Perfection is a word rarely used when talking about gambling. If you’re a regular gambler, then you have had your fair share of soul-crushing losses. In fact, over the course of casino history, it’s become clear that losses are almost synonymous with gambling.
Behind every smiling gambler, there’s a collection of awkward and unforgettable bets that have simultaneously defined their gambling experiences and almost forced them to quit. You know that buzzer basket that throws the spread out of whack, that silly last-minute touchdown that flips an under to over, and folding your poker hand when your opponent clearly has garbage cards.
Yeah, losing happens to the best of us gamblers. But when you hear about the following world’s famous losses, you’ll either feel better about your somehow “small” losses or think twice about betting in New Jersey.
What we cover
1- Gladys Knight Loses $60,000 Jackpot Win Plus $45,000 Own Money
You’ve probably heard rumors about celebrities losing thousands of dollars on a trip to Atlantic City, Reno, or Las Vegas (I see you there Charlie Sheen🙂). But famous musicians also don’t disappoint.
Take singer-songwriter, Gladys Knight, for instance. The Empress of Soul has always been known to be a controversial gambler. In one night, Gladys won a lucrative jackpot worth $60,000 and within minutes she lost the entire prize money. What’s even more fascinating is that she lost the money playing at the same casino.
And that isn’t even all. When she realized that she’d flushed the entire jackpot win down the drain, Gladys made a call to 911. As if that isn’t dramatic enough, she lost another $45,000 of her own money before responding officers arrived on the scene.
Thankfully, Gladys Knight checked herself into a rehabilitation facility, and her compulsive gambling is now under control. While recounting some of the best and worst things that ever happened to her for the Chicago Tribune, Gladys said her gambling addiction and the dramatic loss are right up there on the list.
She told reporters, however, that she will be back to doing what she does best: singing and gambling.
2- Terrance Watanabe Loses Everything
The gambling story of Terrance Watanabe is so sad that it has been used repeatedly as a cautionary tale for the so-called gambler rich-kids. Most people can’t discuss or write about any piece on gamblers who lost it all without mentioning his name.
Terrance Watanabe truly takes the cake when it comes to people who gambled foolhardy away all of their life savings and inheritance. And we’re not talking about tens of thousands of dollars. It’s estimated that he gambled away well over $825 million (yes, you read that right – close to a billion dollars!)
In 1977 Terrance was a very wealthy man after inheriting Oriental Trading Company (OTC), one of the most successful direct merchant suppliers of novelties, toys, arts and crafts, as well as party and school supplies. Berkshire Hathaway acquired it from him back in 2000.
After selling OTC, he somehow got too bored or failed to find something interesting to do. One way or the other, Terrance found his way into the world of high-roller gambling. To make the matters worse, he had little to no prior high-stake gambling experience.
Terrance wagered bigger and bigger bets year after year. He reportedly lost over $825 million gambling at The Rio in Las Vegas. As if that wasn’t too big a loss, he went on to incur more than $127 million in gambling losses at Caesar’s Palace.
As far as famous gambling losses go, Terrance’s losing streak in Las Vegas is thought to be one of the largest the world has ever witnessed. He even attempted to take Caesar’s Palace and The Rio to court, but eventually, he lost the lawsuit and was instructed to pay the casinos their money.
Surprisingly, he has paid off almost the whole debt with only $15 million remaining. He has already been charged with several felony offenses, and he could be sent to jail for close to three decades if he fails to honor the rest of the debt.
3- Rapper Birdman Loses a $1 Million Super Bowl XLVI Bet to 50 Cent
Hip-Hop artist 50 Cent is not a well-known gambler, but he won more than fifty cents from fellow rapper Birdman back in 2012. On the other hand, Birdman is an ardent sports betting gambler who isn’t afraid to put his money where his heart is.
However, placing correct Super Bowl bets has been rather tricky for the long-time music executive and producer. As an avid Patriots fan (when they still had Tom Brady as the quarterback), he was right to peg his money on the then NFL champions to scoop Super Bowl XLVI.
Birdman was so confident in the New England Patriots that was ready to plunk down $5 million on them to win the ultimate game, the super bowl. While he didn’t put down five mill’s, Birdman eventually decided to go mano a mano with 50 Cent, placing a $1 million wager. Unfortunately for Birdman, the super bowl ended with victory for New York Giants and it was 50 Cent who laughed all the way to the bank.
