Nik? said:
With all due respect, that's about as bad an analogy as I've read. It's nothing like that and I'd actually go the other way. If you don't think that the Leafs fans filling the building every night hasn't at least in part contributed to a degree of complacency among Leafs management over the years I'd question a lot about you.
No, Nik, I don't accept that, for two reasons.
I cannot imagine a scenario where the MLSE owners are happy/content/ambivalent about forgoing years upon years of playoff revenue because they're uninspired.
Assuming that they are making so much money that they feel the need to not max out their revenue, for whatever reason, Toronto is a merciless market with expectations far higher than probably 90% of the league. So, even if there might be less financial pressure - but given that there is a board and not a single owner that seems unlikely - there is certainly more media/fan pressure than most other NHL cities.
I think there is a much more logical explanation; they're just not very good at producing good sports teams. There are a ton of reasons why this might be case and none of them are that the Leafs are happy with sabotaging themselves through complacency.
I would equate the "Leafs don't win because they make too much money" theory with other conspiracy theories of its kind, which is pretty much what I did.