But I don't think those events can be fully separated. They signed Tavares when they knew that they would have negotiations coming up with several players in the same tier of talent (not Nylander, but to be fair they pushed that negotiation as far as they felt they could). Not throwing crazy money at Tavares may have saved them cap room in several ways, which would be useful in trying to fix actual team needs.
I feel like Toronto's management team didn't have a long-term plan after they signed him.
They followed up the landmark signing of a total stranger by having Shanahan go on the record to say that their youngsters are being greedy. Then Dubas goes on-record to say "we can and will keep all three."
A few short months later, they cave to Nylander's ridiculous demands to appease their fans and then give Matthews a hilarious paradigm-shifting contract in the off-season to supposedly avoid another contentious negotiation process. In the process, they piss off their best player and GMs around the league.
Comical stuff really