Left Field- Talk to any Boston fan about their 2004 playoff run, and they will tell you that the turning point was Dave Roberts' steal of second base against the Yankees in Game 4 of the ALCS. So what could the Yankees do to trump this? How about two steals on one play by the same person! Johnny Damon did this during Game 4 of the World Series. He will be forever remembered for this heads up play that turned the tide of the series back to the Yankees. With all that said, I would let him walk during free agency. He is 36 years old, and has gone from an above average defensive CF to a mediocre one in LF. Plus, I think it is time the Yanks got a little bit younger. I wouldn't be upset if he came back on a 2 year deal, but it looks like his agent, Scott Boras, is looking for a 4 year pact. That is way too long, so I would see what offers he got on the market before going any further. But we'll always have the double steal.
Center Field- It was a very productive bounce back season for Melky Cabrera, as he won the CF job out of spring training over Brett Gardner, and never looked back. He had a solid season, leading the team in shaving cream pies to the face. I would not hesitate to bring him back as the starter in 2010, but there are rumblings that the Bronx Bombers are looking into Curtis Granderson. Getting Granderson would be awesome, but it would certainly cost the Yanks stud prospect Austin Jackson. If the right deal was available I would pull the trigger. But you could do worse than have Melky keep the seat warm for Jackson for at least one more season.
Right Field- Going into the season, it seemed as though Nick Swisher and Xavier Nady were going to battle for playing time all season long. But thanks to Nady's shoulder injury, Swisher took over the everyday job, and had a good season, with lots of HR's and walks. While he will strike out a ton and never hit for a high average, Swishalicious will continue to show good power and have a solid on base percentage. He is signed at a reasonable rate through the next two seasons, so he should be a fixture in the lineup till at least 2011.
Designated Hitter- If 2009 was indeed the final season in Pinstripes for Hideki Matsui, he went out with a bang, winning the World Series MVP despite only starting 3 of the six games in the series. He was unstoppable at the plate, hitting .615 with 3 homers and 8 RBI's during the 6 game series. Unfortunately, his knees seem to be betraying him as Matsui is no longer able to play the field. It wouldn't be a terrible decision to keep him around, but we could use a little versatility on this team. Mark DeRosa would be the perfect fit here. He could play pretty much every position but catcher. Signing him would allow multiple players to rotate at DH, keeping everybody fresh. Plus it wouldn't break the bank to sign him.