Is Epstein worth Brett Jackson, the Cubs' highly touted outfield prospect who was their No. 1 Draft pick in 2009? Or do the Red Sox want Matt Szczur, another top Minor League outfielder? Or, can the two teams settle on a cash amount?
The Cubs and Epstein have reportedly agreed in principle on a five-year deal, believed to be worth $15 million to $18.5 million. But because Epstein has one year remaining on his contract, the Cubs must compensate the Red Sox, and the value was expected to depend on the number of staffers Epstein would take with him to Chicago.
In recent years, when two of Epstein's co-workers left to take general managers' positions with other clubs, they were each allowed to take two Red Sox staffers with them. When Josh Byrnes went to the Diamondbacks in 2005, he took two people, including Peter Woodfork, then director of baseball operations. In 2009, Jed Hoyer took scouting director Jason McLeod and Sam Ray, now assistant to the scouting director, when Hoyer went to the Padres.
In 2002, the Red Sox offered Billy Beane the GM job and were prepared to send Double-A third baseman Kevin Youkilis to the Athletics as compensation, but Beane opted to stay with Oakland. Last month, the White Sox received two of the Marlins' top five-ranked prospects in exchange for letting Ozzie Guillen out of his contract to manage Florida.
The Cubs would not comment on the GM search.
In a radio interview Friday with CBS Radio in Boston, Red Sox owner John Henry said he could not comment on whether Epstein was headed to Chicago. But asked if he wanted Epstein back, Henry said yes.
"I'd love to have Theo back," Henry said. "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. ... The fact is, I think people don't understand this, the fact is, being general manager in Boston, being manager in Boston, is a terrifically tough job."
If Epstein leaves, he would end a nine-year run with the Red Sox, which was interrupted briefly when he left the job from October 2005-January 2006.
"He never saw the general manager's role as longer than 10 years for himself," Henry said. "Maybe he did early on. Certainly, after a few years, he knew that the stress of this job was too much."
The Cubs, coming off their second straight fifth-place finish in the National League Central, have been looking for a new GM since Aug. 19, when chairman Tom Ricketts dismissed Jim Hendry.
An announcement could come early next week. Major League Baseball discourages teams from making announcements during the World Series, which is to begin Wednesday.
According to a source, the Red Sox want one or more prospects, and not cash, as compensation. Ricketts was handling the negotiations with Red Sox president/CEO Larry Lucchino, and discussing the targeted players with Cubs interim GM Randy Bush, player development director Oneri Fleita, and scouting director Tim Wilken.
The Cubs farm system was depleted earlier this year when the team acquired Matt Garza from the Rays in exchange for five players, including Chris Archer, Brandon Guyer and Hak-Ju Lee. Jackson, 23, is playing for Team USA after batting .297 at Triple-A Iowa; Szczur, 22, batted .260 at Class A Daytona. The top pitching prospects include Trey McNutt, 22, who is pitching in the Arizona Fall League, and Jeff Beliveau, 24, who posted a 1.89 ERA in 41 games at Double-A Tennessee.
Epstein is expected to be replaced as the Red Sox GM by Ben Cherington, who was hired full-time in 1999 and has served the team in several capacities, including director of player development.
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 championship drought, and won 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 race. Manager Terry Francona and the Red Sox mutually parted ways two days after Boston's season ended.
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.