One year, three mayors: A look at the historic transitions 2021 brought to Boston City Hall

From left to right, former Boston mayor Martin J. Walsh, Acting Mayor Kim Janey, and Mayor-elect Michelle Wu.Globe staff

Boston City Hall’s most unusual year will continue with another turn later this month, when city government will see its second mayoral transition of 2021 and the third mayor in a single calendar year.

In a town known for sticking with its incumbent executives for years, it is an unprecedented amount of political change, at least in modern times. (Boston has had more than two mayors in a calendar year at least once before, according to the city clerk’s office. In 1845, five different men took a turn as the city’s top pol, according to city records: Martin Brimmer, William Parker, Thomas A. Davis, who died in office, Bensin Leavitt, and Josiah Quincy Jr.)

With a new mayor will undoubtedly come a litany of City Hall changes. Michelle Wu has yet to announce who will serve in her Cabinet, but if Martin J. Walsh’s City Hall departure in March is any indication, there may be a management exodus. A slew of close Walsh advisers left in the weeks and months after their former boss headed to Washington, D.C., including his chief of staff, chief of policy, the city’s corporation counsel, and Walsh’s communications chief. Walsh’s chief financial officer, chief of operations, equity chief, economic development chief, and the city’s top energy and environmental official also left this year.

There were further transitions in seemingly every corner of the city’s 18,000-strong workforce. According to more than a dozen current and freshly former City Hall insiders interviewed by the Globe, people were worried about sticking around, given that they didn’t know who the mayor or their department head would ultimately be, and there have been more people than usual with “acting” or “interim” in their titles in recent months.

Now, another shakeup is on the horizon. Wu, who bested her City Council colleague Annissa Essaibi George in Tuesday’s general election, will be sworn in on Nov. 16.

It’s a quick turnaround, and Wu herself has acknowledged that “it is not possible for anyone to arrive on Day 1 after a two-week transition with a fully staffed up team.”

The speed is the result of the unusual circumstances of the election. Typically, a new mayor would be elected in early November and sworn in the following January, in accordance with the expiration of the mayoral term. This year, however, due to Walsh’s departure earlier this year, the mayor will be sworn in shortly after the election certification process, which typically takes 10 days to two weeks.

City councilors decided earlier this year that such a move “will clear up confusion between the powers of [the] acting mayor and the powers of a duly elected mayor and follows the will of the voters.” While Acting Mayor Kim Janey, who became Boston’s interim executive thanks to her role as City Council president when Walsh left, was the city’s first Black and first female mayor, Wu is the first woman and person of color popularly elected to that office.

To date, Wu has brought on a transition director, Mariel Novas, and tapped communications firm 90 West to help during the transition period. She also launched a transition website where people can apply to work for the city. (There are currently 420 job postings on the city’s website, according to a Janey spokeswoman.) But significant outstanding questions remain: Who will be Wu’s chief of staff? Her policy chief? What will the search committee for a new police commissioner look like?

City Hall transitions can be rocky. Tension is perhaps inevitable when a new boss takes over with stark differences in style and substance from the old boss. During Janey’s months in the corner office, friction between her tight group of advisers and holdovers from the Walsh administration abounded, with some managers complaining of communication breakdowns, rushed policy rollouts that grabbed headlines but lacked details, internal confusion, and frustration.

Rumors of widespread City Hall discord and low morale have persisted for months. But this week, current City Hall employees, as well officials who have recently left city government, described mixed emotions: Workers are relieved that the election is finally over and that they know who the new boss will be, but, with more change on the horizon, there is also trepidation.

“People are nervous,” said one former City Hall staffer who left in recent months, speaking on background because the person is not authorized to talk to the media. “And it doesn’t have to do with Michelle. It has to do with change.”

There will be workers who are going to see what their options are, said the former staffer, who downplayed past clashes between Walsh and Wu having any real impact on the vast majority of City Hall workers. There are City Hall officials “who are still upset Tom Menino’s gone,” but continue to serve the city, the former staffer said, referring to the former longtime mayor who died in 2014, nearly 11 months after leaving office. Change at the Cabinet level is common, this former staffer said. “You know that walking in the door,” the person said. “You serve at the pleasure of the mayor.”

A current mid-level city manager, also speaking anonymously for the same reason, said bluntly that they expected their Cabinet chief to be let go soon and added they knew of one official who recently transferred jobs in city government because they knew their previous role was desirable and one that the new mayor would probably want to have her own person in.

While workers are glad the election is finally over, “it’s all up in the air, same as it was in March.”

“Good people will stay but it doesn’t mean they’re not feeling apprehensive,” the manager said.

Another city manager had questions about the immediate future: “I could potentially be really safe or unsafe in my job.”

Morale at City Hall, that manager said, is still low and people are anxious about what the new administration will mean for their jobs and their departments.

Another City Hall official with a working knowledge of the Boston Planning & Development Agency, an entity that Wu has supported abolishing in the past, said that people at that organization expect there to be change and that staff turnover, which has occurred throughout the year, will continue. But, the person added, the mood is largely “business as usual.”

Although this person did concede, “There is an adjustment of getting to the new normal” with the incoming administration.

Paul Watanabe, a political science professor at UMass Boston, did not discount Wu considering some Walsh appointments who left during the Janey period. In some areas of city government, Wu will be looking for someone to simply “captain the ship and in other places, someone to design a whole new ship,” he said.

Despite the tensions in Janey’s City Hall after Walsh left, “the day-to-day operation . . . I don’t think people felt there was a big problem there,” he said.

In such a transition, management changes are inevitable, said David Hopkins, a Boston College political science professor.

“Once Wu takes control of the mayor’s office, I would guess that she’s going to want to get some of her appointees in there and she has somewhat different politics and policies from Walsh in particular,” said Hopkins.

Hopkins was among those to point out that the main difference between the upcoming transfer of power and the switch between Walsh and Janey is that Wu was elected mayor, while Janey was serving in an interim capacity.

Wu’s council colleague Michael Flaherty thought Boston’s new mayor-elect “has a good handle of things citywide and has solid citywide relationships.”

“I don’t expect there to be any delays in city services,” said Flaherty, who was reelected on Tuesday. “Mayor-elect Wu is a demonstrated leader and I anticipate there will be less transitions out of City Hall now than under Kim Janey, in part because of the stability a duly elected mayor provides both city employees and residents with.”

Janey, who was eliminated from the mayoral field in September’s preliminary contest, plans to take some time off before returning to the City Council in December. She has yet to announce what her plans are after her council term expires in the new year.