High-stakes gamblers put prices on everything. How much money, for example, would it take for a man to get breast implants on a dare? Las Vegas gambler and magician Brian “The Wiz” Zembic agreed to do it for $100,000 back in 1996.
A well-heeled backgammon player put up the six-figure sum, and Zembic became the proud owner of two 38C breasts, after undergoing a notorious boob job first reported by Maxim in 1998. To win the bet, Zembic needed to keep them for 12 months. But he says he's come to like his surgically-augmented set so much, that 19 years later they remain firmly in place.
“I got lazy, I was busy gambling, and, honestly, they grew on me,” says Zembic, adding that the bet stipulated he had to pay for the implants himself. (The surgeon did it for free, in exchange for Zembic dropping a backgammon debt against him.) “Plus it hasn’t hurt my ability to get girls," he boasted to Maxim this week. "They don’t give a shit.”
No stranger to bizarre wagers, known as "prop bets", Zembic once earned $5,000 spending a night under New York's 59th Street Bridge in the 1990s, sleeping with vagrants — with $10,000 strapped to his leg. More recently, he bet that his nine-year-old daughter, who had never before played piano, could learn to play George Winston songs better than the New Age pianist himself in three years.
Winston himself provided confirmation, and Zembic won $75,000. Later, he bet that his daughter would open a concert for Winston. She did! Fifty people paid to see the younger Zembic and Winston play in Zembic’s home. He's also bet that he could do better hand shadows than a contestant on America’s Got Talent. (If you're interested, you can watch Zembic do hand shadows of everyone from Alfred Hitchcock to Robin Williams here.)
“I kept 40 flashlights around the house and practiced,” says Zembic, who earns much of his income from giving backgammon lessons and betting on ping pong. “A top hand shadow guy verified that I am better. Now I want to go on AMT and get $10,000 for every round that I advance. That money would go toward paying off a gambling debt that I have.”
Here's Zembic shopping for sports bras in a vintage clip from Inside Edition.
Zembic is not alone in making super weird wagers. Poker superstar Antonio Esfandiari bet $500,000 that he would be able to spend a year abstaining from any form of sexual release — kind of like a high-stakes take on that classic Seinfeld sketch. Inspired by a Buddhist friend, Esfandiari was seeking enlightenment. Predictably, he only found frustration.
“After one week, I bought out of the bet,” he says, explaining that he paid off part of the $500K in order to cancel the wager. “I don’t want to say the sum, but it was an amount that hurt. I paid a pretty price. But my opponent [Bill Perkins, an oil and gas trader who also plays in high stakes poker games] knew that if he didn’t let me buy out I would have won the bet. If it would cost me $500,0000 to have sex or masturbate, I would have stayed celibate.”
Prop bets have a long history among poker players and others who’ve been bitten by the gambling bug. They serve multiple purposes, sometimes even providing financial incentive for improving one’s life. Decades ago, after sports bettor Billy Baxter was imprisoned for bookmaking in his home state of Georgia, he made a $10,000 wager with poker legends Doyle Brunson and Jack Binion that he’d be able to go from 204 pounds to below 165 while behind bars.
“As soon as I got out,” he remembers. “I went right to Binion’s Horseshoe and they put me on the meat scale. I weighed 162, collected my money, and moved to Las Vegas permanently.”
Other times, it’s to prove a point. In the middle of a poker game, Esfandiari got into a discussion with another player about whether or not it’s legal to smoke E-cigarettes on Southwest Airlines flights. Esfandiari thought no, the other guy thought yes. A quick phone call, made between hands, revealed the fact that a rule had been put into effect months earlier, banning the ersatz smokes.
Esfandiari explains that making money resides at the core of these bets — after all, when serious gamblers finish dinner, the bill is usually settled via a round of credit card roulette: the waiter holds everybody’s credit card, shuffles them, and randomly selects one at a time; whoever’s card is left at the end picks up the tab — but he’s also drawn by the intellectual challenge.
“The way these things come up, everybody is usually completely new to the situation,” he says. “It’s interesting to see how people gather information on the fly and dissect that information.” Then there’s the sheer act of forced change. Poker player Jeff Gross wagered that he would be able to spend a year-and-a-half without ever checking luggage. He now travels far lighter and more efficiently than he ever did before.
Other times, it’s a ballsy dare that involves potential pain and suffering. One year, during a poker tournament at Atlantis Resort & Casino in the Bahamas, a group of bored poker pros put up a stake for a guy to swim across a shark tank. Online poker legend Ilari “Zigmund” Shamies snorted rails of salt. Alec Torelli, another online poker wizard, stripped to his skivvies, swam across the water surrounding the Mirage’s famous volcano, and scaled the volcano. Torelli escaped with $1,000 earned, lost pride, and a gash on his foot.
Once, the physically fit Torelli made a $200,000 bet with poker player Ashton Griffin: whoever finishes a triathlon in a shorter time takes the money. “Alec was training hard when Ashton went on a $1.5 million poker downswing,” remembers mutual friend Andrew Robl. “Suddenly the prop bet seemed less important to Ashton. He stopped training and bought out for $100,000. It was the easiest money that Alec has ever made.”
For all of that, there are occasions where money is not the thing at all. Esfandiari recalls attending a dinner party at the Las Vegas home of famed gun nut Dan Bilzerian. Wanting to demonstrate how a bulletproof vest works, Bilzerian set one down on the floor and shot at it.
“I thought that was a waste,” says Esfandiari. “I decided that I wanted the max rush of experiencing it. So I put the vest on and let Dan shoot at me. I got my max rush. In that instance, the experience was worth more than any money I could have gotten for agreeing to be shot at.”
Photos by Stewart Cook / Rex