1)Babe Ruth from Boston to the Yankees for $125,000 & $300,000 mortgage in 1920 2)Nolan Ryan from Mets to Angels for 3B Jim Fergosi in 1972 3)Frank Robinson to Baltimore from Cinncinatti for P Milt Pappas in 1966 4)Prospects Derek Lowe & Jason Varitek to Boston from Seattle for Reliever Heathcliff Slocumb in 1997 5)Lou Brock to St. Louis from Cubs for P Ernie Broglio in early 1964 6)Prospects Curt Schilling,Steve Finley & Pete Harnisch to Houston from Baltimore for 1B Glenn Davis in 1991 7)Larry Bowa & prospect Ryne Sandberg to Cubs from Phillies for SS Ivonne DeJesus in 1982 8)David Cone to Mets from Kansas City for catcher Ed Hearn in 1987 9)Jeff Bagwell from Boston to Houston for reliever Larry Anderson in 1990 I didnt see the show so I dont know what the measuring stick was, it appears that this list may be more about perception than fact though. Example, Milt Pappas was not awful for the Reds. Or does it take into account that Lou Brock had nowhere to play for the Cubs since he couldnt handle CF. Or that it basically boiled down to Steve Finley for Glenn Davis because the Astros turned around and made equally bad trade with Schilling. For actual production being swapped the Bobby Abreu/Kevin Stocker trade may be worse then most of those. The Bagwell trade certainly should be higher Edit: and where is Pedro for Delino DeShields? Bagwell for Larry Anderson obviously hurt the Sox long term, so I wont debate that. But they also got a reliever who gave up 3 runs over 22 innings the rest of the season... and they won the division by 2 games. I don't feel like scouring game logs, but it seems like a pretty safe bet that the Sox were very pleased with the short term results when all they gave up was a bad defensive 3B with doubles power. Of course, we all have the benefit of knowing that his doubles would start going over the fence and he'd become a fantastic 1B, but I think it's being a bit dishonest to judge the trade by anything other than the information they had at the time. I think it is real easy to look back 10 yrs later and wonder what a GM was thinking. Often at the time fans of the teams that supposedly lost these trades were probably happy about them. I dont think to many people were questioning most of these trades at the time they occurred. If they were they were probably questioning something like giving up Glenn Davis for a bunch of unproven prospects.