Epstein did some historic things during his nine years in the post Cherington now occupies, foremost among them helping the fabled franchise win its first two World Series championships since 1918.
Simply being the general manager of the Red Sox would seem daunting to most, particularly when you are the one that replaces Epstein.
But somehow it all looks so natural to Cherington, who carries himself in an unflappable manner -- looking almost as if he's done the job his whole life.
"I don't think I'm unflappable," Cherington said. "I think I probably show my emotions a little bit less than some others. When things don't go well, it bothers me as much as anyone else. I may internalize that more than some others."
Considering everything that the Red Sox were coming off at the end of last season, and all that had to be done to get ready for this spring, it's almost as if Cherington -- known for his exceptional organizational skills and strong work ethic -- ascended into his role at the perfect time.
First, there was the perceived mess in the clubhouse that was reported about ad nauseum following last September's collapse. Then, there was a new manager to hire, and Cherington, after a protracted search, brought the charismatic Bobby Valentine back to the Major Leagues for the first time since 2002. Along the way, there were players to acquire, and Cherington traded for some (Andrew Bailey, Ryan Sweeney and Mark Melancon) and signed others (Nick Punto and Cody Ross).
"Ben is off to a flying start," said Red Sox president/CEO Larry Lucchino. "We knew he would be a solid evaluator. He's a good organizer and leader. We couldn't be more pleased with the fast start that Ben has gotten off to."
And not to be underrated was the challenge that came with saying good-bye to Tim Wakefield and Jason Varitek.
"It seems that hardly anything has taken him by surprise," said Valentine. "That's what I know he wants and what we all want. He's prepared for whatever comes his way. We've been faced with some interesting situations. I wouldn't want to be a first-year general manager and having the captain and the guy with 200 wins retire under my watch at the same time, and have to deal with the club's best manager [Terry Francona] not being at his side. He's been saddled with a real difficult challenge, and he's never complained. He's up early and he's working late."
Perhaps the job of bidding adieu to Wakefield and Varitek would have been tougher for a GM who hadn't already built solid relationships with both players. Maybe the message was a little easier to take from Cherington, because he had earned their respect along the way.
"That was one of the most challenging aspects of the offseason, really," Cherington said. "Their accomplishments on the field speak for themselves, and certainly the organization holds them in really high regard. We made a decision that we weren't prepared to guarantee them a job on the team, and based on that, we then had a long period of conversation about what that would mean and left the door open, because we wanted to give them a chance to have a say in the outcome and the final decision.
"But it was hard -- you have guys that have left that much on the field and given that much to the organization. There were times this offseason that I had to deliver news that they didn't want to hear. We tried to do that in as respectful a way as possible. I also know that there will always be a place for Jason and Tim in the organization, and we hope that we can work with both of those guys for a long, long time."
The things that might keep Cherington awake these days are the same things Boston's ravenous fan base obsesses about.
"We need some guys to step up on our pitching staff. We've got a lot of guys here who are capable of doing that," Cherington said. "We're optimistic because we believe we have guys that are capable of taking advantage of that opportunity. We have to see them do that. It's March 7 -- we haven't seen enough of it yet.
"We've tried to build some depth in the outfield in the event that Carl [Crawford] wasn't back at the beginning of the season, and it looks like he may need a little more time. We'll continue to look at that collection of outfielders and figure out [how it] works. As with every Spring Training, we're going to cover every other team's camp and see if there are guys available that might help us. I'd say that the primary focus is on trying to figure out who from that group of pitchers is going to step up and take advantage of the opportunity."
Then, there is shortstop. Perhaps the transaction Cherington has been second-guessed for the most is trading Marco Scutaro to the Rockies for a pitcher who probably won't make the Major League roster in Clayton Mortensen. It's no secret the primary motivation of the move was to clear some salary space to fill other needs on the team. Part of it was used to sign Ross. Perhaps the rest of it will be allocated to fill a need before the July 31 non-waiver Trade Deadline.
