Poker Prop Bet Ideas

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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.

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  • Q: What is a Prop Bet? A: According to Wikipedia, a prop bet 'is a bet made on the outcome of a proposition.' Source: Wikipedia - Proposition Bet As it pertains to the poker world, there are two major types of prop bets that players tend to engage in: 1) Bets based on which cards will hit the flop 2) Unusual bets that will involve performing.
  • If you follow the poker world closely, you should know that Ted Forrest is known for his outlandish prop bets. Well, on Sunday, Forrest and Matusow entered into a prop bet of their own, and it will be interesting to see whether or not Matusow can win the bet. According to Matusow, it will be a piece of cake and a slam dunk.

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.

Jan 27, 2020 The idea with the red/black bet is to bet on the color outcome of the flop with one other player. Each time a player hits their winning flop, they get paid the agreed-upon amount. As I mentioned in the juicing article, the idea here is to bring energy to the table and a sense of gamble. Go Vegetarian for 1 Million Dollars In season 6 of High Stakes Poker, Phil Ivey mentioned that he would give up eating meat for an entire year and he needs an extra incentive in the form of a bet. He initially asked for 5 million dollars, while Tom Dwan was only willing to bet $500,000. After more negotiations, they agreed to bet 1 million.

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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.

.@CardPlayerMedia Correcting the numbers: @themouthmatusow has payed me $70.500 of the 1.8million he owes me for the weight loss bet #4years

— Ted Forrest (@ForrestTed) 9 September 2014


#4 Phil Hellmuth – Shaves Head After 2002 WSOP

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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.

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#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.

Inside Edition

If someone would have bet me whether or not my book, Billion Dollar Hollywood Heist, would end up beating out Molly’s Game after its sales quadrupled due to the Oscar-nominated feature film, I don’t think I would have taken that bet. Yet, as I’m writing this my book is no. 1 on Amazon’s poker category, Molly’s Game is no. 4, and I’m certainly not sad about it.

As card players, winning is often all about the money… but considering how I haven’t seen a dime for my book yet, I’m going to file this one away in the “proud to be on top” category and call it a day. It’s important that we take a little time to remember our wins seeing as how such moments are not only few and far between, but often fleeting when they finally arrive.

And speaking of celebrating a win, let’s get into this issue’s column, which is a subject matter that always manages to squeeze the maximum amount of joy out of every win… Prop Bets!

Ok, I friggin love proposition bets! Chances are if you are reading this then you too enjoy the undeniable giddiness often accompanied by getting the best of it with either friends or foes, while wagering on fun props that are all too often wacky, weird, or just plain wrong.

It’s hard to even fathom anyone in the professional poker community who doesn’t participate in or at the very least enjoy sidelining around the occasional prop bet. The World Poker Tour’s very own Vince Van Patten just released a very funny film called 7 Days To Vegas that is based on poker and prop bets.

Come to think of it, I don’t recall having ever met a card player who didn’t enjoy seeing someone either winning by a long shot on a prop or getting their ass handed to them after being overly confident. So, to satisfy our collective prop bet sweet tooth, expect to see me devote the occasional column to this great gambling past time which will feature a range of tales including never-before-revealed high-stakes props from top players of today and in year’s past.

To kick off this debaucherous, Schadenfreude-filled jaunt, I’d like to share the story of the time I pulled a prop bet show out of my ass, right after bombing out on a courtroom-based reality series pitch back in 2007. The pilot I ended up selling that day was called, I’ll Take That Bet.

Never heard of it? That’s because it never aired. We shot it with the likes of Phil Hellmuth, Mike Matusow, Layne Flack, Erica Schoenberg, Evelyn Ng, and the late Gavin Smith, among others.

The show does exist, however. If you’d like to see it, then keep reading.

Poker Prop Bet Ideas 2019

After producing the Aruba Poker Classic, and more than two seasons of The Ultimate Blackjack Tour, I knew one thing to be certain. Poker players can often be difficult to wrangle.

