Top Ten Insane Poker Player Prop Bets

11 Jun
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Poker players are no strangers to the side hustle, indeed many of us began playing poker as a side hustle, which gradually rose to eclipse our other forms of income or just became an enduring passion. Still, you often see poker pros still playing side games even while they compete in high stakes pots, taking unders or overs on side bets, and more. 

One of the most famous examples of the poker side hustle is the prop bet or proposition bet, in which players put money on the line that one or another participant will or will not manage a specific challenge, often over a specific time period. Not only do some of these prop bets involve big money (often held in escrow by a third party), some of them have become mired in controversy due to defaults on payment or other issues, whilst others are frankly bonkers. These are the ones we’re going to hone in on today at PokerDeals as we explore the wild world of insane poker prop bets with this top ten.

10th - Lodden Thinks

One of the best known poker prop bets, and one which is continually morphing into new versions of itself across live poker tables the world over, is the “Lodden thinks” side bet. This was first initiated by poker pros and buddies Antonio Esfandiari and Phil Laak, when they were seated at a final table alongside Norweigan pro Johnny Lodden in the 2008 London WSOPE.

The idea was that the two friends must bet privately (and quietly!) on Johnny’s opinion on a specific topic, taking their guesses, and paying out based on what Lodden actually states he believes at the end. The original bet was on what Lodden thought was the current world record for holding one’s breath. Lodden answered 6 minutes and 25 seconds, meaning that Antonio won with his guess of 5 minutes 30 seconds. You can find variants of the game going on all over the poker world to this day, and Antonio has been known to take bets on this game up to any amount his opponent wishes to wager.

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

This $340,000 bet was dreamed up in a Las Vegas bar between Lindgren, Phil Ivey and Gavin Smith, although several other pros took action as well. Lindgren had to play four full rounds in a day at Bear’s Best in Vegas, walking all the rounds and playing them back-to-back, as well as playing from the back tees, the pro level, and scoring under 100 for every round. Despite his opponents getting to choose the day, and selecting one of the hottest on record, Lindgren went on to complete the mission, causing all buy Ivey (who had $200k on the line) to buy out of the bet during the fourth, by which point Lindgren was looking sure to crush it. The day was not without its cost for Lindgren who suffered heat exhaustion, dehydration and lost 14 pounds in a single day thanks to the heat.

8th - Vegetarian Phil Ivey

Phil Ivey was keen to turn veggie, and he was well-known for being a huge fan of red meat. During the televised High Stakes Poker Season 6, he famously bet Tom Dwan a cool million US dollars that he could go without meat for a full year. The bet didn’t last long or work out too well for Ivey, who bought out of it after a measly three weeks, paying $150,000 to Dwan for the privilege. 

7th - Biker Bilzerian

Back in 2016 Dan Bilzerian bet Bill Perkins that he could ride from Las Vegas to Los Angeles in just 48 hours, a feat many considered impossible given that a) that’s over 300 miles, b) Bilzerian claimed he had not ridden a bike in 18 years and c) Dan is not a professional athlete! He pulled it off, taking coaching prior to the event from Lance Armstrong, donating $25k of his winnings to Armstrong’s charity of choice and netting himself $1,200,000 in the process. He also, insanely enough, bet his private jet against Rick Solomon’s $250,000 on condition that Solomon would only win if Bilzerian were to either die or become “braindead” as a result of the challenge. 

6th - MMA Madness

Two poker players who seemed to build a bet out of actually not liking each other too well were JC Alvarado and Olivier Busquet, who agreed to wager $150,000 on the outcome of 5 rounds of MMA action in the ring against one another. Despite Alvarado initially being considered a favourite due to his experience in Jiu Jitsu, Busquet entered the ring looking built and dominated the fight, leading to a victory declared after just three rounds on medical grounds. 

5th - Esfandiari Lunges towards Victory 

Antonio Esfandiari is considered quite sporty, and has been known to do some workouts at the live poker table, but this time he made a bet that he would only move around via lunging for a full 48 hours, during the 2016 PCA Main Event. The first day was passed peacefully in his room, but the second was a day full of poker action for Antonio and he lunged his way across the Rio tirelessly. Lunges are well-known for exhausting the legs in a matter of minutes, so Esfandiari, feeling that his legs wouldn’t make it to the bathroom, resorted at one point during a WSOP $5k buy-in to the old pee bottle technique (used by online pros before scheduled breaks), attempting to pee under the table discreetly, he was busted in the act and disqualified from the event! The exact amount of the bet is unknown, but he did win it, and surely it was many times greater than the $5k buy-in he lost out on! Still, funny but pretty gross. Definitely not Covid-friendly, we doubt he would have even attempted this in 2021. 

4th - Titanic Golf Shot

The host of the very first World Series of Poker back in 1970, Titanic Thompson was a bit of a hero of his time. His was one of the first prop bets to become legend, when he made a bet that he could drive a golf ball far further than any golf pro had ever managed, 500 yards. Thompson simply waited for winter and drove his ball far across a large frozen lake, easily winning his bet.

3rd - Amarillo Slim’s Mad Selection

We found it too hard to choose from Slim’s insane prop bets as there were so many to pick from, so here are some highlights. Rafting down the “River of No Return” in the dead of winter, beating a World Champion Ping Pong player using Coke bottles as paddles, outrunning a horse over 100 yards (accomplished by selecting a racetrack with a 180 degree turn halfway), riding a camel through the Casino El Mamounia in Marrakesh, and wagering that a cat could pick up a coke bottle. He was pretty much famed for being the biggest hustler of his day, as this list can testify. 

2nd - Not so “Kwik” Bathroom Break

One of the many things poker pro Jay Kwik was known for back in 2008 when this bet took place was playing poker constantly, and he was said to have not had 10 days away from the game since he first started playing. This must have made the prop bet he made with fellow pro Andrew Robl all the tastier for his competitor as they bet he could not survive 30 days living only in the bathroom of his Bellagio hotel suite. Various conditions were placed on the bet, including a cap of 400 minutes talking time on his phone, no physical human contact, and he must be on webcam constantly. The full bet amount is unknown, but Robl bought out after 20 days for a cool $40k as it became clear that Kwik was, in the words of his rival, just “too good”. 

1st - Zembic’s Bazoongas

Poker pro Brian Zembic became infamous for his prop bet, as he bet $100,000 back in 1976 that he couldn’t go a full year with breast implants. Zembic had to pay for the surgery and went for a 38C cup. The incredible thing about this story was not that he won the bet easily, but that he was so fond of his breasts that after winning the bet he went on to keep them for another twenty years, going so far as to claim that they made him a much bigger hit with the ladies!

Don’t Try this at Home

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! Remember these are trained professionals (or something)! If you do try any crazy prop bets, remember to wager within your means, use an escrow if you don’t have perfect trust with your fellow bettor(s), and for goodness sake, don’t do anything dangerous, and do your homework before laying your money on the line!

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