Zanzibar Buck-Buck McFate said:
I remember having a variation on this debate more than 10 years ago when I first began posting here. The question was whether consistent winning (but no Cup) was satisfying in any way, or if only a Cup win is. I argued that consistent winning is satisfying, that I enjoy watching the Leafs play good hockey and still get enjoyment out of that alone even if they don't win the Cup. Of course I'd like a Cup win on top of it, very much. But I can't agree with people who say that only a Cup win will make them happy.
That's why the last decade or so has been so hard. The only "fun" we've had is arguing over negatives. This last season was the worst, by far. There were only a handful of guys on the roster that I liked to watch play.
I agree with this. I remember Gilmour-Sundin eras, when the Leaf were mentioned along with cup contenders and wasn't followed by a room full of laughter. I remember when we were good enough that other teams actually had rivalries with us. I used to have spirited discussions with random fans from other teams filled with playful jabs, now I say im a Leafs fan and they look at me like I said I had a terminal illness...I get hugs sometimes, they ask me if I need anything, maybe a place to stay ect.
I understand that during most of those eras we were among the oldest teams. We also got some luck on the trade front and its looking like those types of trades don't happen as much or at the very least, its improbable enough to be unreliable.
Developing our prospects is at least within our control. We can create a team we want rather then try to cobble something together to fit the pieces we have. Developing a homegrown powerhouse built for sustained winning will be a lot more fun to watch then this last decade+ of watching them try to swing for a home run and falling flat on their face.
Now if you are proposing a hypothetical where it has to be one or the other; basically a constant contender that never wins vs a guaranteed cup win? I would choose constant contender that never wins for the Leafs, then cheer for another team that doesn't have some weird gypsy curse.