So in the 2008 NCAA pick ’em, The Dren lost and proudly displayed his loser shirt at Wrigley Field. He again lost this year’s pick ’em, but forgot to bring the shirt to a baseball game with him, so he’s wearing the two-time loser shirt at a pool in Palm Desert, CA:
Again, I’m sure his wife loves it.
If you’re wondering what the shirt says (the original is here):
If he loses for a third time, I might have to open up the design to the masses here.