Celebrities love to spend money, and some are known to do it quite recklessly. From luxury homes to expensive cars, celebs can spend millions in a single day.
With a seemingly endless flow of funds, many celebrities turn to gambling for a thrill. There’s nothing quite like wagering a big bet on a single spin of the roulette wheel or round of poker.
Some celebrity gamblers seek their thrills in occasional visits to casinos. Some turn pro and master their favorite games. And some fall into addiction, which can lead even the hottest star into bankruptcy.
Some of Hollywood’s most famous celebs – stars like Charlie Sheen, Ben Affleck, Matt Damon, Tobey Maguire, Shannon Elizabeth, and Ray Romano have joined sports legends Michael Jordan and Charles Barkley in gambling away sizable portions of their earnings in high-stakes games, accumulating debts of millions of dollars.
We have compiled a list of some of the top celebrity gamblers and the stories that surround their games.
Tobey Maguire is very open about his fondness for gambling. The Spiderman star has publically competed in the World Series of Poker, where he played using tips he learned from legendary poker pro Daniel Negreanu.
Maguire is rumored to have accumulated about $10 million in poker winnings, which is great. What’s not so great is that the star loves playing in underground games. This led to legal troubles when he won big pots full of cash from a player who was later convicted of tax, wire, and investment fraud. Untangling himself from his legal woes reportedly cost the star $80,000.
Famous gamblers like Leo DiCaprio and Ben Affleck were reportedly part of the games, but they didn’t suffer the same legal woes as Maguire. Maybe they didn’t win enough to attract attention from prosecutors.
Speaking of Affleck, The Batman star is known to be an avid fan of both blackjack and poker, winning the California State Poker Championship in 2004. Affleck starred with Justin Timberlake in a 2013 gambling drama, “Runner, Runner.” The movie was partially based on the life of Nat Arem, an accountant and professional poker player who helped expose online poker cheating by analyzing thousands of games using statistical methods.
Affleck seems to be one of the compulsive gamblers whose love of gaming has caused him turmoil on occasions, like when he was asked to steer clear of blackjack tables at the Hard Rock Hotel and Casino in Las Vegas under suspicion that he was counting cards.
Card-counting is not illegal; it’s not even cheating. But casinos reserve the right to expel gamers at will, and they’re constantly watching for people who win too much and too often at blackjack.
Affleck denies tabloid reports suggesting he has a gambling problem.
A close friend of Affleck’s, actor Matt Damon, is widely reported to be a poker fan, famous among celebrity gamblers. The “Good Will Hunting” star is said to enjoy Texas hold’em, which he plays in Las Vegas luxury hotels. Like Affleck, Damon has played a leading role in a poker-inspired film: 1998’s “Rounders,” a drama that deals with the underground world of high-stakes poker.
Damon researched the role by taking lessons from professional players and visiting underground casinos in New York. He even managed to participate in closed tournaments organized by the notorious Molly Bloom. According to some sources, he once lost more than $40,000 in a single game. Nowadays, Damon plays only in charity tournaments and with friends.
Michael Jordan is the gold standard among celebrity sports gamblers, but this basketball superstar has seen his share of gossip. When he retired in 1993, people whispered that it was due to his gambling addiction. One widely circulated story suggested that NBA Commissioner David Stern banned him from the game. Not true.
Jordan is a fierce competitor who loves to win. He is known for betting on golf and other games, and he loves playing blackjack. Asked about gambling, he assures people that he could stop anytime.
With a net worth of more than $1 billion, Jordan can afford to gamble whenever he wants. He says he is not a professional gambler but that he loves to bet – and it’s nobody’s business if he gambles now and then because it’s a hobby he can afford.
Another famous athlete turned gambler is Charles Barkley. The legendary power forward’s gambling win-loss record seems to have been much less successful than the one he enjoyed in his basketball career. The NBA superstar has suffered legendary losses, totaling more than $10 million according to his own statement in a 2007 ESPN interview.
Unlike Michael Jordan, Barkley says he has been addicted to gambling. He came to that realization, he says, after losing $700,000 in one weekend of betting on the Super Bowl. In 2008, Barkley vowed to stop gambling after a casino sued him over a $400,000 gambling debt. His hiatus lasted two years. Then it was back to the casinos. Barkley reportedly enjoys playing blackjack and betting on the outcome of sporting events.
He has tried to moderate his bets but now says his lifetime losses exceed $30 million. “No matter how much I win, it ain’t a lot,” Barkley told ESPN in 2007. “It’s only a lot when I lose.” That’s one self-confessed addict’s view of the big wins and losses in high-stakes gambling.
