Worst Casino Losses

It’s safe to assume most people who visit casinos expect to lose a few bucks. In among the avid everyday gamblers and the ones who know how to card sharp, there are the averages: moms and daughters celebrating the latter finally being 21 and her mom’s new gambling buddy, frat boys out for a weekend, a few friends looking for Friday night entertainment. Gaming odds are okay, but they’re definitely slanted toward the house, and for most people, that ends in losing a hundred bucks or so.

But for the unlucky few, it can result in a lot more.

Some of the world’s biggest losses are enough to make your wallet squeak in terror, but what really hurts is how fast a big loss can happen.

Take Robert Maxwell’s loss. He was playing roulette at the Ambassadeurs Club casino in London—three wheels at a time in an attempt to win back some of his earlier lost money. He lost all three wheels, and in a little under a minute, also lost $2 million. Ouch.

Omar Siddiqui, a Fry’s Electronics executive, also had a staggering, staggeringly quick loss. Though he accrued quite a lot of lost money in his time gambling—and it was later revealed that all the money he was gambling with was in fact laundered, oops—his most significant loss was $8 million.

In one day.

Zhenli Ye Gon, who was accused of sneaking pseudoephedrine into Mexico, was also fond of sneaking . . . well, money. And saving money. When his house was raided in 2007, police found $200 million in cash bundled up and waiting (sounds like a fire hazard, to be honest). But despite Gon’s profits, he also lost—a lot. Including more than $80 at the Vegas Venetian alone.

Joe Francis, creator of the Girls Gone Wild franchise—and therefore, as you can imagine, the owner of quite a lot of money—made another name for himself in 2009 when he lost $2 million in Steve Wynn’s Las Vegas casino.

And then decided not to pay it.

Ultimately, it ended in a court case, where Francis was ordered to pay $20 million to Wynn for defamation. Hindsight is 20/20, right? (Or, you know, 20/$20 million . . . )

Though the quick-loss tales may hurt, some of the longer-term ones are painful, too. Terry Watanabe, a Caesar’s Palace high roller, lost an estimated $120 million in 2007. There was controversy after Watanabe claimed the casino gave him alcohol and drugs to keep him playing.

Plying players with free alcohol isn’t unheard of, but drugs? Could be a way to explain the over $200 million Watanabe lost over his gambling career.

Honorable mentions: Archie Karas, who rode into Vegas with $50, made it into $40 million, then lost it all; Akio Kashiwagi, who lost $10.5 million just on baccarat; and businessman Fouad-al-Zayat, who lost £500,000 in less than half an hour.