Top 10 Craziest Prop Bets Made by Poker Players

When somebody mentions poker, it often conjures up images of a pair of figures staring intently at each other across the table, usually wearing sunglasses, trying to intimidate each other.

What outsiders don’t think about is that these figures generally love gambling in many different forms, and as they go about their daily lives they will come up with the most bizarre, unthinkable wagers.

These prop bets mostly aim at challenging not just skill but endurance, creativity, and sometimes sanity.

From outrageous physical feats to daring personal sacrifices, prop bets embody the gambler’s spirit in its most colourful form.

What Are Poker Prop Bets?

Poker prop bets — short for proposition bet — are random side wagers that are agreed during an unrelated activity.

Most of the time these bets crop up at the poker table but often they will be agreed on a golf course or during some other pastime.

While it is the aforementioned gambler’s spirit that gets these wagers agreed, their purpose is really to entertain and build camaraderie.

The best prop bets  are still talked about many years after taking place, sometimes transforming ordinary players into unforgettable characters.

Why Poker Players Love Prop Bets

Poker players love the thrill of competition. They naturally enjoy risk and pushing boundaries.
But after years of competitive play, sometimes long-time players don’t get the same buzz from grinding out hands and this is where prop bets come into play.
Side bets — another name for a proposition bet — offer an escape from the rigor of strategic play.

It might sound strange to the casual player that somebody who plays this game for a living would claim boredom, but it does happen in stretches. Professional poker is not all sunshine and rainbows, even when it’s going well.

Top 10 Craziest Prop Bets in Poker History

#1. Brian Zembic Has Breast Implants Fitted

In 1996, high-stakes gambler Brian Zembic accepted a prop bet that he would undergo breast augmentation surgery and keep the implants in for a year to win $100,000 ($200,000 in 2024).

Initially Zembic declined the wager, but following heavy losses on the stock markets he relented and roped in a cosmetic surgeon who had gambling debts to do the procedure.

The Canadian had 38C implants fitted and refused a six-month buyout for $50,000, determined to collect the full $100,000.

After the prop bet was won, Zembic became a minor celebrity in the gambling community and, incredibly, still has the implants fitted. Some say this is on the off chance that a movie about his story is ever produced.

#2. Antonio Esfandiari Lunges for 48 Hours

During the 2016 PokerStars Caribbean Adventure, Antonio “The Magician” Esfandiari accepted a $50,000 prop bet from Bill Perkins to move from one place to another only by lunging for 48 hours.

Those readers who are not fitness fans will probably not appreciate how physically taxing this movement is. For an average out of shape person, 10-20 reps will have them looking for a comfortable chair to recover on.

Esfandiari was clearly in pain as he moved from poker table to poker table, and then came the decision about what to do when the urge to visit the bathroom became too much to handle.

Poker players are innovative by nature and so The Magician opted for the most obvious choice to this problem: he urinated in a bottle under the table.

Unfortunately, this violated tournament rules concerning general decency, causing his disqualification.

Despite this, Esfandiari honoured the spirit of the bet by donating the $50,000 winnings to charity after Bill Perkins paid up.

We did it. We won the ultimatesweat bet and 150k. I feel so surreal right now.

Thanks to @matthew_stapless @bp22 @mikevacanti friends and family, @beccarr94 and of course all of you rooting us on every day. Inspiring me to be better. Thank you ❤️ pic.twitter.com/Yg6IpfLv5y

— Jaime Staples (@jaimestaples) March 26, 2018

#3. Staples Brothers Weight Bet

Twitch streamer brothers Jaime and Matt Staples turned their sibling rivalry into a 50-to-1 wager against Bill Perkins to reduce the 170lbs weight gap between them over a year to a mere pound or less.

Jaime weighed in at 304 lbs (137.9 kg) and Matt was a slender 134 lbs (60.7 kg).

The pair documented everything on social media over the 12 months, with the poker community following along with every post.

The brothers wagered $3,000 against Perkins, earning them $150,000 when they weighed in at  188.3 lbs (85.4 kg) for a loss of  115.7 lbs (52.5 kg) for Jaime, while Matt gained 54.3 lbs (24.6 kg).

#4. Markus Gonsalves Beats Dan Smith at Tennis With a Frying Pan

Fiery Dan Smith, sixth on the all-time live tournaments money list with winnings of $60,421,591, and fellow pro Markus Gonsalves came up with one of the most bizarre prop bets in recent times, but also one which is amusing when you watch the video.

The pair were to play a standard tennis match, but while Smith would have a normal racquet Gonsalves would have to make do with a frying pan!

Gonsalves had previously beaten Smith in a tennis match while using his weaker left hand. The next match, Smith thought, would see him equal their score.

But against the odds, Gonsalves won the match 6-2, leaving Smith considerably embarrassed and likely to never pick up a tennis racquet ever again.

