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Yankees Potential 2015 Free Agent Target: Jon Lester

Could Lester be the latest in a line of Red Sox to trade Beantown for pinstripes?

Dilip Vishwanat

2014 Statistics: 219.2 innings pitched, 2.46 ERA, 2.80 FIP, 9.01 K/9, 6.1 WAR

2015 Age: Turns 31 on January 7th

Position: Left-handed starting pitcher

Jon Lester has been making Yankees fans miserable for a while now as part of the Boston Red Sox pitching staff. After being traded to the Oakland Athletics ahead of the 2014 deadline possibly signified a true end to Lester's tenure in Boston, the left-hander has hit the free agent market just before his 31st birthday. Seeing as the Yankees have only one left-handed pitcher under contract for next season, and he happens to come along with a giant question mark and degenerative knees, it might be worth it for the Yankees to pursue Lester if the price is right.

With a 6.1 fWAR, Lester had a contract season that many players can only dream of. He turned in a career high in innings, a career low in ERA, and his highest WAR total since 2009 with the Red Sox. Those efforts will no doubt be rewarded with a shiny contract in the six-seven year range from whichever team acquires the lefty this offseason. It's easy to understand why the Yankees might be hesitant to pursue another giant contract, particularly for a pitcher over 30, with their payroll already fairly high after last offseason's spending spree. CC Sabathia's contract extension already looks pretty disastrous and the team shouldn't be in any hurry to double down on that. However, adding Lester to a rotation with Masahiro Tanaka, Michael Pineda, potentially Brandon McCarthy, and one of Sabathia, Ivan Nova, and Shane Greene would certainly be formidable in the AL East after missing the postseason for two consecutive seasons.

The added bonus to pursuing Lester over Max Scherzer or James Shields would be the lack of draft compensation tied to his signing. That will likely make him more desirable to all teams, driving the price up, but the Yankees can certainly spend more money if they choose to. Not losing the draft pick would be appealing after they lost picks in the 2014 draft for signing Jacoby Ellsbury, Brian McCann, and Carlos Beltran. Signing Lester, McCarthy, Chase Headley, David Robertson, and, for example, Asdrubal Cabrera would allow them to keep all their draft picks. It would, however, push payroll to a much higher figure. The Steinbrenners may not be willing to part with the extra precious millions.

Left-handed pitchers have traditionally done well in the confines of Yankee Stadium, and the Yankees would be without a southpaw if Sabathia is unable to stay healthy. In that case, having Lester provide a change of pace from the righty-heavy rotation could be very beneficial. The team will have to decide whether someone like Lester is worth the investment, knowing that there is a good possibility that the end of any contract he signs won't look very good. If they wanted to sign one of the big name pitchers on the market, it seems like Lester is definitely the way to go. Rumor has it that they would rather go after names like Jason Hammel and Chris Capuano after their top choice of McCarthy. That might not be enough to satisfy a restless (and spoiled) fan base to check back in. Wouldn't three seasons in a row of missing the playoffs just continue to mean an embarrassing attendance showing during most home games? The Alex Rodriguez circus likely isn't enough to make up for that.

Would you take a chance on Lester if you were the Yankees, or do you think they are better off staying away? Do you think adding Lester would make a difference in their chances in 2015?