Man where to start with Detroit……
In the O6 days there were a ton of bad moves. Trading Terry Sawchuk. Trading Glenn Hall. Trading Johnny Bucyk. Trading Red Kelly. Trading Ted Lindsay. Basically forcing Gordie Howe to go to the WHA. It’s a long laundry list. Jack Adams and James Norris were pretty awful and petty and made moves just to spite players at the detriment of the team.
Post expansion the team was mostly crap so it’s harder to find good moves than bad ones. Taking Joe Murphy 1st overall in 1986 was pretty bad instead of Jimmy Carson, Vincent Damphousse, or Brian Leetch. Trading Marcel Dionne was bad too but rumor was he wouldn’t resign with Detroit so they made to move him.
During the playoff streak not many terrible moves. The one standout was opting to sign Johan Franzen over Marian Hossa. No clue what they were thinking there. Letting Fedorov walk over Ilitch having hurt feelings was also a pretty dumb move. Trading essentially the Vasilevsky pick for Kyle Quincey is still dumb, especially since the team let him go for free on waivers just 4 years prior.
Recently, passing on Quinn Hughes for Zadina still is a head scratcher. Anyone local who watched him play at UM knew he was a stud.
Worst ever idk. One of those early Adams trades probably. Detroit could have been on equal footing with the Habs dynasty teams if you still had those players instead of giving them away for essentially nothing. If I had to pick one it would probably be the Sawchuk series of trades. First he was sent to Boston for nothing and then reacquainted 2 years later for 500 goal scorer HHOF players Johnny Bucyk. That’s really bad.