From the 70's
Middleton for Hodge is the all-time worst, but giving up Ratelle and Park for Espo and Vadnais sucked. The first trade doesn't happen without the 2nd one.
From the 80's
Ridley'Miller for Carpenter...
...the absolute worst of the multitude of Espo deals.
But giving up a #1 for Bergeron, and giving up the opportunity to draft JR? Criminal.
From the 90's
The Nedved/Zubov deal really sucked, given that Smith could have had either Selanne or KT for a similar package.
But, the Kurri was depressing, especially giving up Norstrom. Imagine having a a top 4 of Leetch/Beuke and Norstrom/Zubov.
From the 2000's
Some of the firesale deals really turned out to be crap, but the one that annoyed me was giving up Nedved for a lesser package to Edmonton, when David Poile said he offered two 2nd round picks for him. Oh, and taking Jozef Balez instead of Tomas Plekanec? What the hell was going on with that scouting staff?