Top 10 Most Insane Poker Prop Bets – The Art of the Wager

1 year ago

You can’t be a poker player without being a gambler – it’s in the job description! However, some poker players like a gamble more than others and will gamble on absolutely anything, including MMA matches, becoming vegetarian for a year, and much more!

These bets are called prop bets or “proposition bets,” and while they have no impact on your poker, they can make for some fascinating stories. It’s those stories we’ll be taking a look at today as we dive into the world of famous poker prop bets.

10. Lodden Thinks

One of the few poker prop bets from this list we’d recommend trying with your friends is a game called “Lodden Thinks.” The game was devised by high-stakes poker pros Phil Laak and Antonio Esfandiari during the final table of the 2008 WSOPE London Main Event. The two were so interested in what Johnny Lodden thought about random topics that they decided to turn it into a betting game. After sharing the game with the world on episodes of High Stakes Poker and Poker After Dark, it quickly swept the poker scene, and soon, everyone was playing this game at the table.

If you want to join in the fun, the game is really easy to play. First, set an amount that you’re going to be playing for – it’s best to keep the amount low if you’re just playing between friends at the poker table. Next, designate someone to be Johnny Lodden (unless he’s already at your table and willing to play!); they’re going to be the ones deciding the answer to your question. Once you have someone to be your Lodden, you need to think of a question. In the very first game of Lodden Thinks, the question asked to Johnny was what he thinks the world record for holding one’s breath is, but you can ask any question you like! The best part about this game is that you’re betting on what someone thinks – so you don’t need to know the correct answer.

Once you have your Lodden and your question, the two players playing the game need to bet on what they think their friend thinks is the answer to the question. The best way to do this is to auction, and one player takes the under or over when they’re happy to. For example, if the question is “How many cars are in the city of London,” Player A may say over 1 million, then Player B says over 3.5 million, then Player A says over 4 million, etc. etc., until one person thinks it’s under the amount. So, if you think it would be under 4 million, you “take the under,” which means if they guessed under 4 million, you win, but if they guessed over 4 million, you lose.

The game is a lot of fun and a great way to get some action going on a boring table.

9. Erick Lindgren’s Four Rounds of Golf in a Day

Erick Lindgren Golf

We quickly move from a bet we’d heartily recommend to one that we’d highly discourage – unless you’re on the other side of it! Notable poker pro Erick Lindgren was challenged by Phil Ivey, Gavin Smith, and others to play four rounds of the Bear’s Best course in Las Vegas back to back. Any golfer will know just how tough playing multiple rounds in a day can be, but add 100-degree Las Vegas heat to the equation, and what is a tough but doable challenge soon becomes much more daunting. Not only that, but Erick had to walk the entire course of Bear’s Best, playing each round from the back tees scoring under 100 every round! To rub salt into the wounds, Erick’s opponents got to pick which day he played, and they picked one of the hottest days of the year – who needs enemies when you have friends like that!

We’re sure many professionals would struggle to complete the bet based on these parameters, but with $340K on the line, Erick was going to give it his best shot. In fact, he did such a good job on his first three rounds that everyone but Ivey bought out during his fourth and final round. However, with $200K on the line, Ivey wasn’t going to give up without a fight and made Erick complete the challenge – which he did. He may have won the bet, but Erick suffered dehydration and heat exhaustion, causing him to lose 14 pounds in a single day!

8. Vegetarian Phil Ivey

Vegetarian Phil Ivey

Anyone who watched Season 6 of High Stakes Poker will be familiar with the Phil Ivey vegetarian bet, as it was a major talking point throughout most of the season. In fact, you can see some of the negotiations happen at the table, giving us a rare insight into how these bets are made. After much deliberation, it was decided that Tom Dwan would bet Phil Ivey $1 million that he couldn’t be a vegetarian for the year. This bet was completely on the honour system, so Tom must have really trusted Phil if he was willing to risk $1 million!

Despite Daniel Negreanu offering to help Ivey adjust his diet, Phil didn’t last very long, succumbing only three weeks into the bet. He called up Tom and offered to buy out of the bet for $150,000 to eat some chicken. Tom obliged, and Phil ate what is likely the most expensive chicken dish in the world – we hope it was worth it!

7. Biker Bilzerian

Biker Bilzerian

Bill Perkins is no stranger to a prop bet, and who better to bet against than millionaire Playboy Dan Bilzerian. Anyone who’s followed Bill’s prop betting will know that they all have an element of physical challenge to them, and this one is arguably one of the most challenging he’s set. He gave Dan Bilzerian 48 hours to bike from Las Vegas to L.A. – that’s roughly 300 miles in just two days! However, if he could do it, there would be a $600K prize waiting for him in L.A. Given that Bilzerian had claimed to have not ridden a bike for 18 years, this seemed like it would be a dead cert for Bill Perkins.

However, after getting coaching from Lance Armstrong (hopefully just coaching) and putting in a lot of hard work and effort, Bilzerian was ready to take on the challenge. As an added bit of motivation, he also bet fellow degenerate Rick Salomon that he wouldn’t die during the challenge. If he did, he would give his private jet to Salomon, whereas Salomon would have to pay out $250K if he did survive the challenge. Bilzerian smashed the bet, completing the journey in around 36 hours – giving him 12 hours to spare. While his body certainly felt the effects of the bet for a little while after, he walked away $850K richer.

