The Sox filled one of those holes Tuesday, as they agreed to a one-year deal with free-agent backstop A.J. Pierzynski.
A year ago, the Winter Meetings opened with Cherington swooping in and agreeing to terms with Napoli, who became a vital power bat and a perfect fit in the clubhouse. Now that the Sox have had a full year to monitor the hip condition that reduced Napoli's initial deal from three years to one and delayed the official signing of the contract until late January, perhaps the sides will be able to find common ground on a multiyear pact.
Napoli has made no secret of how much he loves Boston and that he has a desire to stay.
Should the right-handed slugger slip away -- or even if he doesn't -- Cherington could be on the prowl for some more power.
"It's one of the criteria, one of the things we'd like to do," Cherington said. "We do think if we look across [the roster], even aside from anyone we might add, we think there's power potential on the team, position by position. If Opening Day was tomorrow, we think there's a chance to get pretty solid power production out of most spots on the field. But yeah, we'd like to add more. That would be a criteria we'd be looking at at certain positions."
And what will happen for the Red Sox over on the left side of the infield? Drew was a stud defensively at shortstop, particularly in October. But if he doesn't stay, the position could certainly be manned by top prospect Xander Bogaerts, a future star in the minds of most.
"We certainly believe he's a shortstop," Cherington said. "He could play another position if he had to. He proved that he was capable of doing that. We absolutely see him as a shortstop long-term."
It was Bogaerts who stepped in at third base midway through the postseason in place of the slumping Will Middlebrooks. Perhaps Middlebrooks can bounce back in 2014 and play the same way he did in his rookie year.
But can Cherington bank on that?
"We think if we do nothing, we'll get more out of third base than we did this year," Cherington said. "That's our hope and expectation given the players that are here. We'd like to at least add somebody on the left side of the infield. Whether that's more in the form of an everyday player or depth, whatever that is, it just depends on how the rest of our offseason unfolds."
Then there is Ellsbury, a dynamic leadoff hitter who has been invaluable for Boston when he stays healthy. The center fielder could demand a price tag that's too rich for Boston's blood. And if he leaves, Cherington could go in-house with prospect Jackie Bradley Jr.
There's also the chance the Sox could sign a corner outfielder like Carlos Beltran and move Shane Victorino back to his natural position of center field.
It's important to remember that free agency isn't the only way to fill needs. The Red Sox have the type of depth most teams would love to have in the starting rotation, and they could always use some of that excess to help fill another need.
"I think it's no secret, one area we have a little bit of depth in is the rotation," Cherington said. "That's an area other teams are sorting out, working through free-agent options. Some of the free agents are starting to land, so I think that's probably going to become more clear for other teams, too. We'll see what that means for us.
"I don't know yet really what it means, other than we've had a lot of conversations. We know we'll have to be compelled to do anything there because obviously a supposed surplus can turn into not one pretty quickly, so we want to be careful, not do something just for the sake of doing it since there's downside to doing that. We'll see. We've had a lot of conversations."
And the Winter Meetings, which take place from Monday to Dec. 12, are typically a place where a lot of those conversations lead to transactions.