In the following, we do not necessarily only present the biggest gambling losses of all time, but we do present the most notable ones. For some of those affected, they were the most catastrophic casino losses that were ever possible, for others they were individually manageable, but exceptional for other reasons. Non GamStop casinos losses should not normally reach these magnitudes. Discover best non GamStop casino games on

Our site reveals how you can avoid unpleasant or even threatening surprises when you want to play games of chance online. But now our five examples of negligent losses from gambling; you could also say: Here is the amazing flop list of the biggest, fastest and dumbest gambling losses.

Basketball Star Barkley: $20m in Gambling Losses But ‘No Problem’

Charles Barkley was one of the all-time greats in basketball. This not only refers to his height of 1.98 meters, but above all to his 16-year successful career in the US basketball league NBA. However, it was public knowledge that he lost large chunks of his substantial earnings as a basketball superstar to less successful casino tours. Barley’s take on this was that there was no problem as there was still enough of his money left.

In an interview, he once admitted to having suffered losses from gambling totaling $10 million. A few years later, according to his own statements, it was already 20 million. Barkley once said he lost $2.5 million in a single blackjack session. Eyewitnesses claim to have seen him wager $60,000 on a single spin of the roulette wheel.

In the meantime, however, there seems to have been a problem for Barkley. Wynn Las Vegas Casino claimed $400,000 in outstanding gambling debts from him in 2008. After paying the money, he announced that he would stay away from gambling for the next few years. He didn’t quite succeed, but apparently his gambling losses have been within limits since then – even if they are likely to exceed the personal budget of many ordinary people by far, including online gambling at non GamStop casinos.

Football Great Michael Vick – Total Loss!

Michael Vick is also an American sports star, a football player. He lost more than money; he also lost his reputation and freedom when he was involved in illegal gambling. Vick’s weakness for dog fighting became his undoing. In court, he pleaded guilty to taking an active part in organizing such fights and also to having been involved in the related betting business.

It took the once successful quarterback ten years to get his life back on track. He used up his entire fortune to pay off millions of dollars in debt. His former team, the Atlanta Falcons, took legal action to recover nearly $20 million in bonuses from his ex-star. But these were not his only payment obligations. While incarcerated, Vick had himself declared bankrupt. He cashed in whatever assets he had and raked in more than $17 million in debt. After his release, he began a new career as a sports commentator.

Super Kicker Wayne Rooney – Gambling Losses Out of Boredom!

England football superstar and former international Wayne Rooney is known for his gambling tendencies. To his eye-catching performances on the pitch, he added no less spectacular appearances at the table. According to press reports, the most notable was a trip to the 235 Casino in Manchester. According to the articles, Rooney struck midnight there in May 2017 and lost £500,000 within just two hours, almost €600,000 after all.

According to eyewitnesses quoted anonymously, Rooney had played roulette and blackjack to pass the time. Incurring losses only seemed to spur him on to further operations. He later explained his behavior by saying that he ended up in the casino out of boredom because his then fiancée Coleen was traveling with the children without him. Later, Coleen became his wife and probably took better care of him. Again and again there were reports of marital difficulties.

Real Estate Mogul Harry Kakavas – The Billionaire Gambler

Australian Harry Kakavas is known as the victim of one of the most disastrous casino losses ever. Within just 15 months he bet around €1 billion in casinos. During this period, his losses from gambling amounted to “only” significantly more than ten million. However, that was more than he could actually afford.

Kakavas had known for a long time that he had a gambling problem. The money for this also came from fraudulent manipulations that landed him briefly in prison in 1998. That same year, he made a decision: he banned himself from gambling at Melbourne’s Crown Casinoto to protect himself from making gambling losses. Six years later, however, it was this casino that attracted Kakavas again. There they had learned that he was traveling in Las Vegas and lost heavily. A successful effort was made to win him back as a customer. Kakavas later took this as an opportunity to sue the casino. His accusation: It deliberately exploited his gambling addiction. The lawsuit was unsuccessful. Kakavas went back to his real estate business and put the past behind him – a few million poorer.

The Anonymous Curmudgeon

Finally, a story in which neither horse nor rider are known. It is based on the testimonial of a casino employee on the social media Reddit, who called himself “Citymike”. According to his own statements, after a six-week training phase, he was used at a gaming table that was reserved for a high-risk player. He showed up with a holdall full of cash and bet $350,000 on blackjack within 15 minutes and lost, $35,000 per round. The dealer describes the end of that costly 15 minutes: “He stood up, smiled and thanked me. My boss told me that he checks in every few months and usually brings even more money with him. I was floored: the man had lost more in fifteen minutes than I would make in ten years. He didn’t tip.”

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