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.

Related Articles
  1. Investing Basics

    10 Habits Of Successful Real Estate Investors

    Enjoying long-term success in real estate investing requires certain habits. Here are 10 that effective real estate investors share.
  2. Investing Basics

    5 Types of REITs And How To Invest In Them

    Real estate investment trusts are historically one of the best-performing asset classes around. There are many types of REITs available.
  3. Investing Basics

    5 Simple Ways To Invest In Real Estate

    There are many ways to invest in real estate. Here are five of the most popular.
  4. Investing News

    Super Savings for Your Super Bowl Party? Bet on It

    Prices for wings, avocados and TVs are all coming down, which will make your Super Bowl 50 festivities less costly.
  5. Retirement

    Dollar Shave Club Review: Is It Worth It?

    Learn about the business model of the Dollar Shave Club, and find out whether the razor subscription company is a worthwhile investment.
  6. Term

    The Implications of Nonfarm Payroll

    The nonfarm payroll is a key economic indicator that’s closely monitored by analysts and investors around the world.
  7. Investing News

    Are Super Bowl Ads Worth Their High Cost?

    Are Super Bowl ads worth the investment? A look at the cost and how they're received.
  8. Investing Basics

    Understanding Real Estate

    Real estate is an encompassing term that refers to land, the buildings on that land, and its natural resources, such as crops and minerals.
  9. Investing Basics

    How To Value A Real Estate Investment Property

    Two common methods for real estate valuation are the discounted net operating income and gross income multiplier approaches.
  10. Investing Basics

    How to Calculate ROI For Real Estate Investments

    When it comes to real estate investments, there are two important ROI calculations to know.
RELATED FAQS
  1. What is a derivative?

    A derivative is a contract between two or more parties whose value is based on an agreed-upon underlying financial asset, ... Read Full Answer >>
  2. What is securitization?

    Securitization is the process of taking an illiquid asset, or group of assets, and through financial engineering, transforming ... Read Full Answer >>
  3. Do plane tickets get cheaper closer to the date of departure?

    The price of flights usually increases one month prior to the date of departure. Flights are usually cheapest between three ... Read Full Answer >>
  4. Can hedge funds trade penny stocks?

    Hedge funds can trade penny stocks. In fact, hedge funds can trade in just about any type of security, including medium- ... Read Full Answer >>
  5. Can hedge funds outperform the market?

    Generating returns that exceed those provided by the broader market is the goal of nearly every investor. However, the methods ... Read Full Answer >>
  6. Is Colombia an emerging market economy?

    Colombia meets the criteria of an emerging market economy. The South American country has a much lower gross domestic product, ... Read Full Answer >>
Hot Definitions
  1. Presidential Election Cycle (Theory)

    A theory developed by Yale Hirsch that states that U.S. stock markets are weakest in the year following the election of a ...
  2. Super Bowl Indicator

    An indicator based on the belief that a Super Bowl win for a team from the old AFL (AFC division) foretells a decline in ...
  3. Flight To Quality

    The action of investors moving their capital away from riskier investments to the safest possible investment vehicles. This ...
  4. Discouraged Worker

    A person who is eligible for employment and is able to work, but is currently unemployed and has not attempted to find employment ...
  5. Ponzimonium

    After Bernard Madoff's $65 billion Ponzi scheme was revealed, many new (smaller-scale) Ponzi schemers became exposed. Ponzimonium ...
  6. Quarterly Earnings Report

    A quarterly filing made by public companies to report their performance. Included in earnings reports are items such as net ...
Trading Center