Craziest Gambling Stories

The gambling world can sometimes produce really off-the-wall stories. Every month there are plenty of cases of individuals going to extreme lengths to pay back debts, or of simply bizarre behavior at casino properties around the globe. It can be entertaining and sometimes sad.

We are presenting you with some of the craziest stories.

Poker Player Lost 0M In Single Night, Molly Bloom Claims

The film adaptation of Molly Bloom’s 2014 memoir hit U.S. theaters on Christmas Day, and to promote the project Bloom made her interview rounds. In a chat in November with Ellen DeGeneres, Bloom revealed the biggest poker loss she ever saw first-hand. “I saw someone lose $100 million in a night,” Bloom told DeGeneres. She added that the player “paid the next day.” Bloom said the buy-in for her most expensive and exclusive games, which ran in L.A. and later New York City, was $250,000. That was presumably the minimum buy-in. Celebrities in her games, which kicked off around the height of the poker boom in the mid-2000s, included Alex Rodriguez, Dan Bilzerian, Leonardo DiCaprio, Ben Affleck, Matt Damon, Toby Maguire and Nick Cassavetes, as well as billionaires such as Alec Gores and Andy Beal.

Man Lets Woman Push Slot Button For Him, But She Gets To Keep Entire 0K Jackpot

A gambler in Florida learned a lesson the hard way in January when a woman he had befriended was sitting next to him at a $50-a-spin slot machine in the high-roller room at the Seminole Hard Rock casino. The man, Jan Flato, said that he was feeding the machine money and let Marina Medvedeva Navarro push the button for good luck. The spin resulted in a $100,000 jackpot. Because Navarro had placed the wager, the casino gave her the money—$50,000 in cash and a $50,000 check. Video footage confirmed that she had pressed the button. However, Navarro denied Flato’s version of events, saying that it was actually her money in the machine and that Flato knew that the gambler who pushes the button gets the jackpot.

The 20-Second Win

Ashley Revell, an English gent, went for an all or nothing roulette spin. After emptying his savings account and selling every single thing he owned, Ashley had a whopping $136,000. He let the wheel work its magic and 20 seconds later, he turned his cash into $272,000. Not bad, but we don’t recommend spending every penny you own in one game.

Terrance Watanabe

Terrance Watanabe was a man who made his fortune as the heir to his father's party-supply import company. He is also the subject of one of our crazy casino stories. The Nebraska millionaire treated his money with the same lack of attention as his customers treated the cheap plastic trinkets he got rich selling. Terrance Watanabe became one of the most sought-after whales in the entire world not just because he loved gambling, but because he was terrible at it.

There is no way to know for certain, but it is estimated that Watanabe lost approximately $220m, most of his fortune, in casinos in a five-year stretch from 2003-2007, with him losing an astounding $127m in 2007 alone. For a time he basically lived in various casino high roller suites, his favorites being the Wynn, Rio, and Caesar's Palace. Watanabe was known to gamble drunk, play games with huge house edges like roulette or slots, and make idiotic decisions at the blackjack table. He routinely lost $5m a day, and ended up being barred from most casinos for his drunken behavior and inability to pay his debts.