6 Biggest Sore Losers in Gambling History

Neon Gambling Sign at Casino Entrance, Hand Holding Poker Cards
Nobody likes to lose when gambling with real money. But at the end of the day, most losers are mature enough to pay their debts and avoid causing an incident.

Unfortunately, certain gamblers don’t believe in this code. Some people might refuse to pay up or even cause physical harm to others.

Neither scenario is pleasant. However, there are players who  just can’t handle themselves properly after losing money. Below, you can read about the biggest sore losers to ever gamble.

1 – Harry Kakavas

By all means, Harry Kakavas never should’ve had to worry about money. The real estate developer made an estimated $1 billion by selling luxury homes on Australia’s Gold Coast.

But like many people who get filthy rich, Kakavas got tired of always winning. So, he started gambling in casinos…a lot.

Kakavas became famous for playing some of the highest stakes ever seen in Australian casinos. He would bet as much as $300,000 per hand in baccarat.

The billionaire didn’t fare so well in these games. He quickly lost his billionaire status and more after taking a beating on the baccarat tables.

Unhappy with his luck, Kakavas made trips to Las Vegas and Macau in hopes of turning things around. These gambling excursions didn’t go any better. In fact, he once lost $164 million through a single Vegas session in 2006.

Rather than taking his losses like a man, Kakavas spent several years attempting to sue various casinos. His case revolved around the VIP perks and casino comps that were offered.

He argued that the VIP rewards were merely used to keep luring him back to casinos. Kakavas lost every lawsuit and failed to recoup any of his massive losses.

2 – Jack McCall

Jack McCall may be the saltiest loser on this list. In fact, he’s such a sore loser that he actually murdered “Wild” Bill Hickok over a poker game.

This story began in August 1876, when Hickok was gambling at Nuttal and Mann’s Saloon No. 10 in Deadwood, South Dakota (formerly Dakota Territory). He was drunk and quickly lost all of his money to Hickok.

The latter encouraged McCall to stop playing poker. Hickok also bought the losing player breakfast and offered him money. McCall accepted the money, but he was also insulted by the gesture.

The following day, Hickok was at the poker tables again. He normally sat with his back against a wall so he that he could see any potential enemies coming. However, the only seat available at the time was one that faced away from the entrance. He begrudgingly took the seat.

Casino Poker Table, Ace of Spades Poker Cards

McCall entered the saloon during the game and shot Hickok in the back of the head. Wild Bill died instantly. After murdering Hickok, McCall was summoned to appear in court. He claimed that he was avenging his brother’s death (Lew McCall) at the hands of Wild Bill.

But the poker losses were largely believed to be the main reason behind the murder. Nevertheless, he was acquitted and allowed to go free.

McCall was later reported after bragging about shooting Wild Bill. He was subsequently retried on grounds that the first trial happened on Indian lands, rather than on true American soil.

This time, he was found guilty of murder and sentenced to death. McCall was hanged on March 1, 1877. One interesting side note to this bitter gambler story is that the hand Hickok died with—two black aces and two black eights (fifth card unknown)—is called “dead man’s hand.”

3 – Terrance Watanabe

Terrance Watanabe was once a very successful businessman. As the CEO of Oriental Trading, he helped the company grow to the point where it was selling $300 million annually.

In 2000, after over two decades in the family business, Watanabe decided to sell his controlling stake in the company. The Japanese-American tycoon always had a business-first mentality up to this point. But he decided to relax and start enjoying his fortune after selling Oriental Trading.

Unfortunately, part of this relaxation included long stays at casino resorts. Watanabe would play everything from slot machines to roulette during his stays.

He differed greatly from the average high roller. Rather than playing games with the lowest house edges, he’d gamble on anything—even keno, which has an extremely high house advantage.

Watanabe was treated like a king as a result. Casinos spared no expense when it came to comping him. Watanabe asked few questions and continued gambling away his fortune. His losses hit a peak in 2007, when he dropped over $120 million.

He eventually lost so much that he couldn’t cover his debts. Caesars Palace sued Watanabe for $14.75 million in bad checks. The latter countersued Caesars Entertainment on grounds that the casino gave him drugs just to keep him playing. It turns out that this part of the case did have some validity.

