So I came across this on thestar.com last week and man are Leaf fans screwed. The gist is that bascially Larry Tanenbaum said that instead of winning the Cup right away and then having the Leafs be terrible for like 5 years, he'd rather sacrifice a few years rebuilding so that the Leafs are competitive for the next 10-15 years.
You'll notice that he didn't say he'd win Stanley Cups in those years, just be competitive. His plan is bascially to make the Leafs competitive enough to hop into the playoffs and appease fans, but it doesn't matter if they win the Cup because by then, the shareholders will have more than enough money to invest in real estate ventures.
When the Oilers were terrible in the mid nineties, I kept falling back on the fact that they won 5 cups in 7 years. Living in the GTA, friends would comment on how the Oil sucked and I could comment on how the Oilers more recently won a Cup than the Leafs. If I were a Leaf fan, I'd take the Cup. It would silence the 1967 chants, the endless ridicule and all the fans of all other NHL teams accept the Habs who've won more cups, but the Be-Leafers could just say that they've won a Cup more recently.
Of course, this is not a surprising mentality given that today, Richard Griffin wrote and article in the Star today about how Ted Rogers has no interest in winning another World Series. Even though the Jays are not profitable, they bring all sorts of income to Rogers' company.
Though I am a fan of both the Raptors and the Jays, thank God I'm an Oilers fan in the only sport that counts.