Is it Wu’s race to lose?

Boston will elect a new mayor three weeks from today. Three debates, the first of which comes on Wednesday night, will finally give voters a chance to see the two contenders side by side. 

With those encounters still looming, and no polls yet released on the final election, “I’m not going to bet anybody out or in yet,” said Joyce Ferriabough Bolling, a veteran Roxbury-based political strategist. 

“I’m not willing to say ‘game over’ at this point. There’s a lot of time left,” said John Connolly, a former city councilor who vied in the last race for an open mayor’s seat, in 2013, when he was edged out by Marty Walsh. 

While they both said the race is by no means over, the two seasoned Boston politicos, speaking on a new episode of The Codcast, also agreed that Michelle Wu is the clear favorite over Annissa Essaibi George. 

Connolly supported Andrea Campbel in the preliminary election, while Ferriabough Bolling backed Kim Janey. With the two Black women candidates, who finished third and fourth, now out of the running, Connolly and Ferriabough Bolling say the city’s Black voters will now play a pivotal role. 

Wu “has padlocked” white progressive voters, while Essaibi George “has locked down rooted, lifelong white Bostonians,” said Connolly. “Black and brown voters in Boston, both lifelong, rooted Black and Brown residents and newer Bostonians of color, are going to decide this race. And you have to say at this point, with Ayanna Pressley and [Acting] Mayor Janey having weighed in on Michelle Wu’s side, she has a decisive advantage as we go into the closing stretch.” 

Connolly said a coalition made up of white progressives and minority voters has been the winning formula for Boston races in recent years. 

In a campaign that has so far lacked a sharp edge, things like the recent debate over the length of a candidate’s tenure in Boston have received lots of attention. Asked last month in a radio interview whether it matters that she grew up in Boston and Wu did not, Essaibi George said,  “it’s relevant to me, and I think it’s relevant to a lot of voters.” 

Essaibi George insisted she was just describing an important part of her biography and not suggesting that Wu’s out-of-state background was somehow disqualifying. 

“I don’t particularly like the signalling of it – I have more knowledge because I’m from here than you,” said Ferriabough Bolling. “It’s the carpetbagger theory, and I just don’t like it.” 

Meet the Author

Michael Jonas

Executive Editor, CommonWealth

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

Connolly thought it might have been a play for Black voters. Some polling suggested likely Black voters in the city may be even more receptive to the “lifelong resident” argument than the electorate at large. But he said the comment ignores the reality that Wu “is very much where the sort of center of Boston is today.” Connolly pointed out that the majority of Bostonians were not born here and the fact that “younger Boston is getting more progressive.” 

Policing has become something of a fault line in the race, with Essaibi George winning backing from lots of law enforcement officers, including former Boston police commissioner Willie Gross. Ferriabough Bolling said Boston has escaped the worst of the police-community encounters that have hit other cities, but she said Black voters are still wary of a candidate who is seen as too “cozy” with police. “They’re doing a good job in the middle of the pandemic, but not so good a job policing themselves,” she said of the string of issues involving Boston police officers. 

Connolly said there is less pressure on Wu to turn up the temperature of the race since she’s widely seen as the frontrunner. Essaibi George has to “draw better distinctions if she’s going to mount a real challenge in this final,” he said, “and she’s going to have to start doing it at the debates.”