The Yankees would have to part with quite a bit if, as Peter Gammons reports (MLB Trade Rumors), the Red Sox would have to part with both Casey Kelley and Clay Buchholz. I can only imagine that the Yankees would have to give up Austin Jackson, Ian Kennedy, and maybe one other prospect to get Doc and then an additional $20 million a year to keep him. That is a really hefty price to pay and while I do love the idea of having Doc in our rotation losing three top prospects is not easy to stomach. Add onto that the fact that the Yankees made three blockbuster deals last year and it seems a little unreasonable that they would need to sign Doc. The rotation is far from set but resigning Pettitte while tinkering with Hughes and Chamberlain as well as with a healthier Chien-Ming Wang sounds like a perfectly reasonable option. After all, the Yankees won the world series doing just that.
Would I love to have Doc? Absolutely. But is he worth giving up three top prospects and 20 million a year? If that is the case, Doc might not be the Yankees huckleberry, even if he wants to be.