The 2011 Planning Has Begun

Written For Baseball Digest.

From the moment Alex Rodriguez watched a called third strike to end the American League Championship Series, you could hear the wheels turning inside Yankees GM Brian Cashman’s head. Cashman has a busy winter ahead of him with a number of free agent issues to contend with, both internally and externally.

The two biggest free agents among the current Yankees are their skipper Joe Girardi and the face of the team, shortstop Derek Jeter. Cashman has already stated he wants Girardi to stay and said Jeter will not be going anywhere. The second is nearly 100% true, but Girardi’s situation could be a little trickier.

Girardi would have been in for a mega pay day had his contract expired at the end of the 2009 championship season. But he and his binder struggled at times this season and the Yankees season fell short of both management’s and the fan’s expectations. Which, of course, is easy to do when you’re expected to win the World Series every year.

Girardi also lost some negotiating power when the Chicago Cubs, rumored to be highly interested in the Illinois native, hired interim leader Mike Quade to be the full-time manager. That being said, according to several sources Girardi will sign a new deal shortly, likely three years in length. Should the Yankees and Girardi not work out a deal, Bobby Valentine, Tony Pena,and Willie Randolph would be among those considered for the job.

Derek Jeter is fully expected to be back in Pinstripes next year, but just like Girardi, Jeter’s bargaining power decreased with a subpar year after a huge 2009, and many questions remain. How much money is he willing to accept? How long does Jeter want to play? How long can he play shortstop and will he be willing to eventually move to another position/share time at DH? Will he be able to handle reduced playing time? The right thing to do would be to sign Jeter to a lifetime deal that specifies baseball and post-career life. Jeter should never be out of Pinstripes unless he wants to be. A deal will be made, but just how quickly a deal gets done remains to be seen.

The two other big free agents among current Yankees are two-thirds of the remaining “Core Four”- Mariano Rivera and Andy Pettitte. The main factor in each player’s future is how strong their desire is to return for another year. Both have admitted they have pondered their future beyond baseball. Rivera said at one point not too long ago that he would like to pitch another five years. It was certainly tongue in cheek, but Rivera is likely to return in 2011. If for whatever reason Rivera decided to hang it up, the Yankees would certainly go hard and heavy after free agent closer Rafael Soriano.

Pettitte, as he has done the last two years, will probably take his time over the winter and not declare his intentions until after the holidays. At this point, chances are probably 50/50 that he returns next season. Though he was healthy for the most part, Pettitte suffered a debilitating groin strain that DL’ed him for two months, and then he dealt with back and hamstring issues in the post-season (which was revealed yesterday in a Brian Cashman-Joe Girardi season wrapup press conference.)

Aside from Jeter, the remainder of the infield is set with Mark Teixeira (1B), Robinson Cano (2B), and Alex Rodriguez (3B) returning to their positions in 2011. The Yankees catching situation will most certainly see a change though. Jorge Posada will be back for the final year of the four year contract he signed prior to the 2008 season, but backup Francisco Cervelli will likely be gone. Cervelli started out the season hitting like a house on fire, but his offensive and defensive production decreased with increased playing time. Posada’s time behind the plate is also likely to be reduced to try to limit the number of games he misses due to injuries.

The beginning of the Jesus Montero era, however long or short, should begin in the Bronx next season. In addition to backing up Posada, Montero should see time at DH as the Yankees take a serious look at his powerful right-handed bat. Austin Romine will also be waiting in the wings at Scranton and, as has been the norm for the past several years, the Yankees will sign a Chad Moeller-esque catcher to a minor league contract as a precaution.

The outfield situation is an interesting one. Curtis Granderson (CF) and Brett Gardner (LF) are likely to return, but with free agents Carl Crawford and Jayson Werth looming on the horizon, the Yankees could move Nick Swisher if either outfielder is signed. Everyone loves what Carl Crawford can bring to a ball club, but signing the right-handed, right field-playing Werth may actually make more sense (and could possibly be a less expensive option than what Crawford will demand). The Yankees could use another strong right-handed bat as well.

While it may sound like blasphemy to some Yankees fans, Swisher’s value will never be higher. He had a career year, but Werth is a better ballplayer in every aspect of the game. Swisher has one year ($9 million) left on his current deal with a club option ($10.25 million, $1 million buyout) for 2012. Age isn’t a factor in this one since Werth (31) is actually a year older than Swisher (30).

