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When gambling, whether online or at a land-based casino, you always know the casino has an edge. It may be small but the casino still has a somewhat better chance of winning than you have. For some gamblers, this is a clear warning that they may lose.

For others, this is an invitation to challenge the casino and they take it up without question. The stake during gameplay is always what separates the boys from the men at the table. However, there are those that have no limitations and neither do they rely a gambling budget to make sure they aren’t pushing their luck too hard. They go all in, resulting in massive losses.

Here are some of the biggest casino losses that will remain in gambling’s history books for a long time to come.

#8 Charlie Sheen: $2.5 Million

Coming in at number eight is Charlie Sheen who made a name for himself through the famous comedy series Two and a Half Men. However, according to his admission on gambling, it appears he also made a name by losing a staggering $2.5 million through betting on multiple sports.

As a result, this led to a divorce from Denise Richards, his ex-wife. According to the documents presented during the divorce, Sheen placed bets worth over $200,00 every week for a three-month period that the marriage lasted.

#7 Gladys Knight: $6 Million

You probably know her from hit songs such as “That’s What Friends Are For”, “License To Kill”, and “When a Child Is Born”. Gladys Knight, a talented US Soul musician, had an illustrious musical career but she had a liking for gambling.

The Grammy Award Winner (6 times), admitted to having lost a ton of money through baccarat and blackjack gambling. According to reports, Knight spent $40,000 per night, which translated to at least $6 million in lifetime losses on gambling.

#6 Phil Ivey: $10 Million

You might think heavy losses follow amateurs in the game. Well, you’re wrong because even the most skilled players come up against heavy competition. In the case of Phil Ivey, a skilled and professional poker player, it wasn’t about competition, although the losses came from one.

During a WSOP Main Event in Atlantic City’s Borgata Hotel and Casino, Phil Ivey won at least $9.6 million. However, trouble started brewing soon after when Borgata sued Ivey for cheating in a baccarat game.

Phil was handed a sigh of relief after the court ruled in his favor saying that Ivey did not cheat and that he wasn’t involved in any sort of fraud. However, he was still required to return the money earned from the tournament, leaving a massive dent in his pocket.

#5 Kerry Packer: $13.6 Million

Billionaire, lover of life, and incredibly generous sums, this is Kerry Packer for you. He’s also a lover of gambling and that’s what saw him lose big at the tables. Even then, this billionaire is known as a fighter for the working class.

Stories about him offering massive tips to casino staff exist throughout Sin City. His tips are so big that they can get you out of debt. However, his generosity wasn’t enough for him to avoid a $13.6 million loss in just 72 hours in 2000. While that may be a drop of rain in the desert of Packer’s finances, it’s still an insane amount of money to lose in such a short period, particularly on gambling.

#4 Charles Barkley: $20 Million

Charles Barkley is no stranger to placing the occasional flutter. The prolific forward who had a fine stint at the Philadelphia 76ers and also an inducted NBA Hall of Famer admitted to being an ardent gambler.

Barkley, one of the top 50 Greatest Players of all time and an NBA analyst, lost at least $2.5 million in a blackjack session that lasted only 6 hours. That’s not all because it’s estimated that Barkley may have lost anything between $10 million and $30 million.

#3 Harry Kakavas: $1.5 Billion

Getting around this hefty sum is difficult but it happened. All in a span of 14 months. The victim? Harry Kakavas, a well-known high rolling gambler.

The real estate salesman from Australia rose in the ranks to become a wealthy man by selling homes in Australia’s Gold Coast. Kakavas had been losing before but in May 2006, in just 5 hours, harry lost a whopping $164 million.

According to witnesses present during this epic loss, Harry was placing bets well over $300,000 per hand. His trend in losses continued when he visited Macau at one point. It’s estimated that Kakavas lost over $4 million in 24 hours.

At one point, he attempted to get back $20.5 million he had lost at Crown Casino in Melbourne. According to his petition, Kakavas claimed that the casino was well aware of his gambling problem and instead of placing restrictions, they went ahead to take advantage of the situation. The court ruled against him. He tried to appeal but also lost.

#2 Singaporean Tycoon: $100 Million

Looks like billionaires have a thing for losing at the tables. In this case, it’s all about a local businessman who was gambling – get this – at two different casinos. According to reports, the businessman lost at least $75 million during gameplay.

Reports place the billionaire businessman who was also listed in the top 40 richest people in Singapore by Forbes at the Resorts World Sentosa and the famous Marina Bay Sands.

Unconfirmed reports also place another businessman from Singapore in the same casinos and at the same time. Can you believe that? This one lost $37 million.

#1 Watanabe: $127 Million

Terry Watanabe takes the top spot when it comes to the person who lost the most in Las Vegas history. The high roller is known for being a staunch businessman and mostly as an ardent gambler.

In 2007, Watanabe went on one of the maddest gambling sprees ever seen in Sin City’s casinos. The Rio All-Suite Hotel and Casino and Caesar’s Palace were locations that saw it all. Blackjack was the preferred game that saw the businessman lose a jaw-dropping $127 million.

According to witnesses present at the scene, Watanabe’s playing strategy was so terrible that it appeared as though he was deliberately trying to lose.