#2 Coaching
I’d bet money that by the time the Oilers win a Cup that Todd McLellan is no longer their coach.
Whether it’s loading up the first line, insisting that Draisaitl play wing, or a generally old-school mentality, I don’t think McLellan is a very good coach for today’s NHL.
By contrast, Mike Babcock is pretty much unanimously considered the best coach in the NHL. He’s a master tactician and motivator. He does have some old-school tenancies that hurt him (i.e reliance on checkers and stay-at-home defensemen) but he’s also shown a willingness to evolve that is the hallmark of all successful people.