The World’s Most Outrageous Vegas Bets

While most visitors to Sin City confine their gambling to poker, blackjack, and other casino standards, longtime stalwarts bet on anything and everything. Prop bets, as they’re called, are responsible for many of the most outrageous wagers in Vegas history. If you’ve never been tempted to gamble away your bank account on something crazy, you can at least admire the reckless streak found in the following individuals.

Most Outrageous Vegas Bets

Anywhere But Des Moines

Anywhere But Des Moines

NBC declared Des Moines, Iowa the wealthiest city in America in 2014, but to a gambler used to the insane nightlife of Las Vegas, it might as well have been southern Afghanistan. With three World Series of Poker bracelets, John Hennigan has proven his dominance on the felt. Des Moines, however, proved to be too much for him to handle. His friends bet him $100,000 that he couldn’t live in the Iowa capital for six months. He gave it the old college try, but he was back in Vegas after just two days to pay off the bet.

What a Boob

Brian Zembic made a name for himself in the 1990s as a man willing to go to any lengths necessary to win a bet. The magician/gambler solidified that reputation in 1996 when a friend bet him that he wouldn’t get breast implants and keep them for a year. The average man might realize that $100,000 wasn’t enough money to endure a year of ridicule, but Zembic is no average man. He accepted the bet, got the implants, and kept them in. Interestingly enough, Zembic chose to keep his new rack even after winning the money. As of 2014, Zembic still has his 38Cs.

Betting It All

If you spend any time at the roulette wheel, you’ve probably heard someone say, “Put it all on red.” But when a UK man named Ashley Revell said those words in 2004, he really meant them. Revell sold his car, his clothes, and cleaned out his bank account for one monstrous spin of the wheel at the Plaza Hotel & Casino. Lucky for Revell, the wheel stopped on 7 red, and he was able to turn $135,300 into $270,600 in a matter of seconds. Revell used his winnings to start online poker site Poker UTD, which folded in 2012.

Imagine the PruningImagine the Pruning

Anyone who follows professional poker is familiar with the names Phil Hellmuth and Huck Seed. Both have distinguished themselves as masters of the game, but they are also known as outrageous gamblers away from the poker table. One time, Seed bet the “Poker Brat” that he could stand in the ocean – water up to his shoulders – for 24 hours. At stake: $20,000. Seed lasted only three hours, though, and Hellmuth padded his bankroll.

The Company That Almost Wasn’t

Today, FedEx is an internationally-recognized brand, but founder Fred Smith was struggling to keep the company afloat in the early 1970s. With rising fuel costs eating into his capital, Smith found himself on the verge of bankruptcy. Desperate to keep the company from going under, Smith took his last $5,000 to Las Vegas for a wild gamble. He used the money to play blackjack for the weekend, riding a lucky streak that turned the $5,000 into more than $30,000. He used the money to pay his outstanding fuel bills, keep the company in business, and the rest is history. Today, FedEx is valued at more than $25 billion, making this arguably the biggest bet in Vegas history.


Steep turns and dizzying winnings-Drift Casino

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