Lester dominates hitters during the 2013 postseason

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."

Young arms could surface soon for Red Sox

WS2013 Gm6: Workman tosses perfect eighth in relief

LAKE BUENA VISTA, Fla. -- On paper the Red Sox have a veteran-laden staff with six returning starting pitchers, but paper can blow away in the spring and summer, when attrition can take over.

General manager Ben Cherington doesn't feel the need to force one of his prospects into the rotation at this time. At some point, he realizes, it will probably just happen.

Anthony Ranaudo, Henry Owens, Allen Webster, Rubby De La Rosa and Matt Barnes are all young arms who could be knocking on the door. And Brandon Workman, a valuable reliever this past postseason, could get a chance to start if the opportunity presents itself.

"It could just happen naturally," Cherington said. "Every time we think about potentially moving a starter, something in the back of our head reminds us, 'Don't do it unless it really makes sense.' We know we're going to need more than five starters to get through the season. We'll probably need more than six starters to get through the season.

"Even if we do nothing, it seems likely that at some point one of those young guys is going to get a shot this year. That is important in the long run, because at some point, sometime in the future, in this next year or two, we're going to probably need to integrate another young pitcher in the rotation, and in order to do that, they have to have an opportunity.

"There is some value to [creating an opening], but it seems like it often happens naturally if you let it, rather than sort of forcing it. I guess that's where we are. We're just sort of balancing those things and, again, if it's something really compelling, we'll listen, we'll look at it. We just don't want to do it just for the sake of doing it."

In Spring Training of 2006, the Red Sox thought they had a glut of starting pitching and traded Bronson Arroyo for Wily Mo Pena. That move proved to be disastrous.

Lefty bat preferable for left side of infield

John Farrell at the Winter Meetings on MLB Tonight

LAKE BUENA VISTA, Fla. -- The Red Sox aren't close to acquiring the infielder they are seeking for the left side of the infield, an acquisition they'd prefer to hit left-handed.

Xander Bogaerts and Will Middlebrooks, who lead Boston's depth chart at shortstop and third base, respectively, are both right-handed hitters.

"I guess in a perfect world we would [have a lefty hitter], but we don't live in a perfect world," said general manager Ben Cherington. "There would be other factors. Defense would be important in that spot. Hopefully some other skill, whether it's baserunning or ability to hit right-handed pitching, or something else. Dependability, comfort in the role, all those things, in a perfect world. But we haven't found that perfect guy for that role yet."

As for Stephen Drew, the free-agent shortstop who helped the Red Sox win the World Series, Cherington said there hasn't been any recent dialogue with agent Scott Boras, though he hoped to have some before the Winter Meetings conclude on Thursday.