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The last time Andy Pettitte retired, prior to the 2011 season, he announced it just a week before pitchers and catchers were due to report to spring training. As a result, he left the Yankees, who had hoped to have Pettitte in their starting rotation that season, in the lurch. New York still managed to pull out another division title that year, thanks to the second-best offense in baseball, an outstanding bullpen and a true ace in CC Sabathia.
The 2014 Yankees, however, are unlikely to enjoy such luxuries. Fortunately for them, the timing of Pettitte's second, and likely final, retirement on Friday will at least give the Yankees the opportunity to assemble a proper rotation without having to give 51 starts to veteran non-roster invitees, as the 2011 team did.
In addition to Pettitte retiring, Hiroki Kuroda and Phil Hughes will be free agents this offseason, leaving Sabathia and Ivan Nova as the only sure things for New York's 2014 rotation. Of course, neither of those men is a sure thing. Nova has been inconsistent in his three full major league seasons and can't be relied upon to anchor the front of a rotation. Sabathia, meanwhile, has seen his velocity drop three miles per hour from 2011 and has suffered through his worst major league season this year with career highs in ERA (4.90), WHIP (1.37), home runs allowed (28), losses (13) and hit rate (9.6 H/9) while leading the majors in earned runs allowed.
The Yankees would obviously love to have Kuroda back, as he has been their best starting pitcher in each of his two seasons with the team. However, he played both of those seasons on one-year contracts and has proven to be an idiosyncratic free agent, one who appears to base his decisions far more on personal preference than on the size and length of the offers he receives. When last asked about his plans for 2014, the 38-year-old righty reportedly gave no indication of his intentions.
Beyond Kuroda, there are some viable free agent alternatives. Despite his struggles with the Rangers, Matt Garza, who won't be 30 until two days before Thanksgiving, seems likely to be the belle of the ball in terms of starting pitchers this winter. Ervin Santana, who is a year older, has significantly upped his free agent profile with a strong walk year for the Royals.
The Yankees aren't a team built around youth, however, so plays for reliable veterans such as Tim Hudson (38), Bronson Arroyo (36) or even the suddenly ageless Bartolo Colon (40) could make sense for a team just trying to hang on for another year with Alex Rodriguez (38), Ichiro Suzuki (39), Alfonso Soriano (37), Vernon Wells (34), Mark Teixiera (33), Sabathia (33), and, via the player option he's now likely to pick up, Derek Jeter (39) all under contract for next year. The same holds true for offering a "pillow contract" -- the term agent Scott Boras uses for an incentive-based deal -- to the likes of Roy Halladay or Tim Lincecum, though those are obviously far less reliable options, and the Yankees need dependable starters as much as they need ones with high upsides.
If New York can fill two of the spots behind Sabathia with free agents -- be it Kuroda plus one, or two new faces -- that would push Nova to number four, and they have plenty of in-house options for that fifth spot. Chief among them are 2013 rookies David Phelps and Adam Warren. Phelps posted a 3.63 ERA in his first 10 starts this season before developing elbow problems from which he has since returned, while Warren has pitched well in long relief. The Yankees can also hold out some hope for the return of Michael Pineda from the shoulder surgery that wiped out his first two seasons with the organization, though they can't count on anything from the righthander who hasn't thrown a major league pitch since 2011 or a minor league one since Aug. 2. The Yankees also liked what they saw from rookie Vidal Nuno this season before a groin injury ended his season in early June. Behind that group, the organization's top pitching prospect, Jose Ramirez, hit Triple-A this season, though he also missed time due to injury, and lefty Nik Turley, who spent most of 2013 in Double-A could get in the mix, as well.
None of the free-agent or in-house options are terribly inspiring, though. Recognizing that New York isn't likely to get into a bidding war over any of the above pitchers, one likely outcome might be something like this:
LHP - CC Sabathia
RHP - Hiroki Kuroda
RHP - Bronson Arroyo
RHP - Ivan Nova
RHP - David Phelps
The only real changes there are discarding the free agent Hughes for the less heralded, less experience and thus more easily replaced Phelps, and replacing the retiring Pettitte with another veteran workhorse such as pending free-agent Arroyo.
Of course, for that to work, they'd need Kuroda to come back on another team-friendly deal (he made $15 million this year), Nova to stay healthy and build on his solid showing since returning from the disabled list this season and Sabathia to bounce back from a season in which appeared to be bearing the burden of his heavy workloads from the previous six.
Another season from a 42-year-old Pettitte, who has been merely league average this season, wouldn't greatly improve that outlook. He'd simply replace Arroyo in the above speculative rotation. By announcing his retirement now, rather than waiting until most of the above free agents are off the market, Pettitte has given the Yankees every opportunity to replace him, which short of returning for 2014, is the best thing he could have done for them.