I think one of the problems is that the Leafs have gotten themselves far too complacent in "let's get out of the first round".... losing sight of the goal that with the pieces they have, they should be having home ice in the playoffs, getting #1 seeds, dispatching teams in the first round without having to go 7 games, and losing in round 2 or 3, maybe finals, maybe you win one.
2017 I get the first round loss. They snuck into the playoffs with a team that was probably too young to be there in the first place -- they hung in there with the Caps; so I think it's fair to consier that a success.
2018 First time against Boston, again you have to be a little "Ok" with the loss... they weren't that deep, Kadri gets himself suspended.
However, it's now been 2019, 2020, 2021, 2022, 2023 and 2024 -- 6 years where this team has been stuck in mediocrity and made no appreciable dent setting a higher bar for themselves.
In that time, Tampa has fallen off a bit, Boston has lost a huge number of important pieces to retirement and remained better than them every year, and Florida also rebuilt themselves on the fly.... not to mention the Red Wings, Sabres and Senators upcoming with a ton of young talent.
I don't know who to fire -- as I don't pretend to have full in depth to the politics of who makes what decisions at MLSE, but this blindly loyal attachment to building around Matthews/Nylander/Marner, despite them not being interested in sacrificing money to win, needs to change.