So, you want to hear about poker prop bets, do you? Well, strap in, my friend, because I’ve got some stories to tell you.

As a poker player and writer, I have always been fascinated by the strange and wondrous things that people do for fun. One of the most curious phenomena in the world of poker is the proposition bet (also known as a prop bet), a wager made between two or more players on a particular outcome that may or may not be related to the game at hand. These bets can range from the mundane to the absurd, from rewarding a player who wins the hand with deuce-seven or eating a whole pizza in under five minutes, to spending 30 days in a dark room without human contact. Let’s take a crazy trip and explore some of the most ridiculous prop bets ever made.

A Quick Run and a Burger

Prop bets are said to have originated in the early days of poker when players would bet on anything and everything in an effort to pass the time during slow periods in the game. As the legend goes, one of the earliest prop bets involved a player betting he could run a mile in under a set time. The other players laughed and took him up on the bet, only to be amazed when he succeeded, out of breath, but in time. Prop betting has become a beloved tradition among poker players.

One famous prop bet between two poker players was made over a McDonald’s cheeseburger. Howard Lederer, a vegetarian, was offered $10,000 by David Grey to eat one cheeseburger. Lederer accepted the bet and relented on his vegetarianism for just long enough to consume the sandwich and win the bet. Grey was upset because he lost, but as the story is told, what stung more was that Lederer didn’t get sick and lose his lunch immediately afterward. Allegedly, Lederer offered Grey a way to win back the money by eating a handful of olives, a food he was known to despise. Grey turned it down and Lederer kept the $10,000.

Lunging and Running

Numerous famous prop bets were held between Antonio Esfandiari and Bill Perkins. Topping the list was a challenge in which Esfandiari would have to lunge everywhere he went for 48 hours straight. The rules were simple: Esfandiari had to keep one foot on the ground at all times. Want to go for a walk? Lunge. Need a bathroom break? Lunge. Midnight snack? That’s right, lunges from the bed to the kitchen. Despite the awkwardness, pain and discomfort, Esfandiari completed the bet and won $50,000.

One of the most ridiculous prop bets I’ve ever heard of involved a player named Ashton Griffin, who bet he could run 70 miles in 24 hours. Griffin had never run more than a few miles at a time before, and he only had a few weeks to train. Despite the odds being against him, Griffin managed to complete the run in the allotted time and win, but he suffered a number of injuries in the process, including severe blisters and a broken foot!

Another bizarre prop bet involved two players who bet on whether one of them could stand in the ocean for 24 hours straight. While this bet never materialized, a variation on it almost did with discussions on whether the player in question could float in the ocean for 24 hours without touching the bottom.

peeling two aces


While prop bets can be silly and absurd, they can also be a lot of fun for players and spectators alike. They offer a way for players to blow off steam, have a good time, and provide additional entertainment for the railbirds. Prop bets also provide a way for players to test their physical and mental limits. Of course, not all prop bets end well, and some players have suffered serious injuries or health problems as a result of reckless wagers. Nevertheless, the tradition of prop betting continues to thrive in the world of poker and will likely continue to do so for years to come.

While some prop bets can be seemingly harmless and downright hilarious, others can have serious financial consequences. A prime example of this is the infamous “Howard Lederer Show Bet” that took place during the 2008 World Series of Poker. Howard Lederer, a well-known poker pro, made a $5,000 bet with his friend David Grey that he could shoot a basketball free throw blindfolded. Lederer missed the first five shots, but on the sixth attempt, he made the shot, winning the bet. However, this bet had a dimmer outcome, as it was later revealed that Lederer had borrowed the $5,000 from Grey and never paid him back, leading to a bitter feud between the two players.

$100,000 Breasts

Another example of a potentially disastrous prop bet, not to mention the craziest of all prop bets, is the “Brian Zembic Breast Implant Bet.” In 1996, professional gambler Brian Zembic made a bet with his friend that he would get breast implants and keep them for a year for a payout of $100,000. Zembic won the bet and kept the implants for over 20 years. He gained a reputation as “the man with the $100,000 breasts.” While Zembic may have made a small fortune from the bet, it’s hard to imagine that the experience was worth the pain and health risks associated with undergoing elective surgery.

Despite the potential risks involved in some prop bets, they remain a popular pastime among poker players and gambling enthusiasts alike. Prop bets can be a way to inject some fun and excitement into an otherwise mundane poker game, and they provide a way for players to challenge themselves and each other in creative and unexpected ways. So the next time you’re sitting at a poker table, don’t be afraid to suggest a crazy prop bet – you never know what kind of wild and wacky adventures it might lead to.

What are some of the silliest or craziest prop bets you’ve ever seen?

From the Desk of the Wordsmith

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