LAKE BUENA VISTA, Fla. -- Once general manager Ben Cherington gets through the busy part of his offseason, he could turn to an important longer-term issue -- making sure lefty ace Jon Lester, coming off a solid season and brilliant postseason, doesn't leave as a free agent following the 2014 season.
The Red Sox drafted Lester out of high school back in 2002 and would love to continue the relationship.
"He's a key guy," said Cherington. "Obviously, he's been a horse for us for a long time and didn't show any signs of slowing down this October. Obviously, he's a guy we would like to keep. The timing of those conversations, usually it's a later-in-the-winter or a Spring Training thing, or after the contract [runs out]. We'll see. I think there will certainly be a willingness to have a conversation, so we'll see where it goes, but we haven't done that yet."
Letting Lester get to free agency could turn into a risk.
"We know him personally, and we know what he does on the mound," Cherington said. "And he knows us, so there's a relationship. We'll see if there is mutual interest, I don't know. But we're certainly open to having a conversation at some point."
Ian Browne is a reporter for MLB.com. Read his blog, Brownie Points, and follow him on Twitter @IanMBrowne. This story was not subject to the approval of Major League Baseball or its clubs.