While there has been no formal acknowledgement by the Red Sox that Cherington, currently the assistant GM, will move into Epstein's seat, a baseball source confirmed on Thursday that it's highly likely.
Tim Brown of Yahoo, citing sources, reported that Cherington has already been informed that he will be the team's next GM.
The Red Sox have steadfastly said they won't comment on their general manager situation until there is a resolution. Epstein reportedly has agreed to a five-year contract to join the Cubs.
Though Cherington has long been one of Epstein's top confidants, he actually precedes his presumed soon-to-be former boss, who was hired in 2002, in the Red Sox organization.
In 1999, Dan Duquette, then the GM, hired Cherington to be an area scout but he was moved up to baseball operations in May of that season. He became director of player development in 2002 and stayed in that role for three years.
The Red Sox thought highly enough of Cherington to make him their co-GM along with Jed Hoyer in December 2005. That arrangement lasted about a month, after Epstein, who had left the club, decided to return to his post.
It has been obvious in the early stages of this tumultuous offseason that the Red Sox have been grooming Cherington for a promotion.
When the club met with Terry Francona and made a mutual decision that he would not be returning as manager, Cherington was involved in those meetings. Last week, when ownership was briefed by Epstein on the club's search for a new manager, Cherington was in that meeting.
With a strong background in player development and possessing the perspective of a player -- he played college baseball at Amherst -- Cherington could be the right fit to fill Epstein's post.
Cherington, 37, is also known for his strong organization skills and even temper.
He was named the assistant GM on Jan. 12, 2009, and had since worked closely with Epstein on virtually every phase of baseball operations.
Meanwhile, Epstein's fate hasn't been resolved, as the Red Sox and Cubs continued to spend time on Thursday working out a compensation package for Boston, made necessary because he has one year remaining on his contract with the Red Sox.