Yet there is one star-caliber executive who, above all, continues to maintain intrigue as a subject of speculation: Cubs president of baseball operations Theo Epstein. While the 45-year-old Epstein — who remains under contract with the Cubs through 2021 — represents an obvious potential target for the Sox given both his record of success and his upbringing in and near Fenway Park, it’s also fair to wonder whether either or both sides might be open to exploring the possibility (or if the Cubs would permit such a conversation).

The team appears to be spending as much time examining where it stands with relation to the operation of the other 29 teams and considering what it wants from its next leader(s) as it does thinking about actual candidates. No names have been attached to the team’s pursuit, creating an information vacuum in which inkblots can be interpreted any number of ways.

More than two weeks removed from Dave Dombrowski’s firing as Red Sox president of baseball operations, the search for his replacement remains in its preliminary stages. The groundwork for that search has been, to date, deliberate and methodical.

The recent restructuring that elevated Mike Rikard to VP of scouting and featured promotions within the amateur scouting department suggests the possibility of continuity. At the least, those moves offer evidence that the team’s owners, who had to sign off on them, believe strongly in the members of the baseball operations department.


Related: Red Sox promote from within to fill scouting role

It seems clear the team would like an incoming general manager or president of baseball operations to be able to work well with the existing group. Some see an obvious possibility that the Red Sox could choose an internal replacement for Dombrowski from the current Gang of Four — assistant GMs Brian O’Halloran, Eddie Romero, Zack Scott, and senior VP Raquel Ferreira.


Related: Raquel Ferreira is a natural fit to help Red Sox in transition

The team seems unlikely to limit itself to those with Red Sox ties. There are numerous potential candidates, whether it’s ex-Sox executives such as Arizona assistant GMs Jared Porter and Amiel Sawdaye, Cubs GM Jed Hoyer and VP Jason McLeod, or Mets assistant GM Allard Baird, or those with no prior experience working for the Sox, such as Rays senior VP Chaim Bloom or Brewers assistant GM Matt Arnold.

It may be hard for the Red Sox to lure in an executive like Jeff Luhnow because the job is increasingly perceived as an unstable one. Tim Warner/Getty Images/Getty Images

Multiple industry sources are convinced the Red Sox also will want to see if they have a chance of reeling in some of the biggest fish in the executive seas. Given that the team is forever in win-now mode, the idea of finding an executive with a known track record is significant.

But there’s skepticism in the game that several of the executives with such a track record — Arizona’s Mike Hazen (the former Red Sox executive who just signed an extension with the Diamondbacks); Oakland’s Billy Beane and David Forst; Chris Antonetti and Mike Chernoff in Cleveland; Andrew Friedman of the Dodgers; or Jeff Luhnow of the Astros — would leave their jobs to pursue another that is increasingly perceived as unstable. While the resources that come with the Sox job are appealing, the ouster of Ben Cherington less than two years removed from a championship and the departure of Dombrowski after one down year have led to a perception in some corners that the position comes with impossible-to-satisfy demands.


Epstein understands the particulars of working for the Red Sox better than anyone. For now, there’s little more than inkblots to interpret. But it’s worth revisiting both Epstein’s history with the Sox and his departures from them to gain some insight into factors that could be at work.

When he moved from the Red Sox to the Cubs, Epstein — in an op-ed for the Globe — explained his decision to leave his dream job:

“Football legend Bill Walsh used to say that coaches and executives should seek change after 10 years with the same team. The theory is that both the individual and the organization benefit from a change after so much time together. The executive gets rebirth and the energy that comes with a new challenge; the organization gets a fresh perspective, and the chance for true change that comes with new leadership. This idea resonated with me.”

Theo Epstein talks with Terry Francona early in the season in 2006. Jim Davis/Globe Staff

Epstein’s planned timetable for departure accelerated, however, after the Red Sox collapsed in September 2011 and fired manager Terry Francona.

