I don't now why people are talking about the PK Subban and Roy trades as darkest days. The former was a no-brainer move after Subban made a clown of himself the previous season. It had reached a point where he'd stop playing right in the middle of the game and mouth off to linesmen and referees. There's a reason a lot of Habs players hate his guts. Notice how Gallagher, a true badass of the game, treats Subban. That dude can go poison another locker room and pimp his "brand" for all I care.
As for the Roy trade, it's more of a consequence of an even darker day: October 16th 1995. That day Ronald Corey, who was the president of the team at the time, pushed the panic button waaaaay too early after a bad season start. He fired both the general manager and coach of the team and replaced them with two people who were lacing in experience, intelligence and connections.
GM Serge Savard was a sort of complete package general manager in that he had that aura as one of the former on-ice legend of the game and his aura, charisma and strong presence was recognized league wide. Picture Steve Yzerman and multiply the badassness by 2 because Serge Savard was also recognized as someone with incredible smarts and a passion for business (he wisely invested his money as far back as during his career). His only flaw was an outdated philosophy on scouting which made the Habs the only team in the league that didn't formally interview players before the draft and during the last few years, a propension for drafting huge, useless and talentless WHL players instead of skilled QMJHL guys. He nonetheless packed the team with amazing players and brought two Stanley cups in two different decades and kept the team competitive and with a strong local identity. He was replaced by a bumbling idiot who had been selling beer since retiring, Reggie Houle.
The fired coach was Jacques Demers. Demers had replaced the methodical and harsh Pat Burns and brought more passion and renewed energy. Demers was usually seen as less of a strategist than the wave of defense-first coaches that were the new trend of the time in the NHL. But he was an underrated hockey mind. And more importantly, I believe Demers is one of the first coaches to truly understand the post Gretzky trade era of "hockey as a business". The late 80s early 90s is when players became huge individual economic entities with enormous leverage. Demers became a master at forging alliances with franchise players. He was so good at it that everything else fell into place. Rarely were players unhappy with Demers, who could have probably even dealt with the Ovechkins and Subbans of this world. He was replaced with Mario Tremblay. I don't even feel I have to say something about that.
With Tremblay and Houle, everything turned to crap quickly after a few early wins. Players were clearly unhappy, confused and eventually angry, which led to trades that were awful. The Roy trade is the ultimate exhibit A of this. In addition, because the overhyped Saku Koivu was unable to earn better ice time to the infinitely superior Damphousse and Turgeon, the team had the strange idea that having too many quality centers was A BAD THING and started getting rid of them and making room for the team to become Koivu's. The dude was handed everything on a plate and couldn't have led
couldn't have led a bunch of boyscouts out of the wood if his life had depended on it, yet was asked to lead them to a championship when his only two skills were above average passing and uncanny ability to get injured.
It didn't take long after that day in October 95 for me to stop being a hardcore fan. Seeing great players leave one after the other. The franchise never recovered from that.