I have a lot of trouble with the whole "fan" concept.
I'm a hockey fan, sure. I'm a fan of certain players, sure. But a die hard fan of an organization? I don't think so.
Nowadays, teams are just corporate entities. The don't care about the fans as much (those lockouts... and one to come soon), they do what they can to make money. It just happens winning a Cup is pretty lucrative.
I don't question players/coaches desire to win a cup, and to some extend, GMs, but that's not the point of all that circus.
I live in Montreal. So I got to follow the Habs a lot. The Habs being one of the most titled and prestigious team, fans here are crazy. On a historical point of you, the Habs have their print on the Province. The result ? For too long, the organization took their fans for granted and did whatever they want.
Naturally, without even realizing it, I stopped whatching the Habs, I stopped to care. I started to watch the Blues because I loved Tkachuk, Pronger and Demitra, I don't know if I'm a "fan", though.
This year, I think I only missed two or three Habs game because their style is exciting. So I'll keep follow it as long as I'm entertained.
I know it's not a popular opinion and people will trash this post, but hey, just wanted to share my opinion, humbly.