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Red Sox Face Dilemma with Jon Lester

Red Sox ace Jon Lester throws for the American League All-Star Game from Target Field in Minnesota. (Photo by Elsa/Getty Images)

Jon Lester is the ace of the Boston Red Sox, but for how much longer will he hold that title?

Lester is set to become a free agent following the 2014 season, in which he will have the ability to sign with any team that offers him a contract, which means that his time in the Red Sox organization could be coming to an end. The 30-year-old pitcher was drafted by Boston in the second round of the 2002 amateur draft, and has been at the heart of their two most recent World Series championships.

Lester has also conquered his fair share of demons off of the diamond. During the 2006 season, he was diagnosed with non-Hodgkin lymphoma. His recovery was inspirational as he returned to the major leagues as soon as the 2007 season. On the other end of the spectrum, Lester was at the center of the chicken-and-beer fiasco a few years ago when the clubhouse fell apart. The native of Tacoma, Washington has known no other baseball home than Boston, making this impending free agency crucial for his legacy as one of the greatest Red Sox pitchers of all-time.

From the perspective of the team, the Red Sox have great pitching depth in the minor leagues, but would be missing a clear ace heading into 2015 unless Clay Buchholz keeps up his recent success since returning from the disabled list. The only reported offer made to Lester was an initial four-year deal for $70 million, which was labeled as the team “low-balling” Lester, who would receive much larger offers on the open market.

The deal Lester signs will likely be his last large contract with a team, as he should have the opportunity to sign for more than four years given his incredible consistency. Lester has made at least 31 starts in each of the last six seasons dating back to 2008, and is on pace for his best career year in 2014 with a career-best 2.65 ERA in 129.0 innings at the All-Star break.

The narrative of having Lester return to Boston sounds great, especially if he was willing to take a hometown discount, but realistically the Red Sox shouldn’t block the potential of players like Henry Owens and Matt Barnes by investing in a pitcher on the wrong side of 30. It would be stunning to see the Red Sox sign Lester to a lengthy deal, especially after the efforts by the organization to avoid such deals since the disastrous Carl Crawford contract.

Perhaps the perfect middle ground would be a short-term overpay that would give Lester another opportunity for free agency with years left in his career. A three-year deal for around $75 million would be fair for both sides, as it would keep Lester in Boston for three prime years of his career while overpaying to avoid a lengthy commitment.

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