It makes perfect sense when you think about it. All of us in this profession love the feeling of being free to go where we want, when we want. The only schedule that ever matters might be getting to the main event before you get blinded out or showing up to the cash game before the fish have all been caught. That’s why I chose to shoot the majority of I’ll Take That Bet at one single location, which was my buddy and then-producing partner Sam Korkis’ house in Vegas, on a day when no major tournaments were being held.

There were many issues, such as dragging Phil Hellmuth to the set straight from an all-night Chinese Poker game at the Bellagio sporting fever blisters on his lips and what looked like a 72-hour session of fatigue, or the fact that all the other cast members were placing big side bets on whether or not Mike Matusow would arrive to the shoot either drunk, late, or not at all. But before I star into those stories, first let me tell you how the show got sold in the first place.

The year was 2007 and my agent had set up a pitch a month out for me to meet with Court TV about a courtroom reality series. By the time the actual pitch date rolled around, I had almost forgotten about the show concept I was supposed to show them. Always eager to give it a shot, I gathered up my material for the pitch and went in with the mindset that I was going to sell another TV show. At that time, I had The Ultimate Blackjack Tour airing on CBS, and a pro wrestling series on MTV, plus a couple other pilots in production.

As soon as I started my pitch, the development executive politely stopped me and said, “Didn’t your agent tell you? We are no longer Court TV. We have just changed the name of our network to TruTV and aren’t interested in court room-related series anymore.”

Trying to draw attention away from the fact that I felt like an uninformed jackass, I turned it around and started asking them questions about what they saw for the future of their newly re-branded network. There were three executives in the room including a vice president of development, and a director of development. I was surprised to hear how excited they all were. They didn’t know exactly what they wanted, but they knew it was going to be “cool.”

That’s when I asked them if they knew what a prop bet was. A young assistant literally raised his hand as if it were a pop quiz and answered by saying, “Oh I know what that is. That’s when you sucker somebody out of their money right?”

I laughed and said, “Well, sometimes it can mean exactly that!” And I began to tell them a story about one of the greatest prop bet hustles I had ever witnessed.

So, what was this crazy story that sold them on the idea? Well, if you’ve read my book, Billion Dollar Hollywood Heist, then you will remember the million-dollar golf bet between entrepreneur and poker playboy Kasey Thompson and the infamous, former WSOP champion, the infamous Russ Hamilton. (Hamilton, of course, was later implicated in the UltimateBet scandal, but that’s a story for another day.)

For those that haven’t read it, here is an excerpt from the book that explains how I became the first producer to sell a show concept to the newly formed TruTV.

Out of all the hustlers I’ve ever known, none even came close to Russ. Whether it’s poker, golf, or a gum-spitting contest, you never want to make a wager with Russ unless you’re ready to lose a ton of dough. He might even lose a bet to you on purpose just so he can beat you for more money down the road at something else.

Remember my friend Kasey Thompson? The guy Tobey let off the hook for a million bucks out of the kindness of his heart? Well, one time Kasey had a million-dollar golf game set up with Russ. He was confident he would win because he had a much better handicap than Russ did.

Bet

The day before the game, the two of them were having lunch near a big old palm tree. Out of the blue Russ bets Kasey ten grand that he can’t shimmy up to the top of the tree in under five minutes. Kasey not only took the bet, but he shot up the tree like a monkey and then came back down to collect his winnings, which Russ quickly paid, in cash.

And what happens the next day out on the first fairway? Kasey’s hands were so scarred up and mangled from climbing the tree that he could barely hold his driver and his golf game completely went to shit. Unlucky coincidence? Or as sweet a long-range scam as you’ll ever find? You decide. But suffice to say Russ easily took Kasey for the million bucks on the golf course that day.

As I’m casually telling this story to the TruTV execs their faces lit up like a first time hold’em player with pocket aces. They were hanging on every word, and bought the show in the room, even calling my agent to make a deal before I had time to get back to my office.

