It's not hard to find stories about losing wagers and busted bettors. Michael Jordan may be the greatest basketball player of all time, but as a punter, he's putrid. Tales of Jordan's golf course gambles are legendary. In 1992, "His Airness" admitted to writing a check for $57,000 to Slim Bouler, a convicted cocaine dealer, for money lost on gambling and betting (I know, it's hard to believe that a drug dealer would sully his reputation in such a way).

But Jordan's spat with Lady Luck was nothing compared to Terrance Watanabe's dispute with her. During a yearlong gambling nightmare in Sin City in 2007, Watanabe lost nearly $127 million. According to an article that appeared in the Wall Street Journal, this streak resulted in the loss of his personal fortune which was accumulated over the course of two decades. (Is the stock market the biggest gamble of them all? Find out more in Going All-In: Comparing Investing And Gambling.)

Politicians haven't been immune to the fickle hand of fate either. According to the Associated Press, Jenny Sanford, the soon-to-be ex-wife of South Carolina Governor Mark Sanford, told Barbara Walters on "20/20" that her wedding was a "leap of faith." And we all know how that turned out.

Still, certain gambles do pay off and, at least in the world of sports betting, some of those payoffs can be very handsome indeed. Here are a few wagering returns on the top sporting events of 2009.

Masterful Win
Despite not finishing higher than eighth and failing to make the cut three times in nine previous Masters tries, Angel Cabrera endured a three-way sudden-death playoff to win the 2009 edition of the prestigious event. Those with the courage and conviction to back Cabrera may have been as happy as the golfer; they received a whopping $14,000 for every $100 they wagered.

Yankees Pull It Off
Although the price was on the skimpy side, loyal fans of the New York Yankees would've received $250 for every $100 they staked on their beloved Pinstripers to win the 2009 World Series at the start of the season - enough to buy a year's supply of peanuts and Cracker Jacks.

Slam Dunk
Those who believed in the Lakers as much as Jack Nicholson at the start of last season would've pocketed $350 for every $100 they put where Jack's mouth is. Some, like me, would've paid an additional $350 if they'd used tape. (Debt collectors are becoming more aggressive, and have found "legal" ways to function outside the law. Know your rights and how to counter these new methods in The Dark Side Of Debt Collection.)

No Penalty Here
The Pittsburgh Penguins became just the second team to win the Stanley Cup after losing the first two contests on the road when they defeated the Detroit Red Wings four games to three. Penguins fans were justly rewarded with $60 for every $10 wagered prior to the start of the season.

At The Races
However, it was prescient fans of the Sport of Kings that really struck it rich in 2009. When Mine That Bird topped Pioneerof the Nile, Musket Man and Papa Clem in the 2009 Kentucky Derby, the $2 superfecta, a bet that requires punters to select the top four finishers in a race (in order), returned a stunning $557,006.40.

Super Bets
Of course, no article on sports betting would be complete without at least a mention of the Super Bowl. Last year, $81.5 million was wagered on the big game and, this year, the figure grew to $82.7 million. (You may think it goes without saying that Super Bowl host cities benefit from the event, but as it turns out officials have been using some creative math. Find out more in The Not-So-$uper Bowl)

Among the more interesting betting propositions, or "props," on this year's super spectacle (from BetUS.com):

  • Bettors were offered $10 for every dollar they wagered if a member of The Who, this year's featured halftime entertainment, lit up a joint. Sadly, for those who took that bet, the only thing that Roger Daltrey, Pete Townsend and the boys were puffing on Super Bowl Sunday was copious amounts of air. How old are those guys anyway?

  • The over-under on how long it would take Carrie Underwood to sing the "Star Spangled Banner" was one minute, 41 seconds (an "over-under" bet allows gamblers to wager that a particular total will be above or below a specified line). There have been conflicting accounts, but the consensus appears to be that those in the "Team Over" camp got the money.

The Bottom Line
The next time someone asks you about the status of your 401(k), tell them you'll let 'em know after the season, the next race or the 2011 Super Bowl is over. Of course, if you don't have a crystal ball or a time machine, making these top bets might be just a little tough.

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