I did not mean to imply you do not want to add a solid P in 2026 by waiting for Skubal in 2027.
I am pretty sure that for as long as I have been a Sox fan, 53 years and counting, I have always wanted us to add an ace or solid #2 every season. I hate the idea of trying to improve the rotation by upgrading the #4 or 5 slot, and even attempts at upgrading the #3 slot often fail, especially with the Sox choices.
Okay, you want names: of course I'd start with trying like hell to trade for Skenes or Skubal without giving up Mayer or Anthony, but that may be impossible, even with an offer like Abreu, Campbell, Garcia, Tolle, Arias and Sandlin. I'm not sure who else might be available.
I'm not sure I count Luis Castillo as a #2 anymore, but Pablo Lopez & Cole Ragans are pitchers I'd count as "good enough." (Trade guys) Maybe Joe Ryan or Nate.
Probably Free Agency is the way to go, despite paying way to much and needing 2-3 more years than reasonable. I'm assuming we'll have enough money to keep Bregman and sign a SP'er and Closer, but with JH, nothing should be assumed. These guys fit the bill, for me:
SP: Cease, Gallen, F Valdez, Ranger Suarez and maybe M King, Canning, M Kelly or Seth Lugo (shorter deal) I do not think Flaherty, Eflin and the super old guys make my list.
Closer: Helsley, Robert Suarez, E. Diaz or Chapman (1-2 yr deal.) Maybe Weaver, Iglesias or Finnegan would be okay, if we check all the other high need boxes off, first.