The questions of when and how to replace them is unanswered — and intriguing — at the beginning of another critical offseason.

“It is pretty clear that that executive leadership circle is down not just bodies, but down really talented people. And we’ve got to find the right people to emerge and to put into place there,” Breslow, who is in his fourth offseason as chief baseball officer, said in a phone interview.

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“Hesitant to put a timeline on it, but understand that these jobs [as the head of baseball operations] are massive and they’re not getting any smaller. Finding people who can add to what we are building here, it’s near or at the top of my list.”

Other teams plucking away top lieutenants is something of an inconvenient compliment. It’s great that clubs think so highly of Smith and Toboni, for example, that they want to hire them to run the team. But it leaves the Red Sox dealing with the aftermath.

“The inconvenient piece is that we need to put a great team on the field and we need to win more games in 2027 than we did in 2026,” Breslow said. “Losing leadership like Taylor and Paul makes that harder, but we have to do everything we can to replace them.”

Amplifying the aftermath is when they take other Red Sox officials with them.

Toboni recently hired David Besky, director of baseball sciences, as a major league pitching strategist. Last offseason, his Nationals added Devin Pearson (Red Sox director of amateur scouting) as an assistant general manager and Andrew Wright (Red Sox minor league field coordinator) as a special assistant.

So far, Smith hasn’t brought any Sox peers westward, according to Breslow.

Although Smith ran the research and development department — analytics — he “touched a lot of different aspects of the organization,” Breslow said, including roster construction and “longer-term strategic thinking.”

“We will definitely miss him, but in his absence, I think there’s an opportunity for some emerging leadership to step up and step into that void,” Breslow said.

At least for now, the Red Sox are relying on internal options for that (much as they did throughout 2026 in dividing Toboni’s duties instead of deciding on a one-for-one replacement).

This time, the Red Sox promoted Dan Meyer to vice president of baseball research and Patrick Coglianese to vice president of baseball systems. Both were senior directors under Smith.

Meyer has steadily climbed the analytics ranks since joining the organization in 2018. Coglianese came aboard about two years ago and, prior to that, worked in software engineering for ASICS.

“Those two will work in concert as we continue to evaluate the opportunities in front of us,” Breslow said. “My job is to constantly balance giving those who are ready to step into leadership roles the runway to do so, while also appreciating that any chance we have to add dynamic, talented people to the organization is something we have to explore.”

The Red Sox haven’t made any major front office additions “at this moment,” Breslow said.

“Organizations, generally speaking, benefit from new ideas, fresh perspectives, experiences different from the ones that the rest of us have had, so that we can add just some diversity of thought,” he said.

Breslow still has three assistant GMs: Michael Groopman, Eddie Romero, and Raquel Ferreira. Additionally, Brian O’Halloran is an executive vice president of baseball operations. All four are holdovers from prior administrations, inherited by Breslow upon his hiring in 2023.

The remaining Breslow-era senior addition is Ryan Otero, a special assistant to the CBO.

As for the GM-as-No. 2 question?

“Constantly assessing that situation,” Breslow said. “Exactly what title those people have, I think, is kind of secondary to just understanding who makes us better.”

In a sense, maintaining a front office is much like maintaining a roster of players. It’s an ever-evolving group, never static. A person in Breslow’s position is always on the lookout for frontline talent — and for the next wave that can step up when needed.

“The best thing to do is to understand our current people and their talent and their ability to step into leadership roles, and also where I’ve got voids and blind spots and can find people who can complement me,” Breslow said. “But I don’t think it works great when you go out and say, ‘I have to hire this position.’ We want to hire great people who are going to be additive to our group, wherever and whenever that happens.”

Tim Healey can be reached at timothy.healey@globe.com. Follow him @timbhealey.