The Kessel trade was consistent with a full rebuild though. Its nothing like trading for Nylander, its like a rebuilding team trading for Jack Hughes. Kessel is hall of famer that is going to finish with 400+ goals, 1000 points and 2 cups.
The trade didn't turn out nearly as bad as the haters expected when that pick ended up being #2. Solely because Seguin was overrated and Kessel ended up being the best player in the trade. And Seguin was probably so overrated only because it was the Leafs pick. He was a very talented offensive player, but more like a poor mans Phil Kessel than Ron Francis.
If the Leafs didn't make that trade I'm not sure that history turns out any differently. Swapping Kessel for Seguin and Hamilton certainly doesn't turn the 2008-2015 Leafs teams into contenders, not that we would even want that anyway. There is no way I risk butterfly effecting anything about this current Leafs team.
We even traded Phil for more (Kappy, and 1st (Freddy)) than Boston got for Seguin/Hamilton combined (Louie Eriksson, Rielly Smith, 1st (Zach shenshyn)).