After first baseman Mike Napoli reached an agreement to return to Boston on Friday, one key component from the World Series-winning team, shortstop Stephen Drew, is still a free agent. Cherington would like to keep Drew, and he might have more financial flexibility to do so with Ellsbury moving on to the Yankees.
The Red Sox will likely be active in the pursuit of trade and free-agent acquisitions.
"We're trying to make the team as good as we possibly can, as strong as we possibly can, as deep as we possibly can without making moves that handicap us for the long run," said Cherington. "You know, with every decision we make that there's a range of possible outcomes, and we're going to shoot for the high end of that range."
Shortstop: Although Drew had an inconsistent season at the plate, the Red Sox are firm believers that his defensive excellence outweighed that. The Sox hope they can persuade Drew into a return engagement, but it's not yet clear what his market is.
Xander Bogaerts, Boston's top prospect who came up big in the postseason, could take over the position if Drew leaves. But the Sox's best team would probably have Drew at short and Bogaerts at third.
Center field: There are certain scenarios in which Cherington would be comfortable going into the 2014 season with prospect Jackie Bradley Jr. as the Sox's center fielder. That would entail surrounding Bradley with as many good bats as the team can afford in case he struggles for a while at the plate. Bradley already plays Major League-caliber defense.
Though Shane Victorino has played center field for most of his career, the Red Sox remain adamant that they want to keep him in right, where he won a Gold Glove Award last season.
Who they can trade if necessary
The one thing the Red Sox have as a trading chip is starting pitchers. It's hard to fathom anyone from the big three of Jon Lester, Clay Buchholz or John Lackey would be moved, but Boston also has Felix Doubront, Ryan Dempster and Jake Peavy, any of whom could interest potential suitors.
It isn't as if the Red Sox are looking to deal a starter. But if it helps them fill another need, they'd certainly consider it.
Bogaerts is at the stage where he's just about ready to start being called a player instead of a prospect. However, Bogaerts can still hold that distinction entering 2014, considering he still has his rookie eligibility. It would take a blockbuster trade of epic proportions for Cherington to even consider moving Bogaerts, and the chances of Bradley getting traded are also slim, given the loss of Ellsbury.
Third baseman Garin Cecchini is developing a reputation as a hitting machine. Lefty Henry Owens could be a star in the making. Righties Matt Barnes and Anthony Ranaudo are other pitchers the Sox remain optimistic about. Catchers Blake Swihart and Christian Vazquez are the reason Cherington went for a short-term solution behind the plate for 2014 in Pierzynski.
Boston's farm system currently has a lot of depth, which means Cherington could utilize it if an impact player became available in a trade.
Rule 5 Draft
With 39 players on the roster and a signing or trade acquisition expected at some point, it wouldn't be surprising to see the Red Sox pass on a Rule 5 pick. As for players they might lose, the Sox didn't protect Kolbrin Vitek, a former first-rounder.
Big contracts they might unload
The Sox aren't looking at any contracts they have to get rid of. But Peavy is making $14.5 million in 2014 and Dempster will earn $13.25 million, meaning Cherington could gain some financial flexibility if either of those righties are dealt to help fill another hole.
Last season, the Sox had an Opening Day payroll of roughly $154 million. They will probably stay in that general range for 2014. The Red Sox traditionally have one of the top five payrolls in the game.