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Second in a series of profiles of the historic field of candidates vying to be Boston’s next mayor. For more coverage of the race, please subscribe to On the Cusp, the Globe’s weekly newsletter covering all aspects of the contest, and visit our Mayoral Race page for the latest developments.

In a heated Boston mayoral race, politics can be found everywhere, even on the base paths of a softball diamond behind the Orchard Gardens school in Roxbury.

That was the site of a recent kickball game for neighborhood kids organized by Boston police. There were officers in the infield and outfield and City Councilor Annissa Essaibi George, true to her reputation as a dynamo, was on the move, taking a turn at the plate and rounding the bases, in between chats with cops and residents.

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In a crowded campaign in which multiple candidates are pitching themselves as the most progressive option, Essaibi George has carved her own, more moderate path, most notably when it comes to policing.

At a time when advocates have pushed for deeper structural reforms in the scandal-ridden Boston police, she is calling for hiring hundreds of more officers. She accepted the endorsement of former Boston police commissioner William Gross, who is known as a cop’s cop.

She shrugs at the centrist label affixed to her by some local political observers.

“I don’t really care.”

Essaibi George spoke at the No Books No Ball Pandemic Relief Summer League in Ramsay Park.
Essaibi George spoke at the No Books No Ball Pandemic Relief Summer League in Ramsay Park.Pat Greenhouse/Globe Staff

She instead defines herself as a realist, an outlook honed on the streets of Dorchester, where as the daughter of immigrants she grew up and has lived her whole life, and in the classrooms of East Boston, where she taught for 13 years before representing the city as an at-large city councilor. She pushes back on critics who say that she wouldn’t, if elected, tackle the problems plaguing the Boston Police Department.

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“I’m the candidate who is not afraid to show up, not afraid to have conversations, not afraid to do the work,” she said.

Friends, local advocates, and council colleagues describe Essaibi George as an industrious worker, someone who thrives on a chock-full schedule, who knows the city through her life experience as a city kid who is now a mother of four and through her daily grind of meetings, appearances, and conversations as a councilor.

Paul Nutting, a Dorchester resident and longtime friend, compared Essaibi George to the multi-armed Hindu goddess Durga.

“She always has so many balls in the air,” he said. “She’s so driven.”

Essaibi George, 47, is Dorchester through and through. She speaks with a thick Boston accent and has a history of civic engagement in the neighborhood. A knitting, crocheting, and sewing enthusiast, she owns a yarn shop on Dorchester Avenue called Stitch House.

Essaibi George, who currently lives on Mayhew Street, is the mother of four teenaged sons: 16-year-old Douglas and 15-year-old triplets Charlie, Kayden, and Samir. Her husband of almost 20 years, Doug, is a developer and fellow Dorchester native.

Dorchester is also central to Essaibi George’s political story, which started with local groups such as the Columbia-Savin Hill Civic Association, a collection of concerned citizens who weigh in on planning and projects in the neighborhoods. She ultimately rose to serve as its president. She also served on the Dorchester Day Parade Committee, which organizes the annual parade festivities, and is a former head of Little Miss Dorchester, a talent showcase, among a slew of other community roles she took on.

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 Essaibi George celebrated her election to the City Council in 2015 with a party at her home in Dorchester.
Essaibi George celebrated her election to the City Council in 2015 with a party at her home in Dorchester. Aram Boghosian for The Boston Gl

She first ran for City Council in 2013, but fell short. She ran again two years later, and this time won, placing fourth out of five major candidates. She is now serving her third term, as an at-large councilor.

She grew up on Taft Street in Savin Hill, the oldest of four siblings. Her Polish-American mother, Barbara, was born in a displaced persons’ camp in Germany after World War II and moved to Boston when she was 2 years old. She raised her family while working as a secretary and telephone operator at The Boston Globe, where she spent more than 30 years before being laid off.

Essaibi George’s late father, Ezzeddine, was an observant Muslim who emigrated from Tunisia and worked as a security guard at Boston University for more than two decades to ensure his children could attend the school for free if they wanted. Essaibi George was raised Catholic, but has said she absorbed both of her parents’ cultures. She identifies as Arab-American.

Essaibi George attended the first Seniors Appreciation Day Cookout, hosted by Will Dickerson and sponsored by former police commissioner William Gross at Robert’s Playground in Dorchester.
Essaibi George attended the first Seniors Appreciation Day Cookout, hosted by Will Dickerson and sponsored by former police commissioner William Gross at Robert’s Playground in Dorchester. Pat Greenhouse/Globe Staff

In her own career, Essaibi George taught health, economics, and other subjects for 13 years at East Boston High School, where she also coached softball.

Her youngest sister, Sarrah Essaibi, said Essaibi George has always had an “alpha, take-charge personality and approach.” She joked that she chides her older sister for knitting behind the steering wheel when stopped at red lights.

“She’s always going,” she said.

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Her mother, now 71, recently recalled that her eldest daughter told her she was going to be mayor one day while she was still in high school.

She thought her daughter’s activism was born out of a desire to “know what’s going on and to help people.” At age 16 or 17, her mother recalled, Essaibi George spoke at a demonstration downtown protesting potential school district budget cuts.

“She said to Mayor Flynn, who was mayor at the time, ‘If you don’t put the cuts back, we’ll remember, and we’ll be voters soon,’” her mother said. She recalled being taken aback by her daughter’s forwardness.

