Ben Cherington: Jon Lester Contract Talks ‘Challenging’ For Red Sox

Jon LesterJon Lester and the Boston Red Sox have a mutual interest in extending their relationship beyond 2014. So what’s stopping Lester and the Red Sox from agreeing to a contract extension before the left-hander hits free agency next offseason?

Well, as Red Sox general manager Ben Cherington said Thursday on WEEI’s “Dennis & Callahan,” things aren’t always as easy as they seem, especially when it comes to high-profile players and the open market.

“The devil’s in the details on any significant contract, whether it’s for Lester or anybody else that we’re talking about a long-term deal,” Cherington said. “… The hard part with Jon is that he’s done such a good job, he’s been so consistent, so durable pitching in tough positions, pitching in the postseason. He’s got a lot going for him, and he’s just a few months from free agency at a time when you and we all see what’s happened with starting pitching in the free agent market and (the) contracts (that) have come down over the past two, three years.”

There certainly have been some monstrous free-agent contracts doled out recently. Justin Verlander (five years, $140 million), Felix Hernandez (five years, $135.5 million) and Clayton Kershaw (seven years, $215 million) are among the high-priced hurlers who have signed significant contract extensions over the last 14 months, and Max Scherzer reportedly rejected a six-year, $144 million contract offer. All of this information impacts Lester’s negotiations, even if the 30-year-old isn’t in the exact same ballpark as the aforementioned pitchers.

“That makes it challenging, and we have to look at it through our own lens that what’s clear as we’ve stated — and (owner) John Henry said this and I said this — we want Jon Lester to be here,” Cherington said. “We will work as hard as we can to try to make that work, but there’s things that other teams might do that we just won’t do. … We’re just going to keep working at it. While we’re not currently, we’ll be working on it at the right time and when there’s a desire on both sides there’s always a chance.”

Lester, who was drafted by the Red Sox in the second round in 2002, has spent his entire career with Boston. The veteran lefty is coming off a 2013 season in which he went 15-8 with a 3.75 ERA in 33 regular-season starts before once again elevating his game in the postseason.

Lester and the Red Sox have tabled discussions for the time being, and Boston previously has shown a willingness to walk away from the bargaining table if things get too expensive — see: Jacoby Ellsbury. But both sides clearly want to keep their good relationship intact, so perhaps some sacrifices will be made to get a deal done before next winter.

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