Boston is coming off two tumultuous seasons -- one that ended with a September collapse and the other that fell woefully below expectations.
"I think how I feel is that fans in Boston are sort of tired of hearing how good we are in the winter," Cherington said. "We've got to build a team that wins and does the right things, and a lot of that is the players on the roster. That's the focus right now."
Here is a look at what areas Cherington will be focusing at the Winter Meetings, which take place in Nashville, Tenn., from Monday through Thursday.
First base: Two winters ago, it seemed the Red Sox had filled this need for the better part of the next decade by acquiring Adrian Gonzalez's big bat from the Padres. But after 1 1/2 seasons, Gonzalez was sent to the Dodgers in a blockbuster trade that freed Boston of not only his salary but also those of Carl Crawford and Josh Beckett. So who does Boston turn to now? One player the club's definitely eying is Mike Napoli, who could shift to first base after catching for most of his career. Adam LaRoche is another intriguing player on the free-agent market.
Starting rotation: The Red Sox hope that Clay Buchholz, Jon Lester and John Lackey can return to being frontline starters. However, Buchholz and Lester were inconsistent this past season, and Lackey missed all of 2012 after undergoing Tommy John surgery. Cherington would like to find a starter somewhere, and a trade could be a more realistic avenue than free agency.
Right field: Ryan Sweeney and Ryan Kalish are both options but are looked at more as complementary pieces at this point. Cody Ross remains a free agent, and the Red Sox are still trying to retain his services. He was a good fit in the lineup and the clubhouse last season.
Shortstop: Jose Iglesias was once looked at as Boston's shortstop of the future. Now, the team is wondering if he can serve as a bridge until the organization's top prospect -- Xander Bogaerts -- is ready for Major League action. Iglesias struggled mightily at the plate after his callup in 2012, and he's spending the offseason trying to build strength. The Red Sox could either make Iglesias their shortstop in '13 or find a safer option. One thing is clear -- they can't do better defensively than Iglesias.
Who they can or need to trade
The addition of David Ross as a part-time catcher leaves the Red Sox with some depth at that position. Jarrod Saltalamacchia, who belted 25 homers in 2012, could entice plenty of teams. There is also prospect Ryan Lavarnway, who is at the point in his development where he probably either needs to play in Boston or get regular time somewhere else.
A shortstop with a big bat, Bogaerts might wind up being the next big star in Boston. However, Bogaerts is probably a season or two away from being ready to help the Red Sox. Jackie Bradley Jr., the exciting outfielder out of the University of South Carolina, is on a similar timeframe. Matt Barnes is the best pitcher in the farm system. It would probably take a franchise player for the Red Sox to consider moving any of those three prospects.
Big contracts they might unload
For the first time in years, the Red Sox don't qualify as a team in this category. Several big contracts are now off the books, giving the Sox the type of financial flexibility they haven't had in years.
The Red Sox opened last season with a payroll of $175 million. That was with Gonzalez, Crawford and Beckett on the books. Expect the club to open next season at a lower number, but how big the gap will be remains to be seen. Cherington has vowed to make disciplined decisions this offseason, and going forward. The Red Sox have resources, so if a marquee player becomes available at the right price, don't be shocked if Cherington makes something happen.