Famous Gambling Losses That May Make You Think Twice About Betting In The US
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Famous Gambling Losses That May Make You Think Twice About Betting In The US

Famous Gambling Losses That May Make You Think Twice About Betting In The US

As it turns out, celebrities are not immune to the woes of gambling addiction or major losses at the casino. Sure, it may be somewhat easier for a celebrity to recover from a lengthy losing streak, or that one seriously bad night at the poker table or sitting at a blackjack table or playing baccarat or the slots, but when they lose, they typically lose big. Here is a list of our favorite gambling story losses involving some of the biggest names in the entertainment world.


Air Jordan Loses On The Links

It would be a safe bet to say that Micheal Jordan is the best basketball player of all time. However, he isn’t quite as good with a somewhat smaller ball and a very large arena. Jordan has a history of wagering massive amounts of money while playing golf. Usually to the tune of $100,000 per hole. In September 1991, Jordan went on a ten-day golf betting binge where he lost just about $1.2-million. He did win some of that back on the course and was able to talk that debt down to $300,000. 


Soul Singer Addicted To Blackjack

Speaking of gambling stories, losses can climb into the millions for some celebrities. Take Gladys Knight for example. The six-time Grammy Award winner is partial to playing blackjack and baccarat at the casino. At her peak in her gambling career, Knight was plunking down $40,000 a night on these table games. There is no exact figure, but estimates put her losses over the years in the 6-million dollar range - one per Grammy Award she has won throughout her musical career.


Baccarat Binge Hooks Aussie

Australian billionaire Kerry Packer is probably best known for his generosity at the casino tables where he would routinely tip dealers with enough money to cover their debts. Dealers looked forward to having him play at their tables. He also could put arrogant big-spenders in their place if they were disrespectful in any way. However, in this gambling story, losses at the baccarat table made him famous in a very different way. Over three days in 2000, he lost a total of $13.6-million in what had to be a brutal losing streak.


Baywatch Babe Plunges Deep

In the collection of gambling stories of losses, that one story dating back to 2007 in Las Vegas involving Pamela Anderson can’t be ignored. She was playing poker in a casino for a single night. It was a game that she has never been seen playing in public before and lost $250,000 that night which may explain why Anderson has never been associated with the table game before. However, she said she was able to square up the deal with a make-out session. Could that be true? We'll never know for sure.


Tilly Loses A Dilly

Academy Award-winning actress Jennifer Tilly has a reputation for being a good poker player and is considered to be one of the most successful female gamblers out there. She is so good that Tilly has several World Series wins but during the 2012 event, she was spotted sleeping on benches and is open about how her losses stress her out. At one point, she quit playing poker because she could not handle the anxiety but has since returned. Her total losses, however, are unknown.


Golfer Known As A High Roller

Golf great Tiger Woods is no stranger to gambling. He was a regular in Las Vegas at a club called the Mansion. This place was specifically for the big players at the MGM Grand on The Strip. Woods had a $1-million betting line at the casino and spent as much time as money at the blackjack table. For Woods, it was fairly routine to drop $25,000 a hand. As for what figures Woods lost at the tables, there is no number available but he has admitted to having a gambling problem.


Everyone Still Loves Raymond

Speaking of gambling addicts, actor-comedian Ray Romano had it so bad at one point that he sought help from Gamblers Anonymous that assisted him in kicking the habit. Or at least helped him to get it under control as Romano still gambles but has restricted his gaming activities to virtual bets on the golf course. He is no stranger to the World Series of Poker and still fancies himself as a potential winner. It is not known how much he has lost over the years.


Player Dribbles From Top To Bottom

NBA star Allen Iverson is probably one of the top losers when you examine gambling story losses. He earned well over $200-million during his playing career and thanks to his gambling addiction and a drinking problem, ended up broke and deep in debt. He lost endorsement deals, was divorced by his wife, and lost custody of the couple’s five children. He was also once accused by his ex-wife of kidnapping the children but that charge was later dropped.


