Will Red Sox Sign Give Jon Lester an Extension?

While Boston Red Sox general manager Ben Cherington will work over the All-Star break to explore ways to upgrade his club’s lineup and determine whether or not to trade starting pitcher Jake Peavy, he might also be involved in discussing a contract extension with veteran left-handed ace Jon Lester.

The 30-year-old Lester is just 9-7, but he is having the best season of his nine-year Major League career with a 2.65 ERA, a 1.14 WHIP and 134 strikeouts in 129 innings over 19 starts.

The Red Sox will shed more than $72 million in payroll after the 2014 season, and only three players (David Ortiz, Dustin Pedroia and Clay Buchholz) are signed beyond 2015. Those factors, along with the depth of high ceiling prospects in the Red Sox system that will allow the team to fill several positions internally and at minimal cost, could lead the team to extend an offer that will satisfy Lester.

Media reports indicate that Lester’s camp was displeased with Boston’s alleged four-year, $70 million offer in spring training. Lester has told reporters that he would take a “hometown discount” to remain with the Red Sox, yet it will likely require a deal that includes a higher annual salary for fewer years (four years, $100 million?) or a longer term contract of five or six years north of $20 million a season.

Lester, who turns 31 in January, has a career record of 109-63 with a 3.66 ERA and a 1.29 WHIP. Even more impressive are his post-season numbers. He is 6-4 with a 2.11 ERA over 13 appearances and 11 starts. In the World Series, he is 3-0 with a 0.43 ERA in three starts.

The Red Sox have veteran right-hander John Lackey under contract for 2015 at $500,000, and Clay Buchholz is signed to a reasonable $12 million figure next season (and $13 million in 2016 and $13.5 million in 2017). A veteran tandem of Lester, Lackey and Buchholz leading the rotation would make the Red Sox a World Series contender in 2015. The club also has an array of high-ceiling young starting pitchers like Rubby De La Rosa, Brandon Workman, Anthony Ranaudo, Allen Webster and Henry Owens.

The Red Sox can afford to ink Lester to a long-term contract extension. It could cost them $125 to $140 million over five years, and Lester could wait until the offseason and test the market. Since unloading the albatross contracts of Adrian Gonzalez and Carl Crawford, Boston has exercised restraint with deals. Cherington must determine whether or not Lester is a legitimate ace, and the ownership group must decide if retaining the left-hander is worth the long-term investment.