Upon quick consideration I would suggest3 main reasons for the downfall: Ronald Corey, R. Corey + R. Corey!! But seriously here goes: !- The "Living in the Past" syndrome. Corey wanted to copy the historical Habs blueprint...the Flying Frenchmen. This is evident strarting when he pushed Serge Savard into trading Chris Chelios for an obviously declining Denis Savard. Perhaps the most obvious example is when he hired Houle AND Tremblay to run the whole organisation as though the two retired players were the best candidates based on the fact that they were ex-habs.
2- This syndrome continued to plague them by trading with a clear bias towards Francophone players as w Thibault + Richer for example. More importantly, the trading history was pitiful period.
These trades were often based on poor player evaluations, both re players on other teams and especially on their Own team ! (And again, with myopic bias towards French players). Throwing Captain Keane in w the trade for Thibault; Odelein for Richer; leaving Turner Stephenson UNprotected in the waiver draft so we could keep Patrick Poulin!! (Apparently Stephenson wasn't good enough for the Habs yet the New Jersey Devils specifically traded w the 2nd or 3rd team picking in order to acquire him because he was good enough for the CUP champions) !!
3- Very poor drafting, especially earlly on, but again they were allways biased towards Francophone players which, I think at least, caused them to overvalue some over others.
PLEASE don't think I'm prejudiced against Francophones; I'm well aware of the understandable desire of LES GLORIEUX to have French players on the team. But this desire led to ALOT of bad decisions during the "Dark Years" imo. off to work now!