This is such a great not-ever-done fictional idea wow

Hall deal was the biggest joke but the draft pick deals cant really be predicted

There is but 2 things you can really nail Chia to the board on. The Hall trade and the Eberle trade. Those had so little chance of turning in hi favor that someone in his group should have advised against them.

All the rest are circumstantial. The picks are absolute luck based. No one thought Barzal would be a 80+ point player. Good prospect yes but not as good as he'd been. Lucic signing sucks but you know what, there were other teams willing to sign Lucic so it wasn't only Chia. etc etc

Chia took a leap of faith with Larsson that he'd turn into the next Victor Hedman right before he became a superstar. He also traded a guy that despite being on a terrible team was literally the teams most valuable player ( before McDavid arrived) for a player that wasn't even that high up in the Devils ranks yet.

Eberle trade was also misinformed. Eberle might have had a bad post season but he was still year after year one of the teams most consistent scorers. Sure they saved money with Strome but he only had one year in which he lived up to that potential and nothing else so was he banking on Strome playing the 3rd line and being a really good 3rd liner? IMO That was a wild swing and a miss for Chia on that one.

Had Chia simply not made those two moves, the Oilers would be much better off today as it would have probably meant not signing Lucic as well.