The decision to go with Tavares over quality depth is going to be one of the great Leaf what-ifs.
They had their elite young core and a deep complementary core back in 2018, plus it wasn't like leadership was a need when they were already paying Marleau 6mil to be that guy.
Instead, the 2 centres the Tavares signing helped kicked out the door went on to be key contributors on Cup winners. Plus his signing completely threw off the Leafs pay structure, where Matthews and Marner were able to point to the fact they outproduced the Leafs new 11mil guy to get inflated contracts.
That cap crunch also put massive pressure on their ability to keep quality depth on wing around: JVR, Hyman, Brown, Kap, Johnsson, Komarov, Mikheyev, and Engvall is a ton of quality homegrown (more or less) depth to bleed out over the course of a few seasons.