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Jon Lester Trade Rumors: Should Red Sox sign or trade him?

By Jeff Louderback

Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the second inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports
Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the second inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports /
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Jon Lester’s fortunes have taken an exhilarating rollercoaster ride over the last three years.

Rewind the clock to 2011, and that will uncover a year when the Washington native produced a 15-9 record and a 3.25 ERA but flopped in September, a month that saw the Boston Red Sox plummet from likely American League East championship status to falling out of the wild card picture on the season’s final day.

Amid the dysfunctional circus that marked Bobby Valentine’s lone stand managing the Boston Red Sox in 2012, Lester struggled to a 9-14 record and a career-high 4.82 ERA. He is not an ace, critics argued. The Red Sox are unlikely to pick up his $13 million team option after the 2013 season, they forecasted.

Fast forward to present day. The 30-year-old Lester has followed a solid 2013 campaign (when he posted a 15-8 regular season mark and a 2-0 record with a 0.59 ERA in two World Series starts) with the best numbers in his nine season Major League career. Eligible to become a free agent at season’s end, the left-hander is 10-7 with a 2.52 ERA and a 1.12 WHIP in 20 starts. He is 5-1 with a 1.54 ERA over his last 10 outings, including a matchup with Tampa Bay left-hander David Price on Friday when Lester permitted two runs and six hits with seven strikeouts and one walk over six innings, getting a no-decision in his team’s 6-4 loss.

That Friday night clash in St. Petersburg, FL showcased two of the game’s premiere left-handed starters. Lester and Price are alsocurrently coveted by opposing teams hoping to pry them away via trade. With Tampa Bay thriving, winning nine of its last 10 games, and Boston struggling, Price couldremain with his club for at least theremainder of the season and Lester might be the ace who gets dealt.

Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the first inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports
Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the first inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports /

Lester is authoring the best season of his career at an ideal time. Along with Detroit’s Max Scherzer and Kansas City’s James Shields, he is considered the premium potential free agent pitching prize this offseason. If he reaches free agency, that is.

The Red Sox reportedly extended an initial four-year, $70 million offer to the arm who has generated a 110-63 regular season record and, most importantly, a 6-4 mark with a 2.11 ERA in 13 post-season appearances, including a 3-0 record and a 0.43 ERA in three World Series starts. Understandably, Lester said, “No, thanks.”

Over the weekend, media reports indicated that the Los Angeles Dodgers were interested in acquiring Lester. They are eager to unload disgruntled outfielder Matt Kemp and the cumbersome $107 million remaining on his deal while the Red Sox apparently prefer a transaction centered around 22-year-old power-hitting outfielder Joc Pederson, a prospect the Dodgers are reluctant to trade.

Adding another top prospect to their already deep farm system is more palatable to the Red Sox than losing Lester through free agency and gaining a draft pick. Of course, the team has another option – signing him to an extension before he reaches free agency.

Considering that Lester has emerged as a true staff ace and is a workhorse who routinely tops 200 innings every year and thrives in October, the Red Sox are likely to give him a more attractive offer. It will probably be a proposed deal that exceeds $20 million a year and will cover five to six years. Lester is worth the risk, and the Red Sox can afford to take that chance that he will deliver in the final few years of a new contract.

Boston 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, should inspire the club to extend an offer that will satisfy Lester.

Lester turns 31 in January. The Red Sox rotation also features John Lackey (who is 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 anchoring the rotation would make the Red Sox a World Series contender in 2015.

With the assortment of high-ceiling young starting pitchers like Rubby De La Rosa, Brandon Workman, Anthony Ranaudo, Allen Webster and Henry Owens, Boston has the depth to carry Lester on an annual salary ranging from $20 million to $25 million without sacrificing results.

At 48-57 and 10 ½ games behind American League East leading Baltimore, the Red Sox might have dug themselves too deep of a hole to escape in 2014, but inking Lester to a well-deserved extension would bolster the club’s morale and hopes for the long term.

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