Ben Cherington Anticipates a ‘Constructive Conversation’ with Jon Lester

Over the course of the offseason that started as soon as World Series hero Madison Bumgarner received the keys to a new truck loaded with technology and stuff, the whereabouts of another left-handed pitcher with a dominant postseason pedigree is likely to be a primary focus for many Red Sox fans. And maybe for the team’s front office, too.

With Jon Lester now a free agent, and the Sox needing to fill the vacancy atop their rotation that was created when they traded the ace to Oakland in July, Ben Cherington said Thursday that he’d like to discuss a potential return to Boston with the southpaw.

“We’re going to try to build the best team we can, and we know that one of the areas we need to add to is the rotation. Obviously we know him well, and we hope we get a chance to talk to him,” said the Red Sox GM. “I’m sure we’ll talk to others, and I’m sure he’ll talk to others, so we just have to get into the offseason and see what comes of it.”

With righty Max Scherzer, Lester is likely to be among the two most sought-after free-agent starters — and is accordingly in line to command a commitment of more than $100 million. Before the start of the 2014 season the Red Sox reportedly offered him a four-year deal that would’ve paid him $72 million, and after Lester turned that down it’s believed that no other formal offers were made.

Especially now that other teams can also get in on the bidding, then, in a contractual sense Boston is essentially starting over in its pursuit. But if the Sox are serious in their interest to bring Lester back, they can at least hope the familiarity gives them a head start when negotiations can begin on Tuesday.

“I feel like the relationship is in place that will allow for a conversation, and from there we’ll have to see where it goes,” Cherington said. “He’ll have options, obviously. We will, too, but we look forward to having a constructive conversation at some point.”