"I would love to have Theo back," Henry said on 98.5 The Sports Hub 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. I did everything I could personally, and so did (chairman) Tom (Werner) and (CEO) Larry (Lucchino), to make that happen. The fact is that being general manager in Boston, being manager in Boston, is a terrifically tough job."
For the first time, Henry acknowledged that Epstein has spoken to another team, presumably the Cubs. But a few hurdles remain. The Red Sox are taking a hard-line stance that Epstein not take any of his top aides with him, according to a team source.
Sources said Epstein and the Cubs have reached agreement on a five-year deal for anywhere from $15 million to $20 million, but the two sides also have to reach agreement on compensation to the Red Sox. Cubs chairman Tom Ricketts has given his player evaluators a list of prospects to decide if any should be made available in a compensation package, ESPNChicago.com's Bruce Levine reported Thursday.
Henry has said that there's a shelf life for working for the Red Sox and that Epstein would not be the Red Sox GM forever. He started at age 28 in 2002.
"He never saw the general manager's role as longer than 10 years for himself," Henry said. "I mean, maybe he did early on, but certainly after a few years he knew the stress of this job was too much."
Some Red Sox officials have been told that Ben Cherington, as expected, will be general manager, assuming the Red Sox and Cubs come to an agreement on compensation for Epstein, said the team source. Cherington would step into a tough situation after the Red Sox collapsed in September and allegations about a lack of team chemistry surfaced.
"Tom and my role is to have the best management possible," Henry told the radio station. "We've had great management. Tito (manager Terry Francona) and Theo have brought two World Series, arguably the best general manager in my mind and the best manager. It's just a really a sad day to see them both leave."
Teams only have seven days to communicate and get a deal done after they ask for permission to talk to an employee of another team, two major league sources told Levine Friday.
The source told ESPNBoston.com Friday that he would not be surprised if negotiations continue until Tuesday.
That's the day before the World Series is scheduled to begin, and the commissioner's office prohibits any major personnel announcements from being made during the Series.
"I can't imagine that either team would want to go another 10 days (until after the World Series ends)," the source said.
Henry acknowledged that the timing of an announcement could be tricky.
"It would be unfair to the Cubs, who I don't care that much about, but certainly to the Red Sox, and to Theo and to the people involved to comment about what's going on until there's something to be announced," Henry said during the radio appearance.
The Red Sox would seem to hold considerable leverage in the negotiations, given that Epstein remains under contract for another year and the Cubs have raised high expectations among their fan base that the 37-year-old is headed to Chicago.
It may well be that depending on the players they receive from the Cubs, the Red Sox may relent on banning Epstein from taking any of his top aides with him.
Epstein is already putting together his wish list for a Cubs staff during the negotiating period, a major league source told Levine. On the current staff, interim Cubs general manager Randy Bush and scouting director Tim Wilken have one year remaining on their contracts. Director of player personnel Oneri Fleita has four years remaining after his deal was extended at the end of the season.
Could the whole deal between the Cubs and Red Sox still fall apart?
The Red Sox need only look back to 2002, when Billy Beane accepted the GM job, only to inform the club two days later that he had changed his mind and would remain GM of the Oakland Athletics.
That was not a compensation issue, but there is precedent for a disagreement on compensation killing a managerial hire: The New York Mets wanted to hire Lou Piniella as manager after the 2002 season but could not reach agreement with the Seattle Mariners on compensation.
Piniella ending up going to Tampa Bay after the Rays agreed to send outfielder Randy Winn as compensation.
Gordon Edes covers the Red Sox for ESPNBoston.com. Bruce Levine covers the Cubs for ESPNChicago.com. Information from The Associated Press was used in this report.