Brian ZembicFull disclosure; Brian Zembic is more famous as a personality within the gambling community rather than as a particularly successful blackjack player, but his story is so unique it has to be included here.

That said, he is a high stakes player of both blackjack and backgammon, among other games, and he competed in the 2nd World Series of Blackjack, finishing 9th overall.

Born in Canada in 1961, Brian was always a character and was never interested in making money by working. He has been a gambler all of his life in one way or another, and even when he did have a job as a teenager he found someone else to do it for him and paid them half of what he was getting.

As well as gambling in the traditional sense, Zembic has taken many bets from friends. He became well known for accepting zany wagers to the point that people he doesn’t even know will offer to pay him for his antics.

He slept under the 59th Street bridge in Manhattan with $10,000 strapped to his ankle for a week to win one bet, lived in a box for 2 weeks to win $25,000, and lived in a friends bathroom for a month to win another bet – he was unable to leave even when the toilet was being used. He turned down the offer to cut off his own penis for $1 million, but it’s safe to say that 99% of the time, if you make a dare devil bet with Zembic, you are probably going to lose your money.

$100,000 Boobs

Breast ImplantsThe bet that made Brian famous was made in 1996, when he made a comment about his friend’s girlfriend’s breasts, exclaiming that if he had similar features he could get just as much attention as she did. His friend, known as Jobo, dared him to put his money where is mouth was, which was like a red rag to a bull for Zembic.

The bet was on, but Jobo didn’t think it was serious. Even Zembic didn’t really do anything about it until his lost a substantial amount of money on a bad stock market tip, at which point he approached a New York surgeon, Dr Felix Schiffman, who was also a gambling buddy.

He couldn’t afford to pay for the surgery so instead he challenged Schiffman to a game of backgammon, ended up winning enough to pay for the surgery, and so in effect he managed to get it for free.

When Jobo found out that Zembic was going ahead with the deal he tried to buy him out for $50,000, but Zembic was committed and wanted the full $100k, so he went under the knife.

The Terms of the Bet

Man LaughingThe pair actually handled the bet in a very professional manner, despite the juvenile nature of it.

The terms were officially drawn up, and stated that Zembic must keep the implants for a full year, that they should be a size 38C, and that he had to pay for the surgery himself (he had that covered already).

The money was held in a Swiss bank account to ensure fairness and that payment would be made upon completion, and once the year was through that money would be released.

This all went ahead as planned, Zembic had the implants, his friend laughed like a hyena, and a year later the bet was won.

However, Zembic grew accustomed to his new breasts, and didn’t get them removed for 20 years! It probably helped that the bet was extended to net him $10,000 for every extra year he kept the implants.

Amazingly, he has lived two decades of his life as a man with breasts, stating that he had no problem attracting female attention, even getting married and having a daughter during that time.

He finally had the breasts taken out in 2016 on the American TV show ‘Botched’, but estimates that they have banked him more than $500k over the years in TV show appearances, interviews, documentaries, and book sales – including $100 from talk show host Jimmy Kimmel who paid him for a flash.