Celebrities Who Have Gambling Problems

March 21, 2024
8 mins read

Often ordinary people forget that celebrities are not a unique race exempt from mundane problems and issues such as gambling. Especially when you are a famous person living in a detached reality with enormous sums of money, gambling can be a fun little habit that often turns into a vast, all-encompassing problem. This is our list of celebrities with gambling issues.

Ben Affleck

The Academy-award-winning actor has been known as a passionate card player, particularly a fan of poker and blackjack. Rumors were floating on the internet that the actor entered a rehab facility to deal with his gambling and alcohol addiction at some point. What is interesting is that Ben has a natural talent and is a professional gambler. In the 2000s, Ben participated in Molly Bloom’s high-stakes poker games alongside Leonardo DiCaprio and Tobey Maguire. In 2004 he scooped the $356,000 prize for winning California State Poker Championship, which qualified him for World Poker Tour final tournament. In 2014, he was asked to stop playing blackjack at the Hard Rock Hotel in Las Vegas after a series of wins. The hotel’s management was suspicious that the actor was counting cards, which is illegal in some casinos but frowned upon in every casino. Ben was asked about his addiction in several interviews, but he adamantly denied it.



The famous rapper and maker of undeniable 2000s hits, Cornell Jones Jr., known as Nelly, has battled gambling addiction for most of his life. In 2011 his former promoter, Slim, accused the rapper of blowing all of his finances on gambling and that he was close to foreclosure on his house. In his tweet, Slim wrote: ‘You broke you spent your whole fortune on coke, steroids, Ashanti, pulls and at Harrah’s Casino, you probably there now! Nelly denied all the accusations, claiming that Slim was one of the promoters he worked with back in the day, he revealed: ‘First if you believe Slim was my manager, then this is pointless anyway. Second, don’t nothing go in this body but fish, chicken, turkey, protein, Rozay, Ciroc Remy, and Budweiser! Third, I know some hope the foreclosure statement is true, but I’m sorry, ‘epic fail.’ However, Nelly was spotted gambling and attending poker tournaments several other times. In 2020, TMZ reported that Nelly had a verbal altercation with a poker player at the Mohegan Sun casino in Connecticut.


Charlie Sheen

The globally famous actor Charlie Sheen, perhaps best known for his role in the sitcom “Two and a Half Men,” has been dragged into the media for years for his drug and alcohol addiction. Although everyone knew Charlie’s propensity for illicit activities, it was not until his ex-wife Denise Richards shared personal details about his habits, claiming that he spent 200,000 weekly gambling and even gambled during his daughter’s birthday party. According to her statements, most of his fortune was spent on various games such as poker, blackjack, and sports betting. During an interview, Charlie revealed the biggest bet he had put- $1 million on Pacquiao, who fought against Oscar De La Hoya in a boxing match.

He later claimed that he gave up his gambling addiction and wanted to set his life straight. However, after that statement, he was spotted gambling at a casino. Old habits die hard!


Gladys Knight

Even though some people think that gambling is mainly in the man-domain, women can also fall victim to this addictive vice. The seven-time Grammy winner Gladys Knight was one of those women who struggled with gambling addiction for nearly a decade, winning and losing large sums of money in one night. Intending to raise awareness and share light on the issue, she detailed her experience with the addiction in the autobiography “Between Each Line of Pain and Glory: My Life Story.” Gladys said: ‘I would play, and I would win. And you should never win. Because you think you’ll win everything. I just woke up one day and said this doesn’t make any sense. I had gotten $2,000, and within 25, 30 minutes, I had won 60 grand, and I sat right at that table and gave every dime of it back.’

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She said that her gamble of choice was sports betting and baccarat- in one instance, she reportedly lost over 60,000 while playing baccarat in the ’80s. After this event, she chose to work on her addiction; Gladys joined Gamblers Anonymous and eventually managed to break the nasty habit.

