The Best Poker Prop Bets Gone Wrong

When it comes to gambling, prop betting can take place on almost anything you could imagine-from the outcome of a football game to which cards appear on the flop in poker, to first scorer in basketball and a million other things.

More interesting, and often outrageous, dangerous or just hilariously funny, are the ‘poker prop bets’ which such gamblers resort to for fun, and which often entail a huge amount of money, or sometimes something more extreme….like getting a boob job if you lose!

Perhaps not so awful if you are female, but back in 1996 Brian “The Wiz” Zembic accepted a wager of $100,000 that he wouldn’t get 38C breast implants. Never one to shirk a dare, as we will see, Zembic went ahead with the operation and became the owner of a magnificent pair of tits- which he had to keep for one year to win the $100K.

19 years on and Zembic still proudly displays his ‘chest-ware’, done for free by a surgeon in exchange for dropping a backgammon debt. Such is the way of the gambler.

This wasn’t the first outrageous prop bet Zembic had taken on. He once slept with homeless people under New York's 59th Street Bridge, which earned him $5000. The catch – and you know there always has to be one in prop bets – is that he had to do so with $10,000 of his own cash strapped to his leg.

And it is this kind of detail is what makes prop bets so interesting, amusing and addictive to the gambler. Just like in Luke Reinhardt’s famous novel ‘Diceman’, there also has to be a huge down-side to the bet to make it worthwhile wagering huge amounts of money.

One famous poker prop bet involved Howard Lederer, who had turned vegetarian after some gastric surgery. As explained in the classic poker book 'The Professor, The Banker and the Suicide King', David Grey offered Lederer $10,000 to eat a cheeseburger. Despite the obvious problems to his gastric system, the money proved more appetising, and Lederer duly scoffed the burger, took the money (and probably suffered consequences too ugly to mention here!)

Another poker legend, Antonio ‘the Magician’ Esfandiari, famously bet $500,000 that he could go without any form of sexual release for an entire year. Oil and gas trader – and fellow high-stakes poker player Bill Perkins took Esfandiari up on his bet, not believing that ‘the Magician’ would manage such celibacy (including as it did masturbation!)

Esfandiari had been inspired by a Buddhist friend to ‘seek enlightenment’ through self-imposed sexual chastity – and lasted all of a week before ‘buying himself out’ of the preposterous bet.

Often the other gambler pretty much has to allow this ‘buy out’ to make a profit, as Esfandiari explains:

Not that having to buy out of such bets early has stopped Esfandiari from making other prop bets. Such is the fun -and money -that prop bets entails that it’s difficult for the high-stakes player to refuse such action.

And he also likes the intellectual side of it – though some might not see something like ‘swimming across the shark tank’ or ‘snorting lines of salt’ as having any intellectual integrity at all!

However, experiencing new and weird things is often at the heart of the Magician’s decision to accept prop bets.

He once attended a dinner party at the home of Dan Bilzerian-the ‘Instagram King’ and a poker pro - where his host demonstrated how a bullet-proof vest works by shooting at one lying on the floor.

Not enough for Esfandiari, as he explains:

No money involved, nothing tangible to be gained, but as Esfandiari says:

There is very little in the way of prop bets which hasn’t been done, and won or lost – and the ingenuity of some of the winners is legendary. ‘Titanic’ Thompson, a scratch golfer, once bet that he could drive a golf ball 500 yards – a seemingly impossible task – but when the bet was accepted he drove to a nearby frozen lake and – using the ice as an aid – easily accomplished the 500 yard distance.

With prop bets probably being as old as gambling itself, they have built up a legendary status which is unlikely to ever stop. As long as gamblers have the money, and the balls to wager it, then people are going to continue doing the craziest things – like Johnny Moss deciding to accept a 15-1 bet of a $1000 that he couldn’t beat up a huge, known tough-guy in the pub, a 100-0 record bar fight monster.

Despite cold-cocking the guy from behind, Moss ended up seriously battered and broken in hospital once the streetfighter had finished with him.

According to Howard Lederer, the story goes that fellow poker-legend ‘Puggy’ Pearson turned up to visit Moss at the hospital and told him he was crazy, that he couldn't go on taking these kinds of bets.

Moss, a true gambler, up for any proposition as long as the price was right, looked at Pearson and murmured: