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The Top Eight Ballsiest Bets That Paid Off

by DannyGallagher   April 05, 2010 at 10:00AM  |  Views: 1,987

Mark Twain once said, "Necessity is the mother of taking chances." Now get ready to meet her illegitimate children.

Source: B2M Productions/Photographer's Choice RF/Getty Images

By Danny Gallagher

8. John Heidegger Puts His Ugliness on the Betting Line

Source: David McGlynn/Taxi/Getty Images

It takes a real man to muster enough courage to confront and admit to his shortcoming, but an even bigger man would back his bank account on them.

This famed Swiss opera manager John Heidegger had developed an unusual but proud reputation for being "the ugliest man in Switzerland." His reputation was so legendary that one person attempted to put it to the ultimate test and put a big chunk of change on the line to uphold it. Lord Chesterfield offered the manager a wager that he could find someone uglier and if so, the winner would be paid a handsome amount. Reports vary on the actual amount except that the outcome would make one of the two men considerably wealthier.

Chesterfield eventually found a woman from a nearby slum and arranged a meeting with Heidegger to settle the bet. Upon meeting the woman, he placed her bonnet on his head and legend has it that the lump of female ugly that stood before him was so shocked that she fainted on site. Heidegger won the bet and the money, hopefully putting it towards paper production technology to find a big enough paper bag to conceal his legendary homeliness.

7. A Mysterious Investor Bets on the Collapse of Bear Stearns...And Wins

Source: Chris Hondros/Getty Images News/Getty Images

Anyone who throws their money in the stock market is basically just rolling a giant pair of dice. On one side lies a seven pair that can put you in the penthouse suite and your kids through college and on the other lies a set of boxcars that can kick you down to the gutter and get your young ones rejected for a DeVry scholarship.

One unidentified investor, however, bought thousands of shares predicting the total collapse of the Bear Stearns investment group, a bet that made them the only profitable person ever to come out of the former corporate giant.

Back in 2008, the investor put down $1.7 million on the company's failure when the stock hovered at $62 a share and, within a period of nine days, the company actually went into freefall with the stock tumbling to a measly $2 a share. The bet netted this mysterious douchebag, er, investor 159 times his initial investment. SEC and other government agencies have tried to unmask the mysterious bettor but have been unsuccessful. The man has yet to show his face in public, presumably because he used his insane wealth to buy a new one and having to replace it after the unemployed masses rip it off would void the warranty.

6. Ted Forrest Runs a Marathon in the Las Vegas Heat

Source: PhotoStock-Israel/Flickr/Getty Images

Professional poker players are basically gambling addicts with a better credit rating. They spend their days on the green felt runway tossing cards and playing with chips until the sound of shuffling becomes an inaudible blur in their brains. When they aren't playing, they spend all of their free time betting some more.

Ted Forrest, dubbed the "King of the Prop Bets," has made his money at the poker table but also taking on crazier physical challenges than an episode of Fraternity Double Dare, like vowing to lose a ton of weight in a short amount of time or downing 10 beers in 30 minutes.

Some have even put his body and his life on the line. Some schadenfreude schmuck bet the "stud" that he couldn't run a 7K marathon in the peak of the Las Vegas heat. He not only accepted the challenge, but finished it even as the desert temperature reached upwards of 115 degrees. The bet not only earned him $7,000 dollars, but also a pair of running shoes that melted at the soles and a visit to the hospital for dehydration (which is ballsy in and of itself since his health insurance probably considers "being a dumbass for money" as a pre-existing condition).

5. Brian Zembic's Nice Pair Earns Him $100,000

Source: John Lamb/Photodisc/Getty Images

Whether it's lying in a greasy tub of Kentucky's finest chicken or lying next to them in bed after a night of fuzzy memories, what red-blooded American hetero male doesn't love breasts?

Zembic apparently loved them so much that he hasn't had his removed since the doctor implanted them.

The extreme gambler was involved in a high stakes game of backgammon when a friend who gave him a bad stock tip prior to the conversation challenged him to get breast implants. He not only took the bet and won with a luscious pair of 38C-sized man boobs, but he has kept them more than 10 years after it earned him $100K, making them the most profitable two-pair in all of Sin City.


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