Allen Iverson

The famous NBA player Allen Iverson has been known to the public as one of the greatest players who drank and gambled away his stellar career. A couple of years before he officially retired, rumors resurfaced about his drinking and gambling problems which put not only him but also his family under various financial strains. Although his wealth seemed like a bottomless pit, he allegedly gambled and drank more than he was making at the time. After his wife, Tawanna, divorced him, she revealed to the media that she was forced to sell her possessions and jewelry to pay their kid’s tuition. In addition to his uncontrollable habit, Allen was banned from several US casinos for inappropriate behavior. On one occasion, he urinated in the trash can at the Bally’s Atlantic City casino. On another, he was wrongly rewarded 10,000 after losing a hand in poker, which he refused to return, causing a skirmish at the casino.

Michael Phelps

One of the world’s greatest swimmers, Michael Phelps, has also developed an obsession with gambling, particularly poker. Reportedly, his love for gambling stretched back to his high school days when he dreamt of becoming a professional poker player. In 2012, several media outlets reported on his habit as many friends were worried he might trash his career over gambling. One of them said:’ Unlike Mike, his professional poker-playing buddies know when to fold them and walk away. Michael has a ‘don’t quit until you win’ attitude, which was great while he was swimming but could be costly playing poker.’


The biggest crisis the swimmer experienced was in 2014 when he was caught driving drunk and heading to Horseshoe Casino in Baltimore, where he lost millions to poker. Then, two years later, he was caught on camera gambling on his phone before the semi-finals at the Rio Olympics. But, according to reports, Michael seemingly has turned a new leaf, keeping the issues under control and redirecting his poker passion for charity.


Shannon Elizabeth

Shannon Elizabeth, who is best known for portraying Nadia in the hit movie “American Pie,” has also made a name for herself in the gambling community for her extraordinary poker skills. Her hobby and passion developed into a full-fledged career, which explains why she has not been seen in the film industry. She launched her career at the beginning of the new millennium, slowly rising the ladder. From 2004 to 2010, she won over ten tournaments, becoming one of the celebrities’ most successful poker players. She cashed four times in World Series at Poker, $11,000 at a game. For most stars, casual gambling, which turns into a habit, is a potential hindrance that might cost them a career. For Shannon, it is a second career, which undoubtedly served her well. Even though she has not been seen around the tables recently, she has made over $300,000 playing poker which is just a drop in the ocean of her $10 million wealth.


Tiger Woods

Widely regarded as one of the greatest golf players of all time, Tiger Woods has made the headlines for his record-breaking performances and numerous scandals about infidelity and gambling. There were rumors that Tiger got the gambling bug from Michael Jordan and that their befriending might have caused Tiger to become so addicted. During Tiger’s visits to Las Vegas, he was often caught in the company of ladies, staying at one of the high-stakes blackjack tables. Allegedly, he bet over $250,000 per hand


Phil Mickelson

Another professional golfer caught in the web of gambling addiction is Phil Michelson. In June 2022, in an interview about his financial difficulties, Phil admitted that he had had a problem with addiction; he revealed:Gambling has been part of my life ever since I can remember. But about a decade ago is when I would say it became reckless. It’s embarrassing. I don’t like that people know. The fact is I’ve been dealing with it for some time. ‘In May, he published an autobiography in which he talked about the addiction and its effects on his life and family. Alan Shipnuck, who wrote the biography for Phil, said that the golfer lost approximately $40 million to gambling.


Michael, who has recently joined Saudi-backed LIV Golf, said: ‘My Gambling got to the point of being reckless and embarrassing. I had to address it. And I’ve been addressing it for several years. And for hundreds of hours of therapy. I feel good where I’m at there. My family and I have been financially secure for some time.’

