This isn't a blockbuster deal, but it sticks out in my mind:
4th overall pick in 2002 (Joni Pitkanen) for Ruslan Fedotenko and 2 2nd round picks (which turned out to be also-rans in Tobias Stephan and Dan Spang).
Tampa also spun one of those 2nd rounders later that day to Dallas for Brad Lukowich who gave Tampa some needed depth on the backend.
I remember most of us on HF at the time were completely puzzled that the Flyers landed a top 5 pick for scraps and figured Tampa took yet another step backwards. Much like you, I still kinda question if they got enough "value" out of that deal but I suppose Feaster had a shiny championship ring to console him.
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Don't think it was a brutal trade at the time, but the Devils dealing Jason Arnott/Randy McKay/1st for Joe Nieuwendyk/Jamie Langenbrunner in 2002 basically rendered me catatonic for the rest of that day (I still apologize to my college lab partners about that).
At the time, I was mad because the Devils chose not to resign Mogilny because they thought he was too old and wanted too much money. Then they go out and get Nieuwendyk who was even older and made similar money.
The Devils were having trouble scoring and then they trade away Arnott and get back Langenbrunner who was well on pace for a 4th consecutive sub-20 goal year. The Devils had gone to back to back Cup Finals and dealing our #1 in his prime center just seemed like a terrible decision. Then Carolina bounced us out of the first round.
A year later, Langenbrunner is leads our forwards in points en route to the Cup. Although Nieuwendyk missed the last 8 games of that run with a back injury.
Even though they got the Cup in 2003, that trade still never quite sat right with me. Although Lou seemingly wanted to change the culture of the room and thought Nieuwendyk and Langenbrunner (who Lou had scouted for the '98 Olympic team) would bring in needed leadership.