The Leafs have to make the Finals at least once by 2025
For the first time in the history of the franchise, the Leafs are going to rebuild. So we're selling off expiring assets for future draft choices. That's good.
It should take 5 years to rebuild. It's always possible for the first rebuild to fail, so if the first rebuild fails, the management team should be given a little leeway.
10 years from now gives them two shots at a 5-year rebuild cycle. If by 2025 this team is not a competitive Stanley Cup contender that has made the Finals at least once, then the rebuild will have been a total and complete utter failure. I'd say the Leafs are completely cursed and incapable of succeeding ever again... which would make me sad.
Right now the Leafs drought is worse than you can imagine. Not only have they not won the Cup since 1967. They haven't made the Finals since 1967 either. If that second drought still stands by 2025, then I don't know what to think. I will be 38 years old by then. I became a fan of the Leafs in September 2002 (that's AFTER they were eliminated by Carolina in the third round). So I've never seen my team make it past the 2nd round. *sad face*