The Yankees haven’t been active yet this winter, but now that their organizational meetings are over and they’re prepared to go to the Winter Meetings next week they’re ready to get the ball rolling. Up first on their to do list is resigning Andy Pettitte according to Mark Feinsand of the Daily News.
This makes sense for a number of reasons. First, you don’t want to alienate Pettitte, especially after last winter when they hardballed him. There was a reason then (his shoulder), there isn’t one now. Second, he’s going to expect a raise, but how much? They need to work that out so they exactly know how much they have to spend on other players.
Finally, they need to know as soon as possible what exactly they are working with. Should he retire or even sign somewhere else they need to know know so that they can make alternate plans if necessary.
The best situation for the Yankees is to get this wrapped up as quickly as possible. Hopefully by the end of the winter meetings. If Pettitte drags his feet then things could get interesting.
If he decides to call it a career, and it would be hard to blame him after winning another World Series, the Yankees would be expected to turn their heads towards John Lackey, Randy Wolf, or Joel Pineiro. Again, I doubt the Yankees would show real interest in any of those pitchers unless Pettitte stays home.