The first domino of Boston's offseason fell when David Ortiz was re-signed for two more years. That fills a key middle-of-the-order spot in manager John Farrell's batting order.
But there are so many other holes to fill.
The Red Sox have a big vacancy sign at first base. They have a possible opening at shortstop, depending on if there is enough firepower in the lineup to go with defensive specialist Jose Iglesias. There are two holes in the outfield, if you include the one currently vacated by free agent Cody Ross, who was a popular run producer in his first season with the Sox.
And Cherington has already been on record as saying he wants to acquire another starting pitcher from outside the organization.
Even if most transactions generally don't get consummated until closer to the Winter Meetings, which are from Dec. 3-6 in Nashville, Tenn., the General Managers Meetings is where moves often start to take shape.
"I think it'll be more information gathering, meeting with teams," said Cherington. "I'm sure there will be some agents there. We've already had a lot of conversations on the phone, but face to face, we'll talk a little more about concepts -- both free-agent concepts and trade concepts. The offseason is a bit of a mosaic. We're looking for one piece and how it fits together, but at some point, some of the balls have to fall. David was a big one and we're trying to identify the next one."
Similarly, the Red Sox had hoped to be able to secure the services of Ross before he was eligible to negotiate with other teams. But the sticking point is that Ross wants three years, and thus far, Boston has appeared more interested in a two-year deal.
"We've had a number of conversations. Obviously we're into free agency now. We didn't sign him before that started," Cherington said. "The door will remain open, and we'll continue to talk, but once we're in free agency, he's got opportunities to talk to other teams, and we fully expect him to do that."
One thing that is helping Ross -- and could hurt the Red Sox -- is that there is a noticeable lack of run producers on the market this winter. In other words, the price could be inflated.
"Going back to last fall when I first talked to Cody about coming here, the goal obviously was to do well as a team, but part of the goal was to put him in a better position," Cherington said. "I felt it could put him in a better position by coming here and performing in this ballpark. The good news is that it did. That's to his credit. He's in a good position now. It makes it tougher to sign him. We'll keep the door open. We'll keep talking. At the same time, we've got to consider alternatives, too."
Veteran Torii Hunter is an intriguing name on the outfield market, and he has been close friends with Ortiz for a long time. Mike Napoli could help the Red Sox either behind the plate or at first base. Neither player received a qualifying offer from their previous employer, which means the Red Sox could sign them without losing a Draft pick.
Which hole will Cherington try to fill first?
"I don't know if we can follow an order, because there's enough to do and some sort of impact the other," he said. "I think we have to keep engaged in a number of different things at once with agents and teams. We have a general idea of things we want to pursue the most aggressively. We'll see if any of those land more quickly, and if they do, that might shape us in a certain way. I think we need to keep our options open as much as we can, knowing we have a lot of work to do."
Would the Red Sox try to sign a player who received a qualifying offer? That has a new dynamic this winter for Cherington, considering that Boston's 69-93 record means it will have a top 10 pick in June's First-Year Player Draft. The pick will protected, so if the Sox sign somebody with a qualifying offer, they would lose their second-round selection. Outfielder Josh Hamilton is the biggest name on the market.
"Case by case," Cherington said. "I would not rule out doing that, but you can't rule it in yet, either. It's just case by case. There's still value, obviously, with a pick around that range, and you have to factor that into what it would cost to sign a player. I would say case by case."
Aside from looking into player acquisitions, Cherington will also work with Farrell to solidify the coaching staff.
A pitching coach could be named any day. The Red Sox will start to interview hitting coaches later this week. The team has yet to name a first-base coach or a bullpen coach, though incumbents Alex Ochoa and Gary Tuck are candidates to keep their posts.