As much as I love Johnny Damon, I have a sneaking suspicion he won't be back next year. He is already talking about how he has options, which he definitely does after a solid regular season and strong World Series where his gritty at-bat against Brad Lidge and his brilliant 2-base steal set up a key Yankee win. But it seems like his agent Scott Boras is gearing up to demand a multi-year guaranteed deal and I don't think the Yanks will or should give him one. If they were to give him a two or three-year deal, I would bet that he would have a debilitating injury the first year that would cause him to be ineffective for the rest of his Yankee career.
Hideki Matsui made a great case to stay with the team with his MVP performance in the World Series, especially in Game 6. I think the Yanks should offer him a one-year deal if they can't get Damon to bite on a one year plus an option year contract. Signing Matsui for one more year buys them some time to develop younger players or go the free agent route after the 2010 season.
Andy Pettitte seems to be the surest bet to return, that is if he wants to come back. Pettitte always takes his time during the offseason to think about whether he really wants to pitch again. And as he told Dave Letterman, he has a 15-year old kid in high school who he wants to spend time with. He might decide to take his fifth ring and go back home to Texas. But he seemed rejuvenated this season and it might be hard for him to walk away after playing such a critical role for the Yanks in the playoffs, starting and winning all three clinching games.