The reality is is that teams turn into perennial losers and can't shake that tag no matter what they do, Toronto and Edmonton are like this, The Leafs might get like the Islanders, Flyers, Capitals, Blues, Wild, Predators, Habs, Clippers, Rockets, Bengals, AZ Cardinals, as in pretty good but never taken seriously, because in the end they always lose.
For whatever reason only certain teams can produce a winning culture, ownership is the reason as everything starts at the top. The leafs have too many egos at the top, it will never work, and ownership is laughable.