Players throughout baseball filed for free agency the day after the World Series ended, and that included four players from Boston's primary starting lineup in 2013.
Jacoby Ellsbury, the speedy leadoff man and center fielder, is the most impactful free agent from the Red Sox.
Agent Scott Boras has expressed numerous times how unique a player Ellsbury is. Though the Red Sox have had some productive negotiations with Boras in the past, there seems little to no chance that the club would be able to strike a deal with Ellsbury during its window of exclusivity, which ends at midnight ET on Monday.
"The 2013 Red Sox team is great. It doesn't mean the work stops," said Cherington. "There's still things we need to do to get better at and ways that I can be better and the organization can get stronger. But they won their last game of the postseason, so this team is great for 2013."
The other thing Cherington has going for him is a farm system that could offer immediate help for the 2014 squad. Xander Bogaerts proved in the postseason that he's ready to stay in the Majors. Jackie Bradley Jr. could get a shot in center, depending on what happens with Ellsbury.
"Well, we've got guys coming," said Cherington. "We've got a lot of good guys here that are going to be here again next year and a big part of it. We think we're in good position. We think we have a lot of strengths, but we know we need to get better, too. You can't stop being better."
Aside from Ellsbury, catcher Jarrod Saltalamacchia, shortstop Stephen Drew and first baseman Mike Napoli are all free agents. The Red Sox have until 5 p.m. on Monday to make $14 million qualifying offers to those players.
If proffered a qualifying offer, players have one week -- until 5 p.m. on Nov. 11 -- to accept the offer. They can decline it at any time before then and sign with another team.
However, the Red Sox could still wind up striking deals with any of their existing free agents, whether or not they extend qualifying offers. And if a player gets a qualifying offer and declines it, Boston could still sign that player to a contract.
Just how active the Red Sox will be in pursuing other team's free agents will depend greatly on how successful they are in re-signing their own.
Free agents: OF Ellsbury, SS Drew, 1B Napoli, C Saltalamacchia, INF John McDonald, RHP Joel Hanrahan.
Club option: LHP Jon Lester, $13 million ($250,000 buyout); LHP Matt Thornton, $6 million ($1 million buyout)
RHP Andrew Bailey ; LHP Franklin Morales ; LHP Andrew Miller ; RHP Junichi Tazawa ; 1B/OF Mike Carp.
Non-tender possibilities: Bailey.
Areas of need
Catcher: Will Saltalamacchia re-sign? If not, the Red Sox will likely need to find at least a short-term solution behind the plate before one of their prospects emerges. David Ross is back for one more year, and he can catch more than the average backup. One intriguing name on the market is Brian McCann, who had a great relationship with Ross in Atlanta. If the Sox wanted to go a bit older, A.J. Pierzynski is also out there. The ideal option would be to retain Saltalamacchia, who has good rapport with Ross and the pitching staff and has a power bat.
First base: Much like with Saltalamacchia, Boston's need at this position depends on whether Napoli comes back. Though he's streaky at the plate, Napoli was a strong fit with the Red Sox, and he has said numerous times he'd like to come back. If Napoli doesn't resurface, the club does have some in-house possibilities who could take on more responsibility at first, including Carp and Daniel Nava.
Shortstop: Drew was better defensively than most people expected. In the postseason, his glove was downright spectacular. But his bat disappeared for long stretches. Obviously if Drew departs as a free agent, the Red Sox have a future star ready for the position in Bogaerts. However, Bogaerts could also take over at third base if Will Middlebrooks is traded. This is clearly a position where the Red Sox have options.
Center field: Though there have been some injuries along the way, Ellsbury has been the mainstay for the Red Sox at this position since 2008. His bat, legs and defense would all be missed if he signs elsewhere. Bradley Jr. seems like the heir apparent, but the Red Sox would have to be sure he's ready to be a productive hitter at the Major League level.