The Boston Globe reported on its Web site on Tuesday afternoon that Epstein and the Red Sox have all but agreed to terms on a new deal, though there are still some technicalities to work out before the deal is formalized or signed.
"We are all on the same page with regard to our vision for the organization," Red Sox principal owner John W. Henry wrote in an e-mail to the Globe. "The negotiations were pleasant, and were all about rewarding Theo for the great, great job he has done in bringing two world championships to the Red Sox. We look forward to the difficult task of trying to win a third."
However, Henry backed off from that comment later in the day in an e-mail to MLB.com and other media outlets.
"I got a little ahead of where we are today in commenting on what have been refreshingly private negotiations," wrote Henry. "We are not done, but we expect to have an announcement in the near future. I have asked all involved not to comment until this is finalized."
Things were far different at the end of the 2005 season, when Epstein and the Red Sox went right down to the Oct. 31 deadline and no extension could be reached.
At that time, Epstein announced his resignation, only to return two months later.
Other than that brief bump in the road, Epstein has enjoyed a stable and highly successful run since initially being named as general manager of the Red Sox on Nov. 25, 2002.
Though manager Terry Francona stressed that he was certain a new deal for Epstein wasn't final yet, he was enthusiastic about an announcement that could be imminent.
"I hope they're near the finishing line," Francona said. "It sounds like they obviously are. I don't think they got there yet. I certainly can't imagine being here without Theo. It should get done. He's done a great job. I'm excited that it's getting to that point."
When Epstein became the youngest GM in baseball history in November 2002, he spoke of turning the Red Sox into a scouting and player development machine, and also a team that would be a contender for the postseason virtually every year.
Both goals have been reached, and then some. The Red Sox are on the verge of qualifying for the postseason for the fifth time in Epstein's seven seasons. They've won the World Series twice in four seasons after going 86 years without a championship.
And through it all, prospects like Dustin Pedroia, Jonathan Papelbon, Jon Lester, Jacoby Ellsbury, Justin Masterson and Jed Lowrie have exploded through the farm system and paid immediate and significant dividends at the Major League level.
Epstein has also not been afraid to make a bold trade, such as when he dealt Nomar Garciaparra -- then a franchise icon -- to the Cubs in 2004, or July 31 of this season, when he sent future Hall of Famer Manny Ramirez to the Dodgers in a three-way trade for Jason Bay.
"The one thing I don't want to do is -- I don't need to sit here and rate my boss," Francona said. "But since it's all good, I like to brag about him. I saw some of the statements he made when he came here on how he envisioned the organization would be. It seems like he has met those goals with flying colors.
"I know I love working for him. In a place like Boston, it's hard. You're supposed to have an opinion and you don't get to where I'm sitting or where he's sitting without having a strong opinion. Sometimes those opinions, they're not always the same. Again, when things get really tough though, it's nice to know that he's there. That's the one thing, I know, when things get going here and we're up against it, I know the one guy I can go talk to and I appreciate that."
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.