Last spring, it was easy to look at his team and project 90 victories, maybe 95, certainly a postseason berth. Cherington is no longer talking in those terms. Is he trying to lower expectations?
"I think fans in Boston are sort of tired of hearing how good we are in the winter," he said. "We've just got to get to work and build the thing up."
At the moment, the Red Sox aren't sure who will play right field, left field or first base. Shortstop is a concern, too, but it's down the list.
Now about that starting rotation. It wasn't the AL's worst in 2012, but it was in the conversation. Even if the Sox get nice comeback seasons from John Lackey, Jon Lester and Clay Buchholz, they could still be an arm or two short.
They weren't a great offensive team, either. David Ortiz has re-upped, which helps, but outfielder Cody Ross is exploring the free-agent market. Meanwhile, the AL East has gotten a lot more interesting thanks to Toronto's infusion of talent. The Rays, Yankees and Orioles were all better than the Red Sox when the season ended.
And with the Red Sox coming off a 69-93 season, older free agents, the ones who've made a lot of money and are seeking a ring, are looking at Boston differently than in past years.
"It's a fair question and one that we haven't had to answer in most offseasons," Cherington said. "I think you answer it by telling people that you've got to rely on the track record here and the commitment from ownership to put a lot of resources into the team. And just the reality. This is Boston. We're going to build a team as quickly as we can."
If you're inclined to count out the Red Sox, that would be a mistake. For one thing, there's a core of terrific players.
Ortiz and Dustin Pedroia. Jacoby Ellsbury and Will Middlebooks. Lester and Buchholz. There will also be a dramatically different environment. For whatever reason -- and there were plenty of them -- Bobby Valentine was a terrible fit in Boston.
John Farrell won't have to sell himself to his players because they know him and believe in him. Cherington downplays the difference Farrell can make, saying it's about the players, that the manager's job simply is to create a good environment and put them in position to succeed.
That's a different way of saying that the role of the manager in the collapse of the 2012 Red Sox can't be overstated. If Lester, Buchholz and Josh Beckett had won 50 games and pitched 550 innings, things might have worked out different.
One thing we learned in 2012 is that baseball's top dozen or so teams are bunched closely together in terms of talent. It's about doing the little things right, about playing hard each and every day, and it's about not being sidetracked by issues that have nothing to do with winning that day's game.
From the moment Valentine publicly questioned the desire of Kevin Youkilis early in the season, the Red Sox were pretty much a textbook study in paying attention to almost everything except what counted.
Here's the good news for 2013: Farrell will keep them focused, organized and on message.
The Red Sox need Lester to get back on track. Farrell was Lester's pitching coach when he established himself as one of baseball's best and most consistent pitchers, and he'll provide a comfort level.
If the Red Sox get what they're hoping for out of Lester, Lackey and Buchholz, they'll be a long way down the road toward solving every other problem.
If the main players -- Middlebrooks, Ortiz, Pedroia and Ellsbury -- are all healthy and in the right frames of mind, the Red Sox will be good enough to contend.
Now about everything else. The Red Sox have less than $50 million in salary commitments for 2013, and even though Cherington would like to stay away from big-ticket, long-term contracts, he has all kinds of flexibility to pick through the free-agent market and find pieces that will fill the holes.
Inside the industry, there's a belief that the Red Sox will make a run at Josh Hamilton. Cherington will only say that any long-term deal has to be with the right guy.
The point to all of this is that the Red Sox are positioned to succeed. But nothing is going to be automatic.
Lester, Lackey and Buchholz must be productive. Ortiz must have another great year left in him. Middlebrooks must stay healthy. Cherington will have to make wise decisions in free agency.
But it's silly to think the Red Sox are going to be buried in the AL East again. Any team with the core of talent they have and the financial flexibility to add more is a team that will have to be reckoned with. In other words, don't sleep on the Red Sox.