I wonder why. All in all his tenure as GM was a pretty good one; the Canadiens have an above .500 record with him as GM and have made the playoffs the majority of years.
An above .500 record and a playoff appearance are nowhere near enough to keep fans or the organization happy in Montreal. It's one of those organizations that is Stanley Cup or bust. The Canadiens haven't made it past the second round with Gainey as their GM and missed the playoffs once, which is flat out unacceptable in Montreal.
That being said, I haven't been given the impression that the fans or the organization were displeased with Gainey, so if someone from Montreal could confirm or deny that for me it might give some insight into the situation at hand.
Either way, his moves this offseason were not very good ones. He traded for Scott Gomez, who's getting paid over $7 million this year, he signed Brian Gionta to a $5 million per year contract, and he parted ways with Alexei Kovalev, Saku Koivu, Alex Tanguay, and one of the best defensive defencemen in the game, Mike Komisarek. He probably could have afforded all of those players for less than what he's paying Gionta and Gomez, and they would have contributed more to the team, in all likelihood.