Epstein, 37, and the Cubs have agreed in principle on a five-year deal, believed to be worth $15 million to $18.5 million, for him to take over the baseball operations. But the Red Sox want something in return for the general manager who led the team to two World Series titles, and details have yet to be finalized. Talks continued over the weekend between the two teams.
An announcement may come Tuesday. Major League Baseball discourages teams from making announcements during the World Series, which begins Wednesday.
The Boston Globe reported Sunday that it was possible none of Epstein's assistants would follow him to Chicago, although that could change once their contracts expire.
The Red Sox are seeking a player, or players, in exchange for Epstein, who has one year remaining on his contract in Boston. No Major League players will be included.
There were reports that Brett Jackson, the Cubs' No. 1 pick in the 2009 First-Year Player Draft, was a possible piece in the compensation package, but sources said the outfielder will not be included. Jackson was currently playing for Team USA, which just finished the 2011 Baseball World Cup in Panama City, Panama, and was headed to Mexico for the Pan American Games. He singled and stole second on Friday against South Korea, then scored on Joe Thurston's single, but he had to come out of the game because of a minor foot injury. His status was day to day.
What the Red Sox have to determine is who is the equivalent of Kevin Youkilis on the Cubs' roster. In 2002, the Red Sox offered Billy Beane the GM job and were prepared to deal Youkilis -- then a Double-A third baseman -- to the Athletics as compensation. However, Beane opted to stay in Oakland.
Maybe the Red Sox would settle for a Randy Winn-type player. In 2002, the Mariners "traded" manager Lou Piniella to the Rays in exchange for Winn. Or, perhaps the Red Sox scouts have targeted Minor Leaguers similar to the two the White Sox dealt to the Marlins for manager Ozzie Guillen.
The Cubs would not comment on the GM search, and the Red Sox declined to comment on Epstein's status.
Red Sox owner John Henry did speak of Epstein in past tense during a radio interview Friday.
"I'd love to have Theo back," Henry told CBS Radio in Boston. "I would have loved for Theo to have been our general manager for the next 20 years. That was my hope. That would have been my hope. But you don't always get what you want."
Epstein joined the Red Sox in 2002 at the age of 28, and put together a team that won the World Series in 2004, ending an 86-year wait, and then did it again in '07. Boston reached the playoffs in six of his nine seasons as GM, but the 2011 team went 7-20 in September and blew a nine-game lead in the American League Wild Card. Manager Terry Francona and the Red Sox mutually parted ways two days after Boston's season ended.
The Cubs are coming off back-to-back fifth-place finishes in the National League Central and have been looking for a new GM since Aug. 19, when chairman Tom Ricketts dismissed Jim Hendry.
Epstein was expected to be replaced in Boston by Ben Cherington, who was hired full-time in 1999 and has served the team in nearly every capacity, including director of player development.
Carrie Muskat is a reporter for MLB.com. MLB.com reporter Ian Browne contributed to this report. Muskat writes a blog, Muskat Ramblings, and you can follow her on Twitter@CarrieMuskat. This story was not subject to the approval of Major League Baseball or its clubs.