Just read Mackey's oddseason preview from yesterday and something that jumped out at me is that we got pretty deep in discussions with Keller during the season about an extension. That's a good sign on top of the mutual interest that exists, enough to make me optimistic that we'll check that box at some point this offseason.
I may be reading into it a bit, but he also seemed to allude to a possible Connor Joe trade (I find him a bit maddening sometimes, as he can veer between reporting and his own perspective or speculation without clearly indicating which... it's not a problem and he is really good and straight up about not trying to invent rumors, but minor times like this, I find it annoying).
Anyways, running with that notion a bit, I think it could make a good bit of sense and actually be possible. I'm just throwing stuff at the wall with this one, but I could see something like a swap with an AL team like the Guardians or Mariners for a reliever. If I am not mistaken, Trevor Stephan is Clase's set-up man, but he's in arbitration now and Joe is the Guardians type of pitcher. The Mariners have a wealth of good stuff guys all up and down their org, and DiPoto loves wheeling and dealing, so those would be my hail mary guesses.
From the Pirates perspective, it could be a smart way to improve. Joe is a pretty nice complementary player to have, so I don't think he should be shoved out the door or anything like that, but if flipping him is a way to give yourself another leverage option in the bullpen, it seems like a good call. Assuming Cutch comes back and will play in RF at least occasionally, it also lets the bench become more flexible, which I think is advantageous.
Finally, this wasn't in Mackey at all, but I'll take a small stab at something that I think is unlikely to happen and unlikely to be popular as an idea or if it does happen. If the White Sox would trade Tim Anderson for nothing, or especially if they cut him loose, I think he's well worth taking the flier on as the starting 2B. His stock has cratered but he's had a weird couple of years in terms of injuries, and he's still not too old to get back to the pace of a 3-4 win player. He's a classic fit at the leadoff spot and I think could be a spark plug.
It would be quite a pivot, since given the big needs at SP and 1B, it'd be hard to justify allocating what little payroll space there will be to yet another middle infielder, but I think it's the kind of gamble that could really catapult us, whereas the 1B options for example seem like diminishing returns (to me it just seems kind of obvious to get Santana back and have Triolo/Endy play there sometimes). This is way too much wishcasting, but I'd love to see Cutch brought back immediately + a trade for Quintana, and then see if you can concentrate from the group of Bae, Gonzales, and Peguero by trading for better pitching depth, then see if you can bring Anderson in on a two-year deal to really make a run in the immediate future.
