Top 7 Biggest Gambling Losses in History: Modern Casino Legends

No billionaire in existence is safe when it comes to beating the house. After all, as the saying goes, you can’t win forever. Much has been said about cutting one’s losses at an appropriate time and walking out of the casino without the weight of crushing debt and a personal crisis. However, it is hard to set boundaries when the dice start rolling.

Most players have a hard time defining their limits as they end up at the casino table. Gambling reports have proven time and again that the odds of losing are invariably higher than those of becoming a millionaire overnight. Still, this does not seem to bother the majority of the players, desperate to try their luck when the sun goes down. Below, you will find some of the most legendary names in the history of gambling losses that shook the entire continent.

Umar Siddiqui

Siddiqui, at the start of his career, was a manager for Fry’s Electronics. However, he was soon removed from the company’s executive office when it was confirmed that he spent over $65 million of the company’s money on gambling. It was also revealed that the money was obtained through illegal actions. By the time he was exposed, Umar Siddiqui had already earned the title of one of the most enthusiastic cheetahs at The Venetian.

Siddiqui spent more than $70 million of the illegal money in Vegas, gambling away at his favorite casinos. In exchange for his insane stakes, the casino owners allowed the enthusiastic punter to live out his best life. He had a luxury suite and an impressive gambling credit provided to him by the company’s management. When he finally declared himself bankrupt some years later with a debt of $120 million in cash, the man had no more than $80 on his private bank account.

Kerry Packer

Kerry Packer earned the name of one of the most notorious punters on the planet when he developed his own brand of money squandering while abroad. Although Packer used to spend scandalous amounts all over the world, Britain seemed to have a special hold on the famed Australian mogul. Packer would go around casinos trying to find out how much they had on hand.

If the sum turned out to be anything less than $800k, he would leave the place in search of something more “thrilling”. It was estimated that Packer lost more than $12 million in a single gambling round in London. The casino managers would later publish a statement that said Packer once lost $33 million as he was playing baccarat. However, the sources claim that Packer was extremely cautious when it came to family money and would never waste a penny of his fortune.

Maureen O’Connor

When Maureen O’Connor lost an astonishing $13 million in the game of poker, she was better known to the general audience as the mayor of San Diego. Losing that much money overnight does seem outrageous, but the mayor’s losses would not appear too striking once you learn that her original wagers reached $1 billion.

O’Connor later admitted to having a gambling addiction. She also claimed to have borrowed $2 million from her husband only to spend it in one of her favorite casinos. However, it would be unfair to dismiss O’Connor and her contributions to the economy during her years of service as an incumbent mayor. She openly talked about her gambling problem and went out of her way to restore her good name as she paid her debt in full.

Charles Barkley

Charles Barkley could be construed as a common trope of a basketball star taking his love for gambling a bit too far, but this was clearly not the case with this NBA favorite. Barkley once said that he never thought he would fall victim to gambling fever: he only ever dreamt of going to Vegas and having the time of his life.

It was later discovered that Barkley spent his fortune of $30 million when his passion got out of hand, including the loss of $2.5 million in blackjack. The NBA star added that becoming wealthy was never an issue. Barkley was addicted to the adrenaline high so many players are used to. To restore his reputation, Barkley learned how to control his gambling urges. He is still active at the casino table but will never stake more than he can afford.

Harry Kakavas

Harry Kakavas might be the most prominent example of addiction so extreme that it could not be helped. Kakavas was a top-tier real-estate salesman from Australia who lost $1.5 billion at the Crown in Melbourne. He then sued the casino, claiming that they took advantage of his pathological gambling problem and allowed him to take unnecessary risks.

At the peak of his gambling activity, Kakavas lost $164 million in six hours. He once arrived at the Vegas casino only to lose $4 million in the span of one day. It turned out that the man was gambling on loans, so he eventually declared himself bankrupt. Interestingly, the casino never admitted its fault, which led to Kakavas losing the case. The court claimed that Kakavas was fully capable of dealing with his addiction and walking away from the casino if that was what he really wanted. The judge also issued a statement saying the casinos do not carry any kind of responsibility for one’s addictive behaviors.

Archie Karas

Archie Karas, the American gambler with Greek roots, also known as “The Greek”, arrived in the City of Angels while having $50 on his person. He had to borrow $10,000 from someone he knew to buy himself a pass to the casino table. Three years later, he is said to have accumulated a fortune of $40 million.

However, this run of good luck was destined to come to an end when Karas started to show signs of recklessness. He would ignore any gambling strategies that could potentially help him to beat the house and insisted that the casino owners let him gamble on his own terms. The man spent the last of his money in the course of three weeks, thus securing himself a place in the gambling hall of fame.

“The good things you can’t buy with money. A good friend you can’t buy. A friend can save your life, they can help you when you’re down and out.”

Terrance Watanabe

Terrance Watanabe could easily follow in his father’s footsteps and become a successful businessman in his own right, if not for the gambling addiction he developed in his later years. Back in 2000, Watanabe sold his father’s company shares so he could focus on his one and only passion: baccarat.

Watanabe would go on insane gambling tours while in Vegas, making Caesar’s Palace his residence. Wagering $835 million and losing $127 million, he suffered a gambling loss that was unheard of before. Watanabe then hired a lawyer who stated that the casino owners exploited his reckless tendencies and impulsive behavior while showing complete disregard for his overall mental state. The casino management refused to accept the blame for Watanabe’s actions, claiming that he was fully aware of his gambling habits.