My sense is that most Pirates fans are fine trading Glasnow because it's a question of getting guaranteed 4 years of what we need most from Quintana, vs the possible waiting game with maybe a slightly longer payoff from Glasnow. He had some control issues in his first brief stint in MLB, but more generally I think there's just a question of if he'll need another partial AAA season and then more of an ease into an MLB rotation, still with some growing pains in 2017, etc., than emerge as a contributor for the stretch run + playoffs.
Quintana would be perfect for the Pirates and is the right kind of bold move that they need to do for their current core. He plays well as a contrast off Cole and Taillon, too. I lean just slightly towards the idea that it'd be better to pay for the Tyson Ross 1-year lottery ticket, but mainly that's because I think the asset necessary to get Quintana are Glasnow, Bell, and a third non-neglible piece, which he's certainly worth but I'm not sure it's in the Pirates best interest. Ross is way more of a gamble, but he gives us even more depth, which is less pressure to rush Glasnow right into the rotation, making it more likely that he really shows up as a slightly post-hype prospect and turns in a great rookie campaign eventually.
If the deal could hover more about Glasnow, Tucker/Hayes, and Diaz, i.e. two quite solid hitting prospects and a blue chip pitching prospect, I'd be much more brazen about it, but that's underselling Quintana just a bit and the White Sox have no reason not to be patient in getting the deal they want. I also imagine they might want Meadows instead of Glasnow, if they really want blue chip hitting talent, but that's a non-starter for the Pirates.
I don't think it gets done unless for some reason the White Sox want to completely sell out to a total rebuild. He's got enough of a term to still be a part of the rebuilding plan or be traded in another year or year and a half, and I would just imagine that Huntington is not going to budge on the 2/5 of Meadows, Glasnow, Keller, Bell, and Newman that it's going to take. My best guess is that if Chicago likes 2 players from the 6-15 range of most Pirates lists, a deal could happen, but I don't see any combination of Glasnow/Keller + 2 of those guys that meets the value for the White Sox. Maybe 2 of Hayes, Tucker, Craig, or Diaz, but it's just too short any way I look at it.
