yeah the conversation isn't about GMing overall.
no disagreement with your arguments here - not going to go down the list but the piece I most agree with is the skill idea: that hard negotiating with agents just isn't his forte.
However, i think it's possible to further challenge your assumptions here. We are operating with a shared understanding that the Rangers are a *destination* franchise.
It's mentioned often as fact but I'm just not sure that's true, at least not for the types of players that win Cups. The Rangers attract, and historically value, a certain type of player and personality. Cuylle, for example, is an outlier. Is it possible that guys who want to squeeze every dollar out of the team are more likely to want to play in NYC?
Take the country club culture idea. Is it consensus at this point? Do we all believe it exists? I ask because: if we can tell it exists, if we "know about it" just from outside observation of on ice play, every single player in the league knows about it too. NYR is where you can go get paid and slack off - enjoy the fruits of MSG living and not have to earn it in the gym every day. This is to say nothing of the tax/cost of living comparison that almost certainly inhibits AAV suppression of any kind.
I think we also see that NYC is just not the destination it used to be. You see it with the Yankees too - they used to be the peak of the mountain. Now they're literally just another franchise, just another team.
My point is that the assumption underpinning your argument: "NYR are a destination franchise" needs to be heavily qualified, if not completely abandoned in the context of contract negotiations.
Another, more tinfoil hatty note on what you're asserting: I think Dolan has a lot to do with the way we do business. We know that Drury's communication style and management style is brusque, potentially disrespectful, bordering on ruthless. I honestly believe that players give other franchises' management teams a break to get the deal done based on goodwill. I know it comes down to dollars and cents, money talks, but most hockey players are not trying to stand out. They understand that in a hard cap environment, AAV is zero sum relative to their teammates. There are cultures, hierarchies, and social relationships. When guys want to keep a team together, want to stay someplace, they will bring all of it into the negotiating room. I don't think the Rangers' FO gets those breaks because I don't think there is a culture of openness, respect, and goodwill in the corporate structure of the organization. I think that matters.