Bradley is streaky. When he's hot, he carries your team. When he's cold, he disappears. He might be 26, but he is still really young in baseball terms as a slow developing former college first rounder. Regardless, DD doesn't like to deal established big league talent. Even with Papi gone, you have an up the middle crew (sans C) that could be dominant for awhile, even with Pedroia getting up there. I think he makes a splash this offseason, but without dealing any major big league talent. I think you'll see a FA to fill the DH spot and you'll see a trade to get a starter. There is no way to keep this team together once all guys hit FA. And the problem is, DD and Cherington didn't get deals done with these guys before they became stars. So you have to take advantage of the window you have. Think about it.
Jackie Bradley is a FA after 2019
Mookie Betts is a FA after 2020
Xander is an FA after 2019
Benintendi is an FA after 2022
Who knows what Andrew becomes, but the top 3 guys on this list are all-star caliber players. Bradley and Xander start costing real money next yr, although likely in the $5-6 mil range. By 2019, all three are going to be costing close to $20 mil in arb and a contract as FA's, assuming continued production, will likely take them into the $80 mil per annum range to keep all three. With Pedroia and Price still on the books for 2021, you could be looking at Beni in mid arb with Price, Pedroia, Betts, and Bogaerts costing upwards of $120 million. It would be unlikely the whole crew is kept together at that price without seriously affecting the rest of the team. Hence, I see DD going for it. I see all players not currently in the starting lineup or current staff as being on the block. I think now is the window to win. You spend money on Encarnacion to replace Ortiz. You deal the whole farm for a guy like Sale. You sign one of the big name relievers to pair with Kimbrel on the back end. The sox have immense talent, but they did overachieve a bit this season. You keep the curve swinging upward and add major talent and you have a juggernaut for the next 3 seasons or so