This is a crucial winter for the Red Sox, as Cherington and his staff try to construct a roster that can overcome September's epic collapse.
There are a plethora of decisions to be made.
Can Cherington sign a productive right-handed hitting outfielder like, say, Michael Cuddyer?
Who will replace Jonathan Papelbon in the closer's role?
The starting rotation could have two vacancies, depending on whether Cherington thinks internal solutions are realistic.
And then the big question: What becomes of David Ortiz?
The big slugger has been a force through most of his nine years in Boston, but he is now a free agent. There were preliminary talks at the General Managers Meetings with Ortiz's representatives, but can the sides make a deal?
What happens with Ortiz should have a domino effect on the rest of the roster. If the Red Sox keep Big Papi, they probably won't have quite as much money to spend in right field, or, perhaps, on the mound.
If Ortiz departs, expect Cherington to be aggressive in reallocating that money.
However, it does seem clear that the Red Sox have a lot of motivation to keep Ortiz in a Boston uniform.
"I think there's a pretty good understanding of where both sides are," Cherington said recently. "We're just not at the same point yet, but there's a pretty good understanding of where everyone is. I think there's a mutual interest in returning. That doesn't mean he will, but we'll keep working on it."
If keeping Ortiz in Boston would be more along the lines of a conventional move, Cherington has already indicated he will think outside the box when addressing other areas of the club.
One of those, clearly, is the pitching staff.
At his opening news conference as GM, Cherington said the club needed to hit on some pitchers this winter, much like the Sox did with Alfredo Aceves last offseason.
Low-risk, high-reward signings could be right up Cherington's alley when it comes to a market shallow of prime-time starting pitching targets. Though John Smoltz and Brad Penny didn't work out in 2009, Cherington says that can't deter the Red Sox from making a similar type of signing this year.
"I think we have to," Cherington said. "I don't think we can limit ourselves this offseason. We need to add to our pitching depth. We have some resources to do that. They're finite, so we're going to look at a number of alternatives. I wouldn't rule out signing a rehab-type pitcher just because of what happened before."
On the heels of that September collapse, might Cherington shake things up by dealing some of his prominent players? Thus far, the GM hasn't expressed an inclination to do so. However, he does have a lot of players who are drawing interest.
"There's a lot of trade interest in a number of our guys. None of it really surprises me," Cherington said. "Just a lot of trade interest in them, I guess."
One of Cherington's most interesting dilemmas will be what to do at closer.
Daniel Bard clearly has the stuff to close, but who would replace him as the lead setup man?
Bobby Jenks has been a closer most of his career, but it's probably not fair to project him in that role in 2012, giving all the health woes he is coming off of.
Should Aceves be given the chance to close, or will he start? Then again, Aceves might be most valuable of all in the swing role he pitched in last year.
There are attractive closers on the free-agent market, including Heath Bell and Ryan Madson.
So when Cherington gets to Dallas, he will have no shortage of items to keep him busy.