Category #1: We Made the Worst Trade Ever
Florida: Roberto Luongo, Lukas Krajicek, and a sixth-round draft pick in exchange for Todd Bertuzzi, Alex Auld, and Bryan Allen. Luongo is still regarded as one of the game's "elite" goalies. Bertuzzi had the worst numbers of his career as a Panther and became a pariah for quite a while (still considered by some) until he landed in Detroit...again.
Winner: Detroit (meaning Florida’s trade was worse).
Category #2: We Made Mike Milbury Look Stupid
Florida: Traded away Mark Parrish and Oleg Kvasha to then Islanders GM, Mike Milbury for Olli Joikenen and Roberto Luongo
Detroit: Completely shelled Jose Theodore in the second round of the 2008 Stanley Cups Play-offs shortly after Milbury, now a TV analyst who said that Theodore was “the best goaltender left in the post-season”.
Category #3: Google Image Search- Panthers + Red Wings
Winner: Detroit, trash talking in THOSE jerseys was an automatic disqualification.