Two things, if the Sox bite the bullet and eat the cash, they get a better return. Depends on what the return is though and if it makes the team better. Maybe a RF or a quality SP. However, if they just trade him to free up cash, than they will get a lesser return say a backup catcher. Than they can just use that money to go out and get a RF. I would probably just trade him to free up the cash and try to get a RF but it really all depends on what they can get back if they were to just eat the cash. They can always do a separate trade for a SP.