Let's allow the short or long post season play out to see who performs and who doesn't, then evaluate the payroll. Anything less than a WS appearance will be seen as a failure and could influence JH's checkbook availability. If the Sox drop early again in the ALDS, the pressure will be on DD to remake the pitching staff some how or other. If they win the WS, all pressure is off and you can let guys like Kimbrel take his best offer and move on.
My theory is that if I can't win with these guys, then I need different guys. The current BP with its crowd of medium level pitchers does make for some trade possibilities. Keep in mind of the current 19 active pitchers on the 40 man roster , the Sox will open 2019 with only 13 pitching for them.