The Top Eight Ballsiest Bets That Paid Off

April 5, 2010

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

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By Danny Gallagher

8. John Heidegger Puts His Ugliness on the Betting Line

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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

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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

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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

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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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4. Huck Seed's Desert Golf Course Challenge

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Las Vegas is known for crazy behavior. Who knows what causes the psyche to behave in such weird ways? Is it the copious amounts of free booze? Is it the rush of downing Junior's college fund on a single roll of the roulette wheel? I like to think it's the heat, not the humidity.

Poker player Huck Seed not only racked his fortune at the poker table, but also outside the casino, specifically in the city's never-ending desert.

A gambler bet the World Series of Poker champion to four rounds of golf in a single day and having to break 100 in each round. The only catch (isn't there always one?) he could only use a 5-iron, a sand wedge, and a putter and the entire course took place in the desert. Somehow thanks to sheer will and determination (and possibly the divine influence by some easily-amused deity), Seed finished each round without the aid of a driver, a caddie, or even a golf cart in temperatures that buried the needle into 120 degrees.

His profuse sweating also helped keep Las Vegas from experiencing a water shortage that same year.

3. Archie Karas' Lifelong Winning Streak

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Some people like to push their luck. Legendary gambler Archie Karas enters his in a tractor pull.

Karas has amassed an amazing fortune simply through his prowess at gambling. He started as a teenager with a measly $10,000 that he managed to rack up to clear over $1 million in loose chips. But once he hit the million mark, he refused to stop, apparently until the world ran out of money.

His gambling pot dwindled, costing him more than $2 million in the process. He was so broke that he famously drove to Las Vegas with only $50 bucks to his name and borrowed $10,000 that he managed to double to pay back his debtor and put himself back in the black. But not content with simply having his money and his kneecaps still intact, he parlayed his winnings into other games and eventually earned a $2.22 million seat at the World Series of Poker.

He then promptly resigned from gambling, causing Washington's face on the dollar bill to breathe a well-deserved sigh of relief.

2. William Lee Bergstrom's Holy Craps Run

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It must be expensive maintaining a large, shiny set of brass balls. The ball wax and maintenance costs alone must skyrocket into the thousands.

Bergstrom, however, not only has such a pair. He also has the money to back them up.

The Texas risk-taker walked into the Binion's Horseshoe Casino with $777,000 in a suitcase, walked up to a craps table and plopped the sucker down on the "Don't Pass" line, all before the pit bosses had a chance to convert it into chips. A woman rolled an even seven and the casino forked over an additional $777,000, presumably in a fully-comped briefcase.

Not content with defying the odds and the Gods once, he has since made three similar bets, all of which paid off and netted him an additional $870,000.

1. Ashley Revell's Life-changing Roulette Spin

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If you had one shot, one opportunity, to seize everything you ever wanted, would you capture it or just let it slip and then constantly have that stupid Eminem song running through your head until your brain stopping working? Yo.

British bettor Ashley Revell did just that, but he also put his entire life behind it. He convert every possession he owned from his car to his house to the underwear taking up space in his bureau into liquid cash, then combined it with his entire life savings and let the entire $136,000 roll on a single game of roulette.

Fortunately, he didn't take Wesley Snipes' advice to "always bet on black" (besides, getting money management advice from Snipes is like hiring Ray Charles as your personal hair stylist). Revell put the whole thing on red and walked out $136,000 richer.

He then parlayed his winnings into a new online poker company...and a clean pair of underpants.


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