I think it all comes down to which free agent shortstop they sign after next season -- Lindor, Correa, Seager, Story or Baez. These are arguably the best free agent position players available this year (via possible trade), next year and beyond, and if the Sox don't spend big this winter, the timing -- for being closer to contention and a PR splash -- will be ripe. Maybe one of them slides over to second or third, or maybe X Bogie does... or opts out, depending on if the Big Five make big dough on a rebounding market (or if Boston still stinks).