Some high rollers win exceptional amounts of money and many lose it just as fast without blinking an eye. These players have probably lost the most money over multiple sittings than many make in their lifetimes.
So, if you’ve ever wondered what the most money ever lost in a casino is, then we’ve got a list for you. These are the largest losses ever incurred at casinos in the world, including Las Vegas, Singapore, and Macau.
1. Harry Kakavas – $164 million: Money Most Ever Lost
This Australian billionaire never had to worry about money after selling luxury homes on the Gold Coast. But, that success made the real estate tycoon greedy for more, so he started gambling a lot at casinos. During one of his infamous sessions, he spent $300 000 per hand at a baccarat table.
However, it seems he was only lucky in business, and he quickly lost his billionaire status. Still, he tried to win it back by travelling to Sin City and Macau. In Vegas, he lost a record-breaking $164 million in a single session. Then, he tried to sue the casinos for giving him free drinks and comps (but lost that, too).
2. Terry Watanabe – $127 Million: Most Money Lost in One Spree
Terry Watanabe seemed to be determined to lose a fortune at the tables in 2007. His “insane gambling spree” at Caesars Palace and the Rio All-Suite saw him lose $127 million. According to witnesses, Watanabe was playing like he wanted to lose everything he had.
3. Singaporean Tycoon – $100 Million
A local businessman from Singapore lost nearly $75 million while playing at the Marina Bay Sands and Resorts World Sentosa. While his identity remains a secret, it’s still a massive losing streak that must have stung. There aren’t many details about this high roller, but we hope he cut his losses after that.
4. Charles Barkley – $20 Million
This NBA Hall of Famer seems to have the worst luck in gambling because estimates of his losses are jaw-dropping. Reportedly, Charles Barkley has lost between $10 and $30 million over the years while playing at casinos. And, he admitted to losing $2.5 million in one blackjack session, which makes you wonder if he ever learned the rules…
5. Leonard Tose – $25 Million
There seems to be something about businessmen that sets them up for failure on this list. Leonard Tose is no different because he lost roughly $25 million at Las Vegas casinos back in 1985. At the time, he owned the Philadelphia Eagles but had to sell the team rights for $65 million. His bad luck at gambling carried over to the courtroom after he lost multiple lawsuits against the casinos.
6. Kerry Packer – $13.6 Million: Most Money Ever Lost at Once
When you can’t win in Australia, you go to Las Vegas, if Kerry Packer is the example to follow. This Aussie billionaire reportedly lost a whopping $13.6 million in just three days back in 2000. While it’s just a drop in the ocean for Packer, that’s still a lot of money to throw away.
7. Phil Ivey – $10 Million
When you don’t have a large net worth, spending large amounts of money might not be a good idea. Unfortunately, World Series of Poker Gold Bracelet Winner Phil Ivey learned this the hard way. He was accused of cheating to win by Borgata Casino in Atlantic City.
At the time, Ivery was playing baccarat and won nearly 9.6 million dollars. But, as a prolific gambler, cheating claims were bound to come his way. The judge ruled that Ivey hadn’t cheated, but he still had to pay back the money.
8. Gladys Knight – $6 Million
The Empress of Soul, Gladys Knight, reportedly is addicted to playing blackjack at casinos and shared her experiences. According to current estimates, she’s said to have lost over $6 million over the years in between making hits.
9. Safa Abdulla Al Geabury – £2.2 million ($2.87m)
It’s not rare for a player to get sued, but this Swiss businessman takes the cake after he lost $2.87 million at London’s Ritz Club in 2014. According to the media, Al Geabury lost the money and then ignored the debt until he got dragged to court. Eventually, the Ritz Club won the case, but the businessman still refused to pay up and got sentenced to ten months in jail.
10. Charlie Sheen – $2.5 Million
Since Charlie Sheen is well-known for his lavish lifestyle, his gambling habits probably come as no surprise. According to documents filed during his divorce from Denise Richards, the actor spent $200 000 a week at sportsbooks.
What’s the Most Money Ever Lost?
Based on our list, the most money ever lost over a length of time is Harry Kakavas’ $164 million at the tables. When you consider his total loss, it’s easy to see why casinos make so much money in Sin City. Famous gambling games like blackjack and baccarat seem to be the biggest draws, but the roulette wheel also takes no prisoners.
While it might seem tempting to bet big and win more, we really don’t recommend it, even if you’re a billionaire. After all, any sum of money can still be lost, because the house always wins. So, start a bankroll, stick to it, and don’t fall for the free drinks.
Or, sign up to an online casino so you can walk away whenever you want.
