Greatest Prop Bets Ever Made

We’ve all made the odd wager. It usually starts with “I bet you can’t…” And usually ends with something fairly innocuous like “eat five crackers in a minute” or “beat me at tennis”. These pale in comparison to the crazy proposition bets made by gambling legends over the years. A “prop” bet can refer either to a side-bet during a specific game or a one-of-a-kind personal bet completed unrelated to the game. Take Amarillo Slim, king of the proposition bet, who once bet pool legend Minnesota he could beat him using a broom; and won. Here’s our rundown of some of the craziest ones we’ve ever heard.

Breast implants

In 1996, Brian Zembic, a magician and high-stakes gambler, entered into a wager where he would receive breast implants and if he kept them for a year he would win $100,000. It came about as after a conversation about boob-jobs where Zembic had disagreed with another gambler, Jobo, about the gravity of the procedure. The strangest part of the story is not that Zembic won the bet but that he grew so attached to the breasts, he has them to this day.

70 miles on a treadmill in a day

Young, online poker player Ashton Griffin laid 3:1 odds that he could run almost three marathons in the space of 24 hours. Considering that world records for marathon running sit around the 2 hour mark, the amount of money wagered, $300,000, was incredible for an amateur runner. Thankfully, he won otherwise he would have owed those who bet against him almost a million dollars.

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The fighter

It might seem strange that most of the craziest prop bets come from poker players – however, when you think that they play for high stakes as a day job then it doesn’t seem surprising. However, it might seem strange for a gambler to risk serious injury by taking a bet to have a bar fight. But that’s exactly what Johnny Moss did. He took his friends up on the 15/1 odds to win a fight with a bar brawler who’d never lost. Johnny came out worse for wear with several broken bones.

The sea

Imagine standing in the same place for 18 hours. Now, imagine standing in the same place in the ocean for 18 hours. Poker players Phil Hellmuth and Huck Seed entered into a bet where Seed had to stand up to his shoulders in an ocean for 18 hours. They wagered $50,000 on it and Seed; not surprisingly, only managed to last three hours.

Fast food

Howard Lederer, well known as a vegetarian on the poker circuit, won $10,000 from David Grey bet by eating a single cheeseburger. Then, Lederer offered Grey the chance to win his money back by eating a few olives (which Grey hated). Grey was so averse to the idea that he didn’t even take the bet and promptly handed over the ten thousand.

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