I think the Oilers have no choice but to pay McDavid whatever it takes to keep him through his restricted free agent years. They will have to match any offer sheet, as their fans would be livid if he were to leave.
Once McDavid reaches unrestricted free agency, he has full control. If the team hasn't been able to assemble a supporting case around him, and he is tired of being in a small, cold, depressed market when there are huge financial opportunities elsewhere for him outside of his hockey contract, then he will move on. I suspect, that like Gretzky, he will move on at that time.
I'd be very surprised if McDavid finishes his career in Edmonton. I suspect after this one, he'll have five more in Edmonton before he moves on.
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