Yeah, I have been thinking about this myself. I too think Giolito is too valuable not to trade. But certainly don't think Hahn will pull the trigger until the very last minute unless Sox fall back into 8+ GB range.
Giolito, as it sits right now, is likely the top FA SP after Ohtani and perhaps Yamamoto. His value should be a prospect in the 50-100 range. If you could flip him for a major league ready SP that you can just plug right into the rotation effectively turning 12 Gio starts into 6.5 seasons of a SP, that'd pretty tough to not pull the trigger on. Names like Gavin Stone, Emmet Sheehan (LA), Quinn Priester (PIT), Andrew Abbott (CIN), and AJ Smith-Shawver (ATL) are all major league ready or close and could make varies degrees of sense.