Gambling has always been a popular pastime for those looking for a thrill and a chance to win big. While most people gamble within their means and set limits on their losses, some high rollers have lost astronomical sums of money in a single session. In this article, we will take a closer look at some of the biggest losses in casino history, including the stories behind them and the lessons we can learn from them.

1. Terrance Watanabe: $204 million
Terrance Watanabe, the former owner of Oriental Trading Company, is widely considered to be the biggest loser in casino history. In 2007, Watanabe lost an estimated $204 million at Caesars Palace and the Rio casinos in Las Vegas. Watanabe’s losses were so significant that they accounted for 5.6% of Harrah’s Entertainment’s total revenue that year. The company eventually settled with Watanabe for an undisclosed sum, but it is believed to be around $100 million.

2. Harry Kakavas: $164 million
Australian real estate developer Harry Kakavas is another high roller who lost big at the casino. Between 2005 and 2006, Kakavas lost an estimated $164 million at the Crown Casino in Melbourne, Australia. Kakavas claimed that the casino exploited his gambling addiction and offered him incentives to keep playing even when he was losing. However, the court ultimately ruled in favor of the casino, stating that Kakavas was a responsible adult who made his own decisions.

3. Charles Barkley: $30 million
Retired NBA player Charles Barkley is known for his love of gambling, and it has cost him millions over the years. In a 2006 interview with ESPN, Barkley admitted to having lost $10 million in Las Vegas over the course of six hours. He later upped that figure to $30 million in his 2019 autobiography, stating that he had lost an average of $1 million per visit to the casino.

4. Maureen O’Connor: $13 million
Maureen O’Connor, the former mayor of San Diego, California, is another high roller who lost big at the casino. Between 2000 and 2009, O’Connor lost an estimated $13 million playing video poker at casinos across the country. O’Connor claimed that her gambling addiction was the result of a brain tumor and that she had taken out multiple loans to finance her habit. She eventually pleaded guilty to a charge of money laundering and was sentenced to house arrest.

5. Akio Kashiwagi: $10 million
Akio Kashiwagi was a Japanese businessman and high roller who was known for his love of baccarat. In 1990, Kashiwagi flew to Atlantic City to play at the Trump Plaza Casino. He started out strong, winning $6 million in the first two days, but things quickly turned sour. Kashiwagi lost all of his winnings and another $4 million over the next few days. Kashiwagi was found dead in his home in Japan just months later, and his murder remains unsolved.

Lessons learned

While the stories of these high rollers may be entertaining, they also serve as cautionary tales about the dangers of gambling addiction and the need for responsible gambling practices. It’s important to remember that gambling should always be viewed as a form of entertainment, and that it’s never a good idea to gamble more than you can afford to lose.

In addition, casinos have a responsibility to identify and assist customers who may be struggling with a gambling addiction. This includes providing resources for self-exclusion and setting limits on the amount that can be wagered in a single session.

Overall, the stories of these high rollers serve as a reminder that while gambling can be exciting and potentially lucrative, it can also be incredibly risky. For those who struggle with a gambling addiction, it can be a destructive and life-altering habit that can lead to financial ruin and other negative consequences.

If you or someone you know is struggling with a gambling addiction, there are resources available to help. The National Council on Problem Gambling offers a helpline for those in need of support and guidance, and many casinos also have programs in place to assist customers who may be struggling with addiction.

At the end of the day, it’s important to approach gambling with a sense of responsibility and caution. While the allure of a big win can be tempting, it’s never worth risking more than you can afford to lose. By setting limits and approaching gambling in a responsible manner, you can still enjoy the excitement and thrills that come with playing your favorite casino games while avoiding the risks and pitfalls of addiction.

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