I was trying to think of at least “post pandemic” in terms of recent trades.
Seattle acquired Castillo for “ish” Mayer and Yorke type pieces (Marte, Arroyo and some other irrelevant stuff”, but Castillo was 29 at the time with 1.5 years left.
It‘s damn near impossible to think of trades where a young, controllable, good (or better) starting pitcher has been moved without a top 100 starting pitching prospect going back.
Castillo is the only one I can think of off the top of my head, though I’m sure I’m missing someone. Generally it’s older SPs where it can be arranged (Scherzer, Verlander, Sale, Darvish).
I think @chawson (I think) is right when he says if Breslow can acquire someone, it will be someone less established but with longer control, assuming Anthony, Teel and Mayer aren’t involved.
Singer was a good call. Maybe someone like Detmers (LAA are morons). Chase Silseth is someone I’d think Breslow and Bailey would like. I’d suggest Andrew Abbott but the Sox and Cincy are basically carbon copies of each other in terms of farm systems (all hitting, no pitching). Logan T Allen from Cleveland is my personal “favorite”:in this kind of pure hypothetical.