if you market it properly -
100 years ago, we started from the ground up, and here we are doing it again. we may not be where we want to be, but we're sure as hell going to try our hardest to walk in the steps of the greats. support us as we grow our youngsters into becoming legends (or something)
look at what the negative would be and spin it positive.
Not to get too off topic, but that's the only way a rebuild would work here - if it were sold to the fans properly as a long-term commitment to turn this organization around.
Everyone points to Edmonton as the "LOOK IT DOESN'T WORK ALL THE TIME" example, but people also choose to forget what it was like in Edmonton last year or the year before - tons of excitement watching a team that wasn't very good, but were entertaining to watch.
Do people in Calgary complain about their team much? That's not a very good hockey team that works their ***** off every night and you can see some promising young pieces in that organization.
I looked at StubHub today - if people are still willing to overpay for Leafs tickets to watch this sorry excuse of an effort, people will commit to coming out and watching a young, hard working hockey team behind an organization going in the right direction. I have no doubt about it.
I also have no doubt that any sort of draft / all star / winter classic award to Toronto, wouldn't derail the organization from that long-term commitment. One thing that they appear to have in abundance right now is patience - it would be asinine to throw that away for a single, solitary year of celebrations.