But fans want to know if anyone on the roster is capable of manning shortstop.
"We feel confident in what [Mike] Aviles can do and the protection that Punto gives us," Cherington said. "We think very highly of [Jose] Iglesias and the player he's going to be. He's shown some good things already this spring, and he's making progress. I think I've said, there's a competition. It doesn't mean that competition is on equal footing. Some guys are going into the competition with an advantage, but we're not going to limit anyone. We'll see how things evolve. Again, we'll keep our eyes out, but we feel confident that we have the answers here."
While Cherington got experience in virtually every area of baseball operations in his first 13 years with the Red Sox, his four years as farm director are probably what he draws on the most in his current capacity.
"I think that being a farm director for as long as I was was good preparation for this job in the sense that what you're trying to do is create a system that works the best for as many people as possible," Cherington said. "It's not ever going to be perfect for everybody. Being a farm director helped me understand that the goal is to provide the best opportunity for as many people as possible and to help as many people as possible.
"Within that, there are going to be things that happen that you don't like and people that are disappointed because players are human beings. I think in that sense it's helped me a little bit. In this job, deal with the moments that don't go quite as well."
Players like Dustin Pedroia, Jacoby Ellsbury and Kevin Youkilis have known Cherington since those days he headed the farm system they were such an integral part of.
"Shoot, I've been here since 2004, and I've been with him kind of every year. It's kind of cool," Pedroia said. "He's real smart, and he's approachable. I think that's huge for every player. If you can go up and talk to a guy, especially in that position he's in, some GMs are kind of scary, you don't want to go up and talk to them. But Ben is a guy you can talk to and trust, and that's huge if your team is trying to win a championship, because we need everyone on the same page."
Ross was impressed by Cherington's directness during the free-agency process.
"We were talking to the Giants, and it wasn't really panning out. Ben was one of the first to call," Ross said. "It just so happened I was coming to Boston for a wedding in December and ended up meeting with him in Boston. He was a super nice guy who was a straight shooter. He just told me exactly what the situation was. That's all you can ask for as a player -- is for a manager and a general manager and a front office just to be honest with you."
While Cherington is very much his own person, he makes no secret of the fact he learned a lot about dealing with players from Epstein.
"If I could point to one thing I learned from Theo, it's that sense of humanity that he showed in the way that he made decisions," Cherington said. "You could make tough decisions and do it in a respectful, humanistic way. And that was the right thing to do, -- it was the right thing to do sort of on moral grounds. But it was also the right thing to do on professional grounds.
"It helped give players the security of knowing that even when there was going to be a tough decision, when there was going to be bad news delivered, it was being done with as much respect as possible, and it was being done in a way that helped the team and gave guys the best chance to win possible."
Much like Epstein, Cherington's legacy as GM will ultimately be judged on wins and losses.
That process will officially become real on April 5, when the Red Sox open their season in Detroit.
"It's exciting," Cherington said. "We'll be facing Justin Verlander, and it's probably going to be about 40 degrees. I don't know if that's something you really look forward to. But it's exciting, because I think more than anything, I know the group of guys in the clubhouse are really ready to go be the Boston Red Sox again."
Cherington takes great pride in what the Red Sox should represent.
"Another thing that Theo taught me is that nobody should be judged by one moment," Cherington said. "No team should be judged by one moment, either. It should be judged by a longer time span, a longer period of performance and behavior. I think the Boston Red Sox are much different than September of 2011, and I think our individual players are much different than what the perception of September of 2011 was. I think they are motivated to go show people that. So that's what I'm looking forward to, more than anything else."
The man who brought Cherington to the Red Sox was Dan Duquette, who is now the executive vice president of baseball operations for the Orioles. Duquette has fond remembrances of his time with Cherington.
"Ben loved baseball," said Duquette. "He had really excellent instincts for player evaluation. Ben always wanted to be a general manager."
That's exactly what Cherington is, and he's never seemed more ready for it.