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I'm gonna play the disagree card here. Let's say he gets 250 million, which is the high end. That means that he will be getting 25/year, or 5 wins/year. That means he needs to have 50 WAR over the life of the contract. I don't think that that is unreasonable to expect at all. I think that they would be smarter to front load it, but it doesn't really matter, as you're paying for the production through out the contract. I see the 5 million per win rate going up too, with the new CBA. I see no reason he can't put up 50 WAR over the rest of his career.
Ehhh...let's keep in mind he slipped by his standards this year, which was still beastly. What if he's not really 31? What if he get seriously injured? Fair questions.