It's just that the baseball calendar doesn't stop for anyone, not even the World Series champions.
Monday was the deadline for making $14.1 million qualifying offers to free agents, and Cherington extended them to center fielder Jacoby Ellsbury, shortstop Stephen Drew and first baseman Mike Napoli.
The players who received qualifying offers have one week to accept them. By doing so, they would bind themselves to the Red Sox for next season.
Jarrod Saltalamacchia was the one key free agent who didn't receive a qualifying offer, meaning the Red Sox don't get a compensatory Draft pick if he signs elsewhere.
However, Cherington and Farrell reiterated that the team has interest in retaining all four of those starting position players from the team that just won a championship.
"You know, really with all of our free agents, there's interest in every one of them," Cherington said. "I also think it's unlikely that every one of them will be back, just because that's the nature of the game. It's difficult to do that.
"In between there, there's all sorts of permutations and combinations that could work, and we're going to have to, again, keep a conversation going with all of them and also with alternatives, and see how the market shapes up for them and ultimately see what makes sense for us.
"But we had six free agents, if you include John McDonald and Joel Hanrahan, and four position player free agents who played significant roles on the team. In a vacuum, we'd like to have all of them back. We'll just have to see how it goes and we'll continue to talk to all of them and see how the market shapes out."
In other words, depending on how business unfolds this winter, the Red Sox could have a very similar team for their title defense, or one that has quite a few new faces.
"If we could replicate this group and keep it together and take another run at it, that would be great," said Farrell. "But a lot of questions have yet to be answered. The one thing we subscribe to are stability and continuity. We've already been successful with this group. And if we had an outside chance at reassembling in Fort Myers, [Fla.], next February, I think another year of familiarity would be a really good thing."
The Red Sox obviously will look a lot different if Ellsbury is no longer leading off and playing center field. But given his abilities and the competitive market that could emerge, he might be difficult to retain.
"Jacoby's a terrific player as everyone knows," Cherington said. "Of course, we know we're a better team when he's on the field than when he's not. That's about all there is to say at this point. We'll just keep talking."
Boston does have a pretty good center-field prospect in waiting in Jackie Bradley Jr., but there's no certainty he is ready to be an everyday player.
"You know, I think defensively, he's an everyday Major Leaguer now," Farrell said. "I think we all recognize that the first year for most players, particularly position players, there's a transition he's going to go through, and along the way comes some bumps in the road. I think Jackie went through those.
"The one thing we did see was, as pitchers attacked him a certain way, it wasn't as evident as it was when he first came up. So, he's a better player today for what he's gone through this year. You know, the overall evaluation of him has not changed from the time he entered the organization. We just know this is kind of a natural progression that he has to go through and feel like he's very capable of being an everyday guy."
The one thing the Red Sox don't seem keen on is moving Shane Victorino back to center field. Victorino won a Gold Glove Award as Boston's right fielder in 2013.
"I think I speak for John that we both recognize just how good he was in right field this year and how valuable his defense was in right field," Cherington said. "So I guess we'd have to be compelled to move him. It would have to be a pretty compelling opportunity, but you can't rule that out. He's capable of doing it."
Much like in center field, the Red Sox have some flexibility at short if Drew leaves. The most obvious replacement is Xander Bogaerts, who hit the ground running in the postseason while playing third base in place of the injured Will Middlebrooks.
"I mean, he certainly looks like he's ready to play in the big leagues," Cherington said. "We've obviously thought very highly of him for a long time. You don't know exactly when the stage is going to arrive, but he looked very comfortable on it when he got on it. We'll see. It's very early in the offseason, and there's plenty of time this offseason and in Spring Training to figure it all out. We're glad he's on our side."
As for first base, the Red Sox would clearly love to have Napoli back. But his contract situation could be an interesting one, considering the debate over his hip last winter that reduced his original three-year agreement with Boston to just one.
Napoli didn't miss any time to the hip this season and likely feels he's worthy of more than a one-year deal. He also has said he wants to return to the Red Sox.
"The exit physicals are a process and probably different for each player depending on the circumstance," said Cherington. "There's still some things we're working on to get information we're gathering. And of course, I'm not in a position to share detail on that, but Mike Napoli played a lot this year and was a huge part of our team.
"As I said, we're making a qualifying offer to him, so we obviously have interest in him returning. [We're] certainly comfortable on a one-year deal for $14.1 million, and he'll have an opportunity to consider that. He's one of the free agents that we would certainly have interest in having back."
As for the fourth position where there is a key free agent, it is always vital for any team to have a catching tandem it can depend on.
Though Saltalamacchia didn't have a strong postseason at the plate, he was a big part of what the Red Sox did during the season.
David Ross certainly plays more than the average backup, but don't look for the Sox to overextend the veteran, who is under contract for one more year.
"I think going back to this time last year or when we signed David, it was the thought that he was a 60-70-games-caught type of player," said Farrell. "That's not to put a ceiling on him either. But I think we're probably comfortable in that it's a tandem position. I think that's the way we view the catching position here for a number of years, and David from a physical standpoint, would clearly be able to handle his side of the tandem."
These are all decisions the Red Sox will be faced with in the coming weeks.
Though familiarity always sounds good to a team that wins the World Series, there is always some turnover.
"Yeah, that was felt when we got off the duck boats, knowing that this was that one last acknowledgement of a great run to celebration with millions of people here in the city," said Farrell. "But the reality hits as soon as our feet hit the ground, knowing that some things are going to be out of our control this offseason that could change the face of our roster.
"You relish the moments, how special they are when a group of guys come together and achieve as they did. Hopefully, we're able to retain all of them. The reality is that may not work out.
"And to each guy, whether it's Salty and his progression and the way he performed, particularly offensively this year which was a breakout year for him, to the transition of Mike Napoli, who probably exceeded our expectations on the defensive side, to Stephen Drew -- all have earned the right to this point in their career, and that's to get to free agency and how they can best benefit their family. It would be great to have them back, but we'll see."