The Six Craziest Prop Bets Involving Poker Players

Last Updated on March 19, 2019 Author:Adrian Sterne

Professional poker players are known for being risk-takers as they put their money on the line just about everyday at the poker table and believe they can beat their counterparts and make a successful living.

One of the things that poker players often do to make things more interesting is to take part in unique prop bets that can sometime be outrageous, controversial, dangerous and extremely challenging.

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We list the six most craziest prop bets that poker players have engaged in during the last few years.

#1 Antonio Esfandiari – Lunge For 48 Hours

High stakes poker pro Bill Perks challenged Antonio ‘the magician’ Esfandiari at the 2016 PokerStars Caribbean Adventure (PCA) to a $50,000 prop bet that would require Esfandiari to stop walking for 48 hours and only move around through lunges.

Esfandiari who is one of the most successful poker players in the history of the game with more than $27 million in prize money accepted the bet and got himself into a lot of trouble.

Esfandiari was taking part at the PCA and had more than $115,000 in chips at the table. He did not tell anyone about the bet and soon realized that he was suffering muscle fatigue from his constant lunges.

He decided to bring a bucket to the table and used it to relive himself as he could no longer lunge to the bathroom. Esfandiari’s antics at the table were discovered and as a result, he was kicked out of the PCA. Although he won $50,000 from Perkins, his reputation took a hit and Esfandiari admitted in retrospect that he should have used better judgment. He ended up donating the $50,000 to charity.

#2 Dan Bilzerian – LA to Vegas Cycling In 48 Hours

Bill Perkins was once again at the center of this unique bet with Instagram king and high stakes poker pro Dan Bilzerian.

Perkins challenged Bilzerian to cycle from Los Angeles to Las Vegas in 48 hours for $600,000 and Bilzerian accepted the challenge.

Not many gave Bilzerian a chance as he admitted it was years since he got one a bike but once he accepted the challenge Bilzerian took things seriously. He worked with Lance Armstrong to build his stamina and in the end succeeded in completing the race within 48 hours – although there was some controversy as Bilzerian allegedly drafted behind a van that was filming the event.

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In the end, Perkins accepted that he lost the bet and paid Bilzerian the money.

#3 Ted Forrest – Weight Loss Bet

Poker Pro Mike Matusow put $2 million on the line in 2010 when he challenged Ted Forrest to lose weight and go from 181 lbs to 140 lbs within a short time frame.

Forrest was not allowed to use any diuretics or amputate any part of his body to make weight.

Back in 2008, Forrest had challenged Matusow who weighed 250 pounds to make to 181 pounds for $100,000. Matusow made the weight and Forrest paid him $100,000.

So when it came to Forrest’s turn to make weight, he hired himself a fitness trainer and worked really hard to lose the weight. He made the weight in time but in the end Matusow only ended up paying him $70,500. Forrest isn’t pleased that Matusow hedged on his bet and called him out on Twitter in 2014 but is yet to be paid in full.

#4 Phil Hellmuth – Shaves Head After 2002 WSOP

Not a lot of people remember this bet because it happened way back in 2002 but it is memorable because Phil Hellmuth, considered one of the best poker pros in the history of the game with 14 World Series of Poker (WSOP) bracelets and over $20 million in prize money shaved his head after losing a prop bet.

During the 2002 WSOP, amateur poker pro Robert Varkonyi eliminated Hellmuth from the Main Event and Hellmuth would go on to say that he would shave his head if Varkonyi would go on to win the Main Event.

Varkonyi ended up winning the main event and he was kind enough to let Hellmuth off the hook but since Hellmuth had promised his hair to charity, he ended up shaving his head, donating his hair and then paying $10,000 from his own pocket to charity to buy his hair back.

#5 Phil Ivey – Go Veggie For One Year

Tom “durrrr” Dwan told poker great Phil Ivey that he would pay him $1 million if he could be a total vegetarian for a period of 12 months.

Ivey accepted the bet and tried raising the stakes to $5 million but Dwan declined since he did not have the money.

In retrospect, Dwan should have accepted the bet as within 20 days Ivey decided to pay Dwan $150,000 and buy out the bet as he realized being a complete vegetarian was more difficult than he expected.

#6 Brian Zembic – Boob Implants

Brian Zembic is not remembered for his accomplishments at the poker table but rather for his strange bet than won him $100,000.

Zembic was promised $100,000 if he got boob implants in 1996 and then an additional $10,000 for every year that he kept them. He went through with the bet and got 38C boob implants and won $100,000. He has kept his implants for nearly 20 years and in 2016 stated that he was contemplating removing them as he realized that money isn’t everything.

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