I don't think it would be great for the Leafs, but I see it happening regardless. GMs and front office staff will often make decisions that benefit themselves over the team
I don't see Matthews looking to give the team a cheaper deal as they're likely removing the staff and potentially teammates that he likes.
I agree the Matthews contract length and NMC gave all control to the player and put us in this position and Leafs have the option now of overpaying again to keep the asset or let him walk away for free and Leafs lose their cornerstone player. Pick your poison here as both might be bad for business and cup competitiveness with or without him.
However, I don't believe this is a Shanny problem in isolation now, as even if Dubas were still here and making the call he would face the very same pressure points of pay up what AM wants or walk away situation. There was no discount on the previous deal in fact the opposite might be argued as true as one of the NHLs richest. So no reason to expect any hometown discount regardless of GM this time round either. IMO
As you correctly pointed out GMs will do what it is in their best interest in a CYA move, so isn't it convenient that Dubas 5 year contract nearly overlapped the 5 year only deal he secured for Matthews, and now even if he wasn't extended and let go, it would become someone else's problem and not his? .. Dubas only needed Matthews on a 5 year bridge deal and gave him AAV and term and front-loaded with full NMC (everything he wanted) just to get him secured
Long Enough while he was also employed as GM, needing Matthews productivity for his own next contract extention. That was far from in the best interest of the team on term and AAV and now NMC.
If Dubas had received his new deal he wanted now, then his future financially would have been secured, even if Matthews walks away as a UFA and MLSE says were not willing to meet AM contract demands (as they control the final $$ purse-string decisions), then KD is off the hook for not re-signing him, and
ALL the blame for his loss on ownership not management. Dubas set up a pitfall trap for the organization where
only he could benefit from financially as well as AM.