What Are the Biggest Gambling Losses in History?

If you play properly, you’re likely to always know when to stop so that you may enjoy yourself without going above your means to recover your losses. However, not every player acts responsibly, and history has seen some very enormous losses.

iGamingNJ’s editor, Arsenii, decided to research this topic and found the 5 worst gambling losses in history and how they transpired.

Terrance Watanabe

When Terrance Watanabe’s father passed away in 1977, he inherited the Oriental Trading Company from his successful business father. Watanabe indulged in a year-long gambling binge in Las Vegas in 2007, mostly at Caesar’s Palace. He placed a stunning $835 million in bets and lost $127 million of it. 

According to reports, Watanabe’s excruciating losing streak is the longest Las Vegas has ever witnessed and he was seen drunk during his sessions. The owner of Caesars Palace, Caesars Entertainment Corporation, was fined $225,000 for allowing a drunk Watanabe to continue playing. Even now, Watanabe owes $15 million and risks going to jail if he doesn’t pay.

Charles Barkley

Charles Barkley is arguably the most well-known name on this list. The 11-time NBA All-Star was not a responsible gambler.

Despite his enormous accomplishment as a basketball player, he almost completely lost his $30 million wealth via gambling. Barkley, a lifelong high roller, has acknowledged losing $2.5 million in a single game of blackjack. While Barkley undoubtedly had a problem, he also appears to have enjoyed the game more than many of the other players on this list.

Over the years, Barkley has gained some knowledge about responsible gaming. He took a break from it for a while, and even though he has returned, he no longer wagers more than he can comfortably afford.

Harry Kakavas

Harry Kakavas, a former Australian millionaire, lost $20.5 million, which is actually a little amount given that he bet $1.43 billion throughout his gambling endeavors, similar to the next person on the list.

The real estate magnate sought to sue Crown Casino in Australia’s High Court on the grounds that they took advantage of his “pathological drive to gamble”. However, the judge decided that Harry was capable of making logical decisions, therefore he lost the case.

But it’s obvious that Kakavas had a long-standing gambling addiction. He was imprisoned for four months in 1998 for defrauding a significant Australian corporation of $220,000 and using the proceeds to support his gambling addiction.

Maureen O’Connor

The sole woman on this list is Maureen O’Connor, who is also notable for being the mayor of San Diego at the time of her enormous $13 million gambling loss.

Although she has bet around $1 billion throughout her gaming sessions, it’s actually rather astounding that she managed to lose only around $13 million. O’Connor’s addiction to gambling was so severe that she had to borrow $2 million from the charity foundation of her second husband, only to waste it all playing video poker.

She did a good job as mayor and worked hard and meritoriously for the benefit of her fellow citizens. She also did a commendable job of paying off her gambling debt in full, which obviously was no easy task. She learned the meaning of responsible gaming, this is an important concept that everyone should know about, so visit iGamingnj.com to find out how to have fun and stay safe.

This is a paid guest post.