Reading Cafardo today, I think the manager issue boils down to FO game control--does Cherington want to manage games, like Beane does (and probably Epstein did with Tito), or do they want the manager to have game independence?
The answer probably lies in what Lucchino/Henry think is best for the team at this point. From, the interviews, it looks like they want a guy the FO can micromanage. Maybe.
I hope they recognize that it's about pitching. In which case, Maddux should have the inside track.
But what if they want a guy who has the experience to handle a bunch of beer-drinking millionaires, and who can manage in-game? Cafardo says Valentine is the guy. I've heard Henry likes him, too, and Henry is the supreme sabermetrics guy on the Red Sox. Valentine may well be lurking under the radar.
This may well be the best approach, because sabermetrics is much more important in the FO, picking the right players. You want a manager that is good in-game and has the players' respect.
The other thing is , apparently Cherington's manager list was compiled with Epstein while Theo was still in Boston. That means the Cubs manager search list is probably the same as the Red Sox. If so, Cherington may have to act quickly to get his man.