The real issue with Toronto is none of their GMs found the right mix of guys to play behind the core players, or the right coach to develop those guys into players (some of our best depth acquisitions have been Leafs castoffs on the cheap, which is a big slight to their development department). With the cap space they had the last couple of years, that shouldn't have been a real issue with astute scouting & proper internal evaluation.
Its really not all that different than Vancouver before this season with Petey, Miller, Demko and Hughes, or the Sedins era prior to Gillis. People overlook the bottom half of the roster too often, but its where the best GMs stand out from the rest. Getting Higgins, Raymond, Samuelson, Wellwood, Malhotra, Torres, Ehrhoff, Hamhuis, etc. at reasonable prices is what allowed us to go from out of the playoffs under Nonis to perennial contenders.
Tavares accelerated that team's timeline in the same way Mats Sundin did for us way back. While his cap hit was big, there was no reason they couldn't have built out a better bottom 6 forwards group or bottom 3 defense.