A signing 3,000 miles away from Boston will likely impact the future of the Red Sox starting rotation. The Los Angeles Dodgers agreed with 25-year-old left-hander Clayton Kershaw on a seven-year, $215 million contract. Kershaw won the National League Cy Young Award in 2011 and 2013 and boasts a 77-46 record, a 2.60 ERA, a 1.09 WHIP and 1,206 strikeouts in 1,180 innings over his six-year Major League career.
Jon Lester, who turned 30 earlier this month, is not as dominant as Kershaw – at least not in the regular season – but he does own a 100-56 record, a 3.76 ERA and 1,237 strikeouts in 1,376 innings over eight big league campaigns.
After holding St. Louis to one run over 15.1 innings and two starts (both wins) in last October’s World Series, Lester has a 2.11 ERA and a 1.04 WHIP with a 6-4 record in 13 post-season appearances (11 starts) for the Red Sox.
Picking up Lester’s $13 million team option for 2014 was a no-brainer for the Red Sox, but it is uncertain if they will sign him to an extension before he becomes eligible for free agency this fall. If the ownership group and general manager Ben Cherington want to give Lester a handsome long-term deal, they can likely afford to do so since they could have as much as $96 million trimmed from the payroll after the 2014 season.
Some of those players – like veteran right-handers Jake Peavy ($16.5 million salary for 2014 as calculated for luxury tax purposes) and Ryan Dempster ($13.5 million for 2014) – could be traded before the upcoming season begins. Even if they remain this year, the Sox will probably let them walk as free agents because they have Clay Buchholz and Felix Doubront under affordable team control, and John Lackey is under contract for 2015 at just $500,000.
The organization has a plethora of talented starting pitching prospects. Brandon Workman (who made his big league debut in 2013 and pitched well), Matt Barnes, Anthony Ranaudo, Allen Webster and Henry Owens are poised to help the Red Sox beginning the 2014 season and the following year.
The Red Sox believe they will not have to spend big money on free agents at center field, shortstop, third base and catcher because of top prospects like Jackie Bradley, Xander Bogaerts, Garin Cecchini and Christian Vazquez (and fellow top backstop prospect Blake Swihart).
Will Middlebrooks, who is 25 and has 30 home run power potential, could be traded before spring training if the Sox bring back veteran shortstop Stephen Drew and station Bogaerts at third base. Media reports indicate that the club is reluctant to deal Middlebrooks, though, which could mean that Cecchini will be moved to an outfield spot or even eventually first base.
Since the Red Sox are not tied to long-term albatross deals, feature a well-stocked farm system that can effectively fill multiple holes from within and have high-ceiling arms who can at the least fill the back end of the rotation, Lester could be signed to a substantial contract extension before the 2014 season ends. He has proven himself as a go-to starter in the post-season, and aside from 2012, he has established himself as a top of the rotation arm.
Lester will likely be kept in Boston for the long term. The question is, will he agree to a team-friendly deal like Dustin Pedroia and demand a costly contract such as the one the Red Sox refused to dole out to Jacoby Ellsbury?
