An ‘Outsider’ in Boston Seeks Change, Starting in Her Own Party

CAMBRIDGE, Mass. — It’s not a sight you see every day, certainly not around Boston: A black woman mounting a plausible challenge to a 10-term white congressman from her own party, a politician with vast connections who votes the progressive line and opposes everything Trump.

But here was Ayanna Pressley, a Boston City Council member and rising Democratic star, exhorting volunteers in a Cambridge restaurant with an impassioned performance style she learned as a child at her grandfather’s storefront Baptist church in Chicago.

“This is not just about resisting and affronting Trump,” she declared, garbed in a flowing red jumper. “Because the systemic inequalities and disparities that I’m talking about existed long before that man occupied the White House!”

The crowd went wild.

“Change can’t wait!” she shouted, echoing her campaign slogan, her voice raspy as it took on speed and urgency.

Pressley is herself an emblem of change that can’t wait — and isn’t waiting. She is part of a rising tide of women, including Alexandria Ocasio-Cortez and Cynthia Nixon in New York and Stacey Abrams in Georgia, that is challenging historically white male power structures in politics — not only to advance their policy ideas, but also to reflect the changing diversity of their constituents, who have long lacked one of their own in congressional seats or governor’s offices.

In doing so she is taking on a well-respected Massachusetts Democrat, Rep. Michael Capuano, who was expecting to coast once again unchallenged for re-election in the 7th Congressional District, which includes much of Boston and its suburbs. The primary election Tuesday is one of the last marquee Democrat vs. Democrat battles of 2018.

Massachusetts is well known for deeply entrenched politics that favor incumbents, from the Kennedy dynasty to long-serving mayors, senators and House members. Capuano, 66, has widespread establishment backing, including Boston Mayor Martin J. Walsh, several labor groups, and prominent black leaders like former Gov. Deval Patrick, and Reps. John Lewis and Maxine Waters. He also has an army of experienced election workers behind him, and a 13-point lead in a poll published in early August.

But Pressley, 44, may be the rare Boston insurgent whose ambition is in sync with a national political moment that has favored women and underdogs. Last week she achieved an unusual feat for a challenger: Winning endorsements from the city’s major newspapers, The Boston Globe and The Boston Herald. Her supporters are highly energized, and some polling in other recent races has failed to detect strength for minority female candidates. The congressional district is the only one in Massachusetts with more people of color than people who are white. While Capuano has his advantages, a Pressley win no longer seems far-fetched.

Their race has been hard fought but not particularly negative. The mere fact of Pressley’s challenge gives the primary its frisson. Capuano has tried to ignore her and focus instead on his years of experience, his reputation as a progressive and his opposition to President Donald Trump. She has had the harder task of trying not to disparage a fellow progressive while still making a strong enough case for herself.

The puzzle for many voters is why Pressley is challenging a strong progressive in the first place, one who has brought home millions of dollars for much-needed transit, housing and health care projects. Especially when, as Pressley and Capuano agree, they are likely to vote the same way on most issues.

The answer says as much about Pressley as it does about Boston. For her, voting is where her representation would start, not end. She promises “activist leadership” beyond the votes, whether the Democrats retake the House or not.

“I’m not running to keep things as they are,” Pressley often says. “I’m running to change them.”

As for Boston, it is a city where wide disparities still exist between white and black residents in income, employment, housing and police stops, and where the political hierarchy has rarely welcomed outsiders. And until recently, “outsider” meant not just black people but women.

If Capuano is the consummate insider — born in the 7th District, in Somerville, which he went on to lead as mayor before entering Congress — Pressley has been an outsider in many ways throughout her life. She was a struggling student of color, the daughter of a single mother, at her largely white, affluent, private high school in Chicago. She was a Midwesterner who moved East in 1992 to attend Boston University. And her life experiences are unlike those of many leading politicians: she has long spoken of being sexually abused as a child and raped in college, that her father struggled with drug addiction and spent most of her youth incarcerated.

“What probably makes me an outsider is my story and how I came to this work,” Pressley said in an interview. “I am probably an outsider because I challenge conventional narratives about who should have a seat at the table.” Pressley has also been in the vanguard of a small group of women who have been breaking down barriers in Boston politics. She was the first black woman elected to the City Council and for three elections in a row was the city’s top vote-getter. Today, of the 13 council members, six are women of color.

“She didn’t grow up here, she didn’t have 14 cousins who ran different precincts for her, she didn’t have a mom and dad who went to high school with so and so,” said Jesse Mermell, a close friend, describing advantages of some native Boston politicians.

“There is a shift happening in this city,” she said. “Win or lose on Sept. 4, Ayanna is the face of that shift — generationally, racially and in terms of gender.”

Though Pressley left Chicago more than 25 years ago, her time there was transformative.

She was immersed in public speaking at her grandfather’s church, Rise and Shine Missionary Baptist Church. By age 10, she had volunteered on her first political campaign — for Harold Washington, who became the city’s first black mayor in 1983.

Pressley grew up on Chicago’s North Side in a Lincoln Park mixed-use apartment complex. With her father, Martin Terrell, absent, Pressley said she felt “a fragility of circumstance.”

