And the hard truth of the matter is that the reason Canada hasn't won a Cup is because (whether it's the fault of ownership, management etc) the organizations force themselves wallow in .500 hell. They make trade after trade and sign whoever they can get in free agency just so they can win 42 games and lose in the 1st round.
Captive markets at work. Ownership simply takes the path of least resistance. Market "hope" and "anything can happen in the playoffs" and "we aim to be competitive every year" and watch the fans stream through the gates every night. Toronto is probably the first Canadian team since .. ever? .. to
intentionally blow their organization & roster to hell with the specific goal of rebuilding it from the ground (Edmonton sucked for years mostly by incompetence, by contrast). If Toronto ultimately succeeds, it may force the other Canadian franchises to up their game and take rebuilding seriously, instead of continually trying for quick fixes, hanging on too long, etc.
It appears to me that in the mind of some that doing anything else should be considered tanking, it should be frowned upon and you're a dirty human being for ever thinking to do such a thing otherwise.
There's that, too. It's strange because junior hockey teams do it frequently; they often have no choice because of the rapid aging cycle of the players, but they still make those trades, dealing away 19-year-old for prospects & picks, and put themselves out of contention to build for the future, all the time. Nobody bats an eye at them. If they don't do it, they're just setting themselves up for a longer & harder stay at the bottom of the league anyway.
Meanwhile those pesky Americans markets like Pittsburgh and Chicago who built through the draft keep winning the Cup and are the model franchises of the NHL and have been for a decade since taking players like Malkin and Kane with 2nd and 1st overall picks.
Well.. Chicago was fortunate that their old skinflint owner finally left this earth when he did. If he'd hung around for much longer he'd have found a way to screw up the Kane/Toews era before it ever got started, probably. And Pittsburgh damn near didn't even survive. So those examples are a little on the bleeding edge. Still.