I mean not really. If Chiarelli had taken Tkachuk, even with all his other stupid moves, they probably eventually win a Cup.
He also could have taken any one of DeBrincat, Boeser, Barzal, Kyle Connor, Aho etc. and looked at all those players and said "nope".
The team had a lot of lucky opportunities fall into their lap in 2015 and 2016 frankly and they took 0 advantage of any of them.
The Oilers had a lot more going for them than say what the Blackhawks have with Bedard. That's an actual bad situation.