The Biggest Gambling Losses in History

The Biggest Gambling Losses In History

The Biggest Gambling Losses in History

Casino tables always carry a risk, but with a little common sense, you shouldn’t be too concerned about big losses. Gamblers who have lost everything have been unable to resist temptation. I don’t think it matters if they were seeking a return on investment or acting out of ego.

Here are some examples of professional gamblers who have lost everything. While they are good anecdotes, they are rather poor examples of how to act and behave in a casino. All of their money and more were lost. Among today’s gamblers are those who have lost substantial amounts of money gambling, or have gone from being wealthy to being poor.

  1. Terrance Watanabe

Bets totaled: $825 million

Losses Incurred: $127 million

Choice of Game: Baccarat, Blackjack

Whenever we talk about the biggest gambling losers, there is usually some rivalry involved. Some people who have made a fortune, or have come into money by some other means, have felt inclined to gamble quite foolishly at one point or another. Terrance Watanabe, however, is one of those gamblers who lost it all, or at least a significant portion of his wealth.

Following the inheritance of an Oriental Trading Company in 1977, Watanabe sold it in 2000. After playing over $825 million on Blackjack and Baccarat at Caesar’s Palace and The Rio, he lost $127 million in 2007.

Las Vegas has never seen a losing streak like Watanabe’s, so far as world-renowned gamblers who have lost their entire fortunes are concerned. His attempt to sue the casinos failed, and he was required to pay his debt.

In 2010, Watanabe was charged with four felony counts for $15 million of his debt and to the same extent again in 2020. He has since covered all but $15 million of his debt. Failure to pay could result in a 28-year prison sentence.

  1. Harry Kakavas

Bets Totalled: $1.43 billion

Losses Incurred: $20.5 million

Choice of Game: Baccarat

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Despite not being the biggest loser, Harry Kakavas has made it a point to consistently lose. Even so, Kakavas has been able to minimize his losses through his prescience, skill, and knowledge so that he has certainly not suffered the biggest losses.

Makavas gambled at Melbourne Crown Casino for 16 months between 2012 and 2013, spending a total of $1.43 billion Australian Dollars, and incurring net losses worth $20.5 million Australian Dollars. While Kakavas has had no problem gambling for 16 months straight, but yet he hasn’t approved of the casino keeping the money he lost.

The lawsuit claims Kakavas was exploited by the casino by exploiting his “pathological gambling urge,” a popular defense among famous gamblers who lost everything or at least enough to feel aggrieved.

According to the statement from the judge, Kakavas showed that he could make rational decisions and act in his best interests, including refraining from gambling occasionally.

  1. Maureen O’Connor

Bets Totalled: $1 billion

Losses Incurred: $13 million

Game of choice: Video poker

She developed a gambling problem when she served as mayor of San Diego. It could be argued that where power is, there is money, but in Maureen O’Connor’s case, her gambling obsession became more sinister over time.

Still, O’Connor was quite successful in terms of mitigating risk compared to other unfortunate gamblers, a trait politicians have in common. While she gambled over $1 billion, her losses amounted to only $13 million. A better record than Kakavas and better than Watanabe’s.

Her second husband’s charitable foundation had to lend her $2 million and she spent it all playing video poker, so she is another one of the gamblers who lost it all. Her late husband founded Jack-in-the-Box restaurant.

The gambling addiction of O’Connor may be a little sensationalistic, but she deserves admiration nonetheless. She achieved great success through hard work and merit in her political and professional career.

  1. Archie Karas

Bets Totalled: $40 million

Losses Incurred: $40 million

Game of choice: Baccarat, Poker, Dice

One of the most memorable gamblers who lost everything was Archie Karas. Archie enjoyed playing big with no qualms about taking on all kinds of risks for a shot at something better. Las Vegas was his first stop in December 1992, with only $50 in his pocket and a $10,000 loan a little later. In the following two years, Archie played poker intensely, accumulating $40 million.

The wheels of fortune were set in motion when a destitute Archie spotted an old friend at The Mirage and requested the $10,000 loan. Playing $200/400 limit Razz, he soon turned the money into $30,000. He then returned $20,000 to his beneficiary.


