Yesterday I looked at the state of the Yankee rotation and of the organizational starting pitching depth as it stands right now. Today, I want to try to figure out which free agents best fit into the Yankees plans for 2009 and beyond and how.

To begin with, I want to rerun my chart of the returning 2008 starters, but I’m going to add one name to it. With Mike Mussina’s retirement confirmed (though not yet official), the Yankees are all but guaranteed to bring Andy Pettitte back on a one-year deal. Though Pettitte had a poor year in 2008, I support this move for two reasons. The first is that a one-year deal essentially serves as a stop-gap as the Yankees’ pitching prospects continue to mature. Joba Chamberlain is ready to start the 2009 season in the Yankee rotation, but though the Yankees have nine intriguing starting prospects in their system, none of the other eight is fully ready just yet. Even Phil Hughes would benefit from starting the season at Triple-A. A one-year deal for Pettitte gives Hughes (or Kennedy, or even George Kontos) time to refine his skills, then gets Pettitte out of the way for that pitcher to join the rotation in 2010.

Second, Pettitte’s poor 2008 season wasn’t all that poor and was weighed down by an ugly second half that Pettitte blamed on his failure to follow his usual offseason conditioning program due to a desire to stay out of sight in the wake of the Mitchell Report’s December 2007 release. Even still, Pettitte threw 204 innings, won 14 games, and posted an ERA just a tick below league average. After 22 starts, Pettitte was 12-7 with a 3.76 ERA. He then went 2-7 with a 6.23 the rest of the way. Over his entire career, Pettitte’s second-half ERA has been nearly a half run lower than his first-half mark. I’m willing to give Pettitte the benefit of the doubt given both his durability (four straight seasons of 200-plus innings) and the roster flexibility his one-year deal would provide following the 2009 season.

And so, our starting point for this discussion is this:

*on Opening Day 2009

Given the above list of “in-house” pitchers (pending Pettitte’s signing, of course), if the Yankees were to land CC Sabathia, which would be a no-brainer addition should Sabathia accept the team’s offer, the 2009 rotation would look like this:

I’d be content to stop there, with Aceves available to start the season in Hughes’ place and to compensate for Chamberlain’s 150-innings limit once Hughes (or Kennedy, etc.) arrives to take over the fifth spot. But what if Sabathia decides that returning to his home state and getting the opportunity to become one of the game’s best-hitting pitchers is more valuable to him than Yankee dollars? And is there a way for the Yankees to provide some more insurance in that fifth spot that might allow them to leave Hughes in Scranton for a larger portion of the season and hold Aceves in reserve in case of an injury to one of the top four?

There are roughly 50 major league starting pitchers on the free agent market right now, with only Ryan Dempster having signed, re-upping with the Cubs for $52 million over four years. I won’t bother you with all 50, as at least half of them are sub-Ponson level dreck (i.e. Horatio Ramirez and Jason Johnson, both of whom pitched primarily in relief last year), perpetually injured (Mark Prior, Matt Clement), or as in the case of future Hall of Famers Mussina and Greg Maddux, retired. Tom Glavine and John Smoltz will only pitch for the Braves if they return, and are also both 40-somethings coming off injury. Randy Johnson is another 40-something who, despite having a solid 2008 season, simply will not return to New York. Curt Schilling, yet another 40-something coming off injury and like Glavine and Smoltz a retirement candidate, has said he would not follow Johnny Damon’s lead by turning traitor on the Red Sox. Carving all of those pitchers out of the list and stopping before we get down to Ponson and his ilk, we get this list (all stats from 2008):

*as of Opening Day 2009

This is hardly the most exciting list of alternatives, and in an of itself justifies the Yankees’ seemingly outlandish offer to CC Sabathia (which, I should point out, I’m in favor of, even if I think the team should make Mark Teixeira an even higher priority). Still, there’s a chance Sabathia will sign elsewhere, and if he does, Lowe is cleary the next best option. I say that despite the similarity of his line above to that of Ben Sheets because of the disparate injury histories of the two pitchers. Lowe has made 32 or more starts in each of the last seven seasons. Sheets–who finished the 2008 season on the DL with elbow trouble and was unable to take the ball in the NLDS or as the Brewers’ Wild Card chase came down to the season’s final weekend–had not made more than 24 starts in any of the three years leading up to his walk year this year.

It will be interesting to see just how far Sheets’ stock drops as a result of this most recent elbow injury. Given his recent history, anything more than an incentive-based two-year deal would be too much. However, the word is that a two-year deal is about all Sheets is likely to be offered. Supposedly there is no structural damage in Sheets’ elbow. Given the choice between a five-year deal for A.J. Burnett, who has made more than 25 starts in a season just twice in the last six years, and a two-year deal for Sheets, I’d take my chances on Sheets.

