Its a culture thing man. You either have a winning culture and mindset or you don't. You etiher accept mediocrity and are self-congratulatory easily satisfied or you don't accept mediocrity, don't drink your own koolaid and are always looking for more always hungry for more
Its a culture thing. And it starts at the top with the GM
The Leafs have a tendency of trying to be innovative but without a foundation of success. Because of that they are always late to the party.
Regardless of your opinion of Babcock/Lou, they were at least a GM/coaching match. They would have been better off hiring Dubas and Keefe from the start and letting them grow with the team. Instead our young players got too good (at least in the regular season) too quickly and outgrew Babcock. The pain Babcock spoke of only lasted a season, instead we got an entirely different kind of pain with playoff failures.
Rather, management made a poor coaching/GM match and wasted some of the core's prime with a coach and GM that didn't work well together. Once Babcock was sent packing we got Keefe who has been out-coached in 3 straight playoffs and is learning on the job while the core squanders chance after chance.
They have the best core in decades (at least in the regular season and on paper) and have wasted years letting the coach and GM learn on the job.
Soon they'll waste more time with a half measures coaching/GM change.
Same thing with the contracts. Dubas wanted to be their friend while negotiating and while the rest of the league was signing their young superstars the summer they became eligible for an extension, Toronto waited on not just 1, 2, but 3 of their young players and got burned on price and term for all of them. (To be fair, Nylander not being signed early is on Lou.)
The list goes on an on with players choices, style of play, and types of players.
It's a culture and mentality issue at this point, but they'll probably be late once again to make a change.