With voting timetable unsure, candidate field is in topsy-turvy mode

Walsh resignation date is key

The field of potential candidates to succeed Mayor Walsh, Secretary of Labor-designate in the Biden Cabinet, dwindled down over the last week as city councillors and others eyeing the seat waited warily to see what sort of election schedule they will be confronting during this municipal election year.

The popular incumbent from Dorchester will likely resign sometime next month upon his Senate confirmation, in the process passing his duties off to City Council president, Kim Janey, who will serve as acting mayor until an election is held.

The timing of when voters will get their first opportunity to pick a successor will likely impact who will run, and who won’t. Per the city’s charter, if Walsh resigns before March 5, his departure would trigger a special election— a preliminary followed by a runoff between the two highest vote getters— that would be scheduled for early summer.

The council, however, is considering a Home Rule Petition that would override that statutory provision and leave the entire matter for voters to decide in the regularly scheduled elections in September and November.

The petition, which was debated by the full council last week and sent to a committee for further review, would need to be approved by a majority of the council and by Walsh before going to the Legislature and the governor for consideration. (See related story in this edition.)

As that critical issue is sorted out, the field of possible candidates has been slow to take full shape. So far, only two candidates are firmly in the succession field: Councillors Michelle Wu and Andrea Campbell, both of whom launched campaigns last year when Walsh was still considered a probable candidate for re-election. Last week, two potentially strong candidates – Suffolk Sheriff Steve Tompkins and downtown Boston state Rep. Aaron Michlewitz, chair of the Ways & Means Committee at the State House – withdrew their names from the mayoral mix.

Those still weighing bids for the full-time post, according to multiple sources close to them, include Janey, who will run City Hall for at least a few months once Walsh leaves; Annissa Essaibi-George, an at-large councillor from Dorchester who has built an increasingly strong citywide base over the last three election cycles; and Councillor-at-Large Michael Flaherty, the longest-tenured member of the council who lives in South Boston.

State Sen. Nick Collins, who represents South Boston, most of Dorchester, and parts of Mattapan, is also mulling a run as are Marty Martinez, a Dorchester resident who serves as the city’s chief of Health and Human Services for the city; John Barros, another Dorchester resident who is the city’s chief of Economic Development in the Walsh cabinet, by those who have talked to him; William Gross, the city’s police commissioner, who told reporters last week that he was leaning towards a go; and state Rep. Jon Santiago, a physician who represents the South End and Back Bay in the Legislature.

Wu and Campbell can both claim serious head starts over new entries in the race.

Wu officially announced her bid for mayor last September— two weeks ahead of Campbell. The at-large councillor from Roslindale— now in her fourth term on the council— notched the race’s first big-name endorsement on Jan. 9 when US Sen. Elizabeth Warren threw her support to Wu, whom Warren taught as a professor at Harvard Law.

Campbell, who lives in Mattapan, has represented District 4 on the council since unseating longtime incumbent Charles Yancey in 2014. She announced her bid last September, citing her policy work on the council and her roots in the city.

According to the Office of Campaign and Political Finance (OCPF), Wu had $535,589 in the bank at the end of 2020 and Campbell was a bit behind her at $523,731.

Janey, who will be the first Black person — and the first woman— to serve full-time as the city’s chief executive, has not yet said if she will seek a full, four-year term. She had $96,965 in her campaign account at the end of last year. 

Essaibi-George is said to be seriously weighing a mayoral campaign, according to sources close to her. A former Boston Public Schools teacher and the owner of the Stitch House on Dorchester Avenue, she has been a longtime ally of Walsh, whom she has known since childhood. She has built her citywide base over three terms in office, and is one of several people with ties to Walsh’s political organization and donors who could mount a viable candidacy. She finished 2020 with over $110,000 at her disposal for electioneering.

Flaherty first joined the city council in 1999, and after running poorly against incumbent Mayor Thomas M. Menino, he returned to the council in 2013. He has roughly $198,000 in the bank, according to recent reports.

Flaherty told the Reporter last week that he is “weighing” his options, adding, “There are a lot of factors to consider, including who enters the race and whether we have a special election or not. Our city needs a mayor and leaders in each elected position who are fully committed to both bringing our city through this pandemic and continuing the work of making Boston a better, more resilient and equitable place for all its residents.” 

Martinez, who currently has the high-profile job of leading the city’s Covid response, told reporters last week that his experience in that role would be an asset in the mayor’s office.

“The next mayor … will have a huge responsibility to make sure we can finish this response and get to an equitable recovery, and I’m absolutely considering running for mayor,” he said.

Martinez does not yet have an account registered with campaign finance office and neither does Barros, who is also seen as a likely candidate. A Dorchester resident who ran for mayor in 2013 and finished fourth in the preliminary election, he is now a seasoned City Hall veteran with strong connections to the city’s business and civic leaders.

Of Cape Verdean descent, Barros was the longtime leader of the Dudley Street Neighborhood Initiative before joining the Walsh cabinet.

Gross told reporters last week that he is “90 percent in” as a candidate himself. He was promoted to the BPD’s top spot by Walsh in 2018 and is a popular figure among officers and their families.

A Dorchester resident in his youth, Gross lived in Milton in more recent years before moving back into the city— to Roslindale— after his appointment as police commissioner. 

“I can’t give you an answer 100 percent,” Gross said last week when asked about his candidacy. “But out of respect, I’m going to give this deep consideration. If there’s one thing that rings true, I would never be as presumptuous as just to throw my hat in the ring when the mayor was just announced.” 

Michlewitz, who lives in the North End, said last week that he won’t run for mayor, that he will keep his seat in the Legislature, where, he said in a statement, “I believe I can be most effective to the residents of the city of Boston in my current role as the chair of Ways and Means with a seat at the table leading us through the economic recovery necessary to see the commonwealth of Massachusetts out of the damage caused by the pandemic.”

Tompkins issued a similar statement last week: “While I am greatly flattered by both my inclusion in the discussion as a contender for this honor and by the many calls of support and encouragement I’ve received from friends and colleagues, urging me to seriously consider taking the leap, it is with powerful conviction and a renewed sense of purpose that I respectfully decline this opportunity to serve the people of Boston in this capacity.”