The Insane World of Crazy Prop Bets

On average, professional poker players plays only about 20% of hands dealt to them. This means that they can spend up to 80% of their working hours in a casino sitting around doing very little - thinking of ways to keep boredom away.

And what better way to do so, than by betting against one another to try to earn a little extra money on the side. It seems anyone, who has ventured into the murky world of “prop betting” has at some point bet on losing weight.

Case in point: Mike Matusow famously lost $2 million to Ted Forrest on a weight loss side bet! This was a couple of years after Ted lost $100K to Mike “The Mouth” on Mike losing weight!

Are these pros sick or what?

And the bets just get crazier and crazier. Here's our list of the ALL TIME top five most outrageous prop (side) bets:

#5: Four Rounds of Golf in a Single Day

Although many side bets revolve around golf, Erick Lindgren set himself one of the most difficult. All he had to do was shoot under 100 in each of four rounds of golf (72 holes).

This is a difficult task in and of itself, but there were a few more stipulations:
  • He also had to complete it on one of the toughest courses in Vegas – Bear's Best.
  • All rounds had to be completed in one day, back-to-back, with temperatures reaching up to 108 degrees Fahrenheit.
  • He had to walk the entire course - no caddy or golf buggy.
  • He had to shoot from the pro tees.
The madness started after Erick busted from the $50K H.O.R.S.E event at the 2007 World Series of Poker. The original bet was with Gavin Smith for $100K, but then – never to pass up a chance at some side action – Phil Ivey threw in his hat, adding another $200K to the pot. With Phil in, a few other sharks smelt blood in the water and jumped in too, including American pro, Chris Bell.

Perhaps, Lindgren's judgement had been clouded by the aftermath of another early WSOP bustout, but still Lindgren accepted the bet. On the day in question, he awoke at the devilishly early hour of 5:45 am – possibly making his way directly from a poker table.

It started off swimmingly well for the golf master. He breezed through rounds 1 and 2. After struggling through the 3rd round, he made it to the middle of round 4 shooting 69. Seeing the writing on the wall, both Gavin and Chris cashed in early, deciding the buy out of the bet. Smith settled with Erick for $60K.

Phil was a little tougher and more stubborn. He wasn't going to let Erick off that easily. However, Phil was the one left with egg on his face when Lindgren PROPosterously succeeded, bagging himself a cool $340,000 in total.

#4: Thirty Nights Accommodation in a Bellagio Bathroom

In the midst of a prop bet one-up-manship Andrew Robl and a friend talked about living in the Bellagio Hotel for 30 days straight. Another of Robl's friends, Jay Kwik, decided to take it to another level, arguing that he could live in a Bellagio Hotel bathroom for 30 days. With the gauntlet thrown down, the bet was on.

For a possible whopping gentleman's bet of $250K, Jay Kwik would have to spend 30 nights in a bathroom at the Bellagio without leaving the room once. Andrew lovingly referred to Jay's temporary accommodation as “his prison cell”.

According to Robl, Kwik had never gone 10 days without playing poker. So, the prospect of Jay having to live in a tiny space with no human physical contact or poker seemed an impossible task.

With webcams set up and strict rules on what he could and could not do, including the following:
  • Only 400 minutes of talking time on the phone.
  • No personal physical interaction with anyone.
To make the bet even more secure, Andrew put a $500 bounty on Jay's head for anyone catching him breaking the rules by leaving the room.

Once everything was in place, the prop bet was set in motion. In the actual room, Jay had all the creature comforts of home in the form of a Versace towel “carpet”, 12-inch plasma TV and a wide collection of DVDs.

Wedged in between the toilet and the bathtub was a top-of-the-line air mattress. The tub filled with Chips Ahoy and other nutritious snacks common in every poker player's standard diet, Jay seemed to be in it for the long haul.

After 20 days, Robl declared Kwik was ‘too good’. Jay looked to be enjoying himself so much that Robl bought out of the bet for $40,000! He cut his losses early, waved the white flag - giving Kwik the victory.

Check out the prop bet shenanigans here: 

#3: Lodden Thinks

Quite possibly the most iconic prop bet game popular among poker players is ‘Lodden Thinks’. Johnny Lodden is a Norwegian professional poker player. The game was invented at the 2008 World Series of Poker Europe in London and represented the first televised instance of this type of side be. It occurred at a featured table where Antonio Esfandiari, Phil Laak and Johnny Lodden were seated.

The ever ingenious and creative duo of Antonio and Phil decided to bet on what fellow player Johnny Lodden’s opinion would be on any given topic. In other words, what “Lodden Thinks” about any possible subject.

The original bet proposed by Laak was for £100 and asked, “What Johnny thinks the world record for holding your breath is?” Phil's guess was 4 minutes and 30 seconds. Antonio came back with over 5 minutes and 30 seconds. Antonio won when Lodden answered 6 minutes 25 seconds.

The second Lodden Thinks bet by Esfandiari asked the question,"How many hotdogs could be eaten in 10 minutes". Again, Antonio won with 34. The third bet by Antonio sought Lodden's opinion of Laak's poker prowess on a scale of 1 to 100!

