COL traded a guy that wanted out. They were never going to move MacKinnon. No one is giving the front office a pass, that wasn't the point. It's really easy to say something was mismanaged and it's even easier to say that in hindsight.
Was Bickell's contract bad? He fell apart as a player thanks to his MS diagnosis. Of course, CHI didn't know he had MS when they had to trade him. If he had been healthy, that's a contract you don't need to attach Teuvo to, to move. Was the Seabrook contract bad? Signed Sept 26th, 2015; coming off another Cup; coming off seasons of 53 and 55% Corsi. I think anyone could have predicted a decline but I doubt many thought he'd call off a cliff 3 years later. And then you have the Toews and Kane contracts, where Kane has been meeting expectations and Toews really hasn't. Did you think Toews would follow-up 2015 with three consecutive <60 point seasons and 21 or less goals in 2 of those years?
My two biggest gripes with Stan, given the context *at the time* are the Panarin and Hjalmarsson trades. Those two trades set this team up for failure relative to expectations from finishing 1st the prior year. The organization was stubborn and hadn't been able to come to terms with the fact they aren't a good team -- until maybe now?