The Sox have not yet announced how they will reorganize their front office following Theo Epstein's departure for Chicago, but Cherington confirmed on Wednesday that the club has brought on former Royals pitching coach Bob McClure in a hybrid scouting/advisory role.
And then there's the lingering issue of just what compensation Boston will receive for letting Epstein out of his contract to join the Cubs.
"Theo and I have spoken a couple of times since I talked to you guys last," Cherington said Wednesday at Fenway Park, a week after his last huddle with the media. "We traded some ideas and don't have anything to report yet, but there's at least been a couple more conversations."
Courtesy of the Commissioner's Office, there's time for more conversations.
During the World Series, Commissioner Bud Selig set a Nov. 1 deadline for the Sox and Cubs to reach an agreement, but both teams have since been busy setting up their front offices, engaging free agents and, most time consuming of all, finding managers.
With the General Managers Meetings set to begin Monday in Milwaukee, Cherington said he and Epstein were hopeful they can strike a deal in person next week.
"The Commissioner's Office is giving us some leeway on it if we feel like there's progress being made," Cherington said. "I think we'll give ourselves until next week. We'll see each other in person next week, at least give ourselves until then to see if there's something we can't figure out."
If the Commissioner's Office has to handle the issue, Cherington said a date would be set where both sides present their case.
As for McClure, who turns 60 in April, he was let go by Kansas City after the season, his sixth as the Royals' pitching coach.
"He's going to be kind of a hybrid role, do some professional scouting for us, do some work on the field at the Minor League level as a special assistant to player development," Cherington said. "He's got a great pitching background. He's had a lot of success with young pitchers and had an interest in doing something a little bit different after last year in Kansas City. We're going to expose him a little bit to the scouting side, which he hasn't done a lot of, and get him on the field some. He's a guy both Allard [Baird] and I have a great deal of respect for as a pitching guy, so we wanted to bring him to the organization, and this was a role that fit for him and for us."
Baird, whose title with Boston at the start of last season was vice president of player personnel and professional scouting, was a longtime fixture in the Royals' front office. McClure spent 19 seasons pitching in the Majors, going 68-57 with a 3.81 ERA in 698 games.