What are the other contenders?
The first one that springs to mind, of course, is Brian Sabean's ill-fated dealing of Joe Nathan, Francisco Liriano, and Boof Bonser in exchange for one year of A.J. Pierzynski. It's already a disaster, and has a chance to look even worse down the road.
Texas sending Chris Young, Adrian Gonzalez, and Termel Sledge to San Diego for Akinori Otsuka and Billy Killian isn't looking too great either.
Help me, out Bauxites! Let's find a stinker for everyone! I'll be shocked and astonished if we're unable to find: a) a terrible trade; b) a terrible draft pick; c) a terrible free agent signing for each of the 30 GMs currently employed.
It's a tough gig.
Hindsight is 20/20, and it's always easy to take the test after you know the answer. But I'm sick as a dog (which is why I'm at home instead of work), I'm cranky, and I'm in the mood to be totally unfair, and to make fun of other people.