CHICAGO and BOSTON -- It was a day unlike any other in Red Sox front office history, one that -- emotionally and geographically -- was all over the map.

For those who have worked with both Theo Epstein and Ben Cherington, the two men who were inaugurated to their new posts atop the baseball operations pyramids of their storied franchises, it was a day of transition.

The Sox saw the man who was as much the face of their winning culture as anyone else depart, yet another organizational pillar removed in the aftermath of the team’s season-ending collapse. Of course, Epstein’s departure came under vastly different circumstances than did manager Terry Francona’s a bit more than three weeks earlier -- even though the two developments were related.

Francona and the Red Sox had a mutual parting of ways, with neither the manager nor club wanting to continue a relationship that had been wildly successful for much of eight seasons. But it was Epstein who had asked the team not to offer him an extension, who had declined the offers by team owners to design his own position while staying with the Sox and Fenway Sports Group.

Instead, Epstein made the choice to leave Boston, feeling that a change of organizations was required for renewal -- both his own and that of the club. The idea that Epstein would leave at some point (no later than 2012) had been accepted as inevitable. That timetable accelerated when Francona left, with Epstein feeling that he should turn over the managerial search to Cherington.

Still, for some of his former colleagues, the reality of seeing Epstein unveiled in Chicago, his tie a glinting gray with blue stripes to indicate his new allegiance, was jarring.

Epstein had walked away from the pursuit of adding to the multiple championships he had prophesied and delivered in Boston, instead bracing for the challenge of trying to help another team topple generations of futility. The departure of a leader, even if expected, still represented a challenge to process.

At the same time, it was a day of enormous pride for many who have worked with and befriended both Epstein and Cherington in the Red Sox’ baseball operations offices. After all, this was in some respects an antidote to the devastation of the Sox’ year-ending collapse. This was validation for all the hard work invested in building the Sox over the last decade.

Epstein was viewed by Cubs chairman Tom Ricketts as the ideal man for the complicated task of building an organization into a champion after a wait of more  than a century. The Red Sox’ winning record over the last decade, along with the demonstrated success of their player development model, had led Ricketts to Epstein as the ideal man for the immense challenge of turning the Cubs into winners. That impression was further cemented after conversations with approximately 20 trusted associates throughout the game.

That search process, in turn, led to precisely the sort of new challenge for which Epstein longed. He had the opportunity to choose to move from one of the most coveted jobs in the industry -- a Red Sox GM job, Cherington noted, for which a vacancy would produce a line hundreds deep -- for one of the only ones that could match it in prestige, namely, the opportunity to lead the Cubs out of the desert after 103 years (and counting).

“I wouldn’t trade my time with the Red Sox for anything, but I did think it was time to move on. They’re in great hands,” said Epstein. “I was ready for the next big challenge. This is certainly the ultimate challenge.”

In Boston, meanwhile, the success of the Red Sox model was further underscored with the decision of the team’s owners to promote from within and seek continuity with the work done by Epstein and the baseball operations department since 2002.

The choice of Cherington -- wearing a navy blue tie with red stripes to feature his own team’s colors at his press conference -- suggested that the Sox continue to believe in the people and principles that have been in place for the last 10 years or so, and think that they remain on a path that will yield more championships. It also represented the reward for Cherington’s 13 years in the Sox organization, and a milestone towards which Cherington -- who at different points had been an area scout, international scout, advance scout, director of player development, Vice President in charge of the draft and finally an Assistant GM with significant responsibilities for the club’s major league operations -- had long been working.

“I’ve been preparing for this job ever since my first job in baseball and certainly 13 going on 14 years with the Red Sox, I feel like I’ve been preparing for this job every day of that time,” said Cherington. “As much as I wanted it, I never assumed it would be mine, but I hoped it would.

“I’m really excited about this job. I’ve thought a lot about this job in recent years as I’d hoped I was getting clsoer to this opportunity and thought about the challenges that come with it. My eyes are wide open. There are going to be tough days that come with this job, but there’s so much enormous upside.

“At the end of the day,” he added, “this is what we love to do and what I love to do. This is the job I want. The reason I want it so badly is because of the people I’m going to work with every day. That’s why I don’t have any reservations about taking this job.”

