As City Hall undergoes a historic transition of power, some of Mayor Thomas M. Menino’s top Cabinet members are heading for the exit before the new administration takes charge.
One-quarter of Menino’s 20-member Cabinet has left or has announced plans to resign. More are mulling options. The departure list includes Menino’s chief of labor, John Dunlap, whose last day was Friday after eight years in the administration. He will hold a post with similar duties at the Massachusetts Institute of Technology, he said.
“I’m happy,” he said on a recent evening.
But in the wide corridors of City Hall, where phones are ringing and business still hums, the mood is bittersweet, even gloomy, as uncertainty looms among top officials bracing for sweeping change when Mayor-elect Martin J. Walsh assumes office Jan. 6.
The string of exits has caused political observers to speculate about what will happen next. Who is leaving, who will stay until January, and who will stick around and work with the Walsh team?
“I’ve talked to a whole bunch of people privately, and a lot of people are looking around,” said Larry DiCara, former city councilor. “I would say the mood is very uneven.”
Even the mayor’s longtime snow removal guru Elmo Baldassari is weighing what he will do next. Asked about his plans during and after the transition, Baldassari replied: “I don’t know.”
Menino’s loyal aides, including those inching toward retirement, plan on stepping down with Menino. And some Cabinet members, along with department heads, are keeping their eyes peeled for new jobs, political observers said.
Over 20 years, Menino built a team of top advisers credited with steering the city forward and overseeing a sweeping bureaucracy of roughly 20,000 full-time and part-time employees. As Walsh’s team moves towards power, Menino has let it be known at City Hall that he wants the transition to go smoothly, said Dot Joyce, the mayor’s chief public information officer for the past seven years.
“There are people who have been here for a long time,” said Joyce. “I’m sure there’s emotional attachment to some folks. But by and large, I think everyone is hopeful.”
Asked her plans post-Menino, Joyce laughed. “First thing is, I’m going on vacation,” she said.
Cabinet members who have turned in resignation letters include Carol R. Johnson, who retired as Boston schools superintendent in August after six years, and Edward F. Davis, who stepped down as police commissioner Nov. 2 to take a fellowship at Harvard University’s Institute of Politics.
Roderick Fraser, the Boston fire chief, has not indicated what he plans to do, but said he is keeping his options open.
The list of notable Cabinet departures also includes Marie St. Fleur, who had been chief of advocacy and investment for three years, and Daphne Griffin, the former chief of human services and head of Boston Centers for Youth and Families.
St. Fleur, a former state representative, began a new job Monday at Bessie Tartt Wilson Initiative for Children, an advocacy and early education initiative. Griffin began a new job Nov. 4 at Suffolk Construction Corp., where she is working on community outreach initiatives as project development manager for White Stadium at Franklin Park, according to the company.
Christopher Byner, the former director of the city’s antiviolence Streetworker program, has stepped in as interim director, and department employees are toiling along as though they were going to be there for another four years, said department spokeswoman Sandy Holden.
“We are still business as usual,’’ Holden said. “In general, people are sad that the mayor is moving on, because youth and families was such a priority for him. They are concerned about what will be coming next because when someone new comes in, they usually bring in their own team. You really don’t know.”
Menino’s other lieutenants, Michael Kineavy, chief of policy and planning; Mitchell Weiss, chief of staff since 2009; and Howard Leibowitz, chief of programs and partnerships, have pledged to stay on until Menino leaves office.
“I’ve had great run in this administration,” said Leibowitz, who served as Menino’s first press secretary in 1993 and as head of intergovernmental relations for 10 years. “We’ll see what the future holds. I feel I have an obligation to finish out the administration. I feel a commitment to seeing it through.”
It remains unclear what the next moves are for the city’s chief financial officer, Meredith Weenick; William Oates, chief of information officer; and corporation counsel William Sinnott. Weenick declined to comment about her next moves, and Sinnott did not return Globe calls for comment.
Peter Meade, chief economic development officer, who oversees the Boston Redevelopment Authority, announced this spring that his term will end with the Menino administration. The BRA, which took a thrashing during the election, pledged to follow the direction of Meade and Menino to uphold “their high standards of professionalism,” serve the public, and provide a seamless transition for the new administration, according to spokeswoman Susan Elsbree.
“The BRA looks forward to continuing the success of moving Boston forward with Mayor-elect Walsh,” said Elsbree.Meghan E. Irons can be reached at email@example.com. Follow her on Twitter @meghanirons.