7 Worst Gambling Losses in History

Sir Philip Green

Sir Philip Green is a British businessman who is responsible for the success of multiple brands such as TopShop, Evans, Burton, and Miss Selfridge.

Green was born to a rich family in South London, and set up his first business when he was still a young man, using a $30,000 loan to import jeans from Asia to London. He lives a life of luxury in a hotel in London during the week, and spends the weekends at his home in Monaco with his wife and children.

In 2004, he was rumored to have lost over $3 million in one evening at the London Ambassadeurs Casino, gambling at the roulette tables. He has been criticized in the past for corporate tax avoidance, as well as using offensive expletives to describe the Irish. He was knighted in 2006.

Featureflash / Shutterstock.com

Featureflash / Shutterstock.com

Akio Kashiwagi

In 1992, real estate investor Akio Kashiwagi was killed in his home near Mt. Fuji, Japan. After his death, it was revealed that he left gambling debts totalling at least $9 million, which were owed to casinos in Atlantic City and Las Vegas.

An official from the Dunes casino in Las Vegas said that he saw Mr. Kashiwagi “sit at the baccarat table and bet $100,000 a hand for 80 hoursat a time. The most he lost at one single time playing baccarat was $7 million, at the Trump Taj Mahal casino.


His death was extremely suspicious, as Japanese authorities reported that he was stabbed up to 150 times before his body was abandoned. Kashiwagi claimed an income of hundreds of millions of dollars per year, but was very private about how exactly he made his money.

Sean Pavone / Shutterstock.com

Sean Pavone / Shutterstock.com

Harry Kakavas

Another Australian, Harry Kakavas was a real-estate salesman who made his fortune selling mansions on Australia’s Gold Coast. He was known as one of the biggest gamblers in the world, who never let any sum of money stand in between him and the baccarat tables.

Between 2005 and 2006, he was rumored to have lost more than $30 million playing baccarat at the Crown Casino in Melbourne. Since he was such a good customer, the casino plied him with not only free food and drinks, but also free accommodation and free flights from the casino to his home on the Gold Coast.

After he realized how much money he owed the Crown, he sued them, claiming that they knew that he was a compulsive gambler and exploited him.

TK Kurikawa / Shutterstock.com

TK Kurikawa / Shutterstock.com

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