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Annissa Essaibi George appears to be the underdog in the Boston mayoral race. What would it take for her to win?

First televised debate offers opportunity to recast race

City Councilor Annissa Essaibi George.Craig F. Walker/Globe Staff

City Councilor Annissa Essaibi George emerged from the September preliminary election for Boston mayor as the underdog, trailing rival Councilor Michelle Wu by a full 10 points in the final tally. And in the four weeks since, nearly everything has seemed to break Wu’s way.

But in Wednesday’s debate, the first of the general election, Essaibi George has an opportunity to speak directly to the voters who could still lift her to victory, through appealing to her more moderate base in South Boston, Dorchester, and West Roxbury while introducing herself anew to Black voters who likely hold the fate of the election in their hands.


For Essaibi George, it’s a high-visibility chance to redirect the race. And it is a format that plays to her strengths as a communicator. In forums and one-on-one conversations, she comes across as warm and plain-spoken, combining a folksy manner with a hard-biting Dorchester accent, a style that goes hand-in-hand with her central argument that she will be a more hands-on, down-to-earth leader than her opponent.

“It’s game time for Councilor Essaibi George. She’s running out of runway,” said David Guarino, a Democratic political consultant who is not working on either campaign. She needs “to show voters that there’s an actual race here . . . that this isn’t the foregone conclusion that a lot of people are starting to assume it might be.”

Since the preliminary election in mid-September, Wu has picked up a slew of endorsements, out-raised Essaibi George, and now has more cash on hand than her rival. Acting Mayor Kim Janey, who finished fourth in the preliminary election, has endorsed Wu, as have Representative Ayanna Pressley and several coalitions representing communities of color.

The first post-preliminary public poll — released Wednesday morning — showed Wu with a commanding lead, drawing 57 percent support of likely voters compared to 25 percent for Essaibi George, according to the survey conducted by MassINC Polling Group for WBUR, the Dorchester Reporter, and the Boston Foundation.


In recent weeks, Essaibi George has been making major adjustments in her effort turn a corner in the race. She’s opened up campaign offices in Roxbury, Mission Hill, and Hyde Park. She’s been courting diverse community leaders, and she is getting her message out one voter at a time.

“She’s one of us,” said Bobby Jenkins, an ardent Essaibi George supporter from Mattapan. “Once people meet her, they fall in love with her — she’s that engaging. Wherever she goes in the city, she’s comfortable ... she’s at home.”

Last week, Essaibi George stood in Roxbury surrounded by a diverse coalition of community residents and leaders and released her equity, inclusion, and justice agenda, promising, among other things, a $100 million investment toward implementing the plan in Boston’s Black community and Latino, AAPI, and other marginalized communities if she is elected mayor.

Essaibi George is making the most of any opportunity to distinguish herself from Wu — a pattern she is expected to continue Wednesday evening, when the two will appear together for their first televised one-on-one debate.

For her part, Essaibi George doesn’t deny that she’s headed into November at a disadvantage. “I’ve been underestimated all my life,” she told the Globe. But she denied that Wu is carrying the race’s momentum, saying, “we hear it, we feel it” as she campaigns around the city.


She has won the backing of several influential unions, including the International Union of Painters and Allied Trades District Council 35 and the International Brotherhood of Electrical Workers Local 103. She has connected powerfully in small groups of voters, as she did one morning last week with a group of older Haitian voters at the Forever Young Adult Day Center in Hyde Park. The campaign plans to launch new television advertisements this week in an effort to reach more voters in the final stretch.

Now, if she wants to make headway against Wu, Essaibi George needs to win the support of voters of color, constituencies her rival is courting, too. After three Black candidates were eliminated in September’s preliminary round, Wu and Essaibi George began aggressively competing for the backing of voters of color.

“This race is in the Black community now,” said Frank Baker, a city councilor who represents Dorchester and said he will work to turn out his district for Essaibi George. “There’s a large percentage of the vote that both of these candidates have to go after.”

Essaibi George has been actively courting votes in Black communities, where she drew minimal support in September’s preliminary election. She said without Janey and City Councilor Andrea Campbell in the race, “the dynamic has changed,” and there is a “renewed opportunity to introduce myself to voters in the Black community.”

The 47-year-old former teacher is balancing those efforts with work to boost get-out-the-vote efforts in her base, including areas of South Boston and parts of Dorchester and West Roxbury.


Still, analysts said, even impressive turnout in those reliable areas that formed the base for her preliminary success likely won’t be enough to clinch the race for Essaibi George if she doesn’t earn enough support from Black and Hispanic voters.

Former city councilor John Connolly, who came in second place to former state representative Martin J. Walsh when Boston had its last open mayoral race in 2013, recalled the cascade of endorsements from a diverse array of city leaders that helped land Walsh in City Hall.

This time around, that wave has backed Wu, making it more challenging for Essaibi George, he said.

“She both has to make the case why she’s a better alternative to voters of color, Black voters in particular, but she may also have to answer as to why Mayor Janey’s wrong and what did Mayor Janey miss here?” Connolly said.

As it stands now, the endorsements “give Wu the momentum and a decisive edge, but I don’t think it’s game over,” Connolly said.

Wednesday’s debate — at 7 p.m. on WBZ-TV — is widely seen as a pivotal opportunity for Essaibi George to blunt Wu’s momentum.

For the 36-year-old Wu, the first debate is largely an exercise in avoiding landmines.

“The person in the front just wants to get through the debate unscathed,” said Erin O’Brien, a politics professor at the University of Massachusetts Boston.


Aides to Essaibi George hope she has the opportunity to showcase the pragmatic style she has made her signature — and in particular, to poke deeper holes in some of Wu’s landmark, lofty plans. Wu is well known for her proposal to make the T free, a pitch Essaibi George has flatly said Boston’s mayor cannot achieve since the MBTA is run by a state board.

The message from Essaibi George will be “let’s get real,” as one campaign adviser put it — pushing back on Wu policy proposals that don’t fall fully under the purview of the city’s mayor.

Renee Leona Dozier-Holland, who supports the councilor, says she has to continue to do one thing on Wednesday — be authentic.

“Annissa just needs to be herself. When she shows up and she speaks up for herself, I think she’s going to do fine. She’s got a fighter spirit about her,” said Dozier-Holland, a leader of the influential IBEW Local 103 union, which endorsed Essaibi George.

It’s a safe bet to expect a punchier Essaibi George on stage Wednesday. A debate that doesn’t move the needle is a victory for Wu, analysts said.

“A televised debate is an opportunity to reach a larger audience, but also an opportunity to draw some distinctions between myself and my opponent,” Essaibi George said in a recent interview. With five contestants on stage during the preliminary debates, she said, “it was a little bit more challenging” to make clear how she differs from Wu. Now, it will just be the two of them.

In an interview this week, Wu said she looks forward to the platform the debate will provide.

“There’s always some butterflies with that as well,” she said, laughing.

Whether Wednesday makes a dent in the race remains to be seen. But to call Essaibi George the underdog at this point is “an understatement,” Baker said.

Still, he said, don’t count her out.

“It’s a heavy lift for her, but I think it’s doable,” Baker said. “She’s tough. She’s a Dorchester girl.”

Emma Platoff can be reached at Follow her @emmaplatoff. Meghan E. Irons can be reached at Follow her on Twitter @meghanirons.