To me, the most surprising name on the above list, and thus the biggest sleeper in the group, is former Mets closer Braden Looper. Just compare his line above to that of Burnett, who currently stands as one of the Yankees’ top targets. A career-long reliever who had last started as a 22-year-old minor leaguer in 1997, Looper was moved into the rotation prior to the 2007 season by a desperate Cardinals team and pitched well enough that year to remain in the role. He was even better in 2008, regaining most of the losses he suffered in his strikeout and groundball rates in 2007, and thus putting most of his rates as a starter in 2008 in line with the career marks he compiled out of the bullpen. Looper’s nothing more than a league average innings-eater, but he’s likely undervalued given his short track record as a starter, and he has a record of durability having made either 60 relief appearances or 30 starts in each of the last ten years.

The three lefties on the above list all come with their own individual warnings. Odalis Perez only averaged 5 1/3 innings per start in 2008, which was his first season with more than 140 innings pitched since 2005 and his first season with an ERA+ in the triple-digits since 2004. Prior to making 33 starts last year, Wolf hadn’t made more than 23 since 2003 due to a variety of injuries. Again, Sheets is a far more desirable option among these pitchers with spotty attendance given the fact that he brings a high-reward with his high level of risk.

Oliver Perez is a very different case. Just 27, he’s made 30 or more starts in four of the last five seasons, but two years ago ten of those starts came in the minors due to his poor performace in the majors. His poor K/BB rate is entirely the fault of his alarming walk rates (105 walks or 4.87 BB/9IP in 2008), which is a big red flag. Perez is a frustratingly inconsistent pitcher, who could easily pull a Jeff Weaver in the Bronx (or become the Yankees’ answer to Daniel Cabrera), though he does have the advantage of having already endured two and a half seasons in New York, including two late-season collapses by the Mets. Still, the Yankees are already up to their eyeballs in young, raw pitching talent. What they need is someone to hold down a spot in the major league rotation until that talent is ready, not another project pitcher who needs on-the-job training.

That brings us down to Paul Byrd, an aging junkballer who is good for some league average innings-eating, but will get absolutely torched every so often and is an inferior alternative to Looper, and Jon Garland, whose youth, World Series ring, and pair of recent 18-win seasons have made him overvalued (he made $12 million in 2008), though he does earn points for durability (32 or more starts seven years running). The big warning flag on Garland is the fact that his strikeout and walk rates have been converging over the past couple of seasons. Indeed, his K/BB above is the worst on the list, save for Penny, who was injured last year.

Penny is an interesting case and straddles the line between the viable candidates above and another group of veterans coming off injuries. In 2006, Penny started the All-Star Game. In 2007, he was third in the NL Cy Young voting, posting a 151 ERA+, and compiling 7.3 SNLVAR, though with a still-underwhelming 1.85 K/BB. This year, he was derailed by shoulder problems, and it’s telling that the Dodgers declined his $9.25 million option earlier this month. Penny is one of the sextet of pitchers who started for the Marlins earlier this decade and has since been plagued by injuries. The others include Burnett, Dempster, our pal Carl Pavano, Matt Clement, and Josh Beckett.

Penny brings to mind Freddy Garcia, who had the great misfortune of needing surgery on his labrum and rotator cuff just as he was becoming a free agent a year ago. Garcia spent most of the year unsigned while rehabbing his arm and finally caught on with the Tigers at the end of the year, making three middling starts for Detroit. Now 33, Garcia has made just 14 starts over the past two seasons and was only slightly above league average in 2006. Other notable pitchers who returned from injury in 2008, though with underwhelming results, include Pavano, Mike Hampton, Bartolo Colon, and Pedro Martinez, none of whom deserve anything more than a minor league contract with an invite to spring training. Certainly it’s possible that some team will look brilliant for signing one of these reclamation projects to an incentive-laden deal, but I wouldn’t want to count on any one of them for anything. After that bunch we get into the Ponsons and Livan Hernandez’s of the world, or start speculating about the effectiveness of a 39-year-old Jon Lieber who spent most of 2008 pitching in relief.

As far as the free-agent market goes, that’s all there is. Given that, I think the Yankees should limit themselves to Pettitte plus a maximum of two pitchers from among Sabathia and those listed in the table above. Assuming the Yankees sign either Sabathia or Lowe to be the big addition to the rotation, but not both, I’d recommend either a two-year deal for Ben Sheets, whose ace potential is worth a short-term gamble, or a low-cost offer to Braden Looper to eat innings at the back of the rotation with the understanding that he could always move back into the bullpen once the kids are ready. What the Yankees shouldn’t do, is sign multiple starters to long-term deals, thereby blocking their in-house talent at the major league level, and most of all, they should stay the hell away from the overrated and chronically infirm A.J. Burnett.