Gainey had his shortcomings, of course, but nothing is all black or white.
Gainey +/- inherited "Peanut" Houle fiasco.
There was Andre Savard in between, who did a great job at clearing away the dead/rotten wood.
But under Gainey, MTL stopped patching and the organization went all in on drafting and developing.
He took a team that was more or less scorched earth and built it from there.
Markov, Ryder, Ribeiro, Theodore, Komisarek, Higgins, Plekanec were young players, drafted by the previous managements, that spread their wings under Gainey's tenure.
Gainey was a master at not giving his coaches older "has been/wanna be that never gonna be" players, that most of Habs conservative coaches would have naturally preferred to fill up their roster, over young guys.
He was constantly leaving holes in his rosters, so Mtl prospects had opportunities.
Furthermore, they drafted and developed Price, Subban, Pacioretty, Halak, Streit, the Kostsytsyns, Latendresse, Lapierre, Emelin, Grabovsky, etc..
It wasn't perfect, but at least under him the Habs had a vision/plan and they were sticking to it, with relative success.
To evaluate his tenure in a rational manner, we have to consider where he took the team and where he got it in the end.
All this without picking high apart from A Kost at 10 and Price at 5.
We can say whatever we want, but the team MB inherited, maybe it missed the playoff the year prior (2011-2012), but they had a young and strong nucleus. A lot stronger than the mess MB left behind.
I'm not trying to tell you that Gainey was a hockey management genius. But surely he was above some GMs we've had since Serge Savard.
He had excellent leadership and he was methodical. I'd say those were his two best attributes.