Boston Red Sox Catching Up With Old Friends: Jon Lester


You know that nostalgic feeling that you get when catching up with an old friend that you haven’t seen for a while? This offseason the BoSox Injection staff will be checking up on a number of former Red Sox players to see what they have been up to since leaving Boston, while reflecting on how the team has managed to replace them since they left.

Jon Lester

Red Sox Nation was devastated when the team failed to bring Jon Lester back to Boston. After being shipped to the Oakland A’s in a trade deadline deal, Lester hit the open market for the first time in his career last winter. While the Red Sox remained in the mix until the bitter end, the veteran lefty ultimately signed with the Chicago Cubs on a six-year, $155 million deal.

You can’t really blame the Red Sox too much for refusing to match that offer. The front office has been understandably hesitant to grant long-term contracts to pitchers over 30, so a six-year deal wasn’t particularly appealing. Chicago made Lester the third highest paid pitcher in the league on an average annual basis, yet he’s not even close to being one of the three best pitchers in baseball. Lester is very good, but he’s not even the ace of his own team. Jake Arrieta is the Cubs pitcher garnering Cy Young votes this year, while Lester isn’t even in the conversation.

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It’s not as if Lester had a poor season. He had a losing record at 11-12, but that’s not entirely his fault given the young team playing behind him was bound to suffer some growing pains. The 3.72 runs per game that his offense provided him with was the 6th lowest in the National League.

In 2014 Lester produced the best season of his career in a contract year, only to settle back down closer to the pitcher he had always been before. Despite leaving behind the powerhouse offenses of the AL East for the weaker lineups in the Senior Circuit, Lester posted a 3.34 ERA that wasn’t much lower than his career average. That was still good for the 21st best ERA in the majors, to go along with a 2.9 WAR that ranked 39th. Those numbers are great, but not quite elite. If he’s not pitching like one of the top-20 pitchers in baseball in Year 1 of his mega-contract, it’s hard to see how he’ll ever live up to it when factoring an inevitable decline at the tail end of the deal.

Even if Lester didn’t exactly fit the description of an elite starter this season, he was still significantly better than anyone on the Red Sox staff. Boston’s rotation ranked 13th in the league with a collective 4.39 ERA, which improved from dead last only after the infusion of a pair of rookie pitchers.

Would the Red Sox have been better off with Lester in their rotation this season? Absolutely. Would it have made enough of a difference for them to have made the postseason? Probably not.

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Let’s pretend for a moment that the Red Sox had extended Lester and the deadline deal with Oakland never happened. Boston wouldn’t have acquired Yoenis Cespedes, who was the trade chip sent to Detroit last winter for Rick Porcello. While I’m on board with almost anything that retracts the ill-fated Procello trade, Lester’s value to the Cubs this year was worth only about two wins more than the 0.6 WAR Porcello produced this year. At best the Red Sox get a few extra wins with Lester leading the rotation instead of Porcello. They may not have finished in last place again, but they still aren’t a playoff team.

There’s no doubting that the Red Sox could use a pitcher of Lester’s caliber. Would it have been worth it to overpay for the sake of having a top of the rotation starter to rely on? Not when they can wait a year to dive into a more enticing batch of free agent pitchers or cash in a few chips from their top ranked farm system to acquire a younger, cheaper pitcher that may be even better than Lester.

Don’t expect the Red Sox to make the same mistake again of thinking they can compete with a collection of middle of the rotation starters. Passing on Lester led to a poor result this season, but we’ll have to wait to see how they rectify that to determine if it was the right move in the long run.