Below is a look at the club's offseason checklist heading into the Meetings, which start Monday in Dallas.
A right-handed bat for the outfield: Last year, the Sox had three left-handed-hitting starting outfielders. With J.D. Drew's five-year contract off the books, Cherington will try to find a right-handed bat to complement Crawford and Jacoby Ellsbury. Michael Cuddyer is perhaps the most intriguing name on the free-agent market. Boston could also go for a more complementary piece like Cody Ross or Josh Willingham. Josh Reddick and Ryan Kalish, two left-handed-hitting prospects, could still be part of Boston's equation in right field.
A new closer: For the past six years, the Red Sox didn't have to worry about last call. Jonathan Papelbon's job was to pitch the ninth inning. However, Papelbon left for the Phillies and Boston has a big decision to make. Cherington could fill the role internally by promoting Daniel Bard, but then he will need to find an elite setup man.
Starting pitching: Beyond the big three of Jon Lester, Josh Beckett and Clay Buchholz, there are no certainties in Boston's rotation. In other words, Cherington will be searching long and hard for some more starters in Dallas. Don't look for the Red Sox to spend what it will take to land C.J. Wilson, but veteran righty Roy Oswalt, who is coming off an injury-plagued season, could be a nice piece to the puzzle.
Big Papi: It's hard to imagine a Boston lineup without Ortiz. Not only has he been perhaps the face of the team the past several years, but he remains an imposing bat from the left side. If Ortiz departs, it could be hard for Cherington to replace his production. Carlos Beltran is one bat that could be a nice fit, but he has a recent history of durability issues.
Who they might trade
Jed Lowrie: Though Lowrie's name has been on the trade block in winters' past, the Red Sox might be more motivated to deal him this offseason because they have a player with a very similar skill set in Mike Aviles. Despite Lowrie's durability issues, he is a switch-hitter with defensive versatility, making him attractive to other teams.
Reddick or Kalish: One of these players could be a nice piece for Boston's lineup and outfield, both in 2012 and going forward. But they are both left-handed hitters, making them a bit repetitive. Kalish fits more with Boston's organizational mold because of his disciplined approach at the plate. He is also coming off injury, which would make him harder to deal. Don't be surprised if Reddick is part of a trade package.
C Ryan Lavarnway, 3B Will Middlebrooks, RHP Anthony Ranuado, Reddick, Kalish, SS Jose Iglesias and RHP Matt Barnes.
After dealing three top prospects to land Gonzalez last winter, it's hard to imagine Cherington will give up any top Minor Leaguers this winter.
Big contracts they might unload
Right-hander John Lackey would have been the top candidate for that distinction, but he's coming off Tommy John surgery and won't pitch next year. Nobody else really fits this category.
Ellsbury; Bard; C Jarrod Saltalamacchia; Lowrie; Aviles; RHP Matt Albers; RHP Alfredo Aceves; OF Darnell McDonald; RHP Scott Atchison; LHP Franklin Morales.
McDonald, coming off a tough year at the plate, is probably the most likely candidate.
The Red Sox have a policy of never discussing payroll flexibility in a public manner. However, there's no reason to think Boston won't remain as one of the top-spending franchises in the game. The Sox should again weigh in somewhere in the range of $160 million. The biggest contract coming off the books is Drew's $14 million.