In the past, it is the sort of conversation that would never happen with the Red Sox . The idea of trading a front-of-the-rotation starter who is in his prime, with a track record of considerable success, healthy, affordable and under team control for multiple years? There wasn’t a point to the Red Sox discussing such players, and other teams never bothered to engage the Sox about them.
Now, after a 69-93 2012 season, the world looks different. The Sox already showed a willingness to make the type of trade that they never would have considered in the past in August, when they dealt Adrian Gonzalez , Josh Beckett  and Carl Crawford to the Dodgers in one colossal reshaping of the team’s roster and payroll. And so now, perhaps, it should come as little surprise that the team is at least in a position where it has to consider discussing anyone in the rotation in a potential trade, including a pitcher like 28-year-old Jon Lester .
That’s not to say that the team is eager to let Lester go. But if there’s a team that’s willing to consider offering a potentially massive asset — someone like, for instance, Royals outfielder (and Baseball America Minor League Player of the Year) Wil Myers, then the Sox are in a position to listen.
GM Ben Cherington has said that the Sox are looking to add a fifth starter via trade or free agency to a group that already includes Lester, Clay Buchholz , Felix Doubront  and John Lackey . But, Cherington acknowledged on Saturday at the Christmas at Fenway event, he won’t rule out the possibility of dealing one of those four pitchers, thus creating a need to add two starters this winter.
‘Anything is possible, but certainly it’s harder to do that, to subtract somebody from the rotation,” said Cherington. ‘We have a number of players that teams like. We’re in a perhaps different situation than we have been in the past coming off the year we did. Maybe in light of that, teams not surprisingly are inquiring about things that maybe they wouldn’t have in the past. Look, we have to be open-minded; we lost 93 games. But our primary focus is to build the best team we can for 2013 and one that doesn’t in any way get in the way of a great team for a long time. That’s our focus, and that will guide us for the next several weeks. But you’ve got to be open-minded when you have a year like this, and we’re trying to build a team that will sustain a level of success over a long period of time.”
Cherington repeated a theme he’s brought up on a number of occasions this winter. Asked what profile of starter the team is looking to add right now (in a world where it has the aforementioned four starters), he declined to commit to whether the team wanted a pitcher who profiles as a No. 1 or No. 5 starter.
“I think generally [the rotation] needs to improve. The core of the rotation wasn’t good enough last year. I think the combination of the entire group, we need to get improved performance, and as I said before, I think that will mostly come from the guys that are already here,” said Cherington. “That will make a bigger difference than anything else we add, likely. And so, in terms of the order, I guess the way I see it, once the season starts and you get into the schedule and someone’s taking the ball every day, I’m not sure the order matters much. We need guys that, every time they take the ball, give us a chance to win. That didn’t happen enough last year.”
That said, he added that he still feels that Lester and Buchholz can profile as the proverbial top-of-the-rotation pitchers.
“They have in the past and have done that for consistent periods of time in the past, and we’re counting on them to do that going forward,” he said.
Still, that doesn’t rule the Red Sox out from making an aggressive play for other pitchers who might fit that category. That, in turn, marks a change of the Sox’ means from a year ago.
In 2011, Cherington was upfront in saying that the Sox were likely to remain on the sidelines in the bidding for pitchers like Yu Darvish  and C.J. Wilson and Mark Buehrle , given the lack of financial flexibility that the club had and the fact that the team had already made huge commitments to its rotation. This year, the Sox have tens of millions of dollars that they can potentially channel towards the 2013 team, and with Daisuke Matsuzaka  and Beckett now off the books, the team can push considerable resources towards the rotation.
As a result, the team has the ability to play for the top offseason targets — pitchers like Zack Greinke  and Anibal Sanchez . Still, Cherington cautioned that the team won’t necessarily jump into the deep end of long-term megadeals just because it has the means to do so.
“I think certainly we have more flexibility this offseason, so it allows you to consider things that we probably couldn’t have last year. With every guy, we go through the exercise in drawing the line on where we would go, and many times, that line is below where it ends up going. So, that sort of instructs us,” he said. “I wouldn’t rule anything out categorically. We just want to find ways to improve the team, the rotation. We’re working on a lot of ways to do that. Generally, I think every team would say they prefer shorter-term deals to longer-term deals. I think that’s any team’s preference. You know, the guys that have been the most consistent performers and healthiest and have done that, they’ve earned a fair amount of leverage and have earned the right to get significant guaranteed dollars. If you want to add that type of player to your team, then sometimes you have to step up and do that. It’s just case by case, and we’re still going through the process of trying to find who the right fits are there for us.”
Cherington said that Rubby De La Rosa, acquired in the Dodgers trade, is being considered as a starting pitching option, and the team expects him to contribute at the big league level in that capacity in 2013. However, as he’s working his way back from Tommy John surgery (which he underwent in 2011), the team isn’t sure precisely when he will be able to contribute in the big leagues.
“He’ll be in a starter’s role in spring training and we’ll bring him along. Obviously coming off a year where he didn’t pitch a lot, we’ll probably take it a little bit slow,” said Cherington. “He’s out in Arizona working out. A couple guys saw him working out last week. He’s getting into really good shape. He’s a guy that is a big part of our future. We want to make sure we handle the first few weeks and first few months of our experience with him the right way, bring him along the right way. We envision him as a starter and that’s the way he’ll be treated in spring training. … [When he can contribute next year] will be determined later on, spring training or during the season, but he’s a guy that we could certainly see helping us in 2013.”
That, in turn, means that De La Rosa will not be treated as the answer to the fifth starter’s spot for the start of next year given the uncertainty about his timetable. Still, his presence (along with that of a number of talented minor leaguers, such as Allen Webster, Drake Britton, Brandon Workman, Matt Barnes  and others) could influence the profile of starting pitcher that the Sox pursue, and the team’s relative willingness (or unwillingness) to hand out long-term deals of more than four years along the lines of what Greinke and Sanchez are seeking.
Cherington also said that the team will wait until later in the offseason to make a determination about the 2013 role of Alfredo Aceves , who was tendered a contract on Friday.