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5 Most Insane Gambling Losses of All Time

5 Most Insane Gambling Losses of All Time

While most gamblers tend to brag about their winnings, they rarely talk about their losses, especially when it comes to the incredible amounts of money. In this article, we decided to shed some light on this reverse side of gambling and tell you about the players who have become “legends” due to their unprecedented losses. They violated the key principles of responsible gambling, and this approach has definitely cost them a lot.

Maureen O’Connor – $13 million

When a person gains access to a colossal amount of money due to their position in the government, he/she is often tempted to spend that money on his own needs. Maureen, who was mayor of San Diego, became one of the victims of this widespread trend and began to use the money entrusted to her for high roller gambling. This woman has wagered over $1 billion during her gambling career. However, she managed to stop her losing score at $13 million. And unlike millions of other players, she paid off her debt in full, which is quite an impressive achievement.

Harry Kakavas. $20.5 billion

Harry experienced most of his gambling losses at one single gambling establishment, the Crown casino based in Melbourne. Being an Australian billionaire with more than a $1.4 billion fortune, Kakavas certainly had a gambling addiction, and it led him to enormous losses. When it was said and done, his gambling losses exceeded $20.5 million, and the player decided to recover these funds through a lawsuit against the casino. But the court did not support the gambler and his accusations, and he lost a fairly substantial part of his impressive fortune.

Charles Barkley – $30 million

Unlike previous players, this gambler is an incredibly famous and popular sports personality. He competed against Michael Jordan in the most prestigious basketball league in the world NBA and became one of the most recognized basketball players in history. And yet, few people knew that Charles loves to play for real money and that he loses serious amounts due to his gambling passion regularly. Nowadays, many gambling enthusiasts claim that his losses reach $30 million. However, this fact does not stop the former basketball player, and he still risks absurd sums of money from time to time.

Archie Karas – $40 million

This gambler is undoubtedly one of the most iconic players of all time. According to an unconfirmed legend, Archie came to Las Vegas with $50 and turned it into $40 million through gambling over the course of three years. Many gamblers know him as the author of one of the most impressive winning streaks in history. However, all good things must come to an end sometime, and Karas is no exception to this rule. It took him just three weeks to lose every single penny he generated from 1992 to 1995. Therefore, his total losses reached a whopping $40 million mark.

Terrance Watanabe – $127 million

When this player’s father died in 1977 and Terrance inherited his Oriental Trading Company, he did not plan to hit any new business heights. Instead, Watanabe decided to devote as much time as possible to his gambling passion and went to Sin City. As a result, he has wagered over $835 million and lost $127 million at various Las Vegas casinos. His favorite gambling venue was Caesars Palace, and Terrance has yet to pay off all of its debts to this establishment. Some reports say the player’s debt is as high as $15 million, and if he does not return this money, he may go to jail indefinitely.

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