Charles Barkley

The former NBA star Charles Barkley’s gambling addiction has been an open secret for years, and he has discussed it on various occasions. In his 2007 interview with ESPN, he openly admitted his problem but claimed that it was not a big issue given that he has enough money to support the habit; Charles disclosed: ‘It is not a problem. If you’re a drug addict or an alcoholic, those are problems. I gamble for too much money. As long as I can continue to do it, I don’t think it’s a problem. Do I think it’s a bad habit? Yes. Am I going to continue to do it? Yes, I’m going to continue to do it.”‘ In these interviews, he said he lost over 30 million to betting sports, although he is no stranger to poker and blackjack. On one occasion, he lost 2.5 million playing blackjacks; on a different occasion, he lost over 700,000 by betting on Super Bowl. After a series of losses and problems, he took a two-year break but returned to his habit, saying that he had been practicing moderation.

Michael Jordan

Arguably the most famous basketball player in the world, Michael Jordan is yet another well-to-do and prosperous celebrity that has battled Gambling. According to one of his interviews, he began betting in his teens, playing poker and blackjack, and continued occasionally betting in college. After rising to fame, Michael acquired enough money to indulge in his habit, losing mind-boggling amounts to poker and blackjack. In his 1993 interview, he was asked about Gambling, and he said that it was just a hobby and not a problem cause if it had been a problem, he would have starved or sold his house to support the habit.


Although Michael thoroughly enjoyed playing cards, his most expensive form of Gambling was golf. In 1993 he was subpoenaed to testify over a $57,000 check he gave to Slim Bouler, who was sentenced to nine years of prison for money laundering. Michael initially claimed it was a loan but later testified it was a gambling debt.

In 1998 one of his golfing partners, Richard Esquinas released a book entitled “Michael and Me: Our Gambling Addiction,” in which he revealed that Michael owed him $1 million from golf bets. According to reports, Michael was willing to bet on literally anything, and his most significant loss was $5 million, which he gambled at a Las Vegas casino.


Dana White

The president of the Ultimate Fighting Championship, Dana White, revealed in a 2021 interview that he was ‘a degenerate gambler’ and lost a $1 million boxing bet in one night. Dana the notorious blackjack player, revealed: ‘It makes whatever you’re watching a lot more fun, a lot more interesting, so I’ve always been for it. But I’m from Vegas. I play table games too much. I’m a degenerate if you’re not getting it. I’m a degenerate, yes. I love to gamble.’ Although he had lost much money, he has also won some interesting amounts. He said that he often gabled at the Palms Casino in Las Vegas where he allegedly won 1.6 million and later was banned from the casino. Dana said: ‘Then, as soon as the Palms was sold, the people who came in asked me to stop playing there. Las Vegas is all about losing, not winning. They don’t like people who f**king win! Dana, whose estimated net worth is a staggering $500 million, in a 2014 interview, said that his habit is not a problem because it had not disrupted his personal life and caused him to go bankrupt.

Gambling is a severe problem that breaks families apart and causes one to behave irrationally. Celebrities who are humans like everyone else are not immune to it. On the contrary, it seems that having deep pockets might just elevate your chances of becoming a compulsive gambler if you cannot contain it.

Martha Clifford

As an Author at Net Worth Post, I guide a dedicated team in the art of revealing the stories behind the world's most influential personalities. Fueled by a relentless curiosity and a knack for uncovering hidden stories, I immerse myself in the intricacies of our subjects' lives, weaving together accurate data and compelling narratives. My involvement spans the entire editorial process, from the seed of research to the final flourish of publication, ensuring that every article not only educates but also captivates and motivates our audience.

At Net Worth Post, we are committed to providing thorough investigations into the net worth and life achievements of innovators across diverse sectors such as technology, culture, and social entrepreneurship. My method merges meticulous research with eloquent storytelling, designed to bridge the gap between our readers and the remarkable individuals who redefine our tomorrow. Through spotlighting their journeys to success, the hurdles they've surmounted, and their contributions to society, we aim to give our readers a deep and inspiring insight into the luminaries who are paving the way for progress and ingenuity in the modern era.

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