So you know that there was a bet made between Tim and Stephanie/me on the outcome of the football game between Michigan State and Michigan. The picture below tells that the winner was the Spartans (of course.) The bet was to hold a decorated pumpkin (designed by Stephanie), and Tim added the facial expression himself. I don't know if he is referring to his having to hold a Spartan pumpkin, or to the way the Wolverines played. 
Well, better luck next year. You'll need it!
Well, better luck next year. You'll need it!