Epstein is now free to work for any team in the Major Leagues, though it remains to be seen how quickly he will pursue new opportunities. There are currently general manager vacancies with the Los Angeles Dodgers, Philadelphia Phillies and Tampa Bay Devil Rays.
Back on Nov. 25, 2002, after an unsuccessful attempt at convincing Billy Beane to leave the Oakland Athletics, the Red Sox took a chance on Epstein and made him the youngest general manager in baseball history at 28 years old and 11 months. That distinction has since been taken by Jon Daniels with the Texas Rangers.
Epstein rewarded the faith of club president/CEO Larry Lucchino (who he had worked for his entire career in baseball) and principal owner John W. Henry, making several bold moves that helped the Red Sox win 95-plus games for three straight years.
For the past couple of weeks, Lucchino and Epstein -- who appeared to have a classic mentor-protégé relationship -- spent a lot of time trying to hammer out a new deal. However, in the end, money did not seem to be an issue for Epstein.
Instead, it seemed as if he was in need of a change for reasons which aren't completely clear at this point. Epstein, who grew up in Brookline, Mass., which isn't much more than a Manny Ramirez homer from Fenway Park, seemed to have his dream job. If so, it was one that came to an abrupt end.
"First, I want to thank John Henry, [team chairman] Tom Werner and Larry Lucchino for the opportunity to serve as general manager for the last three seasons," Epstein said in a statement released by the club. "Their support and friendship mean a lot to me, and I wish them all well. I also owe a debt of gratitude to the players, Terry Francona, the coaching staff, the front office, the baseball operations staff and the fans for making my Red Sox experience so meaningful.
"Growing up in the shadow of Fenway Park, I never dreamed of having the chance to work for my hometown team during such a historic period.
"My decision not to return as general manager of the Red Sox is an extremely difficult one. I will always cherish the relationships I developed here and am proud to have worked side-by-side with so many great people, in and out of uniform, as together we brought a World Championship to Boston.
"In my time as general manager, I gave my entire heart and soul to the organization. During the process leading up to today's decision, I came to the conclusion that I can no longer do so. In the end, my choice is the right one not only for me but for the Red Sox.
"My affection for the Red Sox did not begin four years ago when I started working here, and it does not end today. I will remain on the job for several days as we finalize preparation for next week's general managers meetings. Thereafter, I will make myself available to the organization to ensure a smooth and stable transition.
"My passion for and dedication to the game of baseball remain strong. Although I have no immediate plans, I will embrace this change in my life and look forward with excitement to the future."
The Boston Globe reported Monday that Epstein and the Red Sox had agreed to a new three-year deal (reported to be close to $1.5 million per season) that just needed to be formally announced. Apparently, that was not the case, as Monday's stunning news came forth.
Red Sox players were disappointed to hear that Epstein was gone.
"Surprised," Red Sox right-hander Bronson Arroyo said of his reaction to the news. "Probably a little disappointed. I enjoyed having him around. I think he brought a lot of honesty to the table as a GM and also, he was kind of closer to our age group, so it was easy to communicate with him."
Before Monday, the most recent public words from the Red Sox had come Thursday, when Epstein and Lucchino issued a joint statement that stated the following:
"We had a meeting over lunch today to continue our discussions and to conduct other business as well. We made progress, but we anticipate no further statement until there is something to announce. We are hopeful that these discussions will work out for the best. In the meantime, we continue 'business as usual.'"
But business was anything but "usual" on Monday, a Halloween that produced more of a trick than a treat for Red Sox fans.
While Epstein inherited a talented core of players -- some who remain and others who have since moved on -- he successfully added to that nucleus, while at the same time, overseeing a farm system that made a dramatic turnaround the last couple of years.
"Every move he made seemed to be the right move at the right time," said Kevin Millar, Boston's primary first baseman the last three years. "It definitely shocks me."
The Red Sox said they would hold off until Tuesday to comment on Epstein's departure, at which point Lucchino will probably be heard from, and perhaps Henry and Werner.
Epstein's tenure was relatively short, but highly memorable.
The move Epstein might never top is the free agent signing of David Ortiz for just more than $1 million after the big designated hitter was released by the Twins following the 2002 season. All Ortiz has done since his arrival is emerge as one of the elite sluggers in the game, not to mention one of the most popular players in franchise history.
And in another master stroke, Epstein was able to reach a two-year extension with Ortiz (including an option for a third year) in May 2004, ensuring that the left-handed slugger will remain in Boston through at least the 2007 season.
There have been some other memorable moves, including the dramatic trade and subsequent signing of Curt Schilling over the Thanksgiving holiday in 2003, not to mention the bold deal that sent one-time icon Nomar Garciaparra out of Boston for Orlando Cabrera and Doug Mientkiewicz on July 31, 2004.
Other less-heralded moves have helped stabilize the team, including the one that brought third baseman Bill Mueller to Boston in 2003, though the switch-hitter is now eligible for free agency. Ageless Mike Timlin, one of Epstein's first free agent signings, has been the rock of the bullpen the last three seasons, and he will officially sign a new deal this week that will keep him with the Sox in 2006.
As with any GM, there were moves that didn't work out so well. Side-winder Byung-Hyun Kim, for one, never got comfortable in his time in Boston. Ditto for fellow right-hander Ramiro Mendoza. Shortstop Edgar Renteria was signed last winter for four years at $40 million and struggled in his first year with the Red Sox.
By and large, Epstein's moves worked out, making him popular among the team's rabid fan base. His local roots did nothing to hurt that popularity.
Though he was the classic local boy who made good, Epstein made his youth a non-issue from the start, hitting the ground running and seemingly never stopping until Monday.
With the Red Sox front office now in a state of limbo, the team has several key baseball decisions ahead of them.
Johnny Damon, the team's center fielder and leadoff hitter the last four years, has filed for free agency. Veteran left-hander David Wells -- a 15-game winner in 2005 -- has already told the team he'd prefer to be traded to a West Coast team for what will likely be the final season of his career.
Superstar slugger Ramirez, according to a report, has yet again asked to be traded out of Boston. As a 10-5 man (10 years in the league, five with existing team), Ramirez must approve any potential trade, which would make it a highly complex endeavor.
The bullpen, which played a big role in the 2005 team not clinching a playoff berth until the final game of the regular season, also appears to need a retooling.
But it's a retooling that will take place under the watch of someone other than Epstein.