"I talked to David's agents since I've been here at the GM Meetings," Cherington said. "I think there's a pretty good understanding of where both sides are. We're just not at the same point yet, but there's a pretty good understanding of where everyone is."
While Jonathan Papelbon, Boston's other marquee free agent, swiftly moved on to Philadelphia, there seems to be motivation from both sides to keep Ortiz in a Red Sox uniform.
"I think there's a mutual interest in returning," Cherington said. "That doesn't mean he will. But we'll keep working on it. We've had good dialogue since we got to Milwaukee."
Cherington also surveyed the landscape on potential free agents and trades during his time in Milwaukee. On Wednesday night, he spoke to agent Bob Garber, who represents left-hander C.J. Wilson and right-hander Roy Oswalt.
The latter, who is coming off an injury-plagued 2011, would seem to be more in line with what the Red Sox are looking for on the free-agent market.
Though Boston didn't have much success with John Smoltz and Brad Penny two winters ago, that, Cherington said, wouldn't preclude him from pursuing some other low-risk, high-reward type of signings.
"I think we have to [explore it]," 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."
The Red Sox also might be able to fill a rotation vacancy through a trade.
"A lot of names have come up," Cherington said. "Surprises? No. You get to the end of the season and start planning for the offseason, you have a pretty good feel for who might be available, teams that are, whether it's salary issues or some team with surplus. You can identify the teams that have surplus in certain areas. That might be the team that looks to move a guy for a need somewhere else. You can pretty much predict. There haven't been any surprises so far, to me."