The ole cup or bust strategy. Why even watch?
It's not "Cup or bust." It's....Are you on a path to a Cup or not?
Only 1 team wins it each year so that means that this year of the Hurricanes, Bruins, Knights, rangers, Lightning, Avalanche, Devis, Leafs, and Stars, only 1 team is going to be happy.
Yet I would call all of those teams "Cup contenders." Being a true Cup contender means you have a legit shot to win it all and that's all you can ask for.
What this means is you need to have a certain level of talent combined with coaching to get in that "Cup contention" conversation. If you don't have it you need to find ways to get it. Typically it is done by drafting well and being patient.
As a result there is nothing wrong with tearing it all down and rebuilding. It's something that takes courage because this is a business and you may be alienating a large portion of your fanbase (who spend money) to do so. But it's a fool's errand to think that if you're an average team that you're eventually going to become a Cup contender just by waiting for an group of average talent to gain more experience.
Thus I think teams like the Canadiens and Blackhawks, who are stockpiling picks and prospects, are potentially closer to the Cup than teams like the Jets or Flames, who have older/aging vets and not enough talent nor great ways to improve their rosters. Unless you have a very young team with some blue chip talent learning their way, being average is about the worst thing you can be in the NHL.
I'd rather have to wait to be a contender in 3-4 years by going young, then fool ourselves that an average/aging team with average coaching is all of a sudden going to be able to compete with the best teams in the league.