A Problem Under Control, Maybe

Former NBA star Charles Barkley admits to having a gambling problem. He has worked with others to bring it under control to where Barkley can just go out and gamble for fun, which he says is not as easy as it sounds. With total losses at over $10-million from gambling, the athlete says he gambles because he can afford to so he doesn’t view it as a problem. Some of us call that denial. Barkley does state it isn’t healthy to be broke after all the years he played in the NBA.


Poker Player Plays Poker Role

Academy Award-winning actor Ben Affleck is a well-known poker player. He also participated in one of Hollywood’s “secret” underground poker games where he lost a total of $400,000 in a single hand. He checked himself into rehab in 2001 to battle both a gambling addiction and drinking problem. He has since recovered and soon after took a role in the movie “Runner, Runner” which was described at the time as being a “gambling-themed thriller.”


Swimmer Treads Water At Poker Table

Michael Phelps is an Olympic swimmer who has amassed a total of 22 medals. He also likes to play poker. When comparing gambling stories, losses usually help you to define how good a player is. As for Phelps, the numbers are unknown, but he has a reputation for being extremely competitive and estimates put his losses in the neighborhood of “millions of dollars” which also puts him on a list with other notable gambling losers.


Sports Betting Has A Shine To Sheen

Actor Charlie Sheen is no stranger to unusual, compulsive activity. In 2006, when his wife Denice Richards filed for divorce, she stated he was spending roughly $200,000 weekly gambling. She even recounted an incident in 2005 where Sheen, traveling to the hospital for the birth of a daughter, was on his cellphone with his bookie placing a bet. Sheen, who favored sports betting to any other wagering, claims he no longer gambles or is involved in any other addictive activity.


Spiderman Weaves A Web Of Debt

Actor Toby Maguire was sued in 2011 for his role in a multi-million dollar illegal gambling ring. He is also very skilled at Texas Hold ‘Em where his winnings are estimated at over $10-million. He has been connected to secret underground poker games in Los Angeles and New York and has been successful most of his playing career. Sadly, Maguire admits to having an addictive personality which means he has likely lost a bundle along the way.


Rapper Takes On Super Bowl

Rapper Birdman is a big sport betting fan. His favorite betting target is SuperBowl but in his gambling stories, losses outnumber wins. He was going to bet $5-million on SuperBowl XLVI and a sportsbook challenged him to do so. Instead, Birdman bet $1-million head-to-head with fellow rapper 50 Cent and lost. Then for SuperBowl LII, Birdman bet rapper AR-Ab $100,000 and lost that match as well putting his losses at a super total of $1.1-million over two games.


A Whale Of A Tale

High roller Terrance Watanabe is legendary in Las Vegas. Partly because he preferred to play casino games that had a high house edge (meaning the odds were in favor of the casino) and partly because he lacked any real gambling skill. He did take Caesars Palace to task for knowingly taking advantage of his poor gambling skill. He won $225,000 in court over that. But Watanabe’s losses were far greater than that - close to $112-million.


Vegas Dave And The Cool Million

Dave Oancea, nicknamed Vegas Dave, plunked down $1-million in 2016 on a female MMA fighter participating in the UFC 200 event. In three minutes, the fighter, and Vegas Dave were declared losers. Dave, who had been using social media to boast about his supposed betting skills, turned to the medium to focus more on the condition of the fighter, who suffered a broken nose, than on his major loss. Again, some of us call that denial. Know what we mean there, Dave?


This Gambler Goes Missing

Probably one of the most interesting stories on gambling losses dates back to mid-1883 and concerns a self-professed compulsive gambler by the name of Matthew Webb. Webb was a daredevil who took on several different challenges like swimming across the English Channel and winning a fair deal of cash by betting against the public on whether or not he would succeed. Webb won a lot of money. But in his last challenge, at Niagara Falls, $10,000 was up for grabs. Webb’s body was never found.


Tycoons Take A Bath

Speaking of gambling losses, stories like this one seem to be common. One Singapore businessman gambled at two different local casinos - the Marina Bay Sands and Resorts World Sentosa - and lost an estimated $75-million. The same two casinos were implicated in the gambling losses of another Singapore businessman who was betting on various casino games at roughly the same time as the other gambler. His losses totaled $37-million. A coincidence?


