Doesn't make sense for an NHL player no matter how good he is to force himself to another team. Imagine if Ovi had done this after losing to Crosby year after year. If the team is flat out ignoring its needs and not trying to get better that's one thing but its not what's going on with the Oilers. The only other time it makes sense is if he's a pending free agent and has made it clear he's not signing again. Then send him at TDL to a contender and he gets a shot there but good luck finding a team giving up anywhere near the assets.
I don't think the money or the organization is 100% the problem. Its probably a mix of them both. If he made less they could spend on more resources, of course it could all just go to a Nurse contract. If he makes more, it has to be on a team that is loaded with young cheap talent and the Oilers have no way to get there because they aren't drafting high and have most spots spoken for.
Fact is the Oilers are a playoff team every year with these guys and they just have to keep taking their shots at it. No way out there to guarantee yourself a Cup, you just earn it by having things fall into place.
Unless he pulled a LeBron and actually demanded the Oilers hire Jeff Jackson as the president (and now apparently GM) then yes, he's a big part of the problem. But there's no indication 97 actually asked them to do that. Just seems, at least to me, like yet another clumsy and panicky gesture from ownership to appease an increasingly frustrated franchise player.
And just *trying* to win don't mean shit if you keep hiring gloriously incompetent general managers to do it. Peter Chiarelli was unbelievably bad, and Holland actually hasn't been that much better, much to my surprise.
Again, never, not once has McDavid had a legit starting goaltender or true #1 franchise defenseman playing behind him. I'd even argue their depth at center is not as good as people think it is, even with that guy atop it. As for his cap hit, that's not the real problem when they've got somewhere around $5 million tending goal in Bakersfield and Nurse is making more than Cale Makar. I will say I think Draisaitl is overpaid but no egregiously so. Still, there's an argument to be had that even a GM of average abilities would have a much better roster built around those two.