After winning $3 million at Binion’s Horseshoe, Archie traveled around Las Vegas and amassed fortunes in every casino he encountered. Over time, Archie’s bankroll increased to $5 million, then $7 million, but he wasn’t interested in searching for another opponent.

He would simply place a sum of cash on a table and wait for his opponent to approach. There was great interest, not least from players like Stu Ungar, who were popular but tragic figures. In two straight games, Archie defeated Stu.

The first was heads-up Razz, where Stu lost $500,000. His second win came in 7-Card Stud, where he won $700,000. His downfall began when he strayed away from skill-based games and began to play dice and baccarat. Throughout his career, Karas beat some of the top players, including Johnny Moss, Chip Reese, Puggy Pearson, and. Why take on the risk of more risky games? We’ll let him speak for himself.

“Something must be understood. I don’t care about money. For me, it is not important. Material possessions are not important to me. All of it. You can’t buy health, freedom, love, or happiness with money. Consequently, I don’t fear money. I don’t worry about losing it.”

Casinos would allow Archie to wager way above the limit if he bargained effectively. Binion’s $5,000 denomination chips were all won at one point by him, thus leaving the casino without its highest denomination chips.

The gambler managed to lose 40 million dollars in three weeks, quickly becoming one of the most unfortunate of all gamblers. Probably the most well-known gambler who lost it all is Archie.

  1. Charles Barkley

Bets Totalled: $30 million

Losses Incurred: $30 million

Choice of Game: Baccarat, Roulette, Dice, Blackjack

Charles Barkley

It is no secret that Phoenix Suns’ ace Charles Barkley has suffered from a gambling addiction on numerous occasions. The entire fortune of Charles Barkley was lost to gambling, which was $30 million. Yet, Barkley, who has always been candid about his gambling problem, has never regretted his gambling.

He claimed he lost millions of dollars playing at 30 casinos during his active gambling years. It’s interesting to hear his perspective on the subject. Barkley has accepted the good and the bad in his habits, whereas others have tried to sue casinos:

“I was in Vegas several times and won a million dollars. At least ten times. Nevertheless, I’ve also gone to Vegas and lost at least three times as much.”

As a result, Barkley developed a mindset where he could accept losses of up to $200,000 in a single session. “I enjoy the action, I enjoy the justice,” he explained. However, he added that everything should be done in moderation.

Charles Barkley is a fascinating individual. Definitely one of the biggest gamblers, but he lost everything – or at least most of it. Even so, he has remained calm.

  1. Michael Vick

Bets Totalled: $20 million

Losses Incurred: $20 million

Choice of Game: Operating an illegal betting ring

Michael Vick has a mixed past, but most of it is his own doing. Vick was one of the gamblers who lost it all, but not just financially. The great quarterback for the Philadelphia Eagles that was a former National Football League (NFL) player had a gambling problem.

A significant portion of the money for the gambling element of the operation came from Vick’s illegal interstate dog fighting ring, Bad Newz Kennels. As a result of Vick’s conduct, the NFL suspended him immediately. Commissioner Goodell argued that Vick’s misconduct was not only against professional standards but also was highly unethical in nature. Vick’s team, the Falcons, didn’t sit idly by either.

Vick was notified that he now owed them $20 million out of the $37 million bonus he received. Vick’s bonus money was used to fuel a gambling ring, according to the court ruling in favor of the Falcons.

After a long and tortuous trial, he was sentenced to 23 months in prison. In the jury’s view, Vick didn’t take full responsibility for his actions because he failed both a drug test and a polygraph.

Even though he’s made mistakes in the past, Michael has made amends, and he’s back in the spotlight. FOX signed him as a studio analyst for the NFL, a position he deserves. Michael Vick definitely qualifies as a famous gambler who lost it all.

  1. Frank Saracakis

Bets Totalled: $13 million

Losses Incurred: $13 million

Choice of Game: Roulette

As heir to a large Greek Automobile Company, Frank Saracakis decided to indulge in his favorite pastime, gambling, while visiting London casinos in 1995. The glitz of the Melting Pot lured him to spend $13 million at Crockford’s Casino in London.

The game he chose was roulette, which he played for quite some time before losing every single chip he had. Although Saracakis didn’t lose everything, he suffered one of the largest gambling losses in history.

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