I'm hoping that if (when) Q is moved, Cherington's comment about "not wanting to get an "A ball pitcher who might be a reliever in a few years" is still something that rings true.
Just to give an example of a name that is too familiar to me for years of reading around, one guy who might fit that description is RHP Matthew Thompson. Projectable, still just 21, but seemingly not moving in the right direction. He's the kind of talent that a team could acquire earlier in its rebuilding phase in order to hope he puts things together, but it just doesn't really make sense at this point for us, especially when you consider the marginal cost of more strain on important arms if Quintana is dealt.
Cherington really needs to hold firm, and it will be a good test of his negotiating skills. If he moves him simply because this team isn't going anywhere, then it won't be a good result. It makes a lot of sense that teams will drag their feet as other things play out before they turn to Quintana, but he needs to be ready and willing to take it up to the deadline and keep him if the right offer isn't there.
I do think part of the conversation has to be about what Quintana himself wants, and to the greatest extent possible, what kind of interest he'd have in coming back next year. As a veteran without a ring, I have to imagine that he'd like a shot with a contender, and also that this would weigh on his decision this offseason, but at the end of the day, Cherington has to make a deal that actually improves the Pirates in 2023, even if the path to do that is to ride out Quintana for 10-12 more valuable starts worth of innings, in order to help reduce stress on the arms of guys like Crowe and Bednar.
The other looming question is what kind of alternative trades we might be able to look at. Cleveland is always a team who is willing to sell and buy at the same time, and maybe we match up pretty well for a Zach Plesac trade. He's not looking like a world beater, but he's somewhat comparable to Brubaker on paper and might at least be able to hold down 150 innings or so for you next year, which is pretty valuable when you consider how paper thin our depth is. If we could pry him away for an OF prospect and some lower minors guys, that's the kind of deal that would make taking anything for Quintana (even if it's just "an A ball pitcher who might be a reliever in a few years") more palatable.
Skubal would be a bigger ticket but I don't know that we have the prospect headliner who would make sense. If Peguero's offense were better or Gonzales had not gotten hurt, maybe that's who could start a package off, but I just don't see it. Another guy who I think is some adjustments away from being pretty effective is Daniel Lynch, but who knows what the Royals would be planning on doing (I hear some speculation the other day that if their pitching can't get better results, maybe they'll revamp the coaching staff this winter).