5 of the Greatest Gambling Losses in History

You’ve probably read some of the more famous stories regarding massive betting shortfalls; the losses of Jimmy White, Terry Watanabe and Kerry Packer are legendary, and extensively covered on the internet. These people blew more dough than most of us poor schmucks could hope to see in a lifetime, but it didn’t really make much of a dent in their finances. Packer alone frequently lost millions in table games, yet his net worth at the end of his life was still in the billions. Rather than retread that ground, we look at a few tales you might not have heard.
A man with empty pockets.
Published on: 29 June 2019

These individuals may not have lost the largest amounts of money in their gambling endeavors, nonetheless, they perfectly represent how not to approach bets. Throwing good money after bad, making incredibly poor wagers, and taking part in unlicensed activities lead to losing more money in ways you might not even think possible.

Here are some of the stranger incidents of people who made reckless gambling choices and didn’t know when to quit, in ascending order of magnitude.

No Win for Mr. No-Tip ($350,000)

Picture the scene: A dealer, fresh out of training, is assigned to a private table used by a solitary high-roller. The player arrives with a duffel bag full of cash amounting to $350,000 and proceeds to put down five grand bets per slot in blackjack, or $35,000 per hand. In a quarter of an hour, the duffel is empty.

Don’t take our word for it, read the account of the baffling episode given by Reddit user Citymike, who was the rookie dealer working the table. In a thread of gambling stories shared by casino staff, he told this extraordinary tale of the anonymous big spender.

The most peculiar part? The guy didn’t tip at all. You would think, after blowing through $350,000, that he could have tossed Citymike a few bucks.

Wayne Rooney’s Roulette Regret ($650,000)

A renowned lover of gambling, the famous footballer took his hobby to another level in 2017, when visiting the 235 Casino in Manchester. According to British tabloid newspaper The Mirror, Rooney managed to lose £500,000 – more than $650,000 – in just a few hours. Witnesses quoted in the story claimed that he did so on only two games, namely blackjack and roulette, and that, “He kept losing but that just prompted him to bet more.”

Resultant media speculation was that the soccer star’s spouse would blow a fuse once she learned of the massive losses, with one paper even going so far as to suggest that she (Coleen) might prevent her future husband making a big-money move to China. Given that Wayne admitted to having gone gambling out of boredom in his then-fiancé’s absence, the notion that she keep a closer eye on him was probably a sensible one.

Rooney never made his mooted trip to the Far East, though we have no way of knowing whether that was down to the infuriated intervention of his partner.

Addicted Harry Kakavas ($15 million)

In 1998, the Australian real estate mogul was incarcerated for four months after being found guilty of defrauding a large corporation for more than $200,000. He had used his fraudulently-acquired funds to fuel his gambling addiction, so in addition to his custodial sentence, Kakavas banned himself from Melbourne’s Crown Casino. Alas, these attempts to gain control over his betting habit apparently came to nought.

From 2005 to 2006, Kakavas wagered well over a billion dollars in casino games, which makes it almost impressive that he only lost $15 million in the process. Where did he lose all this money? Why, at the Crown Casino, of course.

Kakavas subsequently sued the casino to recoup some of his outlay, claiming that Crown had exploited his addiction for their own gain. He proved as unlucky in court as he had been at the tables, as the judge found against the plaintiff despite agreeing that Crown Casino had indeed made every effort to entice Kakavas into spending as much money as possible at their establishment.

In a 2013 Gold Coast Bulletin interview, Kakavas declared himself “finally free from the distraction of the litigation” and back to his real estate day job. Hopefully, after such a grueling and expensive legal feud, he has learned a little something. Only time will tell.

All-Star with No Limits Charles Barkley ($20 million)

Basketball figures don’t come much bigger. This legend of the game was an All-Star eleven times and one of only fourteen players in NBA history to have more than one jersey retired in his honor. Barkley was even made 1993’s MVP. All in all, this power forward had an extremely successful career…yet still managed to lose almost every cent he had made in his 16 years of league basketball.

Barkley’s addiction to gambling more than matched his prowess on the court. In an interview with ESPN, he admitted to losing about $10 million, including $2.5 million in a single session of blackjack. One Reddit user even claimed to have seen Barkley bet $60,000 on a single roulette spin when the NBA giant was still with the Houston Rockets. Despite all this, Barkley maintained that he did not have a problem.

That changed in 2008, when the Wynn Las Vegas casino sued the Hall-of-Famer for unpaid gambling debts of $400,000. Seemingly chastened at being forced to cough up the money he owed, Barkley pledged to quit the betting scene for a few years. Nonetheless, he continues to lose more money than most people will make in a year.

Michael Vick Throws it all Away (Everything)

This NFL superstar lost not just a significant sum of money, but also his freedom and reputation, for his part in illegal gambling activities. Vick had helped finance and organize a dog-fighting ring, so when the law finally came calling, he had no option but to enter a guilty plea in exchange for a suspended sentence.

Unsurprisingly, he was immediately suspended by the NFL and taken to court by his team, the Atlanta Falcons, who demanded that he repay a substantial portion of his signing bonus. The court ordered Vick to hand over an eye-watering $19.97 million, which he was able to do. However, in 2008 he filed for bankruptcy, claiming to owe anywhere between 10 and 50 million dollars in debts.

Over the course of the next decade, Vick endeavored to pay back all his creditors, liquidating his assets as necessary. By November of 2017, ESPN could report that the fallen idol had made his final payment of $1.5 million. In so doing, he had wiped out 99.9% of his debt, approximately $17.5 million.

If you are ever worried about your gambling habits, or you found that these stories hit a little close to home, then check out our page on responsible gambling and make sure that you get help if you need it.

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