Top 10 Craziest Poker Prop Bets of All Time

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Poker players are known for being risk seekers. They’re also known for being willing to put money on the line for just about anything if they think there’s a chance it can be profitable. We’re sharing these statements with you so you can begin to understand the basis behind prop bets between poker players. When we talk about prop bets in this context, we’re talking about two individuals betting on another’s ability to accomplish a certain task. For example, if I bet you $50 you can’t go the whole month without eating candy, that’s a prop bet. If I bet you $20 that I can beat you in a race, that’s a prop bet.

Now, the examples we’ve given are for small amounts of money and are relatively “normal” in the grand scheme of things. What we want to talk about today are the obscure, wild, high-stakes, and downright odd prop bets that poker players have been a part of over the years. The motivation behind these bets is always a little mixed. The main driving force usually is that both parties think they can make money. If you accept my $20 prop bet to race, you are doing it because you think you can beat me and win $20. I am doing it because I think I can beat you and make $20.

Occasionally prop bets are driven by a desire for entertainment or out of the goodness of their heart, but these are rare. This would be like us betting you $20 that you can’t go to school dressed like a clown. We know you are fully capable of it and will probably do it. We know we will lose the $20 bet, but it is worth it to us to get to watch you prancing around campus like a clown. Prop bets out of the goodness of someone’s heart are usually attempts to get someone to better their life. For example, if we were to bet you $20 that you couldn’t lose 10 lbs in the next two months. We might do this hoping that we lose the bet and that you get in better shape because you’re our friend. Again, these two are much less common than the financial motivation. It’s pretty safe to say that most of the examples of crazy prop bets we’re mentioning today will be financially motivated.

Know the Lingo

Before we go any further, we want to make sure you’re up to speed on the gambling prop bet lingo. These are the keywords and phrases that professional gamblers use when talking about these types of bets as well as other bets. Take a quick second to read them, and you’ll be talking the talk in no time.

Booked

This means when a bet is set to go, and all terms have been agreed upon. This is similar to signing a contract, although the backing here is only the player’s word and reputation.

Buyout

When a player no longer wants to compete in a bet, they can ask for a buyout option. If granted, a buyout allows the player to admit defeat and pay less than the full amount of the bet. Bettors are never required to grant a buyout, though, they’re usually granted if an amount to be paid can be agreed upon.

Giving Odds

This refers to offering better payouts to try and entice someone to take a bet. For example, let’s say I want to bet you $10 that I can make five free throws in a row. You might not take that bet because there’s a good chance I can do that. But I might offer you odds, or give you odds to try and sweeten the deal. Let’s say I offer you odds of 8 to 1. This means that I will put up $8 for every $1 you put up. That means that if you bet $10 and I win, you will owe me $10. But, if you win the bet, I will owe you $80, because of the odds. This can really help to push action and get bets rolling.

Action

Action just refers to someone taking your bet. If you say that someone is giving you action, it means that they are willing to bet with you on your proposed wager.

How We Ranked Them

We didn’t. Someone bet us $100 we wouldn’t. Kidding. The actual reason that we didn’t rank these or put the bets in any particular order is that each one is special in its own way. Some of these bets are for less money but are much more classic than the others. Some are much more interesting depending on what your interests are. Basically, we decided that it would not do the list justice if we were to put them in any kind of order. Feel free to let us know which ones are your favorites, and we may come back through and put them in a fan selected order.

The Main Course | The Bets

Vegetarian for a Million Dollars

Phil Ivey and Tom Dwan are two of the highest stakes players in the poker world. They’re also two of the biggest action junkies on the planet always looking for a rush from some sort of wild bet. On season six of High Stakes Poker, a GSN show of a high stakes invite only poker game, Dwan and Ivey began talking about how capable each of them would be to go vegetarian for an entire year. Ivey was looking for someone to bet him that he couldn’t go the entire year without eating any meat. The numbers fluctuated back and forth, but before the night was over the bet was booked.

