I think the proof is in the pudding with Sweeney. He has already tried to do a retool. It was a huge failure.
@cshea already talked about it but in 2015 Chia had his hands tied behind his back for the trade deadline and they fired him in the offseason. They elevated Sweeney with the mandate of retooling the team on the fly.
This was his retool:
Dougie Hamilton - for a 1st and 2 2nd rounders. Ironically he was acquiring picks to move up and pick Hanifin who the canes picked and traded for......dougie Hamilton along with Elias Lindholm a couple years later. Cool. Reports after were that Dougie, a premium RHD offensive D coming off an ELC, wasn't offered around the league. This trade was a massive failure and I'm still mad about it.
Milan Lucic - Retained half of the last year of his deal and got a first, Martin Jones and Colin Miller. He then flipped Jones for another first rounder and Sean Kuraly. I was ready to forget the Dougie trade. This was such a genius move. I was so excited.
The draft happens. I watched it with my father in law, an Islanders fan. I wanted Zboril, Barzal and Erickson-Ek or Connor. When they picked Zboril I was so excited. When they picked Debrusk, I was nervous but at least they will get Barzal. Ok well we know what happened. The worst thing was Barzal fell to the Islanders and my father in law was now excited, rightfully so.
Then he trades Reilly Smith for an objectively worse player in the late Jimmy Hayes. ugh.
Then he trades a 3rd round pick for Zac Rinadlo. double Ugh.
On July 1st he signs Beleskey.
That was it. Most of the success the bruins have had in Sweeney's tenure has been because Cassidy is a better coach than Claude was at the time and used Bergeron/Marchand and Krejci in much smarter ways and Pastrnak matured He did pick McAvoy as well, so he gets credit for that. I wanted Fabbro.
He's been mostly fair to good over his tenure as a whole. His contracts with internal players have been mostly good, even aided by good fortune in the timing. But we've seen what he does when given the keys to a retool and it was basically to set assets on fire. I don't trust him to do it.
I'd want someone like Darche in Tampa, MacFarland in Colorado, the number 2 guy in Anaheim who was the player development guy and now the AGM or maybe someone working for Wadell in Carolina that I dont know about. They need someone more aggressive who has a strong understanding of player development, drafting and the salary cap. Tall order, but its a premiere franchise and they should be able to attract someone like that. Unfortunately the Bruins have only brought in one GM from outside the organization in the last 50 years, so it seems pretty unlikely.