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

[David04]

A friend of mine was 100% positive that the Super Bowl MVP had to be on the winning team. I even tried to explain to him why I thought this was untrue, but he thinks he is never wrong, so we put up some small amount of money.

We go on the internet, and it's like the 3rd or 4th SB, I believe it was Roger Staubach who was the SB MVP on the losing team.

Not really a dumb bet, but certainly the dumbest thing I've ever bet on.