Epstein is now eight years into his position as Cubs president of baseball operations. Chicago is spiraling, having gone from a 63.6 percent likelihood of making the playoffs on Sept. 17 to a 2.1 percent chance entering Tuesday. Manager Joe Maddon is almost surely out after this year, meaning that Chicago will soon embark upon a search for his replacement.


In other words, the organizational circumstances facing Epstein right now bear some similarities to those that prompted him to leave Boston with one year left on his contract.

Meanwhile, there are factors that might appeal to Epstein about a potential return to the Sox.

In contrast to his sometimes strained relationship with former CEO/president Larry Lucchino, Epstein is extremely close with Lucchino’s successor, Sam Kennedy, who went to Brookline High with Epstein.

Moreover, any bad feelings that may have existed with principal owner John Henry (who also owns the Globe) or chairman Tom Werner at the time Epstein left for Chicago seem to have been soothed. In recent years, the Sox have supported charitable activities of Epstein’s Foundation To Be Named Later.

Related: How Dave Dombrowski’s firing took place

Meanwhile, the Boston area events of the foundation underscore that Epstein’s Boston roots remain strong. He worked closely with many members of the team’s baseball operations department. While Epstein at times struggled with the visibility of his life in Boston early in his GM career, he seemed to make peace with the role over the course of his tenure. It’s not hard to imagine why a return could carry appeal.

On the other hand, there are reasons the idea of Epstein coming back right now wouldn’t make sense. The Cubs are amid a structural transition that runs deeper than just the manager, with a chance to reorganize their scouting and player development in ways meant to push Chicago forward in a changing era — exactly the sort of process-based challenge that Epstein loves.


Epstein’s immediate family is now established in Chicago, and whenever Epstein does move on from the Cubs, after the round-the-clock grind of being at the baseball operations helm for the past 18 years, it’s fair to wonder whether a.) Epstein might want a “life buffer” before jumping into another baseball job and b.) whether another job as a president of baseball operations appeals to Epstein, or if he is more likely to seek a different role such as ownership.

Henry and Werner tried to persuade Epstein to stay in Boston in 2011 with a position that went beyond the same thing he’d been doing as GM.

“John and Tom were kind enough at some point late in the summer to tell me that they wanted me to stay with the Red Sox, to stay with [Fenway Sports Group] in any capacity I could imagine. I could tailor my role or do what I wanted,” Epstein said at his 2011 introductory news conference at Wrigley Field. “It meant a lot to me. I was really appreciative . . . [But] I just couldn’t envision a role at the Red Sox that would have satisfied the principles that [Bill] Walsh espoused that were resonating with me so much.”

Would Theo Epstein want another GM job? Or might he pursue something else, like ownership? Elsa/Getty Images/Getty Images

Might his outlook be different now, at a different life and career stage? If so, if he does eye a broader range of interests and responsibilities and curiosities, then the varied holdings of Fenway Sports Group might represent a particularly intriguing challenge, much as Beane (who has an ownership stake with the A’s) has found ongoing satisfaction in Oakland while mixing his involvement in the team’s baseball activities with partial ownership of soccer teams.

In other words, at some point, the Red Sox could make an awfully interesting pitch in hopes of bringing back Epstein. Whether he’d be willing to listen now, however, is another matter entirely — with a decent chance that even if the Red Sox could present a perfect job to entice him, they’d be doing so at an imperfect time.

Still, speculation about Epstein seems unavoidable. After all, in December 2005 — at a time the Sox hired Cherington and Hoyer as co-GMs when Epstein temporarily had left the organization — Lucchino somewhat famously suggested the team would “leave a light on” for Epstein’s potential return. The next month, Epstein responded to that beacon, returning to the GM role.

Might the team once again flip on a bat signal for Epstein, either by pursuing him directly or hiring someone who was close to him? And if so, would he be interested in responding? Would the Cubs permit him to do so? These are just a few of the many questions associated with the Red Sox opening, where silence has created a void filled not by information or a known candidate list but instead by conjecture.

Related: From Dave Dombrowski to Antonio Brown, we need more answers from ownership

Alex Speier can be reached at alex.speier@globe.com. Follow him on Twitter at @alexspeier.