A few things jump out from the list and checking habs drafts with games played:
Not many prospects make it.
Way too many horrible first round choices. So very many bad ones.
Most other teams don't do that much better, but most don't mess up first rounders as often. Lots of randomness.
A few discards were good and should have had more chances: Vokoun, Hainsey, Beauchemin, Conroy
Trades were hit and miss, Vujtek, Balej were good, McDonough was bad, Sergachev could go either way.
Habs scouting was just horrible for years. Knock Timmins but he's a step up from the previous regimes. The top picks were terrible for years and lots of mediocre players were given way too much time and effort.
A few guys just go hurt, Wilkie, Leblanc, Chipchura...
Some personality conflicts, behaviour, and general weirdness: Kostitsyns, Grabovski, Leblanc again, Perzhogin, Hainsey
The habs just could not scout D... Bilodeau, Brown, and all the other big slow guys, Fitzpatrick, were given chances while Beauchemin was overlooked. They traded from the best D in the league to a pretty bad D; the braintrust didn't even know their own team was good. The guys they liked were all great in the AHL but not in the NHL, there was no view for progression. The habs had great farm teams for years, all those failed prospects. Sort of like Rychel and company. Now the farm team is just bad...
Not many prospects make it.
Way too many horrible first round choices. So very many bad ones.
Most other teams don't do that much better, but most don't mess up first rounders as often. Lots of randomness.
A few discards were good and should have had more chances: Vokoun, Hainsey, Beauchemin, Conroy
Trades were hit and miss, Vujtek, Balej were good, McDonough was bad, Sergachev could go either way.
Habs scouting was just horrible for years. Knock Timmins but he's a step up from the previous regimes. The top picks were terrible for years and lots of mediocre players were given way too much time and effort.
A few guys just go hurt, Wilkie, Leblanc, Chipchura...
Some personality conflicts, behaviour, and general weirdness: Kostitsyns, Grabovski, Leblanc again, Perzhogin, Hainsey
The habs just could not scout D... Bilodeau, Brown, and all the other big slow guys, Fitzpatrick, were given chances while Beauchemin was overlooked. They traded from the best D in the league to a pretty bad D; the braintrust didn't even know their own team was good. The guys they liked were all great in the AHL but not in the NHL, there was no view for progression. The habs had great farm teams for years, all those failed prospects. Sort of like Rychel and company. Now the farm team is just bad...