Gambling has long captivated individuals with its allure of high stakes and the possibility of great winnings. However, the world of gambling is not without its share of heart-wrenching tales of colossal losses. In this blog post, we delve into the top 10 biggest losses in gambling history, exploring the fascinating stories behind them, the reasons for these defeats, and where they took place. Brace yourself for a captivating journey into the realm of gambling’s most remarkable downfalls.

Terrance Watanabe

Terrance Watanabe, a successful businessman, is known for his extraordinary gambling losses in Las Vegas. In 2007, he managed to lose an astounding $204 million in a single year. His addiction to gambling led to significant losses at the Caesar’s Palace and the Rio casinos. Watanabe’s penchant for high-stakes gambling and his inability to control his urge to continue betting led to his downfall. His loss is definitely one in the top 10 biggest losses in gambling history.

Harry Kakavas

Australian businessman Harry Kakavas earned notoriety for his massive losses at Australian casinos. From 2005 to 2006, Kakavas lost an estimated $1.5 billion at Melbourne’s Crown Casino. His gambling addiction, fueled by the casino’s relentless pursuit of his patronage, caused him to suffer significant financial and personal setbacks.

Akio Kashiwagi

Akio Kashiwagi, a Japanese real estate tycoon, experienced one of the most memorable losses in the history of gambling. In 1992, during a baccarat marathon at the Trump Plaza Hotel and Casino in Atlantic City, he lost a staggering $10 million in a single night. Kashiwagi’s ambition to become the world’s biggest gambler and his high-rolling lifestyle ultimately led to his downfall.

Charles Barkley

Renowned basketball player Charles Barkley is no stranger to gambling, having wagered millions of dollars over the years. However, his losses reached a pinnacle when he admitted to losing approximately $30 million in various gambling sessions. Barkley’s highly competitive nature and desire for action caused him to chase losses, resulting in significant financial setbacks.

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Zhenli Ye Gon

Zhenli Ye Gon, a Chinese-Mexican businessman, made headlines in 2007 when his gambling losses came to light. He lost around $125 million in various casinos in Las Vegas, allegedly using illicitly obtained funds. Ye Gon’s extravagant gambling habits and his involvement in illegal activities ultimately led to his downfall.

Maureen O’Connor

Maureen O’Connor, the former mayor of San Diego, experienced a colossal gambling loss of approximately $13 million over a span of 9 years. O’Connor’s addiction to video poker and her misuse of funds intended for charity led to her financial ruin. Her case serves as a poignant reminder of the destructive power of gambling addiction.

Archie Karas

Greek-American gambler Archie Karas achieved legendary status for his remarkable gambling winning streak, but his subsequent downfall was equally notable. After turning $50 into $40 million through a series of successful wagers, Karas experienced a colossal loss of $30 million in just three weeks. His insatiable appetite for high-stakes gambling and reckless risk-taking were the primary factors behind his demise.

Robert Maxwell

Robert Maxwell, a British media mogul, is remembered for his dramatic downfall in the gambling world. In the early 1990s, he lost an estimated $2.5 billion in a series of high-stakes wagers on the stock market. Maxwell’s overconfidence, combined with his high-risk investment strategies, eventually led to his financial ruin and subsequent suicide.

Kerry Packer

Kerry Packer, an Australian billionaire and media tycoon, was renowned for his extravagant gambling exploits. While his losses were not as significant as some others on this list, his penchant for high-stakes gambling and his willingness to wager millions on a single hand of blackjack made him a notable figure in the gambling world. Packer’s gambling losses served as a testament to the inherent risks associated with high-stakes gambling.

John Daly

Professional golfer John Daly has had a tumultuous relationship with gambling throughout his career. He admitted to losing between $50 million and $60 million due to his addiction. Daly’s extravagant lifestyle and frequent visits to casinos led to significant financial troubles, highlighting the devastating impact of gambling addiction.


The top 10 biggest losses in gambling history serve as cautionary tales, shedding light on the destructive power of gambling addiction and the risks associated with high-stakes wagering. These stories illustrate the human propensity for both triumph and tragedy, reminding us that even those who seem invincible can be brought down by the allure of gambling. It is essential to approach gambling responsibly and with self-control to avoid the potentially devastating consequences that can arise from unchecked habits.

Disclaimer: Gambling can lead to addiction and financial losses. It is important to gamble responsibly and seek help if you or someone you know is struggling with a gambling problem.