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Red Sox Should Extend Jon Lester’s Contract

Keep this man in Boston. (Photo by Greg Fiume/Getty Images)

After Dustin Pedroia received a seven-year $100 million contract extension from the Red Sox, the question could be raised as to which other members of the team are due for similar contracts, especially aces Jon Lester and Clay Buchholz. But if only one of these pitchers could receive such a contract, which would be a better fit to be extended?

Jon Lester has seen his ERA rise over 4.00 in each of the last two years, and his status as rising veteran ace fall to uncertain second or third starting option, especially with the addition of Jake Peavy.

Yet Lester remains the most viable candidate to receive a team extension because of his consistency. And while that certainly hasn’t been because of results since the start of 2012, Lester continues to take the mound every fifth day unlike anyone else in the Sox system.

The 29-year-old southpaw has started at least 30 games in every season since 2008, as opposed to Buchholz who has yet to reach that plateau in his career.

Additionally, after his $13 million team option in 2014, Lester is set to reach free agency. Regardless of his numbers, a left-handed starter without significant health concerns will draw interest from across the league—unless Boston locks him up through his prime.

Buchholz, on the other hand, is under Red Sox control through the 2017 season, should Boston continue to pick up options that will pay him at most $13.5 million. Buchholz’s continued injury problems should make it hard for the Sox to even consider passing the options that are lined up and giving him guaranteed money.

So while Lester may not be as strong a quality of pitcher as Buchholz, his value is much greater as a healthy left-handed starting pitcher with a career 2.57 ERA in 42.0 postseason innings–as opposed to Buchholz who has made just a single start.

Given his unexpected recent struggles, Lester could be in line for an incentive based contract that would possibly pay him more money than he’d be able to get on the open market based on his success.

For example, I think it would be very reasonable for the Sox to offer him a four-year contract for up to $58 million, giving him $10 million in 2014 (less than the $13 million team option), and giving him the opportunity to earn as much as $16 million in 2015, 2016, and 2017 depending on his durability and effectiveness. The contract could be based from about $10-$12 million for those years.

Jon Lester has been the face of the Boston rotation for years–and that’s not about to change with the success of Buchholz or the addition of Jake Peavy–so the Red Sox should do what it takes to keep him a valuable member of the rotation through the prime years of his career.

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