Top 10 Crazy Gambling Losses

in Casino blog
Created: 16 November 2017
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While the house tends to win in the long run, there have been plenty of cases where players have won life-changing amounts, but this time some of the biggest and strangest gambling losses are the centre of our attention. And this is not only about the money lost, the stories behind them are just as interesting, so read on to find out more about these unique individuals.

10. How to Lose $250,000 in a Single Spin

Have you heard of The Buried Life, the MTV show featuring four guys on a mission to complete a list of "100 Things To Do Before You Die"? One of the things which have appeared on someone's bucket list in 2010 was to make $1 million, and gambling was chosen as they way to do it. The guys have managed to accumulate $125,000 budget which they wagered at a Roulette table at The Golden Gate Casino. Having won on Black, they reinvested quarter of a million on the same colour, but alas! It came Red and $250,000 was gone in a blink of an eye. Wonder if the lads have found another way to cross that item off their list….

Video: MTV Guys from The Buried Life bet $250,000 on Black at the roulette table at the Golden Gate Casino

9. Las Vegas Claims $500,000 from a Guy in One Weekend

Mark Johnston was a 52 year old businessman looking for good times in Vegas during the Super Bowl weekend. Looks like he found it, as Mr Johnston apparently got blackout drunk while betting on table games. Realising he has lost a hefty amount of $500,000 must have been sobering. Anyway, the unfortunate gamer argued that the casino deliberately continued serving him booze even when he was unable to see his cards. Moral of the story? Don't gamble when drunk, there's only one way that can end.


8. Software Glitch Nulls £650,000 Win

Bruno Venturi, a 41 year old pet shop worker from Italy, started gambling on Eurobet site with only £17. Three and a half hours later, he managed to turn this modest investment into a juicy £650,000 sum. Unfortunately, Mr Venturi was not to benefit; the gambling company argued his winnings were null because of a software glitch which made the game charge him only one in six bets. Bruno claimed he didn't realise this was going on and there was no message to let him know something was wrong. True or not, it didn't help. Learn from the Italian's mistake and keep your eye on the balance at all items – for more reasons than one.


7. Playing Three Roulette Wheels Simultaneously Results in $2 Million Loss

Media tycoon Robert Maxwell started playing at a Roulette table with more than $2 million, and apparently at some point decided wagering at a single game wasn't exciting enough. Playing at 3 Roulette tables simultaneously, he managed to lose the lot in only 9 minutes. What can we learn from Mr Maxwell's experience? Focus is key when gambling with real cash!


6. Don't Bet Against Mr Trump

Akio Kashiwagi, a Japanese real estate tycoon who allegedly fostered ties to the Yakuza, was known to bet $200,000 on a single hand at Baccarat. Mr Kashiwagi was apparently lured to Atlantic City by the current USA president to play at Mr Trump's three casinos and initially won almost $6 million of Trump's money. But the crafty casino owner stroke a deal to get Kashiwagi back to wager $12 million until either doubling the amount or losing it all. Having gambled away $10 million, Akio chucked the cards and went home, but sadly that was not the end of his troubles. Gambling debts worth $15 million might have had something to do with the fact Kashiwagi was later found stabbed 150 times (!) with a samurai sword. If you didn't know gambling could be lethal, well, now you do.

Read here the story in the New York Times


5. Girls Can Lose Big Too

Losing fortunes at land-based and online casinos is not a man's privilege, as evidenced by Maureen O'Connor, a former Mair of San Diego who spent $13 million on video poker games over a period of 10 years. Where did the money come from? The lady was married to the founder of successful fast food chain Jack in the Box, and his estate came in handy for financing her gambling passion. Clearly yet another example of an addiction, because when the money ran out, Mrs O'Connor stole further $2 million from her late husband's charity. The lesson? Gamble only what you can afford to lose.

jack in the box


4. From Rags to Riches and Back

Archie Karas was a poor Greek immigrant who came to the States while working on a cruise ship. That's where he got introduced to poker and soon became one of the famous LA poker players. In only a few years, Mr Karas has won and then lost about $2 million, and in 1992 took himself to Las Vegas with no more than $50 in his pocket. Within the next two years he has experienced what's known as the longest winning streak in poker history, earning him close to $40 million – only to lose it all again over the next 3 weeks. Eventually, the legend got arrested after being caught on surveillance cameras marking cards at a Blackjack table.

archie karas


3. Betting Hundreds of Thousands Can Lead to Epic Losses

Harry Kakavas, one of the biggest high-rollers in the world, made fortunes dealing in real estate on Australia’s Gold Coast. He was reported to lose $164 million in only five and a half hours while betting as much as $300,000 per hand. This betting style is probably to blame for the staggering $1.5 billion loss generated over the course of 14 months. Mr Omar Siddiqui has gambled away „only“ $65 million with a similar type of wagering strategy. When you're betting as much as $125,000 a hand at Blackjack, losing $8 million in a single day should probably not come as such as big surprise.

Harry Kakavas


2. Multiple Judgment Errors Lead to $127 million Loss in a Single Year

Having inherited a small fortune from his dad, the founder of the Oriental Trading Company, Terrance Watanabe was set for a life of leisure. When money comes served on a platter, perhaps one doesn't fret losing up to $5 million per day during 24-hour gambling sessions. Mr Watanabe was playing 3 hands of Blackjack simultaneously (mistake No. 1), kept his seat at a table for way too long (mistake No. 2), and apparently drank like a fish (though he claimed the casino was intentionally liquoring him up and even slipped him pain medication). Eventually, Terrance owed up that he's lost almost $127 Million in 2007 to Harrah’s Entertainment in Vegas, after which he recognised he had a gambling problem and signed up for treatment. The message? Don't be shy to admit your addiction and ask for help before you've gambled your life away.

Terrance Watanabe



1. It Could Be You

We'll leave number one empty as a warning. Gambling can be tons of fun if you do it responsibly, but it can also ruin your life if you don't. Play smartly!.




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