Actor Ray Romano became hugely popular with his sitcom, “Everybody Loves Raymond,” in which he played a middle-class family man dealing with all the challenges of suburban life in America. Fame and fortune followed as Romano became one of television’s most highly paid actors.
What few people know is that when the show was over, he struggled with a severe gambling addiction that almost cost him everything he owned.
From 2009 to 2011, Romano produced and starred in another TV show, “Men of a Certain Age.” He portrayed a middle-aged man who is addicted to gambling. Most people at the time didn’t know the main character, Joe, was based on Ray Romano himself. It wasn’t until a few years after the show ended that the actor admitted Joe was modeled on himself, and that at one point he went to Gambler’s Anonymous for help.
Today, Romano places virtual bets but doesn’t frequent the casinos or live betting sites that he enjoyed in the past. He does take part in the World Series of Poker, joking that it’s safe because it’s not really gambling. He knows that he doesn’t stand a chance of winning. Romano says he doesn’t consider himself one of the top celebrity gamblers.
Jennifer Tilly made a name for herself in famous movies like “The Fabulous Baker Boys,” and “Bride of Chucky.” She played Shorty’s girlfriend in the popular sitcom “Modern Family,” and she even got an Academy Award nomination. Among her hidden secrets is a passion for poker.
Unlike other gambling-addicted celebrities, Tilly has taken her love of the game to a whole new level. She took poker seriously, studied it conscientiously, approached it strategically, and is now one of the few celebrity gamblers who can hold their own in games against the pros.
Tilly won the World Series of Poker Ladies bracelet in 2005 and took the prize of $158,625 in a Ladies’ No-Limit Texas Hold’em event. She regularly participates in celebrity and charity tournaments, and she says that she has earned nearly $1 million playing poker.
What is it about gambling and basketball?
Allen Iverson is commonly thought of as one of the best and most successful basketball players in NBA history, but not many people know that he’s one of the famous gamblers who went broke because of gambling debts. Iverson earned about $200 million during his NBA career, but he lost it all gambling.
Although Iverson’s basketball earnings grew over the years, he never seemed to earn enough to get out of debt. At one point, his problem became so big that he lost most of his endorsement deals, including a Reebok deal worth $50 million. Iverson’s example shows that no matter how big a star someone is, no matter how much they earn, it is not all that difficult for celebrities with a pathological gambling addiction to get themselves into very unpleasant situations.
Several of his casino visits ended in feuds, and he’s been banned from entering many of them.
Shannon Elizabeth started playing draw and stud poker with her family at an early age. It wasn’t until much later, when her career was on the way up, that she discovered Texas hold’em.
Interestingly, Elizabeth says she didn’t like it at first, especially not being able to discard and draw new cards. But befriending female celebrity gamblers like Jennifer Tilly helped her find a way to love the game.
By 2006, Elizabeth had become a well-known celebrity poker player. She traveled to Las Vegas monthly to play cards and work on her “second career,” as she called it. That year, she participated in the fourth edition of Celebrity Poker Showdown and took the title at the inaugural Nicky Hilton New Year’s Eve Poker Tournament.
Between 2006 and 2010, Elizabeth won 12 major poker tournaments. In 2010, she finished second in the World Series of Poker’s $5,000 Ante Up for Africa charity event and took home winnings of nearly $80,000. Elizabeth then retired from gambling and winning until August 2013 when she finished in a disappointing 165th place in a Seminole Hard Rock Poker Open field of 338, taking home just over $11,000.
Film and TV star Charlie Sheen has always had a bad-boy reputation. He has battled his addictions in rehab clinics and the pages of the tabloids. Among his most notorious addictions: gambling. In a 2006 divorce proceeding, ex-wife Denise Richards stated under oath that Sheen spent about $200,000 per week with his daily sports gambling.
Although he now claims that he is not addicted to gambling anymore, Sheen used to lose enormous sums of money at casinos betting on sports events and playing poker. He admits that he once placed a bet over the phone while on the way to the hospital where his wife was giving birth.
Sheen’s addictions cost him more than money. The actor’s career suffered and he announced in 2015 that his wild lifestyle had left him infected with HIV. According to Richards, he squandered millions on gambling but forgot to pay child support.
By early 2011, Sheen had begun describing himself as an ex gambling addict, promising that his betting days were over.
The world’s most famous golfer became interested in gambling when he befriended high rollers Michael Jordan and Charles Barkley. The more time Woods spent with them, the more he gambled. But the golfer had a different concept of gambling.
It’s commonly known in Las Vegas that Woods is a disciplined gambler. He has a strict $1 million limit in every casino in Vegas, and he bets no more than $25,000 per hand. His favorite venues are the MGM Grand and the Mansion, considered by many to be among the best gambling establishments the city has to offer.