"Sweet Action: 8 Big Bets Made by Famous People "

From Mental Floss:

Most people limit their gambling to friendly Super Bowl wagers or the occasional trip to Vegas. Celebrities, of course, tend to do everything on a grander scale. Let’s take a look at some famous people and the high-profile bets on which they cashed in or lost big.

1. Truman Defeats Dewey, Jimmy the Greek Defeats Vegas

Everyone remembers the “Dewey Defeats Truman” headline from the 1948 presidential election, but Harry Truman wasn’t the only big winner that night. Legendary gambler Jimmy the Greek had bet $10,000 on Truman at steep 17:1 odds. His logic? His research showed that female voters weren’t too keen on candidates with facial hair, which didn’t bode well for the mustachioed Dewey.

2. Arnold Palmer Bets on Romance

When golfing legend Arnold Palmer met his wife, Winnie, he had a problem that a lot of young guys run into: he couldn’t afford an engagement ring. He was still an amateur golfer at the time, and he was barely scraping by on his meager income. Eventually, he borrowed money from a group of pals to cover the rock.

Palmer wasn’t crazy about having this sort of debt, so when the same group of buddies proposed a trip to New Jersey’s Pine Valley Gold Club, he jumped on the chance to chisel away at his obligations. When they hit the links, Palmer offered the boys this bet: he would get $100 for every stroke he finished under 70. If he played poorly on the notoriously tough course, he would shell out $100 for every stroke he finished over 80. Although he bogeyed the first hole, Palmer repeatedly used this system along with a variety of side bets to wriggle out from under $5,000 in debt in a single weekend.

5. Phil Mickelson Has a Nice 2001

PGA golfer Phil Mickelson had a hot hand during 2001. Fans might remember that two longshots won titles that year: the Baltimore Ravens won the Super Bowl, and the Arizona Diamondbacks knocked off the New York Yankees in a classic World Series. Mickelson was part of betting groups that had picked both squads. Their $20,000 bet on the 28-to-1 Ravens yielded a cool $560,000, and they hit again with $20K on the 38-to-1 Diamondbacks. And to think people used to say Mickelson couldn’t get a big win.

8. Computers Are No Match for Chess Master

In 1968, Scottish chess champion David Levy attended a conference on artificial intelligence and discussed the future prospects for chess-playing computers. Although Levy was optimistic about the future of chess-playing computers, he thought developing great AI would take a while. After some debate, he bet four professors 1,250 British pounds that nobody would make a computer that could beat him within the next 10 years.

Although it took a while for chess programs to pose a serious threat to him, Levy ended up winning the bet when he defeated the program Chess 4.7 in a six-game match at the 1978 deadline. The man-vs.-machine showdown was such a big deal that even Sports Illustrated covered it.

After his win, Levy put up another $1,000 as a bounty for the first chess program that could beat him in a four- or six-game match. He eventually fell in 1989 to Deep Thought, a precursor to famed chess computer Deep Blue....Four MORE