What's the dumbest bet you've ever made?

[Duke]

I had an existing bet that the NASDAQ would fall below 2000 by the end of February 2001, and it was sometime around Christmas 2000, or maybe early January 2001. I was drinking with some buddies, and there was a Duke basketball game on. I'm not a Duke fan, and do not follow college basketball at all, but Shane Battier was playing and I remembered him as a pretty good High School baller. I took even money (for $500 - the same size as the NASDAQ bet) that Duke would win the NCAA tourney that year.

I should have won the NASDAQ bet too, damnit. I thought that was a lock when I made it in November 2000.

~D