#5. MMA Fight Between Olivier Busquet & JC Alvarado

Poker pros Olivier Busquet and JC Alvarado faced off in a five-round MMA fight with $270,000 riding on the outcome.

Busquet posted an open offer for the fight, claiming he was seeking extra motivation, and Alvarado accepted, assuming that his previous MMA training experience would see him through.

The only problem for Alvarado, however, was that Busquet had a significant size advantage at 187.5lbs to the Mexican’s 165 lbs. In the fighting world, this is a complete mismatch.

Even so, Busquet would put up the smaller sum of $120,000 to Alvarado’s $150,000.

The fight turned out to be worth watching. Both fighters displayed an incredible will to win, but in the end the Frenchman’s size won the day with Alvarado unable to utilise his jiu-jitsu background.

We did it!! Thank you from the bottom of my heart to everyone who supported me. So much respect for @JCAlvarado1 pic.twitter.com/EWgQtk3pFI

— Olivier Busquet (@olivierbusquet) April 22, 2016

#6. Mike Noori’s $1000 McDonald’s Food Challenge

There’s nothing like a good, old food challenge. In fact, the internet age has seen a rise of content focussed on such challenges around the world.

With this in mind, WPT Executive Tour Director Matt Savage offered poker player Mike Noori 5-1 odds that he couldn’t consume $1,000 worth of McDonald’s food within 36 hours.

Drinks were allowed but they couldn’t be deducted from the $1,000 total. No more than $200 could be spent on salads and at least $300 must be spent on hot foods with $50 of that coming from burgers. Even forced vomiting was banned!

Noori stood to win a reported $200,000 if successful but in the end he didn’t even manage a paltry $100 worth of McDonald’s food after going out drinking the night before.

#7. Jay Kwik’s 30-Day Bathroom Stay

Jay Kwik’s prop bet to stay in a bathroom for 30 days is arguably one of poker’s most extreme endurance challenges.

Known for his poker stamina in the early days of online poker, Kwik accepted this prop bet from Andrew Robl where he would be deprived of electronics and external distraction. He would also be watched on camera for the entire 30 days.

At the start of the challenge observers were concerned for Kwik’s health if he went deep into the 30 days but, in fact, Robl bought out of the bet for $40,000 four days before it ended as Kwik was showing no signs of suffering.

#8. Huck Seed’s 18 Hours Neck-Deep in Water

Huck Seed, winner of the WSOP 1996 Main Event, was known for his wild prop bets back in the day, and mostly successful with them.

Phil Hellmuth, though, was the man to come up with an irresistible challenge that would soon have the American running. And, as it happened, he was absolutely right.

Hellmuth, winner of a record 17 WSOP bracelets, bet $50,000 that Seed could not stay neck-deep in water for 18 straight hours.

Within only three hours, the wetsuits up Seeds was running for cover as the cold temperature and strain of staying upright in the water was too much to handle.

#9. Howard Lederer’s $10,000 Burger Bet

Howered Lederer, one of the villains of the Full Tilt Poker fiasco in 2011, once raised eyebrows by accepting a $10,000 wager to eat a cheeseburger publicly, despite being a committed vegetarian.

Now we all know just how committed your average vegan or vegetarian is; not many of them would accept cash in return for breaking their vow, and certainly not a millionaire.

But Howard Lederer is a poker player and when somebody dangled cash in front of his nose with a dare behind it, he just could not resist.

This lighthearted bet did end with Lederer picking up the cash but he did offer his friend David Grey the chance to win it back by eating a jar of olives; his least favourite food in the world.

#10. Dan Bilzerian’s Vegas to LA Bike Ride

Millionaire playboy and poker player Dan Bilzerian accepted a $600,000 prop bet with Bill Perkins to bike roughly 300 miles between Las Vegas and Los Angeles in under 48 hours.

Now that’s not exactly a Sunday afternoon ride but Bilzerian was once a candidate to join the US Navy SEALs.

So having not ridden regularly in years, Bilzerian hooked up with cycling legend Lance Armstrong and set about getting back into shape.

Audacious and grueling, Bilzerian completed the ride in about 33 hours, easily beating the time limit.

As a bonus, Bilzerian also won $250,000 from high-stakes pro Rick Salomon as a side bet for not dying or suffering brain damage during the challenge.

Risks and Consequences

While often humorous and seemingly harmless, prop bets can carry serious risks if the gamblers get carried away with themselves. It’s easy to let these shenanigans get out of control.

Physical challenges may lead to injuries, health issues, or long-term consequences. Socially, failed bets could cause permanently damaged relationships.

Poker prop bets are supposed to be a bit of fun so make sure that they stay that way and don’t get serious.

Prop bets have become a part of poker’s rich and colourful history. They are integral chapters in poker’s vibrant story and are another vehicle for us to remember players by when they are no longer with us.

Poker wouldn’t be where it is today without the characters that we have to entertain us and sometimes transform poker from a simple card game into an arena of human endurance and spirit.