Well, I'll take a crack at it. I won't be including any deals from the 2008 season, because we don't really know what to make of those deals just yet. Besides, I've found that as time has gone on, the deals have gotten substantially more reasonable.
Here we go:
- Mercer AutoWreckers trade Hanley Ramirez and Jeff Francoeur to Stewies SexyParties for Freddie Sanchez and Jeremy Hermida, July 2006 - At the time, I really didn't think this was that terrible a trade. Hanley was a speedy rookie who was playing pretty well, but Sanchez was leading the NL in batting average (and did end up winning the batting title). Obviously, though, Hanley has become arguably the most valuable player in fantasy baseball, and neither Sanchez nor Hermida are fantasy starters.
- The Usual Suspects trade Juan Uribe, Danny Bautista, and their 2005 11th round pick to ________ for Lance Berkman and their 2005 13th round pick, May, 2004 - Yes, unfortunately, the top two lopsided trades in our history were both at the expense of the AutoWreckers (formerly named "_______"). Bautista is out of baseball, and Uribe's career has slipped every year since 2004. Meanwhile, Berkman, while inconsistent, has been a keeper every year since. Chip was able to trade two guys who will be taken in the first two rounds this year and still finish ahead of me last season. Ouch.
- Cleveland Enforcers trade John Lackey and their 2007 4th round pick to Those Guys for Andruw Jones, February 2007 - While Lackey has blossomed into a star pitcher, the real reason this trade is on this list is because of how colossally bad Andruw Jones has been. Colossally, inexplicably bad.
- Riders of Rohan trade their 2006 5th round pick to Big Bounty Blokes for Zach Duke and their 2006 14th round pick, February 2006 - A bit of a mistake for the Riders, Zach Duke ended up doing substantial damage to my ERA and WHIP. I probably should've known better, but I wanted to get on the train and pick up one of these young stud pitchers that everyone seemed to have. Now, all I want is six Greg Maddux's on my team.
- Cleveland Enforcers trade Eric Gagne and Jim Edmonds to The Usual Suspects for Victor Martinez and Miguel Cabrera, July 2004 - While the value difference on this trade is fairly substantial, I pushed it down to #5 because the Suspects had a plan, and the trade didn't kill the plan. They moved a couple of youngsters in an attempt to get the premier closer in baseball at the time and make a run at the title. While they fell just a half a point short, certainly Gagne's 22 second-half saves didn't hurt the Suspects' title run.