There is no big rush here IMO. He will see good money, of that I have no doubt and I do think he will stay with the Sox. The way he is pitching right now and has done ever since TJS is well good enough to warrant another contract with decent money attached to it. He seems to be a good clubhouse guy, dedicated and driven to stay a competitive pitcher, so even if he tails off a bit, he will be a valuable piece to the rotation. From his standpoint I think it makes a lot of sense, too. Fenway suits him IMO, after being kind of a villain at the start of his time here he has seriously turned things around and become a bit of a cult hero, so he is well liked in Boston. At his age he won´t be playing too long anymore, so why go somewhere else, unfamiliar and risk playing in an environment that doesn´t appreciate you?
Also, I´ve always had a mancrush on him, even before he became all skinny :-), so I want him to stay.