Oates trade might be the worst trade in NHL history. (For Detroit of course)
Oates would have been traded or released anyhow after sneaking Sergei into the United States. However it's still one of the worst for Detroit.
I'll give a pass on Graves as he didn't really blossom until New York. Meanwhile the man who we acquired(Carson) was later shipped out for Paul Coffey. Who became a key piece for several seasons.
The '89 Wings were never good to begin with. They just happened to play in the NHL's worst division. Same really can be said for Detroit's playoff stints those two years prior. Fun because it had been so long and showed possibly things to come. But that division was trash with the Wings the best of a bad bunch.
You bring back the same poor goaltending and defense coupled with multiple player off-ice issues. Complete with no Probert that season whatsoever and possibly forever. Doomed from the start only to crash even further the next season.
There is however one significant brightside to that '89 season. A couple of months later was the '89 Draft which set up the Wings for years to come. 1990 only wielded two worthwhile picks but both ended up crucial as a complimentary winger(Kozlov) and eventual trade bait(Primeau).