The Nevada Gaming Commission hit Caesars with a $225,000 fine for letting Watanabe use drugs on their property and sexually harass waitresses. But the countersuit didn’t save Watanabe from having to pay the casino. He ended up settling with Caesars out of court for an undisclosed amount.

4 – Safa Abdulla Al Geabury

Safa Al Geabury bears similarities to Terrance Watanabe. He’s a very wealthy individual who refused to cover his gambling debts when the time came.

The Swiss businessman owns an Islamic art collection that was once valued as high as $1 billion. He received a huge marker at London’s Ritz Club in 2014 as a result of his wealthy reputation.

But when it came to pay the marker, Al Geabury was very cheap. He lost £2.2 million at the Ritz Club and ignored the debt. The casino eventually sued him for the money. Al Geabury defended himself by saying that the Ritz took advantage of his compulsive gambling problem.

London Ritz Club Entrance

If true, this might have helped his case. But the Ritz produced signed documents from Al Geabury where he agreed that he no longer had a gambling problem.

The judge in the case ruled in favor of the Ritz Club. He saw too many inconsistencies in Al Geabury’s testimony and didn’t believe that he suffered from compulsive gambling.

Even after the court ruling, the art collector still refused to pay up. Al Geabury was ordered to make another court appearance, which he skipped under the guise that he couldn’t afford the trip.

The judge reached his limit and charged Al Geabury with contempt of court. He was sentenced to 10 months in prison as a result.

5 – Arnold Rothstein

Arnold Rothstein became a legendary bookmaker and gambler. He originally built his fortune by winning in poker games and sports betting.

However, part of Rothstein’s success was attributed to match fixing. He was the central figure behind the Chicago Black Sox Scandal of 1919.

Rothstein had his friend and employee, Abe Attell, pay players on the Black Sox team to throw the 1919 World Series. He was able to escape legal consequences by denying everything in court, but privately, he admitted to fixing the World Series.

This blackmark didn’t affect his finances. Rothstein became wealthier than ever after opening brothels and nightclubs across New York City. He also had a very respected image in the criminal underworld. Case in point, he was once paid $500,000 just to mediate a feud between two gangs.

At one point, he was worth an estimated $50 million. This amount is worth approximately $730 million when adjusted for inflation.

However, Rothstein would suffer a fall throughout the late 1920s. He went through a long losing streak in different forms of gambling.

In September of 1928, he lost $320,000 in a poker game. Rothstein refused to pay after alleging that the game was rigged. He was invited to another poker game in October. Here, he was fatally shot over what was certainly retaliation for not covering the $320k debt.

Rothstein was asked to identify his shooter as he was dying. But even in his last moments, he wouldn’t snitch on a fellow gangster.

6 – Leonard Tose

Leonard Tose is yet another successful businessman who went down the wrong path with high stakes gambling.

Tose earned a $20 million fortune through his trucking company. In 1969, he used $16.1 million of this amount to buy the Philadelphia Eagles.

$16.1 million would only buy a fraction of an NFL team today. After all, some franchises are worth billions of dollars. But the amount that Tose paid for the Eagles was a record at the time.

Philadelphia Eagles Fans and Mascot

Tose held onto his football franchise until 1985, when he sold the team for $65 million. He was forced to sell after losing over $25 million at Las Vegas casinos.

He attempted to sue various casinos for $500,000 apiece on grounds that they kept serving him free drinks and encouraging him to gamble. Tose lost every one of these lawsuits.

Things didn’t go much better for him afterward. He continued losing his fortune and everything else that he’d accumulated through trucking and the Eagles.


Anybody who sits down to a casino table or engages in other types of gambling must be prepared to lose. After all, they’re dealing with negative expectation games in many cases.

However, the gamblers discussed here weren’t prepared to lose. And when they did suffer losses, they either didn’t want to pay up or wanted revenge.

Jack McCall is the most extreme case discussed here. And Rothstein is the one person on this list that died as a result of gambling debts. Kakavas, Watanabe, Al Geabury, and Tose all fall into the category of businessmen-turned-gambling-addicts.

As you can see, it never pays to be bitter over a gambling loss. You’re better off paying the cost and moving on.