Find out what happened next here:

The rules of this game are very simple yet entertaining and amusing, and can be played with 3 or more players. To start, take any given scenario and add a large helping of imagination to come up with new questions.

This is one prop betting game that can continue on and on, long after the actual tournament has finished.

#2: Amarillo Slim Hits a Golf Ball over a Mile with a Hammer

“Amarillo Slim” referred to himself as “the greatest gambler that has ever lived”. No one ever accused the 1972 WSOP Champ of being a humblebrag! He also entered into a massive number of side bets that were both weird and unbelievable.

From betting that he could hold onto a horse' tail for a quarter of a mile to beating Willie Nelson out of $300K playing dominoes in Vegas, he was the quintessential gambler. Look up the word “gambler” in any dictionary and Slim's face would be right next to it.

And, after this next unbelievable side bet, it is hard to deny the validity of his statement.

He took a bet against Evel Knievel, asserting he could hit a golf ball over a mile. And if that wasn’t already hard enough with a golf club, he claimed he could achieve this with a hammer.

The bet was inspired by American gambler, golfer and hustler, Titanic Thompson (aka Alvin Clarence Thomas). With his skills as an ambidextrous golfer, cardplayer, pool shark and marksman, he bet on any and everything his imagination could conjure up.

Taking a page straight out of Titanic Thompson's playbook, and in what seemed like an impossible challenge, Amarillo played his shot on a frozen lake, succeeded in winning the bet and taking the money from the (somewhat shocked) Mr. Knievel.

Amarillo Slim’s Top 5 Greatest Bets:
  1. Beating a horse in a hundred-yard dash. (No one ever said nothing about the race being a said that he had to run in a straight line!)
  2. Winning the 1972 World Series of Poker Championship at Binion’s Horseshoe.
  3. Riding a camel through the Casino El Mamounia in Marrakesh, Morrocco.
  4. Betting that George W. Bush would win the 2000 Presidential election.
  5. Beating American tennis pro, Bobby Riggs, playing Ping-Pong with a skillet.

#1: Dwan's Bracelet Hunt

In all honesty, a lot of the $1,500 entry WSOP bracelet winners tend to get overlooked and forgotten with time. However, Simon Watt is not one of those names. He is the player who came between Tom Dwan and what he claimed would have been his biggest one day win of all time. 

Tom ‘durrrr’ Dwan took a bet against the poker elite that he would be able to bag himself a bracelet at the 2010 WSOP. With many big names in on the action, such as Phil Ivey and Daniel Negreanu, Dwan managed to battle all the way to a one-on-one face off for a bracelet and a reported $9-$12million in side-action money.

With so much money up for grabs in actual poker events, the question comes to mind as to why the other pros would even consider such a bet. Cash game specialist and 3-time WSOP bracelet holder, Eli Elezra, waded in with this response:

"I have a big bet against Tom," he said Eli Elezra. "I have 3-1 odds against his winning a bracelet. I can lose $750,000 or win $250,000. He's a friend, but I do it because I think it's profitable. I'm ahead in all those bets. It's mostly for financial reasons, but it's for fun too. I love a good sweat; it keeps things exciting. If Tom makes a final table, I have a good sweat, you know?"

With so much side-action money on the line, all that stood between Dwan and a massive payday in the 2010 WSOP Event 11 was a relatively unknown Kiwi player called Simon Watt. Unfortunately for Dwan, Watt proved to be his undoing. His takedown of the high-stakes phenom wiped the sweat from the brows of the punter railers and bagged him a bracelet in the process – along with a tidy $600,000+ pay packet.

Bonus Side Bet: Phi Ivey's No Meat Bet

The action went down in 2010 during the now defunct High Stakes Poker TV series. In Season 6, the talk turned to prop bets and brought out the “gambler” in high stakes pros, Phil Ivey, Tom Dwan, Gus Hansen, Daniel Negreanu, and Eli Elezra.

Ivey, always on the lookout for some side action, proposed a bet that would involve him giving up meat for one entire year. Phil later quipped, “ I was thinking about doing it for a while, so this is kind of like an added incentive”.

Equally down with the prop-betting action, Tom Dwan mentioned that he'd be willing take a bite. Never one to sit around lolly-gagging, Phil worked his magic trying to get Dwan to agree to a sum of $5 million to quickly close the deal. Dwan countered with $500K, but Phil just wasn't feeling that “small” amount. He was looking for something bigger to make it worth his while. He came back with $2 million, but Tom was still a little reluctant.

After settling on $1 million, the bet was set in motion. Phil would “go veggie” for a whole year. Even though the bet was Ivey's idea to start with, he seemed less than confident that he could win the bet:

“I'm going to lose. I know I'm going to lose. I'm going to be begging to settle in, like, 4 days."

With Phil still licking his chops over the idea of taking money off Dwan – away from the table, the talk turned to the upcoming 2010 World Series of Poker.

“Let's do some bracelet bets now while we're on it”, he said.

Phil had more to worry about than any future prop-betting. Twenty days later, he folded and bought out of the bet for $150K.

Never mind, his rumoured $3 million bracelet-hunting bet against Dwan at the 2010 WSOP made it all better!