Nor did Cherington’s colleagues have any reservations about celebrating his promotion. Upon Sox president and CEO Larry Lucchino’s introduction of the new Sox GM, boisterous applause erupted from the members of the Sox’ baseball operations staff at the press conference.

That enthusiasm echoed in Chicago, where Epstein remained mindful of his close friend’s ascent. As he shuttled between media obligations in Wrigley Field, Epstein requested updates on Cherington’s press conference, even listening to brief snippets of the WEEI broadcast of the event on a mobile phone.

“Ben is more qualified than anyone in the game to take this job over. I know I’m biased, because I’m a close, loyal friend, but he is really the best guy for the job,” Epstein beamed. “He’s had such a well-rounded development. He’s got so much integrity. He’s so bright. He’s got great management skills of people. This guy is going to do a fantastic job. I’m excited to see it happen. I wouldn’t have left the Red Sox if he weren’t the guy who was going to take over, and if I wouldn’t have had assurance that there would be continuity with the whole baseball operations team.”

Of course, mixed with pride was also a sense of some relief that resolution to an odd state of limbo had finally arrived. For as much as Tuesday represented an important day for the two franchises, the previous week or two had represented a somewhat awkward state of limbo for the two franchises as they prepared to move forward.

In Boston, in particular, the days leading up to Tuesday’s press conferences had featured a bizarre dynamic. Epstein continued to work with his colleagues in the basement of Fenway Park and retained the title of Red Sox GM, but the authority for the position had already been conferred upon Cherington.

Initially, Epstein had remained a part of the Sox’ offseason work, helping to assemble a list of managerial candidates among other tasks. But then, as the compensation negotiations dragged on, there was less and less for Epstein to do. As his departure became a foregone conclusion -- albeit one without a definite date -- his responsibilities were whittled to almost nothing.

“It would have been awkward but for my relationships with all the guys down there. We were laughing about it together, making joke upon joke upon joke about it,” said Epstein. “There was equal parts them trying to kick me out of meetings, and me pretending to assert my authority as general manager and firing all of them. It was just hilarious.

“I felt like that guy in the movie Office Space, who just had the red Swingline stapler,” Epstein added, referring to the character of Milton Waddams. “When I was at Fenway Park, I’d just keep showing up to work, and it was as if someone forgot to tell me that I didn’t work there anymore. I did end up in the basement with just a cubicle and stapler, and I knew it was time to go to Chicago.”

And that he did. But despite the humorous portrayal, and the fact that Epstein’s final days at Fenway had created an eagerness by both organizations to move forward (indeed, something that led the two teams to push ahead even before resolving the matter of how the Cubs will compensate the Sox for Epstein’s move), there was the matter of parting’s sweet sorrow. 

“I think he truly believed it was the right time to move on, but still this is where he made his name and this changed his life forever,” said Cherington. “He's a friend, so that part of it was hard for a lot of people in our office to see him go. And it was emotional for him.

“As much as I knew he is excited about this opportunity with the Cubs I do think it was really hard to walk out that door for the last time,” he added. “We didn't know what day was actually going to be the last day he walked out the door for the last time. There were a few days we thought it might be the last day. So one of the guys in the office made up this computer generated, feminine voice goodbye. So he walked out and each day was a little different message. So he got a kick out of that.

“It was challenging I guess because it did go on for a while,” he continued. “There had been enough goodbyes, but actually the last one may have been a little anticlimactic. But before that a lot of heartfelt goodbyes from him to us as a group and to different people individually.”

Yet as difficult as those goodbyes had been at the end of last week, within both the Sox and Cubs organizations, there was a sense of a new beginning. For the Sox, it is a familiar and trusted voice who is being given the podium. In Chicago, meanwhile, Epstein experienced the rush of being given carte blanche to direct a baseball organization from the ground up, to try to channel the same hard work into a Cubs franchise that had proven so rewarding with the Red Sox.

Whereas Epstein’s star power had dimmed somewhat in recent years in Boston -- the result of both the team’s failure to make the playoffs in the last two years and simple familiarity -- it once again proved luminous in Chicago on Tuesday. On a day of new possibility, when Cherington embraced the goal of bringing Boston its next championships, Epstein was promising the same in Chicago, to widespread acclaim.

“I should probably have another press conference right now to resign,” he joked. “My popularity is definitely at an all-time high. It’s peaked and it’s only going to go downhill.”