Crawford, who will start next season at age 29, can of course wreak havoc on the basepaths as well as hit for power. He’ll most certainly be looking for a long term deal (5-7 years minimum?), though the economy could impact his future. Crawford has always been a center or left fielder and he isn’t your prototypical rightfielder. So if he were to be signed, it would likely mean moving Granderson or Gardner out of town, and that doesn’t make any sense from a baseball or economic standpoint.

The starting rotation for now consists of CC Sabathia, Phil Hughes, and a beleaguered A.J. Burnett. Javier Vazquez will be gone and NOT brought back a third time. While Pettitte contemplates his future, Cashman and the Yankees will be firing on all cylinders as they go after free agent-to-be Cliff Lee. But Lee’s signing isn’t as automatic as most pundits and fans thought several months ago. Lee likes it in Texas and he’s the guy front and center leading the team to its first World Series. The new ownership has plenty of bucks and has already vowed to do everything they can to keep Lee in Arlington.

The World Series outcome should have no impact on Lee’s decision. WFAN’s Evan Roberts believes Lee is much more likely to stay if the Rangers win, but just the fact that they are there could play a major factor in Lee’s decision. The Yankees will argue, of course, that they have a better chance of reaching the World Series in any season. And, of course, the Yankees will not be outbid.

If indeed the Yankees succesfully land Lee, they could look into dealing Burnett, who was a train wreck in 2010. With three years remaining on his five year deal, it’s a trade that could be accomplished, especially if the Yankees pick up some of the cash. The Yankees will also look at back end of the rotation options to replace Vazquez and/or in case Pettitte retires.

The bullpen, a key to the team’s 27th title, was a let down this season. Outside of Rivera, there wasn’t much consistency. Damaso Marte will be out until after the 2011 All-Star break after having surgery on a torn labrum. Boone Logan stepped up and did a decent job as the left-handed specialist. He should remain in that capacity next season. David Robertson had a hugely disappointing follow up to his breakout season in 2009. His spot is certainly not guaranteed for next year. Some of the young arms in the minor leagues will certainly get a chance to make the squad out of spring training. And then of course there is Joba Chamberlain.

In yesterday’s press conference, Girardi said Chamberlain will be a “bullpen guy”, a back end of the bullpen reliever. If not for the fact that he’s out of options (thanks to the guys at River Ave. Blues for that information), the Yankees could have had Joba working his way back as a starter in the minor leagues like they should have in 2008 or 2009. But that ship has sailed. Of course there is the very real possibility that Chamberlain could be dealt.

The Yankees won’t pick up the $11 million option on Kerry Wood, but will definitely be interested in resigning him if they can get him at a good cost and if he doesn’t mind remaining as a setup man. Wood excelled once he was acquired from Cleveland at the trade deadline.

The utility infield position will be up for grabs, with Eduardo Nunez having a solid chance to push Ramiro Pena out of the job. While Pena has the better glove, Nunez has much more offensive potential. The Yankees are also likely to bring in a Miguel Cairo type to compete for the position as well as to push the youngsters.

The bench was a key to the second half of the Yankees regular season though it was a bit exposed during the playoffs. Lance Berkman’s option won’t be picked up and there is a good chance he’ll return to Houston and/or the National League. Both Marcus Thames and Austin Kearns are free agents that may or may not be back. Thames put up solid numbers, but is a defensive liability, while Kearns battled injuries and has always had an erratic bat.

One surprise that came out of the season ending press conference: pitching coach Dave Eiland, for reasons kept private, was dismissed by the team. Early candidates to replace him are bullpen coach Mike Harkey and minor league pitching coach Scott Aldred, who spent the last four seasons in the Yankees organization in Trenton and Scranton.

Finally, Brian Cashman himself has to do a better job this off-season. The GM himself admitted that last winter was not one of his best as moves for Vazquez and Nick Johnson, (who will also not be making a third trip back), blew up in his face.

Whatever moves are to be made this winter, you can bet the Yankees will be right in the middle of things. After all, there’s a 28th championship out there to be won.

Drew Sarver is the Yankees content editor and contributor for BaseballDigest.com. You can also read his work at his blog, My Pinstripes. He can be contacted at mypinstripes@gmail.com and can be followed on Twitter at @BD_Sarver and @MyPinstripes.