Can The Yankees Swoop In And Steal Jon Lester Too?

Jun 28, 2014; Bronx, NY, USA; Boston Red Sox starting pitcher Jon Lester (31) pitches during the first inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports

This coming winter is a long ways off. The New York Yankees have bigger problems to think about than who might or might not become available during next winter’s free agent class. However, there may be an opportunity to once again weaken their bitter rivals, the Boston Red Sox. Jon Heyman of CBSSports.com, is reporting that Red Sox’ ace, lefty Jon Lester, and the team, have decided to not re-engage in contract talks until at least October. By then, the Red Sox will most likely have been mathematically eliminated from playoff contention, and Lester may have a better idea of how his market is going to shape up.

Why talk Lester now? As with other Red Sox greats of the past, by entering free agency rather than signing an extension, it gives the Yankees an opportunity to swoop in, overwhelm the would be free agent with an offer he can’t refuse, and before the ink would dry, Lester could be holding up a pinstriped Yankees jersey, with former teammate Jacoby Ellsbury there to welcome him to the Evil Empire with open arms. As per Heyman:

"“One person close to Lester said he believes Lester has a desire to continue with the Red Sox, though of course as a free agent, there will be plenty of suitors. One of those pursuers is expected to be the Yankees, who are said by a source to be great admirers of Lester, especially for his big-game pitching record. He has helped the Red Sox win two World Series, pitching brilliantly in the fall classics of 2007 and ’13.”"

(h/t, Jon Heyman, CBS Sports and MLB Insider)

With an uncertain future surrounding former ace C.C. Sabathia, the continuing injury problems of Michael Pineda, and nothing to support Masahiro Tanaka, Lester could provide a vital new cog for rebuilding the Yankees’ starting pitching rotation. Not only that, but to weaken their most hated rival, would be just double the pleasure. Having to give up a draft pick is of minimal cost when the Yankees as a franchise, continue to fail in developing their own talent.