That's one example over decades of winners that have demonstrated that the opposite is true: past playoff success is the best predictor of future playoff success and eventual Cup wins.
I agree.
The Leafs aren't going from perennial 1st round losers to Cup winners overnight. That's ridiculous.
Probably not.
If (and that's a MAJOR if) it ever happens with this core, it will be because they've won some rounds and come close once or twice.
Most likely.
This is basically the easiest year they'll ever have to win a playoff round and if they do, that's what literally everyone will point to as evidence that the program is working - true or not.
I agree. That being said, if they don't have any postseason success, it'll likely be the last season this core group is together.