No one should be surprised if he tells them he wants to play out the year and see where things stand.
That is absolutely what he should do if his goal is to win a cup, Leafs or no Leafs. Why commit early to this Oilers team? It's not going to be improving based on the roster it has, and the goaltending situation has never been addressed, so what's the rush. If anything, you force them to make the team much better to convince you to stay. He's already made a shit ton of money. He can afford to risk the very unlikely catastrophic injury he might suffer in the contract year.