She said her late husband, who was active in his union and liked to talk politics, would have loved his daughter’s mayoral run and may have inspired her political inclinations. He had experienced discrimination in France, where he lived for a time and met his future wife, and in the United States, where he felt like he had to prove himself.

She recalled when the United States invaded Iraq after 9/11, “people thought that was the best thing. And he said, ‘No this isn’t a good idea. It’s a mess over there.’”

Essaibi George spoke with Serafina Lemus during a tour of the Bunker Hill housing development.
Essaibi George spoke with Serafina Lemus during a tour of the Bunker Hill housing development. Pat Greenhouse/Globe Staff

Now, Essaibi George is speaking her mind on the mayoral campaign trail.

Touring the Bunker Hill housing development in Charlestown a few hours before the Roxbury kickball game, she made friendly small talk with ease, chatting with residents about their dogs and asking a Boston Housing Authority official about vacancy rates as she walked past boarded up buildings slated for demolition. At this stop and others, she is willing and capable to get into the policy weeds on an array of issues. She is plainspoken and direct in her analysis.

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While touring the sprawling development, Essaibi George spoke about bringing back all out-of-service public housing units. An audit needs to be done, she said, to find out how much “there is there.” An analysis should also be performed of the city’s waitlists for affordable housing, she added. If an applicant doesn’t qualify for one of the priority groups — seniors, the homeless, domestic violence victims, and teenagers who are pregnant — they’re generally out of luck, Essaibi George said.

She suggested that for projects that are 100 percent affordable, there should be a separate permitting track, which would streamline and speed up the process and cut down on red tape.

During the Bunker Hill tour, Janine Day, who is homeless, offered a frank assessment of the city’s housing crisis: “They need to build.”

“You know how many homeless people there are? Women and children? A lot.”

“That’s her thing,” replied an Essaibi George spokeswoman, before Essaibi George petted Day’s dog, a mutt named Turbo.

Indeed, Essaibi George has long been a fierce advocate for the homeless and for mental health services. Last year, she spearheaded an effort that set up a city commission to examine family homelessness. One of government’s roles, she has said, is to help the most vulnerable.

Since ascending to the council, Essaibi George has found a way to navigate Boston’s political currents, winning elections in three citywide races, and, on some issues, her politics are more nuanced than the “moderate” label she’s been tagged with. Even on policing, Essaibi George aligns with progressives on some fronts. She supports ending Boston police’s information-sharing relationship with federal immigration authorities and backs the district attorney’s do-not-prosecute list for low-level offenses. She thinks white supremacist sympathies are a problem within the department.

Yet on other issues, she stands in contrast with some of her more left-leaning rivals: She opposes safe drug consumption sites, removing police from Boston Public Schools, shutting down the department’s gang database, and reallocating funds from Boston police to other programs. She does not have a problem with the four-hour mandatory overtime minimum that is baked into the police union contracts.

Her approach enabled her, as a councilor, to run citywide campaigns in which she would manage to pull “about 50 percent of the vote in the most progressive precincts in the city and 50 percent of the vote in the most conservative,” said Jonathan Cohn, chairman of the Ward 4 Democratic Committee, who is supporting Michelle Wu in the mayor’s race.

Her tenure as councilor, Cohn said, has been in many ways a balancing act of trying not to alienate progressive constituencies while still defending institutional forces.

Progressive critics say that Essaibi George’s candidacy lacks boldness when it comes to housing justice and climate issues and that she is not a change agent when it comes to Boston police. Her call for more police officers reflects a misdiagnosis of the problem, they say.

“If elected, she would in many ways be a continuation of the Walsh administration,” said Cohn, referring to the previous mayor, Martin J. Walsh, who left City Hall in March to join President Biden’s Cabinet. It’s a common refrain from some on the left who see her as a status quo candidate.

Essaibi George acknowledged she has a close relationship with Walsh; she was viewed as a political ally of his on the council, and the pair grew up on the same street in Dorchester. But she also countered that there were times she disagreed with the former mayor, particularly when it came to education. She has clashed with his schools superintendents and voted against his schools budget in 2016 because it “didn’t acknowledge students who are experiencing homelessness the way that it should.”

Walsh has said he will not endorse in this race. Essaibi George’s campaign does include prominent staffers who had worked for Walsh.

She swats away the progressive criticism, saying that those who label her a status quo candidate “aren’t paying close attention to my vision, plans, or record.”

“I refuse to over-promise for political points,” she said. “My plans are rooted in reality.”

Essaibi George’s campaign has maintained that any notion that she is the “cops’ candidate” is an oversimplification, saying that she has been upfront about both the need for reform and the need to work with the police department. But Essaibi George’s mere presence at the police kickball game itself was a political statement, underscoring her willingness to literally play ball with officers amid continued calls for systemic change in the department. Weeks before, two of her top rivals in the mayoral race declined to participate in a candidate forum put on by the local patrolmen’s union.

When it was Essaibi George’s turn to kick the ball, someone from the crowd yelled out jokingly: “She might be able to fire ya’ll, so you better watch out.”

A police officer on the mound rolled the ball toward her, and she booted it in the direction of third base, then hurried toward first.



Danny McDonald can be reached at daniel.mcdonald@globe.com. Follow him on Twitter @Danny__McDonald.