I've been a Leafs fan all my life, dating back to the 70s. In all that time, I felt the Leafs were serious Cup contenders only twice: the 1992/93 Clark/Gilmour team, and the season immediately after they drafted Matthews, Marner, and Nylander as the team's centerpieces. I’m intentionally excluding the Quinn years, I know they made Conference Finals runs, but for some odd reason, it never felt real to me.
The post 2016 era has been a massive failure by management. They wasted three amazing draft picks by failing to build a competent defense or goaltending solution around them. It is baffling to watch such potential squandered. I can't imagine how frustrating it must be for Matthews to see the team crumble around him. We are entering a decline with no high draft picks or top prospects in the system and frankly, this is exactly why I expect Matthews to leave.