Birdman’s bad luck with Super Bowl bets didn’t end there. In 2018, he went head to head with fellow rapper AR-Ab, betting $100k on New England Patriots to defeat Philadelphia Eagles. Again, this time Eagles came up on top and he lost $100,000.
4- Dave Oancea (Vegas Dave)
Some big gamblers put down large sums of money on exciting options like Super Bowl, boxing matches, NBA finals, and so on. When Dave Oancea, aka Vegas Dave, placed a $1 million bet on an MMA fight between female fighters Miesha Tate and Amanda Nunes at UFC 200, he thought he’d wait for several rounds of bloodied fights to determine the fate of his wager.
He was wrong. It Amand Dunes only 3 measly minutes to down Miesha Tate and flush Vegas Dave’s million-dollar bet down Las Vegas drains. With a showy nickname like Vegas Dave, you’d think that Oancea would be an avid sport betting regular.
However, after losing a cool $1 million on that single, three-minute MMA fight, it seems Dave chose to quit sports gambling altogether. On his social media posts, it appears that he’s following Tate’s recovery and often addresses her health after she suffered a broken nose in the course of the fateful fight. We hope that Vegas Dave is nursing his gambling wounds, too.
5- Singaporean Mogul Loses $5 Million
While the world was still grappling with the raging coronavirus pandemic, one local Singaporean Tycoon was gambling away almost all of his net worth playing casino games. The unnamed business mogul (most Asian casinos usually keep the identities of their big players secretive) is said to have lost a whopping $75 million (or over S$100 million) at two Singapore-based casinos.
One of the casinos is the renowned Marina Bay Sands in Bayfront Singapore and the other is Resorts World Sentosa. The tycoon is said to have appeared on many occasions on the Forbes List of Billionaires and is among the top 40 richest persons in the Asian Pacific country.
That’s not the only big gambling loss to have come out of Singapore in the last few years. Reports also state that another Tycoon from Singapore lost around $37 million gambling at around the same time at the same two casinos, Resorts World Sentosa and Marina Bay Sand.
6- Former San Diego Mayor Maureen O’Connor Loses $13 Million
Some politicians have been caught red-handed playing fast and loose games. However, it is the former mayor of San Diego Maureen O’Connor that took this phrase to a whole new meaning. After serving her term as the city’s mayor, she quickly fell into a compulsive gambling rabbit hole.
Compared to some of the biggest gambling losers like Terrance Watanabe, Maureen O’Connor is a small fish in an ocean full of whales and sharks. Even so, she managed to lose around $13 million after betting around $1 billion on video poker.
Be that as it may, Maureen O’Connor’s losing streak remains one of the most famous losses in the gambling world. That’s partly because she lost almost everything she had to her name. What’s most certainly laughable, if not disturbing is that she borrowed $2 million from a charitable organization that was run by her then 2nd husband, Robert Peterson.
As you’d expect, she lost the entire $2 million bankroll to video poker. While problem gambling has certainly tarnished her name, Maureen O’Connor was actually a prudent mayor. She led San Diego through one of the most trying moments. Her professional and political career also speaks for itself.
7- Michael Jordan Loses Close to $1.2 Million in Golf Bets
One of the most celebrated and respected NBA MVPs; Michael Jordan is a legend through and through. His prowess on and off the court is something that hasn’t been matched yet in the NBA. Turns out, his competitive nature on the court bled into his gambling habits.
It’s no secret that Michael Jordan is an avid gambler, golf player, and golf lover. At some point, he was known to place very huge bets on the golf course. His golfing friend Richard Esquinas narrated that the Greatest NBA player went on a ten-day golf wagering spree in the month of September 1991.
In the 10 tens, Jordan lost around $1.2 million in golf bets. Luckily, he was able to negotiate his losses down to roughly $300,000. That’s right; the G.O.A.T. got off easy, but losing $300K on golf betting is no small joke. According to Esquinas, Michael Jordan had a habit of plunking down huge bets on each hole, with up to $100K on a single hole.
8- Charles Barkley, $30 Million Loss
The former player of the NFL outfit Phoenix Suns has always had some bad stints with problem gambling over the years, and there’s no question about that. It is estimated that Charles Barkley gambled away his life’s fortune worth around $30 million to gambling on baccarat, blackjack, dice, and roulette.
