Seems to me that at the rate he is going everybody including the Sox are going to be in the same place on Jon. They will all be looking at a pitcher that is more cutter happy than ever who will likely have lost a little more on his FB by then. Hitters are hitting his FB more and getting it in the air more. Jon is throwing it when he can locate it but appears to be losing confidence in his ability to get hitters out with it. When he can't locate it, he throws the cutter at an even higher percentage than usual. By varying degrees he is slowly but surely throwing all of his secondary pitches other than the Cutter less with his FB usage changing significantly up or down depending on his ability to locate it. Hitters are missing his Cutter less over time as well which would seem to indicate that they are expecting it more. I don't like the way the dif in velo on his FB and his Cutter is narrowing. If Jon misses with the Cutter when the hitter was expecting FB, it makes the Cutter an easier pitch to hit as it just ends up looking like a poorly thrown FB.
His Curve has been a very reliable pitch for him but I think it benefits from being utilized judiciously. It is clearly a set up pitch for him.
Anyway I think teams including the Sox will believe they have seen the best Jon has to offer and will consider his ability to eat innings his most endearing quality when the time comes. It would appear that he will be a cut above the Dempsters of the world but might be a cut below somebody like Lackey if Lackey continues on the path he appears to be on. Lester is just becoming more and more predictable over time I fear and I don't think there is an answer out there for him at this point.
None of that would suggest Jon is headed for the scrap heap. I just don't think teams will be looking at Jon in terms of $20M per for 5 years or something like that. If it has to be 5 years then I would think the number might be something like $15-$17 per. If Jon is interested in max money per, then maybe $20 per on a 3 year deal.