At this point, I think a complete rebuild would be pointless.
It would mean another 6 years before the Leafs would even think about contending and another 3 years before you would see a resemblance of a rebuild. And by that time, it would mean a new GM and the possibility of a whole new scheme if the board doesn't see any sort of production.
Right now as the team stands, I think that you have enough good complimentary players that would help bring along your cornerstones of the franchise, but you need to find those guys. If Morgan Rielly is a franchise player and you are going to do a complete rebuild, then he needs to play right now and you have to forgive any mistakes that he makes. If James Reimer is your franchise goaltender, then he needs to play 80% of the games and again, fans should forgive any mental or other mistakes that he makes throughout the season.
So here's what a complete rebuild would look like:
Forwards
xxxx -xxxxx - Kessel
-----> Lupul played well with Kessel, but Lupul hasn't played a full season in a couple years and might get you something for a team that could be contending. Bozak isn't going to be your 2nd line centre for the future and is gone.
van Riemsdyk - Grabovski - xxxx
------> Grabo's contract says that he's going to be an important piece in the top 6 and although I like JVR, he could play on the 1st or 2nd line.
xxxxx - McClement - Fattin
------> McClement stays on this team to surround the young talent with leadership and guidance. Frattin is young and can score, but should be expected to learn how to kill penalties and play more special teams.
Broll/Creszeni -xxxx - Brown
-------> The 4th line plays a big part on a young and developing team. Generally in a long season, you are going to have guys that will have off nights and fatigue will have an issue on young guys. So you are going to have guys set a standard of play and inject some life into the line-up. But you should also expect them to kill some penalties.
Traded: Connolly, Lupul, Lombardi, MacArthur, Bozak, Steckl, Kulemin
Defence
Gardiner - xxxxx
Rielly - xxxxxx
Liles - Holzer
Traded: Phaneuf, Komisarek, Franson, Gunnarsson
- Phaneuf is your captain, but if you are hoping for a complete rebuild, then you have to accept that for younger guys to play a lot and learn, Phaneuf can't be logging 25 minutes a game. I added in Gunnarsson too because he's not a veteran enough to support such an offensively dynamic players like Rielly and Gardiner.
Goalies
James Reimer
xxxxx
------> The goalie situation is such a tough one to pin point. You need to have a goalie that has an easy going personality and won't get rattled if he gets shellshocked. With such a young team, Reimer is the perfect goalie because of a couple reasons. 1. Goalies don't hit their peak until they hit 26 or 27. Look around the league as to when goalies started winning a lot and playing their best. (Pekka Rinne, Luongo, Schneider, Quick, etc.) 2. Reimer is a big goalie and before his injury, didn't move around a lot and played angles very well. 3. Reimer has an easy going temperment and should be good with the workload.