I trust the Sox know which pitchers we have in our system with very minimal chances at giving us lasting value. Of course, the ones we identify, are likely the same ones other teams don't want. The trick is to find one some other team likes more than we do, and hope we know more than they do.
Unlike some, I think we have begun to improve the pitching pipeline in our system. Counting Whitlock, who we acquired as a prospect, we have seen these pitchers at the MLB level:
DD's guys: Houck, Crawford, Bello & Perales (Better than Bloom's combined guys)
Bloom's guys: Whitlock, Wink, Dobbins, Guerrero, Early, Kelly, Valera, Monegro, Paez, Mullins, Wehunt
Breslow's guys: Slaten, Fitts, Priester, Sandlin, Tolle, Cason, D Reyes, Delzine (This group may be better than Bloom's, too.)
I'd avoid trading any of these guys, but for something good, fine.
(Notice I did not list Penrod or the vets acquired.)
I'm not trying to take anything away from our ring seasons, but those teams were not built on our farm pitching pipeline.
2018: Trade or FA: Sale, Price, Porcello, Nate, ERod (as a prospect) Kimbrel, Kelly, Hembree, Pom, Wright. FARM: Barnes, Velazquez, B Johnson, Workman.
2013: Non Farm: Lackey, Dempster, Doubront, Uehara, Miller, Bailey, Breslow, Peavy, Aceves, Webster, Mortenson. FARM (more this year) Lester, Buch, Wilson (Taz?)
2007: Non Farm: Beckett, Wake, Schill, Tavarez, Timlin (Okajima & Dice K?) FARM: Lester (11 GS) & Papebon
2004: Non Farm: Pedro, Schill, Wake, Lowe, Arroyo, Foulke, Timlin, Embree, Williamson, Leskanic, Mendoza. FARM: basically none
Certainly, we have moved in the right direction on building up a pitching pipeline since 2018, but we have failed, badly on our non farm additions.