So you want to get rid of Crawford? You'll have to eat $15 mil a season to deal him right now. Is it worth it to deal Crawford and $90 million for nothing? No, you gotta keep Crawford, and you kinda have to. If he plays up to his potential, then he's still overpaid, but the sox wont want to move him. If he plays like 2011 again, he'll be worthless again.
Ellsbury is making it to FA, and if somehow he continues to have 25-25 to 30-30 seasons, he's going to outearn Crawford by a lot. Crawford set the market for a 5 tool OFers in their prime. Ellsbury is going to wreck the market. He's gonna get CC money (7yrs $161 mil) on the market.