are great in the pool. However, in the gambling world, not so great. In 2012, Michael was caught gambling for 8 hours in a casino in Baltimore, Maryland, after which he was arrested for driving under influence of alcohol.

Since then, the Olympic gold medalist has battled his addiction, and is now at peace.

Tobey Maguire

Tobey is one of those celebrities that don’t try to hide their fondness for gambling. In fact, the former Spiderman star has participated in World Series of Poker where he used the tips he got from professional poker player, Daniel Negreanu.

Some sources say that over the years, Tobey has won $10 million playing poker, and they might be right. But the problem is, Maguire is also playing underground poker. In 2011, he was part of a lawsuit for organizing illegal gambling ring. Other actors, such as Ben Affleck and Leonardo DiCaprio participated, but they were not part of the lawsuit.

Ben Affleck

Speaking of Affleck, he is the next celebrity on the list. The new Batman is known for his fondness of both poker and blackjack, and in 2004 he won the California State Poker Championship.

Fun fact: Affleck has played in the gambling themed thriller “Runner, Runner” alongside Justin Timberlake. Affleck’s gambling addiction forced him to check into a rehab facility in 2001. The reports were neither confirmed neither dismissed over the years.

Michael Jordan

The gold standard in celebrity gambling is Michael Jordan, a former basketball player that has seen a fair share of gossip linked to his name. For example, back in 1993, when Michael Jordan retired, some rumors surfaced that the best player in the NBA has retired due to his gambling habits. One rumor went as far as saying that then Commissioner David Stern banned Jordan from the game.

Nowadays, MJ is worth more than $1 billion, and he can afford to gamble as much as he likes. He first admitted he has a gambling problem in 1993 in an interview with a close friend that aired during the Finals. Jordan classified his gambling addiction as a “hobby that he can afford”. Another story that surfaced during the 93 playoffs, one in which MJ was accused of gambling during the series with the Knicks. The Bulls were down 2:0, and after the article was published, the Bulls went 4:0 to close out the series and advance to the Finals.

Allen Iverson

The “Answer” is a classic story of a celebrity going from hero to zero in a matter of seconds thanks to gambling. Iverson somehow managed to gamble $200 million, money he made during his professional NBA career. At one point, Iverson asked former teammates for money to pay off his debt. He was also banned from casinos in Atlantic City and Detroit due to his debts.

Iverson accumulated money for years from his basketball career, but also endorsements. He had a lifetime contract with Reebok, but he lost the contract at the end of his career, when his gambling habits surfaced. His wife divorced him, and at one point during the trial for divorce, Iverson said to his former wife that he doesn’t have money for a cheeseburger.

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Thomas B.