If Ivey could go an entire year without eating meat, Tom Dwan would have to pay him $1,000,000. If he couldn’t make it, he would have to pay Dwan $1,000,000. 365 days of green eating would result in 1,000,000 green slips of currency. Ivey made it three weeks until he was begging to be let out of the bet. As is customary, bettors are sometimes given the option of buying out of the bet for a certain negotiated cost. This isn’t discussed when the bet is booked, but only when someone wants out. If no agreement is made for a buyout, then the bet continues as originally booked. Technically, no buyout is required to be offered but is sometimes done as a courtesy. Tom Dwan let Ivey buyout for $150,000.

Run 70 Miles in 24 Hours for $285,000

While we’re on the topic of healthy eating and healthy living bets, let’s talk about one of the more insane prop bets of all time. Regarding health, we highly recommend that no one try this one, no matter how much money it’s for. Enter into the ring, Ashton Griffin. Griffin, for those that don’t know him, was a 22-year-old poker pro at the time from Orlando, Florida. Griffin was looking to bet that he could run 70 miles in a 24 hour period. Now, for those that are wondering, Griffin was not a professional runner by any means but did have a background in cross-country running and was rumored to be in great shape. Even for a professional, 70 miles in 24 hours is an insane and somewhat dangerous task.

After some intense negotiations, the bet was finally booked with Griffin’s roommate Haseeb Qureshi, also a professional poker player. Unlike the first bet we talked about, Griffin was giving odds to entice action. That means that Griffin was willing to put up more money than he were going to win if he lost the bet. If Griffin won the bet, he would be paid $70,000. If he lost the bet, he would have to pay Qureshi $210,000. He was willing to put up $3 for every $1 Qureshi put up to make the bet more enticing and get some action.

While these dollar amounts are already absurd, they weren’t the ending point of the bet. The two continue to push the size of the bet upwards even after the bet started. The final numbers were $285,000 if Griffin won and $855,000 if Qureshi won.

You would think that Griffin would plan out his strategy and begin carb loading and resting days out from the bet. This would be the smart way to approach the bet. Griffin had different plans. After a long night out of drinking and just a few hours of sleep, Griffin decided to snag his running shoes and head to the local gym to start the bet. Starting at 12:30 PM, the bet was underway. We personally remember a lot of chatter going on while the bet was underway worried about Griffin’s safety. His parents even drove up from South Florida to try and persuade him to stop the bet. Griffin was too determined, though. 23 hours and 15 minutes into the bet, he crumbled off the treadmill $285,000 richer.

Dan Bilzerian Biking from Vegas to LA for $600,000+

Vegas to Los Angeles is about 263 miles. Dan Bilzerian, sometimes known as the king of Instagram, decided that we willing to make a prop bet that we could bike this trip in less than 48 hours with no mechanical assistance. The bet was taken by Bill Perkins, an American hedge fund manager and film producer from Houston, Texas. Bilzerian spent about $150,000 and extensive time prepping and training for the ride. He even flew in famed bicyclist Lance Armstrong to help with his training.

Bilzerian completed the trip in 33 hours, well under the required limit but not without controversy. Apparently, Bilzerian drafted behind a van for four to five hours of the last leg of the trip. This counted as mechanical assistance, though Perkins still decided to pay the bet because he felt Bilzerian would have still completed the ride regardless. A lot of bettors said he could have gotten out of paying, but with a man with a net worth of $40 million +, he was ok with keeping things friendly.

There was an additional side bet that was placed on the ride between Bilzerian and Rick Salomon. Salomon is not a hedge fund manager but is famous for his sex tape with Paris Hilton. Salomon bet Bilzerian that if he didn’t die during the ride or directly after the ride, Salomon would pay him $250,000. If Bilzerian did die during or right after the ride, Salomon would get Bilzerian’s Gulfstream IV jet. The last rumors we heard were that Salomon is attempting to get out of the bet because of the drafting incident.

Living in the Bathroom of The Bellagio for Six Figures

This is one of our favorite prop bets because it is so out of the ordinary and yet, so awesome all at the same time. Poker players Andrew Robl and Jay Kwik found themselves in a high-stakes showdown in January of 2008. Another poker player was trying to get action on a bet that they could stay in The Bellagio for 30 days without ever going into one of the rooms. In an attempt to top that, Jay Kwik said that he could easily stay in the bathroom of one of the rooms without leaving for 30 days. Effectively, the bathroom would become his prison cell for 30 days.