For those of you who are wondering if selling a TV show is your ticket to fame and fortune, I’ll spare you the mystery and just tell you it’s far from it. Once a network decides they like your concept, about 100 other things need to go right before the show will ever see the light of day.

In my case, I wanted to produce one big prop per episode, similar to the one I told them about in the room. However, they wanted to turn it into some form of a competition. Doing a competition would be fine, but to do it right would require a bigger budget and a lot of moving pieces to pull it off correctly.

Sadly, If I remember correctly, they offered up about $20,000 for a presentation tape when a full-blown pilot budget for a show of this nature could range anywhere between $125,000 to $400,000 depending on the scope.

Needless to say, wasn’t going to cut it, so we decided to do a bare-bones presentation. What we came up with was a fun little show that fit into a log line that went kind of like this: Seven professional gamblers put their own money on the line… winner takes all!

Poker Prop Bet IdeasPoker Prop Bet Ideas

It was a fun little concept that included basketball wagers, mini golf, some eight ball and other fun bets. Hollywood Dave Stann bet professional gambler Brian Zembic, (the man who got breast implants for $100,000 and then decided to keep them) on who could borrow a stranger’s cell phone and use it the longest. Mike the Mouth and Gavin Smith were betting on who could hit tennis balls over a house and make them land near the basketball court on the other side. And meanwhile, my buddy Phil Hellmuth, forced awake and wearing a ton of makeup, played host, and officiated over all the wagers.

It was actually a really fun atmosphere for people to see Hellmuth in. While I enjoy seeing him yell at the tables, Phil can be very endearing and even more entertaining away from the poker table, especially playing a host to a bunch of poker pros and gamblers.

The show was designed to have an elimination format so at the end of each episode, so somebody had to go! After a long day, and lots of laughs, the person who lost the most would be kicked off the show. So, between Matusow, Flack, Schoenberg, Smith, Ng, Zembic, and Stann, who do you think was the first to be eliminated? Stay tuned to part 2 of this article to find out.

The more important question is, why didn’t the show air? Since it was just a presentation, we never thought it would air, but hoped it would be a stepping stone towards a real budget so we could add more bells and whistles into the series if it got picked up.

Things were looking promising, but it wasn’t long after that when 60 Minutes ran a piece on the god mode superuser online poker cheating scandal involving Hamilton. After that, networks didn’t want to touch a show about gamblers, card players, and prop bets.

So, as much as the network enjoyed the show, they ultimately passed. Would they have done better with a smash hit show centered around props? Who knows? But if you think that means my show will never see the light of day and is gone forever… well, I’ll Take That Bet!


And remember… stay sharp! Stay KardSharp!

Houston Curtis, founder of KardSharp.com and author of Billion Dollar Hollywood Heist has lived a successful double life as both a producer and card mechanic for nearly 30 years. His credits include executive producing gambling related TV shows such as The Ultimate Blackjack Tour on CBS, The Aruba Poker Classic on GSN and pioneering the poker instructional DVD genre with titles featuring poker champion Phil Hellmuth.

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Barred for life from Las Vegas Golden Nugget for “excessive winning” at blackjack, Houston is one of the world’s most successful card mechanics and sleight-of-hand artists of the modern era. Curtis, who rarely plays in tournaments, won a 2004 Legends of Poker no-limit hold’em championship event besting Scotty Nguyen heads-up at the final table before going on to co-found the elite Hollywood poker ring that inspired Aaron Sorkin’s Academy Award-nominated film Molly’s Game.

Curtis resides in Phoenix, Arizona where in addition to running a production company and independent record label, he is also a private gaming/casino protection consultant to clients across the globe seeking insight into master level card cheating tactics via advanced sleight-of-hand technique. To reach Houston for a speaking engagement, consulting or production services send email to stacked@Kardsharp.com.

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All views expressed in this article are those of the author and do not necessarily reflect the views and opinions of Card Player.

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