I don't really think it's that much about management. The Avs, like most franchises, lives and dies with their core players. They have one of the best, if not the best, line in hockey with Landeskog, MacKinnon and Rantanen, and then on top of that they got a Norris Trophy candidate in Cale Makar who stepped in completely seamlessly to the NHL. The rest of their team is really nothing special. They lucked out in the draft finding the right players, similar to the Hawks with Toews, Kane, Keith and Seabrook. That's really it.
Oilers don't have a core. They have two superstars and nothing else. Hall, RNH, Yakupov were all super disappointing picks despite being the consensus picks in those spots. As for the Leafs, they haven't found that game-changing defenseman to shore up the blueline, and they obviously screwed up big time with their massive deals to their core players. But in the end it comes down to having the right mix of players and the Leafs simply don't have it. They have a bunch of egoistic superstars who are only looking out for themselves. That's not a winning recipe. Avs on the other hand is a team through and through.
Oilers could have been where the Avs are now if Chiarelli hadn't traded away his picks in 2015 for Griffin f***ing Reinhart. They should've had one of Barzal, Connor and Chabot plus a good depth forward in that draft and that would've made all the difference. Oilers would be a different team today and have the depth required to compete. The Reinhart trade set the Oilers back years and they basically have no other option now than to wait until Bouchard, Broberg and Holloway becomes impact players before they can compete.