6. MMA Madness

JC Avalardo and Olivier Busquet mma

Poker pros are no strangers to beef – if you think the modern disagreements between players like Doug Polk, Matt Berkey, and Nik Airball are a new thing, you’re sorely mistaken! Back then, players weren’t so keen on heads-up for rolls challenges, especially if one of the opponents was known as an expert heads-up player. So, when JC Avalardo and Olivier Busquet had a disagreement, they decided to bet $150K on a 5-round MMA match.

Alvarado went into the match as a favourite thanks to his experience in Jiu-Jitsu, but Busquet used his training time well and came into the fight looking like a pro fighter. The jacked poker star dominated the fight from start to finish and was declared the winner after the third round on medical grounds.

5. Esfandiari Lunges towards Victory

Lunges are one of those exercises that look a lot easier than they actually are. After a couple of minutes of lunges, your legs are on fire, and you can’t wait to start walking like a normal person again. One person who seemingly didn’t get the memo on just how painful lunges are is Antonio Esfandiari, who bet Bill Perkins $50,000 that he could only move via lunges for 48 hours during the 2016 PCA.

The first day he got off easy, spending the majority of the day in his room at the Atlantis Resort and Casino, but day 2 saw him play the Main Event. To make matters worse, his room was about as far away from the playing area as it could have been, making things even tougher. After an exhausting day of lunging from place to place, Esfandiaria was on break in the tournament and needed the bathroom. Rather than face another lunge-filled trip to the bathroom, he decided to relieve himself at the table by covering himself with a jacket and using an empty water bottle.

However, he wasn’t as subtle as he thought, and several people witnessed the event. He was shortly ejected from the tournament due to a “breach of etiquette,” but Esfandiari did win the bet with Perkins. Embarrassed by his actions, Antonio decided to donate the entire $50K bet to charity, splitting the money between One Drop and REG. It’s not often that spending a penny will cost you $50K and a tournament entry!

4. Titanic Golf Shot

One of the best known old-school gamblers, Titanic Thompson would bet on anything and everything. He was well known as a sharp gambler, but people couldn’t help themselves when he offered such outlandish bets. One of those bets was that he could drive a golf ball over 500 yards. Even today, that would be considered an outlandish bet, but over 60 years ago, an expert player’s drive was only around 200 yards; so, you’d be silly not to take that bet, right?

Well, someone did take that bet, and they realised why you should never bet against Titanic Thompson. Thompson waited until the winter, then drove the ball onto a frozen lake. The ball bounced way past the required distance, and Titanic Thompson won the bet.

3. Amarillo Slim’s Mad Selection

Amarillo Slim bet

Another old-school gambler with plenty of insane prop bets to pick from is Amarillo Slim. In fact, we found it so hard to pick just one bet we’ve settled on a list of some of his greatest hits. These include:

  • Rafting down the “River of No Return” in the dead of winter.
  • Beating a world champion ping pong player using coke bottles as paddles.
  • Beating a horse in a 100-yard dash (achieved by running 50 yards, then doing a 180-degree turn before running back).
  • Riding a camel through Casino El Mamounia in Marrakesh.
  • And, our favourite, betting that a cat could pick up a Coke bottle.

With a list like this, it’s no wonder that Amarillo Slim is often considered the greatest gambler of his generation.

2. Not so “Kwik” Bathroom Break

Back in the heyday of online poker, Jay Kwik was known for his levels of endurance. It was said that when he first started playing poker, he played for 10 days straight! Some of his friends, including notable high-stakes pro Andrew Robl, wanted to put that endurance to the test and challenged him to spend 30 days in the bathroom of his hotel suite in the Bellagio.

Depending on your need for social interaction, this may either sound like a walk in the park or your idea of hell. However, to make things even harder for Jay, there were limitations placed on the bet. He would have no computer, no contact with his friends, and must be on camera constantly. You’d think that anyone forced to live in these conditions would quickly go mad, but Jay excelled at the challenge – so much so that Robl bought out for $40,000 four days before the end, saying that Kwik was “just too good.”

1. Zembic’s Bazoongas

zembic boobs

Arguably the most insane prop bet we’ve ever seen was made by poker pro Brian Zembic. He bet $100,000 back in 1996 that he could go one full year with breast implants. You read that right, Brian bet that he could live with breast implants for an entire year. Brian would have to pay for the implants himself and not have them removed for an entire year to win the bet. While it may seem like the jokes from your friends and loved ones would be too much to handle, Brian embraced the bet and went under the knife to receive 38C cup breast implants.

Not only did Brian easily make it the whole year, but he became so fond of the new implants that he decided to keep them! As far as we know, he’s yet to have them removed, saying that they’re now a big part of his life and made him a much bigger hit with the ladies. According to the terms of the bet, Brian wins an additional $10,000 for every year he keeps the implants after the initial year, meaning that he’s won over $350K from this bet alone.

We hope you’ve enjoyed this round-up of PokerDeal’s favourite insane poker player prop bets, but please do take care before making any insane prop bets of your own! If you do try any crazy prop bets, remember to bet within your means, use an escrow where possible, and for God’s sake, don’t do anything dangerous!

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