There's no real point imo of keeping him. You can say you have him... but you aren't contending in '26, and '27... so you are hoping it comes together in '28 when he has 2 years left of control.. Better off cashing in now, and getting back a huge return. JMO.
Man....4 pages of Pirates discussion without me. Excellent. I'm going to agree with most of the other comments.
The point in keeping him is to contend and while you're focused on (I'd argue the phony) narrative of rebuilding as someone else pointed out, this isn't just about competing, it's about maintaining any level of accountability with the fan-base. Trading Skenes doesn't answer any questions because they can answer nearly every question with Skenes still on the roster.
....so instead of being aspirational about why a team that is clearly trying to be more serious about winning in 2026 should trade their best player, why not lean the other direction? If Cherington asked recently signed Ryan O'hearn to give him the name of an undervalued bat they could acquire....who do you think he'd share? The Pirates roster today doesn't have a RHed batter that you could project >10 HR. If he asked RO his opinion on Kjerstad....what do you think he's say because the Pirates could take a risk on a LHed RF bat. Any names you think RO would share about 3B? The Pirates are kicking around who their 5th starter is....would they rather buy low on someone like Povich and leave Hunter Barco at AAA for 2026?
Sending Mountcastle, Kjerstad and Povich (plus whatever) to the Pirates would clear some roster crunch for the Orioles and would actually add to the performance, opportunity and depth of the current Pirates roster.
...and if I could add one guy to the Orioles MiL from the Pirates system, I'd target SS Wyatt Sanford.
I'm an Elias fan.
...and that's fine, but hasn't he proven to be ineffective (in year 8) at the approach you are advocating for? Shouldn't your argument be that you like Elias as the PBO and the Orioles probably need to get a new GM for the ML roster/trades, etc? Leave Elias working internal ops with Player Development, scouting, draft, IFA, and analytics....