Robl took the action, and Kwik moved into his bathroom “home.” He moved in an air mattress, a 12 inch TV, and got settled in for the long haul. Kwik was said to be spending his days relaxing, watching movies, and meditating. He also mentions some other activities involving some lotion that he details in this hilarious interview with High Stakes Living, an internet TV show.

While the exact amount of the bet was never disclosed, it had to be a sizable amount because Robl chose to buyout early for $40,000. This means that the original amount bet must have been significantly over this amount. Robl was banking on the fact that Kwik would go insane from lack of human contact and not being able to play poker. The bet was policed by placing a webcam outside of the bathroom and offering up a $500 bounty or reward to anyone that caught him leaving the bathroom.

Lose 48 Pounds in Three Months for $2 Million

While we used a weight loss bet as an example for “from the heart bets,” this one doesn’t fall into that category. This was a bet with profit and dollar signs flying through all of the involved parties heads. The bet started after a hearty meal at the Commerce Casino between professional poker players Mike Matusow, Ted Forrest, and Justin Smith. At the time Forrest weight 188 pounds. Matusow and Smith were willing to give Forrest 20 to 1 on $50,000 that he couldn’t get down to 140 pounds by Septemeber 15th of that year. This means he stood to win $1,000,000 if he could pull it off. The two gave him an additional bet of 10 to 1 on $100,000 that he couldn’t do it before July 15th. Ted Forrest was putting up $150,000 to win a possible $2,000,000 dollars. 48 pounds in three months.

Forrest began barely eating and working out upwards of six hours a day. He said he was walking upwards of 16 miles a day to cut the weight. Leading up to the weigh-ins, he went on a 10 day fast of zero food and spent long sessions in the hot tub to sweat out water weight. He weighed in on July 15th at 138 lbs. Matusow commented on how dangerous the bet was and how he feared for Forrest’s safety (he did say because he was worried he wouldn’t get paid out. We’re not sure if he was joking or not, but we will give him the benefit of the doubt).

Unfortunately for Forrest, it sounds like at last reports that he has only been paid about five figures of the bet. Apparently, after the bet, Matusow pointed out that he did not have the money to pay the bet and that he was going to pay Forrest in installments. Matusow said his reasoning for this was because he truly thought it was physically impossible to do. Hopefully, Forrest has gotten some more of his winnings from this bet as we haven’t heard an update in several years.

Here’s a great video of Forrest and Matusow talking about the bet while it was going on.

An MMA Battle for $150,000

One of the more popular recent trends in prop bets among poker players is bets involving combat sports. We’ve seen kickboxing matches, boxing matches, and now a high-stakes MMA battle between poker pros JC Alvarado and Olivier Busquet. The two agreed to a five round MMA fight with full rules (nothing watered down). While Alvarado did have some background in Brazilian Jiu Jitsu, the two were both brand new to the idea and world of mixed martial arts. The agreement was they would both train for a full six months and then meet in the octagon at a local gym facility in Las Vegas

Alvarado was the clear favorite going into the bet as he did have some background in martial arts. The odds on favorite quickly changed when you saw both fighters on fight night. Busquet looked like a massive beast with a perfectly chiseled fighter’s body. Alvarado was in good shape, but nowhere near the size Busquet was. The fight only lasted three of the five rounds with Busquet pummeling his opponent. The only real threat to Busquet was an attempted triangle choke that was quickly shaken off and turned into a guard pass followed up by some ground and pound. Medical staff decided to call an end to the fight after the third round declaring Busquet, the winner.

Here’s a Cardplayer video detailing the fight as well as some clips. The player Terrence Chan being interviewed in the video is a former high-stakes player who also has a strong background in competitive Jiu Jitsu.

Lunging For Cash

This is the second time hedge fund manager Bill Perkins has found his way onto our craziest prop bets list. This time Perkins was placing a bet simply for his own amusement. While this bet was only for his amusement, the amount wagered was still rumored to be in the six figures. If we recall correctly, the winning party did make a $50,000 donation to charity from some of their winnings which mean the bet was for at least $50,000.

