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The Most Jaw-Dropping Gambling Losses Online and Offline

If you’re an experienced player at an online or traditional brick-and-mortar casino, you know losses are a regular feature of gambling. Some days you win, and others, you lose your wagers. So, it is important to always place a limit on how much you spend. This way, you can gamble responsibly while still having fun. Play your favorite games at Spin City casino for a lucrative adventure.

Millions of people engage in these activities, and we have recorded different stories of renowned individuals whose poor decisions cost millions of dollars while gambling. This article highlights the craziest losses in history.

Top 3 Craziest Gambling Losses 

In this piece, we will be starting from the lowest to the highest losses. Grab a snack because it’s about to get more interesting.

  • Charles Barkley: $30 Million 

Charles Barkley was Known as a Professional basketball player and TV personality in the 90s. Throughout his 16-year NBA career, he played for the Philadelphia 76ers (1984-1992), Phoenix Suns (1992-1996), and Houston Rockets (1996-2000). Some of his achievements include being 11 times NBA all-star, and in the year 1996, he became one of the 50 greatest players in the history of the NBA. Charles Barkley is the fourth player to accumulate 20,000 points, 10,000 rebounds and 4,000 assists over a 16-year career in NBA.

He was no doubt a great basketball player, but just like every human, he wasn’t perfect and had a gambling problem. This became apparent in a 2006 interview with ESPN when he claimed to have lost $2.5 million in just 6 hours of gambling. Barkley further recounted that he lost $10 million in 2006 alone. However, he went on gambling until 2008, when this habit landed him in legal trouble. After the whole situation blew over, Barkley took a 2-year break from gambling before going back at it. In total, he has lost over $30 million from gambling.

  • Archie Karas: $40 Million 

Archie Karas is a Greek-American gambler born on November 1, 1950, in Antypata Cephalonia, Greece. He is known for holding the record for the longest and biggest winning streak in casino gambling history. His story began in 1992, when he was destitute and struggling to survive. In December of the same year, he drove to Las Vegas with just $50 in his pocket. There, he got a loan of $10,000 from an acquaintance. By the start of 1995, he had won more than $40 million from gambling.

Karas claims to have gambled more money in casinos than anyone else in history. He made so much money that transporting it became a problem as he had to move around with millions of dollars in his car at a time. He often carried a gun, having his brother and the casino security follow him around. His downfall started at the end of 1995 after he lost most of his winnings in 3 weeks. All in all, he lost $40 million to gambling. The story of Karas is one of great success, but it ended on a sour note due to poor judgement resulting in heavy losses.

  • Terrance Watanabe: $127 Million 

Terrance Watanabe is an American Businessman, Philanthropist, and high-stake gambler, known for his luxurious gambling habits. His father, Harry Watanabe, was the founder of the Oriental trading company supplying arts and crafts, toys, novelty, and school materials.

In 1977, he became the president and proprietor of his father’s company. By 2000, he resigned and sold all his stake in the company to Brent wood Associates, a Los-Angeles based private equity firm.

His whole ordeal started after he sold off the Oriental Trading Company. Although he decided to become a philanthropist, Terrance Watanabe got caught up in the fast life of substance abuse and high-stake gambling. In 2007, Watanabe went to two casinos, the Las Vegas- Ceasar’s Palace and The Rio. In one night, he wagered a total of $825 Million, losing about $127 Million. His gambling habit was so bad that he got banned from Wynn Las Vegas for compulsive gambling. All in all, he was estimated to have lost $204 Million.


Gambling either at an online or brick-and-mortar casino is highly entertaining, and you still get to win money. Also, casino games help with skill enhancement, improve pattern recognition, social skills, and more. However, things stop being rosy when you start losing money. Since losses are always lurking, you have to exercise self-control. High rollers usually suffer a more significant financial impact when they lose games.

In severe cases, this could lead to terrible consequences like personal harm and suicide. Therefore, you should advisably limit the portion of your income consumed by your gambling habit. Once you suffer two back-to-back losses, it is best to take a break and re-strategize. Increasing wager sizes to win back your funds will only lead to regretful decisions.

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