You can't start Toronto's timeline from Rielly, because we really didn't rebuild that time. It was just one more failed year, that Burke benefit from. In hindsight you should start Blackhawks rebuild from drafting Keith, but basicly, it started years after and that organizational capital is always there, when you start rebuild. Change of vision and culture is more or less the start point. Early 2010s we tried to compete and the vision was to retool that bunch of mediocrity to cup winner with trade magic.
It nice to have hindsight on those moves, but you should always have some understanding over context and maybe look it from other franchises stand point also. You wont win every transaction, all top teams bleed assets. Slowly but steadily. It's name of the game at the moment with hard cap.
Marchment and Verhaeghe given free is nice statement of AHL players back then, that took years to develop after that. You can't keep two teams of worth of AHL players in the AHL. Marleau could have been kept, but that would have mean one lost season from this core, in hindsight easy to say that keep him for year since we lost anyway. You can pile that up with Kadri's trade and say that we shouldn't have signed Tavares, but in the end we'd lost Kadri now and don't have replacement here. That Kapanen take is terrible, it was good trade for us that ended up being real bummer, because of the cancer. Why is it there?
If I make one reasonable take now and here, because it's hindsight. I look up that list and say, we could have made slower build. Trade away those assets we had and don't push into playoffs. Don't sign Tavares at all. Would it have been better, might have been, but you never know. In reality we we're bubble team when we really tried and ended up being playoff team straight away. If you look other failed rebuilds it isn't that easy to become perennial playoff team with +100p seasons.
There is one big clear mistake, we didn't draft Aho instead of Dermott. I would have also changed Holl for McCann now and it can be argued if we could have made that decision even back then? But though Holl have progressed every year until now his development went backwards. That Holl-Muzzin could have been really good second pair like it was earlier.