The Biggest Casino Losers: 5 Greatest Land-Based Casino Losses of All Time

Casino gaming is a big source of entertainment and a revenue-generating industry. Like huge prize winnings, the industry has also witnessed some of the biggest falls.

The excitement of the game has lured people into betting enormous amounts resulting in unimaginable losses.

Gambling is often cited as a ‘game of luck,’ but there are also games that demand skills. Read on to learn about the massive losses in the history of casinos.

The Top Five Losses at Casinos


Amidst huge wins, there are moments when players lose money due to addictive betting.

Although losing money is a part of gambling, players should be careful and practice responsible gaming. Many platforms like iMoon casino advocate for responsible gaming to ensure a safe gaming experience.

The five top losses in gambling history are listed under the following names:

  • $127 Million by Terrance Watanabe
  • $40 Million by Archie Karas
  • $30 Million by Charles Barkley
  • $20.5 Million by Harry Kakavas
  • $13 Million by Maureen O’Connor

$127 Million by Terrance Watanabe


In 2007, Terrance Watanabe, successor to a business empire, suffered a heavy loss due to his gambling addiction. He lost $127 million dollars while on a gambling spree over baccarat and blackjack games at Caesar’s Palace in Las Vegas. Watanabe’s addiction to gambling and drinking has been cited as the main reason for his loss.

$40 Million by Archie Karas

Known as one of the best gamblers of all time, Archie Karas had a special interest in baccarat, dice, and poker. He suffered a huge loss by betting above his limit.

The owner of the largest winning streak in the history of gambling lost $40 million dollars due to his gambling mishap.

$30 Million by Charles Barkley


The celebrated NBA star Charles Barkley tried his hand at gambling and lost 30 million dollars.

According to the reports, Barkley was addicted to various casino games and knew losses were part of the game. Even though he enjoyed the thrill of gambling, he took a break from the game and restrained himself from betting over his limits.

$20.5 Million by Harry Kakavas

As a billionaire who loves gambling, Harry Kakavas lost $20.5 million at Crown Casino in Australia. He gambled for a whopping amount of $1.43 billion and was known as a gambling addict.

Kakavas tried to sue the Australian casino by citing the exploitation of his urge to gamble. But the court rejected his plea for the reason that he was fully aware of the decisions he made while gambling.

$13 Million by Maureen O’ Connor


Maureen O’Connor was serving her term as Mayor of San Diego when she lost $13 million by gambling over $1 billion.

As a gambling addict, she even borrowed $2 million to gamble on a video poker game. However, she excelled in her role as a Mayor and also paid back her gambling debts in full.

Big Misses at Casinos by Celebrities

Celebrities and their love for gambling are quite popular. While some have tasted success, there have also been incidents where they lost hefty amounts.

The craze for gambling still continues among celebrities. The following are some incidents where the stars were not favored by their luck.

  • Ben Affleck
  • Wayne Rooney
  • Pamela Anderson
  • Tiger Woods
  • Michael Jordan

Ben Affleck


The Hollywood star is a huge fan of poker and blackjack. But the poker championship winner of 2004 lost $400,000 on a single hand. It was indeed one of the most dramatic losses in gambling history.

Wayne Rooney

The former Manchester United and England team superstar is also an alleged gambling addict. He lost 500,000 pounds in under 2 hours while playing roulette and blackjack. It was one of the quick losses in the gambling industry.

Pamela Anderson

The popular American actress and model Pamela Anderson is a regular in Las Vegas. She loves playing poker and lost an amount of $250,000 in a single night while trying her hand at her favorite game.

Tiger Woods

Tiger Woods, a popular golf star, is also alleged to be a gambling addict. Reports state that a Las Vegas casino offers him a $1 million betting limit. While trying his hand at blackjack, the golfer lost $25,000 on a single bet.

Michael Jordan


Michael Jordan, the American basketball legend, is known for his love of gambling. According to reports, he gambles above $1 million a year. But Jordan lost $5 million dollars on a single bet due to his alleged addiction to gambling.

The Importance of Responsible Gaming

Despite all these big losses, people still fall into addictive gambling and lose huge amounts in single or consecutive bets. Some people have lost a fortune by betting recklessly or without proper awareness about gambling.

Gambling is one of the most sought-after entertainment activities in the world. People indulge in gambling mainly for the thrill and excitement. But responsible gaming is an important aspect of gambling.

Operators should provide players the choices to self-exclude or take a break to relieve the urge to gamble over the limits.

Furthermore, players should be aware of the risks involved and restrain themselves from indulging in activities like regressive betting.