Is Jon Lester worth the long-term deal? It’s not so clear anymore


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One of the biggest questions revolving around the future of the Red Sox is whether they will decide to extend Jon Lester this season, resign him once he hits free agency at the end of the year or simply let him walk and pitch in another uniform going forward. Most Sox fans truly like Lester. He defeated lymphoma, works hard, will take the ball every fifth day, has a hard-nosed demeanor on the mound and doesn’t cause distractions with unnecessary talking out of turn to the media. However, is this all enough for the Sox brass to want to keep him on Yawkey Way for the foreseeable future? It may not be. What seemed like a given the last few seasons may not be so set in stone.

The Red Sox will have John Lackey and Felix Doubront for very manageable contracts next season for sure. It is obvious that Clay Buchholz has had his struggles as of late, but he most likely will be with the club as well. We all know about the well-touted Henry Owens, who according to most MLB scouts, has all the makings of a budding superstar. That leaves one spot open in the rotation. Some would say that Boston will have to sign Lester to have a formidable staff and to have a true ace, though one could argue that John Lackey is a veteran who has pitched like an ace over the course of the last two seasons.

It is widely understood that Boston’s ownership has plenty to spend, but they’ve taken a new approach ever since the famous deal with the Dodgers set them free in 2012. So while I think they would love to sign Lester for three to four years, he is going to be looking for five to seven years in a new contract. He has thrown a ton of pitches and total innings in his career so far (1410 IP in 226 total games). It is a valuable asset, but Cherington and company could be getting weary of wear and tear.

The Red Sox operations staff will have to weigh all of this and decide their best option for the future. There are other free agents who will certainly be cheaper and will most likely sign for less than Lester – Justin Masterson, Ervin Santana, James Shields – just to name a few. Sure, not many of these names are going to sell tickets on their own, but they may fit the new Red Sox mold much better than signing Lester long term.

It will be interesting to see how the Red Sox approach any further negotiations since the Jon Lester “hometown discount” comments and the leaking of the Red Sox low offer of four years at $70 million. My advice to Lester lovers: get your fill while you can and enjoy watching him now, because the future looks a little murky for this relationship.