The former pro football player is still adamant about his previous run-ins with gambling addiction. He always claims that he learned to live with his big losses gradually. People close to him say that he would lose up to $200K per night in Las Vegas.
In fact, during his time as the ace for Phoenix Suns, Charles Barkley is estimated to have blown through millions worth of dollars gambling at over 30 different casinos. He has never tried to sue any of the casinos for preying on his compulsive gambling habits, though. He lost it all, but he never lost his charm and ability to keep it cool.
9- Harry Kakavas Blows Through $1.5 Billion in 14 Months
Credit sources show that the world’s renowned high-roller Harry Kakavas lost more than $1.5 billion while playing at casinos across the world in a matter of 1 year and two months. His gambling spree is often regarded as one of the costliest in the history of casino losses.
The Aussie real estate mogul minted his billion-dollar empire selling properties on Australia’s Gold Coast. There are reports that Harry Kakavas gambled away a staggering $164 million in less than five hours in the month of May 2006.
His game of choice is baccarat, but he was occasionally seen playing blackjack. Some witnesses claimed that he wagered up to $300K per baccarat hand. Even more astounding, the Aussie billionaire is said to have lost $4 million on a one-day trip to Macau casinos.
Later, Kakavas tried to win back $20.5 million of the gambling losses he made at the Crown Casino in Melbourne, but the judge threw out his claim that casinos took advantage of his compulsive gambling behavior. He also lost a subsequent appeal to get the $20.5 million back.
10- Harry Packer Drops $13.6 Million on a Baccarat Gambling Binge
If you’re looking for a classic example of a whale gambler, look no further than Harry Packer, an Aussie billionaire. At the time of his demise, Packer was one of the most influential and the richest Australians.
Perhaps Harry Packer was better known in Las Vegas for giving out playing chips and tipping casino floor workers enough to settle their student loans. He’s also known for reprimanding arrogant whale players for being disrespectful to staff and other gamblers.
Unfortunately, the house always wins, and the same fate befell the humble billionaire. Packer’s casino game of choice was baccarat. People who witnessed one of his baccarat binges in 2000 said that Packer lost roughly $13.6 million in 3 days.
While a loss of $13.6 million was a drop in the ocean for the Australian billion, it still doesn’t change the fact that it’s one of the most famous gambling losses. Just imagine losing close to $14 million in a matter of 72 hours!
11- Charlie Sheen Loses $2.5 Million in Sports Bets
Hollywood veteran Charlie Sheen is not one to shy away from trouble. He’s the poster child of Hollywood excesses and living life on the edge. If you paid attention to Charlie Sheen in the TV hit series Two and a Half Men also starring Jon Cryer, his character also named Charlie was a raging alcoholic with a soft spot for sports betting. His sport of choice was basketball.
Turns out, Charlie Sheen behaved the same way in real life. The former Anger Management star has admitted that he lost $2.5 million on sports bets at various sportsbooks in 2006. Court documents filed during his divorce with former wife Denise Richards showed that Charlie Sheen was burning through around $200K every other week back in 2006 betting on sports.
12- Archie Karas Loses Life Fortune, $40 Million
The story of Archie Karas is that of rags to riches, then riches to rags (well, not exactly). Still, he is one of the most famous gambling losers who gambled it all away. Best known for his bravado and taste for high-rolling, Karas has very little trouble when it comes to taking a big risk if it means getting something better in return.
Archie Karas landed in Vegas in the closing days of 1992 with just fifty bucks to his name. He would later borrow $10,000 from a fellow gambler at the Mirage. He managed to turn the $10,000 bankroll into a fortune of $40 million in the next couple of years.
While poker was his poison (especially Razz), he also played the game of dice and baccarat. He made so much money that he paid his beneficiary double the money he borrowed.
Archie beat the best of the best at poker, including Stu Ungar, Johnny Moss, Puggy Pearson, and Chip Reese. He started losing money when it changed his playing style from skill-based poker to games of chance like dice and baccarat.
Having requested the casinos to lift their maximum betting limits for him, Archie went on to lose his entire $40 million fortune in just 3 weeks. To this date, he made one of the most famous and tragic losses in the gambling space.
