I don't think another RH bat is needed in this lineup. Cespedes is definite a power bat and would love to have him and a contract around to what Hanley got last year is what he will probably get, some think his value exploded after the World Series but I think a month later when teams are looking at the big picture he will be right around Hanley's deal.
As it sits now we are a very RH team. Betts, Bogey, Pedoria, Hanley, Vaz, & Castillo. Add Cespedes and that's 7 out of nine that hit from the right side with Fat Boy and Papi from the left.
I just read an article where Henry said he would like to add another arm but not moving core young pitchers. He said nothing about position players. So I'd say the Winter Meetings will see Cespedes go off the board along with Davis within the first two days and with all the power off the board I could see the focus move back to the rotation and bullpen. We still need a shut down LHP out of the pen along with maybe another starting pitcher.
I like the idea of going after the Guardians arms but if Tito and company wont let one go then with the current rotation is ok until the All Star break when Bucholtz breaks down. So a pitcher like Cliff Lee, Tim Lincecum, Henderson Alvarez, or one of Tampa Bays young arms which apparently all other than Archer are being shopped. Other than the young boys throw Lee or Lincecum a one year deal and see if you can get fire in a bottle.
I think the Sox are in a position of strength now heading into the Winter Meetings. They got their Ace, Bullpen Help, & 4th OF. So any move DD makes is just an added Bonus.