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Top 5 Craziest Gambling Losses

Gamblers call it the thrill of victory and the agony of defeat. But as any experienced sports bettor knows, there's always a risk you'll lose big. In fact, losing big is one of the biggest risks when betting on your favorite team or athlete. Gamblers who play for high stakes with the potential to win big often make news when they lose their fortune in a single blow. It's not uncommon for bettors to blow an entire trust fund or leave their kids uneducated because of gambling addiction. These stories are cautionary tales for those looking to get into risky bets that go beyond watching the game and keeping tabs on Fantasy leagues.

While it is good to stay cautious, who says you can't have fun while at it? Visit our casino and use the Ice Casino 25 euro bonus to win a little extra. Here are our top five crazy gambling losses you won't believe.

Top 5 loss-making gamblers:

  • Maureen O'Connor
  • Charles Barkley
  • Harry Kakavas
  • Archie Karas
  • Terrance Watanabe

    Maureen O'Connor
    Maureen O'Connor is the only woman on this list of top losses in gambling history. She was mayor of San Diego when she lost $13 million in gambling! There are many things to admire about O'Connor's gambling losses. Taking into account that Maureen gambled $1 billion, losing $13 million was quite impressive. O'Connor ended up borrowing an amount of $2 million from the charitable foundation of her second husband in order to gamble away all her money on video poker.

    Although we remember her for her considerable losses, we must not forget how well she served as mayor and what she achieved in her career by working hard and earning her positions. It was an impressive feat for O'Connor to pay back her gambling debt in full.

    Charles Barkley Despite his tremendous success as a basketball player, big-spending Charles Barkley was not a discreet gambler. He squandered most of his $30 million fortune on gambling. He has been open about losing $2.5 million in one Blackjack hand. Although Barkley had a problem, he seems to have gained more pleasure from the game than some of the others on this list. He gambled in a lot of casinos, and he enjoyed a variety of games, from Blackjack to Baccarat to Dice and Roulette.

    For him, it was never about winning a huge amount of money but instead about the thrill of the game. He understood that there were losses. Barkley has educated himself a little bit about responsible gambling over the years. He has quit playing in it for a while and is back at it, but now he knows how much he can afford to lose.

    Harry Kakavas
    Kakavas lost $20.5 million over the course of two years at the Crown Casino in Melbourne, Australia, but his losses were nominal in comparison with the amount he lost in a single sitting. He bet $1.43 billion over a two-year period starting in 2012.

    When he was confronted with the consequences of his gambling habit, he sued the Crown in an attempt to defend himself. Harry was not able to defend himself on his behalf, as the court found he was capable of rational decision-making. Harry had a gambling addiction that went back many years, as proved by his prior conviction for defrauding a large Australian company of $220,000 in 1998 to support his gambling habit. He ended up losing millions at the Baccarat tables in Las Vegas despite his self-exclusion from the Crown Casino.

    Archie Karas
    Even though he was the biggest loser in gambling history, Archie Karas is one of the most well-known gamblers. He holds the record for the longest and largest winning streak in gambling history, despite being one of the biggest losers.

    In 1992, he arrived in Las Vegas with only $50 in his pocket and slowly became one of the biggest gamblers in history, turning the $50 into $40 million with the help of a friend, who loaned him $10,000.

    Soon after, he started taking more and more reckless calls and blew it all away. He gambled on Poker, Baccarat, and Dice. After he won $7 million, he would allegedly lay out the money and wait for someone to approach him. His reckless wagers and bargaining with the casino led to an all-out loss of over $30 million in three weeks.

    Terrance Watanabe
    Terrance Watanabe inherited the Oriental Trading Company in 1977, after the death of his father. He sold it in 2000, so he could focus on gambling. Baccarat and blackjack were his interests. He gambled in Vegas in 2007, particularly at Caesar's Palace. With a wager of $835 million, he lost $127 million.

    According to witnesses, he consumed two to three bottles of vodka daily, in addition to cocaine. Caesar Entertainment Corporation, which owns Caesar's Palace, was fined $225,000 for allowing Watanabe to continue gambling while intoxicated. He owes $15 million as of this day and may face jail time if he does not pay it.

    Gambling is no easy task, and one must be careful when actually betting hard-earned money. A moment of misjudgment can cause catastrophic losses, as we have seen above. So, next time you go gambling, keep your eyes and ears open and try to stay sober to be able to make well-thought decisions.