The bet was that poker pro Antonio Esfandiari would have to lunge anywhere and everywhere he walked for 48 hours. If you aren’t sure what a lunge is, Google the exercise lunge. People usually do about 30-40 of these at the gym, and their legs are exhausted. Imagining having to do them for every step is exhausting to think about. Esfandiari took the bet, and it took place the Pokerstars Caribbean Adventure tournament series at the Atlantis in the Bahamas. Esfandiari sailed through the first day by not going many places and staying in his room because he knew the second day would be a challenge with tournaments to play in and long treks across the widely spread out casino.

Esfandiari took advice from a trainer and loaded up with salt water, ibuprofen, and stopped every few lunges to lie on his back and stick his legs in the air to stretch and help them recover. Esfandiari was playing in a poker tournament at the time that he was actually disqualified from because he was caught peeing into a bottle underneath the table during a $5300 buy-in tournament. This can give you a little idea as to the size of the bet as they were playing for a lot of money. Esfandiari just didn’t think he’d be able to make it back from the bathroom without his legs giving out.

Here’s a Cardplayer story on the pee incident.

Esfandiari’s plan was that if his legs gave out at some point, he would just lie there until he could move again or until it was midnight and he had won the bet. Esfandiari made it the 48 hours and claimed the cash in the bet. Bill Perkins also came out the victor as he was rumored to be just paying to watch Antonio suffer through the bet. Both sides won in this crazy prop bet.

Fake Boobs for $100,000

If we did rank this list, this one would definitely find its way towards the top. Back in 1996 Brian Zembic, a high-stakes gambler became famous as the man that would do anything to win a bet. This truly got tested in the summer of 1996 when one of Zembic’s friends, a gambler by the name of Jobo, offered Zembic $100,000 if he got breast implants and kept them in for a year. Zembic would pay for the surgery and have 38C implants put in under his pec muscles.

For a while, the bet didn’t go through, but Zembic went on a bad gambling run and decided to complete the bet. To this day, Zembic still has the implants in as he’s become a bit of a celebrity from the bet making international news. His story has been documented in a book, and Fox Searchlight Pictures has bought the rights to his story to make a movie. Zembic, of course, won the bet and collected his $100,000 prize. He was offered $50,000 to cancel the bet, but he decided to push through and see the bet to the end.

Shaving Your Head if an Amateur Wins

This bet doesn’t have any money attached to it but is still a classic moment in poker prop bet history. When Phil Hellmuth was knocked out of the 2002 World Series of Poker Main Event by amateur Robert Varkonyi, he was confident that Varkonyi had zero shot of winning and bet that if he did somehow pull off the miracle, he would shave his head. As you probably guessed, Varkonyi pulled off the unthinkable and won the 2002 WSOP Main Event for $2,000,000.

Varkonyi did give Hellmuth a chance to get out of the bet, but he decided to be a man of his word and shaved his head. He also agreed to sell his hair and donate the proceeds to charity. Apparently, Hellmuth eventually bought his own hair back for $10,000.

Erick Lindgren; Play Four Rounds of Golf for $340,000

This classic prop bet started at the bar after several drinks. The bet started out between Erick Lindgren and Gavin Smith (both poker pros) and quickly included Phil Ivey who wanted to get in on the action. The bet was the Lindgren would have to golf four rounds in one day. Seems simple enough, right? There were stipulations.

  • He had to play four full rounds at Bear’s Best in Las Vegas
  • He had to walk all of the rounds back to back and carry his clubs.
  • He had to shoot a score under 100 for every round.
  • He had to play from the back pro level tees.
  • The bettors could pick the day he had to play.

The bet was $100,000 between Lindgren and Smith and an additional $200,000 between Lindgren and Ivey. There were also additional bets with other professional players.

As you can imagine, they picked a day in the dead heat of summer when it was 120 degrees + outside. Lindgren came out on fire too, though. By the halfway point of the fourth round, he was in cruise control. Everyone except for Ivey decided to buy out of the bet. Ivey banking that the pressure would get to him stuck to the bet but came out a loser in the end. Lindgren took home $340,000 and a great tan from his day on the course.

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