I'm guilty of buying a Wittenberg shirt (my first team), but the background story is far more interesting. My buddy got me to start playing HD, so I joined his conference. Every year, my buddy, 14 of our good friends, and myself compete in a 3-day competition of pseudo sports. Events are pool, air hockey, ping pong, darts, bags, foosball, croquet, HORSE, bowling, and mini golf. With the exception of the last 4, everything is head to head, double elimination bracket style. It's the greatest weekend of the year. 16 guys get together and grill out, drink, and talk trash. Winner gets his name engraved in a 40oz. beer mug, gets the mug for a year, and endless pride and bragging rights. My first season in HD, the first time I played my buddy in conference play was this particular weekend. So I decided to buy a shirt and taunt him all day the day before our game, even though his team was far better than mine. Turns out, he he had the same idea, bought his team's shirt, and was wearing it as well. Our other friends knew about the game and found it pretty comical when we both showed up wearing our respective apparel.
As for who won the game...I was up 6 with :30 to play, but missed something like 6 straight FTs and lost by one. Just gave my buddy more trash talking ammo for the weekend. Looking back, it's probably also worth noting I followed in Wittenberg's footsteps. Solid lead going into the last event (mini golf), only to crumble and choke the victory away. Sad face.