I'm thinking that the biggest thing that Brian Cashman is going to look for this offseason is a guy to be able to slide into the starting rotation behind CC Sabathia that he can count on. I think a solid #2 starter behind CC and in front of A.J. Burnett would be exactly what the Yankees need, before Phil Hughes and a mystery fifth starter could finish out the rotation. But what is definitely needed is another top of the rotation starting pitcher. They need to acquire one somehow.
The first way of acquiring one would be through the system, but I don't think Phil Hughes is ready to be a number two yet. He had a great season this year but I think he still needs to develop and if the Yankees find a starter he's going to end up being the 4th guy probably. There's nobody else in the system that can really even come close to being the type of dependable top of the rotation starter the Yankees need.
The second way, probably the most popular and most likely, would be via Free Agency. The only name that comes to mind is Cliff Lee. No other free agent pitchers are even close to his level. Brandon Webb is alright, but he's recovering from injury and is a huge question mark at this point. The Yankees obviously, whether you like it or not, are going to make a run for Cliff Lee. They are going to call him up, and offer him a ton of money to try and come to New York and solidify the starting rotation. I'm not sure that I agree with this. At first I thought that the Yankees had to get Cliff Lee and I was all for it. Lord Duggan's two posts against it, plus figuring out how old he actually is, has turned me against that idea a little bit. Cliff Lee has been historically injury prone, is 33 years old, and is going to demand a multi year contract worth over 20 million per year. Is that something you really want on this team? The Yankees have enough of these huge contracts that is going to keep people under contract making millions until they start growing grey hair. Another one isn't necessary, especially since the Yankees don't need him. If they desperately needed an ace like they did after 2008 it's one thing. But it isn't. They have an ace. They need another top of the rotation starter, no doubt, but one at Cliff Lee's level and salary isn't necessary. I think it would be smarter to try and find a cheaper, younger option rather than to break the bank for Cliff Lee. That way the Yankees have more money to spend on other needs this offseason like improving their bench and bullpen. Unfortunately, there are no pitchers that fit this mold in the Free Agent Market, which brings me to the final way of acquiring a pitcher...
A trade. The Yankees could always turn to other teams to see if they have pieces they are willing to trade. The Yankees have pieces of their farm system that A) May not have any place in this organization in the future because they are blocked, and B) would make terrific trade bait because of their young talent. To me, I look at any prospect not named Jesus Montero as a guy I would be willing to trade if I were getting the right piece. Yes, that includes Austin Romine, Manuel Banuelos, and Dellin Bentances. I would try to avoid trading Banuelos if I could, but if the Yankees were getting the perfect starter that fits their need, I'd be open to trading him. Here are a few guys the Yankees should look at acquiring via trade.
Zack Greinke- Obviously. The Royals are shopping him around and want to trade him. Greinke is 27 years old with a respectable contract. He's one of the most talented pitchers in the game. People will say that he "doesn't want to come to NY so it's dead". No, it doesn't mean that. Curt Schilling didn't want to go to the Red Sox, remember? He still ended up there. People thought that CC didn't want to "pitch out of the NL and pitch on the East Coast", and yet here he is, leading the Yankees pitching staff. It's not as if it's impossible to get Grienke. The Yankees have the right pieces to get him and I'd be open to getting him as long as it didn't involve trading Montero. Greinke could stabalize the Yankees staff for years. I hope the Yankees will at least look into him.
Jair Jurrjens- This guy is also a possibility. He's on the Braves now and they're looking to deal him. He's only 24 years old (will be 25 when the season starts), and had a bit of a rough year this year and was hurt. However, he's young and has pretty good stuff. In 2009 he won 14 games, had a 2.60 ERA and threw 215 innings, very respectable for a young guy. He may or may not be a big time top of the rotation starter, but he does have a lot of upside and he's incredibly young. He would bring a young right handed arm to the Yankees rotation and probably would not cost too much in terms of prospects or money.
Derek Lowe- On the subject of Braves pitchers, Derek Lowe is another one that comes to mind. I'm not as fond of this guy, but I'd be open to him and he does have good qualities. He's older and more expensive than Jurrjens, but he also comes with something that Jurrjens does not. Experience pitching in the AL East and experience in the postseason. He has been a terrific postseason pitcher throughout his career and the sinkerballer, while I wouldn't prefer it, may not be an awful option for the Yankees to look into.
Josh Johnson- This is wishful thinking completely. I do not expect this at all and if it does happen, there is no chance it doesn't cost the Yankees Banuelos at least, if not both him and Jesus Montero. Josh Johnson is one of the best in baseball. He has nasty stuff and is really young. Nobody could be against having him in the rotation. Unfortunately I think the cost of getting him will be too high. I'm willing to trade some prospects, but not too many. Montero should be untradeable.
Chien-Ming Wang- He isn't a trade guy. He's actually a free agent. The Nats want him back too (unfortunately). However, Wang is still young, and we know the upside the guy has. I'm not suggesting he be a number 2 starter, but I think the upside he could bring the Yankees could be of that quality. He'd be incredibly cheap with a ton of upside. Plus, I loved Chien-Ming when he was here. I was upset when the Yankees didn't resign him last year. Why not take a shot on him now if he doesn't sign with the Nationals? Give him a chance to resurrect his career in the place where he had so much success.
Is there any more guys that the Yankees could get via trade that anybody can think of? I thought of a few but I think there are more the Yankees can target.
While I would prefer the trade route, I still acknowledge that the most likely scenario is the signing of Mr. Cliff Lee. I still give the Yankees the edge in signing him, and while I don't think it's the best choice, there's no question he will improve the rotation tremendously. Here in my mind is next years most likely starting rotation.
Joba Chamberlain/Ivan Nova/ect.
If the Yankees sign Cliff Lee he would fit right into the rotation. I'm assuming that Andy Pettitte retires. Just a gut feeling. If he comes back he'd slide into the rotation and Chamberlain would be in the pen for another year. But if he does retire, I think the Yankees will have another Spring Training battle for the 5th starting job between Joba, Ivan Nova, maybe Brackman. I don't know. This time however, if Andy doesn't come back I want Joba in the fifth spot, to give him a chance to finally get to pitch 200 innings with no restrictions and see how he does.
This is all speculation. I think the offseason can be a fun time because of all the speculation that occurs. I don't think the Yankees get any of the guys I mentioned as possible guys they could trade for. Cliff Lee is most likely, and if they don't sign him then maybe they'll go after one of those guys. I would prefer Greinke but thats just me.
Either way it's going to be an interesting offseason. I hope that whatever happens, it makes the Yankees more likely to win #28 in 2011.