Now that the Yankees have signed Andy Pettitte, they are pretty much done with their offseason spending. And for all of you Manny Ramirez hopefuls out there, you should probably understand this before you embarrass yourself in front of a friend or co-worker: ahem…MANNY RAMIREZ IS NOT GOING TO THE YANKEES!!!! GET OVER IT!!!
Okay, so now that i’ve gotten that off my chest, it’s time to go over what this article is really about: who (if anyone) will the Yankees go after next offseason after spending a gagillion ($422mm to be precise) dollars on CC Sabathia, A.J. Burnett, and Mark Teixiera alone. Well, there really isn’t that much choice. With most of the top free-agents likely to exercise options or sign long-term deals with their current teams (Josh Beckett and John Lackey to name a few), really the only top-knotch player out there, is Matt Holliday. After being traded to the A’s this offseason, it appears that Holliday is headed for free agency (unless of course he gets traded to a club that then signs him to a long term deal, which is extremely unlikely considering his agent is Scott Boras).

Of course that brings us to the question of “will the Yankees pursue him?” It’s the same question that was brought up earlier this offseason with A.J. Burnett, Mark Teixiera, and Manny Ramirez (there was never any question about Sabathia). The Yankees will have $45mm coming off the books as Jose Molina, Johnny Damon, Xavier Nady, Hideki Matsui, and Andy Pettitte will be free agents. More importantly however, with Damon, Nady, and Matsui leaving, it will mean the Yankees will have a vacancy in the outfield and in the DH hole. Now a lot of things could happen with that. Prospect Austin Jackson will be ready to man centerfield, which may or may not put Brett Gardner or Melky Cabrera in left, and would also give Nick Swisher the right field job. For DH, the Yankees could either switch Jorge Posada over there and use a prospect such as Francisco Cerevelli to man the catchers position, call up maybe an Eric or Shelley Duncan, or sign a Carlos Delgado or a Hank Blalock to a one year deal. However, the option that you’ve all been waiting for: signing Matt Holliday.

Now there are many reasons why the Yankees could probably sign him. Number one, the money. Holliday would probably require Mark Teixeira type money, which the Yankees actually have room for. In fact, they could even sign him and another player if the really wanted to. They have room for him financially. The next reason is that he would fill a potential hole. If the Yankees had an outfield of Matt Holliday, Austin Jackson, and Nick Swisher, I’d be just fine. Plus if someone really didn’t like Holliday in the outfield, and wanted Gardner there instead, the Yanks could just slot Matt in the DH spot and it would work perfectly. However, that would have a few ramifications. It would mean that Jorge Posada would be forced into being the full time catcher since he wouldn’t be able to turn to the DH role as backup. However, I see the Holliday playing left field scenario as more likely.

Another thing this would do, would be to allow Jesus Montero the time he needs to develop. I know that some people view him as the predecessor to the Jorge Posada throne, but that’s just not very likely for two main reasons: Number 1, when Posada’s contract expires after the 2010 season, the Yankees will likely try to sign Joe Mauer (which is a story for another day). But the more important, reason number 2, is that Montero is really lacking as a defensive player. He’s overweight, and slow behind the plate. In fact, many scouts and people around baseball see him as a first baseman/DH type of player (just like Jason Giambi). And if the Yankees were to sign Holliday (or just leave things as they are for that matter) it would give Montero the time he needs to fully develop as a hitter and get used to that DH role which he would most likely occupy in the Bronx. A quick note, for those of you who are not familiar with Jesus Montero, check him out. The guy hit over .320 last year in Yankees single-A and has frequently been called the best hitter in the Yankees system.

If the Yankees signed Matt Holliday, it would all but signal the end of Johnny Damon’s years in pinstripes, and let me be the first to say “it was a hell-of-a-run.” Johnny has really had some great times in the Bronx, with probably the highlight coming last year when he went 6-for-6 in a hot afternoon game against the Royals. However, Damon’s leaving really takes a toll on the Yankees’ defense as Damon was frequently sacrificing his body for the team. More importantly though, it leaves the Yankees without a true, number one hitter. But not to fear, Austin Jackson is (almost) here! Jackson fits the leadoff hitter model perfectly (speedy guy with decent power who can get on base). Plus, if he can’t handle it, they can always try Gardner, or Cabrera or whoever the hell is manning center for the Yankees these days. The Yankees have really seemed to take an over-the-top interest in centerfield lately, I mean, Mike Cameron?? What??!! But I’m getting off topic.

There has also been some speculation that the Red Sox, fresh off of getting beaten by the Yankees in the Mark Teixeira derby, will go all-out for the young left fielder. However, I don’t see it. They just don’t really have room for him with 2 young players (and J.D. Drew) manning the 3 outfield spots. Of course I mean Jacoby Ellsbury and Jason Bay, both of which are very talented players. And if Ellsbury’s not going anywhere (I bet the Twins are regretting not taking that Ellsbury, Lowrie, and Lester for Johan Santana deal right about now), than it seems as though Jason Bay would be the odd-man-out. But hold on a second, the Red Sox are actually quite fond of Jason Bay and aren’t about to let him leave. So if there’s no room in the outfield, where do you put Matt Holliday? DH? *Buzzer Sound* Big Papi’s already got that and isn’t about to give it up to some hot-shot kid. Well then is there any where else? No. That’s it. The Red Sox just don’t have room for Holliday and thus I don’t think he’s going to go there.

The final point (finally) that I’m going to make has to do with Matt Holliday’s family, mainly his Dad. Holliday’s Dad is a big fan of the Yankees and it would be a “dream come true” for him to have his son don the pinstripes (of course Scott Boras may beg to differ but that’s beside the point). Last year at the 2008 All-Star game at Yankee Stadium, when his son Matt hit a homerun for the NL squad, his dad Tom literally jumped out of his seat and rejoiced. Before Matt had been traded to Oakland, Tom Holliday said, “if someone would have called me today and said Matt had gotten traded to the Yankees, I’d have been hunting for a place to celebrate.” Well for now Tom’s going to have to stay up watching his sons games on the West Coast. However in future, he might just be playing in a city closer to home: New York.