Entering the offseason "hot stove," free agent negotiations, the Yankees seem to be in agreement on every organizational level that their pitching rotation must be the first issue addressed.
CC Sabathia and A.J. Burnett will once again lead the New York squad but after those two front line individuals, the situation gets murky.
Andy Pettitte, despise multiple clutch postseason performances last season, is no longer a true third starter. With Joba Chamberlain or Phil Hughes probably holding down the fourth spot, it is likely that the Yankees will shift Pettitte into the five-hole and try to sign a solid arm to provide more consistency at the front end of the staff. And while Roy Halladay will likely be traded somewhere this winter and free agent Joel Piñeiro may provide a fine addition to some team's roster (likely in the NL), it seems like the early indications are pointing toward another Red Sox/Yankees offseason rumble, this time over John Lackey. 
For the Yankees, Lackey would provide a key stabilizing force in the rotation at what will likely be a bargain price (relatively speaking). John has all the proven tools necessary to perform successfully in a big market, pressure-filled residency. Ever since he started and won Game 7 of the 2002 World Series against San Francisco, Lackey has been known as a consistent, clutch, and big game hurler.
In 2009 — at age 30 — Lackey was very good despite injury issues, posting a 3.83 ERA and a 1.27 WHIP. While his hit total (177 in 176 2/3 innings) isn't ideal, he walked only 47 batters in that span while striking out 139, demonstrating the early onset of a crucial evolution from the power pitcher who struck out over 190 batters twice in his career to a savvy veteran who uses his control, command, and resourcefulness to get the job done. And while Lackey was only 11-8 in '09, his other figures clearly show this was a case of a lack of run support from an offense that was at times anemic. Lackey's strikeouts have decreased but so have his walk and hit totals, indicating that he is a pitcher who still has a number of productive seasons ahead of him as he adjusts to his new capabilities.
Because of the projected, depression-induced, stricter spending habits of nearly every team in baseball this offseason, there may be no better time for the Yankees to snag a pitcher of John Lackey's caliber without a large financial investment or minor league fire sale. An MLB executive told 1050 ESPN New York's Andrew Marchand that Lackey may be "lucky" to see AJ Burnett money ($82.5 million over five years).
Article comments
1 - momus
Absolutely the WRONG place to spend money - why is Lackey viewed as the pick of the litter in this season's free-agent market of pitchers? Because he is the ONLY one of any note. Let someone else pick up the 20-million-a-year-for-5-years tab that his agent is floating - Cashman has wasted more money in the past decade chasing down overrated pitchers and ignoring the ones in his own back yard, the Yankees do not need another Weaver, Contreras, Pavanno, Wright, Vasquez, Brown, Johnson ... and remember he gave up 2 southpaws for all these jackasses - Ted Lilly and Andy. This mook's track record with pitchers is terrible.
2 - Tony
Lackey will be much cheaper than most of those pitchers were and he is better. His numbers are that of a very good 3rd starter which is exactly what he would be. It is not a "pick of the litter issue." If anything, Halladay (who will be traded) is the "pick of the litter."
I don't think I suggested anywhere that Lackey will come in and dominate but if he adds another 5-7 wins in the season over their previous rotation he is worth the money, especially with his postseason experience.
You're right, Cashman has a terrible history with pitchers but that was before he started to understand the sabermetric peripheral measurement necessary to sign the correct talent. Those moves prove you can't buy a championship by Lackey is a solid 3 year commitment.