He was too loyal to a fault. Personally, I think the emotions that came out after the Gallagher signing indicated that he tried to play hard ball and failed/cracked and just gave into what both Petry and Gallagher wanted and tried to play hard ball on Danault where he let him walk.
Paying people in their 30's for what they did in their 20's is bad business. The rebuild should have started years ago but Covid came along and gave us a chance where we showed some "upset" potential and we did get a cup finals out of it.
It's all lead to this and I said it years ago. The rebuild is coming but it's a little later than you might expect. Weber on LTIR, Price dealing with an injury, Danault walking has forced us to make the management change and do the rebuild.
He was loyal to the wrong people in many cases. Well, he correctly got rid of some of the guys he traded, but Bergevin showed a lot of loyalty and generosity to guys like Gallagher, Byron, Alzner, and less to Radulov, Danault, KK, and others. Why play Staal in the playoffs after he showed he was done in the regular season? I mean it worked out for a few key games, but what was the decision making process? Where was the loyalty to Markov? He was very loyal to Lefebvre, Daigneault, and Therrien, less so to Julien.
I found it mostly came down to keeping people who, like Gallagher, always say good things about the coach and GM, relatively silent guys, and foxhole buddies who would never criticize the GM or threaten to advance in the organization. I got the impression that he decided not to keep Danault when he did his pizza thing on TV, got laughs, and didn't explicitly praise Bergevin. Similarly with Subban when he got media attention and didn't say much about Bergevin he went. Many of his contract negotiations, KK, Radulov, Markov, Danault, included reputation attacks, media leaks, and personality conflicts.
Weber is great, but I think Bergevin appreciated his taciturn nature as much as his play on the ice. I expect it contributed to dumping Domi as well, though that worked out well. While MB was in town there wasn't room for another big CH ego or media presence.
It wasn't all bad, but it was pretty random. I think Bergevin's ego prevented him from doing what he would have needed to do to build a coherent team. He couldn't just acquire players based on talent and fit and fade into the background, he had to be front and center with no one blocking any of his camera angles.
I'm not exclusively bashing Bergevin, he made some good moves, but I think vanity was his tragic flaw.