Atlantic City Casino Wins Losses

Legendary poker professional Phil Ivey found himself in court in a dispute with the Borgata Hotel Casino and Spa in Atlantic City. The casino claimed Ivey cheated when he won $9.6-million playing baccarat. The judge ruled that Ivey won the jackpot fair and square but informed the World Series of Poker bracelet winner that he still had to hand over the cash. Again, even though there was not enough evidence to verify that an act of fraud had taken place.


Aussie Gambles Away Fortune

Australian realtor and well-known high roller Harry Kakavas spent 14-months on a worldwide gambling tour that saw him lose close to $1.5-billion. In May 2006, he lost $164-million in just five hours. Blackjack appears to be his weakness and he has been seen placing $300,000 bets per hand in the casino. He even tried to claim back $20.5-million in losses from the Crown Casino in Melbourne stating the casino had taken advantage of his gambling addiction.


Footballer Can’t Kick The Habit

Manchester United player Wayne Rooney is on this gambling stories/losses list for a good reason. That’s because his gambling addiction is one of the worst kept secrets in the sporting world. He is best known for a loss of $685,000 that took place on roulette and blackjack in the record time of under two hours. He shrugged it off saying he was playing out of boredom as his wife and children were not home at the time. Again, we usually call that denial.


Her Name Didn’t Help At All

Paris Hilton was banned from her family’s Las Vegas Hilton casino in 2006. She had been playing there and having a good time but when she started losing, it must not have looked very good to other family members. What sealed the deal was when Hilton bet and lost her $240,000, Bentley, during a high-stakes game. Her game of choice was poker and she is probably the first person ever to be banned from their own family’s casino.


Play Hard And Bet Hard

UFC President Dana White is considered to be a very good gambler. There are some nights he has reportedly walked away from casinos with the winning of up to $5-million just from the blackjack table. He has a habit of betting $50,000 per hand and has been banned from several venues. What we don’t know is how much White has lost along the way. You can’t win all of them which means even this high roller would have had some dismal nights at the casino.


Billionaire In The Wrong Circle

Cirque du Soleil co-founder Guy Laliberte could afford to lose a little gambling. Sadly, that’s the excuse used by more than one celebrity or famous gambler. In the case of Laliberte, he was playing the high stakes games on Full Tilt Poker and lost over $30-million. Naturally, he turned on the online site claiming that he was cheated by the system that permitted unlimited bankrolls of players at his table. Regardless, a major loser no matter how you look at it.


This Guy Needs A New Tutor

Chun Lei Zhu, who also goes by the names Patpatman, and Patpatpanda, has one of the most unusual gambling loss stories you will ever hear. He had hopes of becoming a star high stakes online poker player. But instead of hiring someone to teach him the ins and outs of the game, Patapatpanda chose to go it alone and try to figure out the game at home. That proved to be a costly mistake as he ended up losing nearly $15-million in the process.


A Rose By Any Other Name

One of the biggest betting losers in the history of sports has got to be former MLB star, Pete Rose. It was his gambling addiction that essentially ended his baseball career. He was known to make wagers between $3,000 and $10,000 per day on his baseball team to win. Oddly enough, after being banned from various levels of the game and the Hall of Fame, Rose continues to wager on baseball and his former team. Now he does it for fun, or so he says.


Boxer Hooked On Sports Betting

In our last selection of gambling stories/losses, we look to undefeated professional boxer Floyd Mayweather, Jr. Sports betting is his hobby and he has won $3-million from a single college football wager and typically places bets at $400,000 per event. At one time, his ex-wife had to cover a $700,000 bet he was placing. In January 2014, media reports indicated that Mayweather had placed a $10-million bet on the SuperBowl. His losses are not noted.


In Conclusion

Think gambling is easy and that luck will be on your side the moment you set foot into a casino and get comfortable at the poker table? It’s not all fun and games if gambling becomes an obsession that causes you to incur major losses like the well-known examples noted above. One thing is for sure, nothing turns a celebrity into a loser quite as fast as the house edge combined with the demons that lurk within the mind of a gambling addict.

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