Even if we assume the Leafs are guaranteed to re-sign him I still don't think I'd do it. The 1st round pick figures to be top 5-10 (I think more around 5), Nylander's upside is very high, plus Gardiner and JVR seems like too much. Even if it's not, who is left for him to play with? The Leafs have some building left to do before making a move like this, IMO.