Will Red Sox break from philosophy in Jon Lester contract talks?

The Red Sox’ initial contract extension offer to pitcher Jon Lester was $70 million over four years.
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The Red Sox’ initial contract extension offer to pitcher Jon Lester was $70 million over four years.

The Red Sox have the resources to re-sign Jon Lester now or when he becomes a free agent. The question is will they do it?

A team philosophy has developed over the past two years that no player is worth a long-term commitment of more than five years, and that philosophy has been reflected in both the Jacoby Ellsbury and Jon Lester negotiations.

The Red Sox were not willing to go to even $100 million over five years on Ellsbury, according to a major league source, and their initial offer of four years, $70 million is a reflection of where they will go on Lester.


It’s hard to imagine there wouldn’t be a deal that would include vesting options after a fourth year. The Red Sox could always break from this philosophy in special cases, but what we don’t know is whether they view Lester as a special case.

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The Red Sox have now gotten a look at their young pitchers in the majors and they like what they see from Brandon Workman and Rubby De La Rosa, with Henry Owens, Matt Barnes, and Anthony Ranaudo to come.

Obviously, none of the youngsters are Lester. At least not yet.

When ESPN reported Sunday that the Red Sox and Lester had re-opened contract talks, it seemed as if the Red Sox had suddenly changed their stance.

But people within the organization, and then Lester himself, said the report wasn’t true.


“I don’t think they’ve started anything. I know the conversation has been there throughout the season with different topics,” Lester said. “Like I said from the beginning of the season, the conversations were amicable and conversations continued. Nothing as far as contract or numbers or anything like that.”

Lester wanted the focus to remain on the team, which took two out of three in New York..

“It’s an added distraction we don’t need right now. We just need to focus on playing baseball and get back to competing in the East,” he said. “We don’t need to worry about my contract stuff. That’s the last thing I want these guys to worry about.”

There’s more optimism with the Red Sox, who are just five games out in the loss column in the AL East. With Lester, John Lackey, and Clay Buchholz as the cornerstone of the rotation and Workman as the fourth starter, the Red Sox seem to be in better shape with their pitching than other AL East teams.

The one sore spot has been Jake Peavy.


The Red Sox have pretty much made Peavy and Felix Doubront, who has been relegated to the bullpen, available in trade talks.

The Milwaukee Brewers and Texas Rangers were scouting the Red Sox in New York.

Red Sox general manager Ben Cherington said the team has not ruled out pursuing another hitter, even with the call-up of Mookie Betts. Two other Red Sox rookies – Jackie Bradley Jr. and Xander Bogaerts – have struggled offensively. So the Red Sox could be in line for both an outfielder and possibly another infielder.

The Red Sox seem set at catcher. John Farrell said that there could be more opportunities for David Ross, who has seen an upswing in his offense of late. Farrell said that there could be matchups where they could utilize Ross more than having him be Lester’s personal catcher.

Follow Nick Cafardo on Twitter at @nickcafardo.