I think this team can give us some fun baseball to watch and maybe even make some noise this postseason with one more solid starting pitcher and a right-handed bat with power.
If I were in Breslow’s shoes, I’m signing Jordan Montgomery because he’s a good bet to solidify the rotation for the next three seasons. For an innings eater, he’s pitched relatively few innings for his age and his TJ surgery was recent enough that he’s unlikely to blow out his elbow again anytime soon. Sure, they’ll probably be paying half his salary to pitch for someone else on the backend, but they should be able to swing that with all the young hitters moving up through the system.
Next, I’d trade Kenley and Duran for the best upper minors starting pitching prospect(s) I can get. If Verdugo can get a guy like Fitts and an interesting reliever then I’d think that package should be able to fetch something similar. Then, I take Kenley’s money and use it to sign Soler or Rhys Hoskins to bat in between Devers and Casas. Whichever of the two who requires the lesser commitment should be fine. Either Soler splits time with Yoshida between LF and DH or Hoskins becomes the primary DH and backs up 1B.
I think these moves make the team competitive and potentially even dangerous while still remaining under the CBT tax this season. I’m not against going over, but maybe there’s an argument for waiting until more of the young players in the system are producing in Boston.