“Coming home to an eviction notice on the door,” she said. “Coming home alone. I’m an only child. My mother was raising me alone. We couldn’t afford child care; child care hours didn’t work according to her schedule.”

Her mother, Sandra, a social worker, community organizer and legal secretary, was a ferocious champion for her daughter

“Everything she did was for Ayanna,” said Myrna Smith, a close friend of Sandra Pressley, who died in 2011. She said the elder Pressley made “personal and financial” sacrifices for her daughter.

Pressley recalled: “It was me and her versus the rest of the world. Cagney and Lacey. Thelma and Louise.”

One of her mother’s achievements was enrolling her daughter in the Francis W. Parker School. Named for the founder of the progressive school movement, it is consistently ranked among Chicago’s best private schools. When Ayanna Pressley attended, it was largely inaccessible to lower middle-class black children like her. Daniel B. Frank, the longtime principal, said the school helped Pressley “try out another part of herself.”

“She had her own family struggles, but she found at Parker a place that would not only support her, but give her an opportunity to be something other than a kid who had struggles at home,” Frank said. “Here she could just be, and grow, and develop, and have voice.”

By senior year, Pressley was much less of an outsider. She was a member of student government as well as a cheerleader, and had developed a reputation for being politically inclined. At graduation she was named both class salutatorian and “most likely to become mayor of Chicago.”

“If nothing else, I am a survivor,” read one of her senior quotes.

“Oh, I do not talk loud, I just get my point across,” read another.

Terrell, Pressley’s father, recalled that as he watched her salutatorian speech, he realized his bubbly little girl had become a young woman with powers of public speaking that she could wield in a new, politically astute manner.

“She electrified her classmates,” said Terrell, who is now an author and retired director for the United Negro College Fund. “And I felt that, although she was a good writer, she was a great public speaker.”

Capuano, a mild-mannered man who speaks in a thick Boston accent, moves with the ease of a seasoned politician, talking knowingly about local issues with a range of leaders he has cultivated for years. He has opted to campaign only on his progressive record, rather than attack or insult Pressley.

“I don’t compare myself to the councilwoman,” Capuano said in an interview. “In my mind I’m running on the basis of my record both back in Washington and back here.

“We’re in the fight of our lives with Donald Trump in the White House, and this district — like all districts, but particularly this one — needs the best fighter we can get in Washington, someone who’s experienced.”

In Somerville, his hometown, Capuano has held nearly every political office of import — alderman, mayor and now congressman — and he uses his campaign stops to gently remind voters that his history of leftist activism could stand next to anyone’s. Capuano has stressed to voters that, if Democrats retake the House, his seniority and relationships with other lawmakers would make him a prime candidate to sponsor bills and serve on valuable committees that are critical for achieving results. Pressley would be a freshman.

Pressley has long been an advocate for girls and women. She volunteered at little-known nonprofits, served as a mentor and Big Sister and has been a regular presence at events like the Boston Area Rape Crisis Center’s annual Walk for Change.

It was this background that led some of Boston’s “kingmakers,” Pressley said, to suggest in 2009 that she not run for City Council and instead pursue a career with nonprofits.

Pressley ignored their advice. From her years of working for Rep. Joseph P. Kennedy II and former Sen. John Kerry, including as Kerry’s Massachusetts political director during his 2004 presidential campaign, she had built an extensive political network of her own. Kerry even knocked on doors for her.

Pressley won that first race. And in 2011, in her first bid for re-election, she pulled in more votes than anyone else.

If the outsider was now working on the inside, Pressley still focused her energies on helping marginalized people like those who were incarcerated, homeless or caught up in human trafficking. And while she doesn’t often talk in detail in public about her personal experience with sexual assault — “I’ve just kept going, like millions of people do every day, because life does not allow them to do anything else,” she said in the interview — she said she wanted to be a voice for those who have gone through traumatic events. It has given rise to a central point in her current campaign stump speech: “The people closest to the pain should be closest to the power.” Pressley, who lives in Dorchester with her husband and stepdaughter, was so plugged in with her community that she was already meeting privately with some of Boston’s female firefighters before the media aired their complaints about sexual harassment and discrimination, said City Councilor Michelle Wu. Just 16 of Boston’s 1,500 firefighters are women.

“Ayanna is in rooms that no other elected officials are in,” said Wu, who in 2013 became the first Asian-American woman elected to council and in 2016 the first woman of color to serve as its president. “Whenever she stands up and speaks on the floor, everybody stops and listens because she speaks with moral authority.”

Boston’s strong mayor form of government generally precludes City Council members from making much of a splash, but Pressley is credited with at least one major accomplishment: increasing the number of valuable liquor licenses so some could be distributed to help restaurants in disadvantaged neighborhoods become more economically viable.

“For the issues she’s speaking on, she does the work and is prepared,” said Sam Tyler, president of the Boston Municipal Research Bureau, a nonprofit research group that monitors council activity. “She has a penchant for coming late,” he added, “but she does come.”

Erin O’Brien, a political scientist at the University of Massachusetts Boston, said there were two different assessments of Pressley’s standing in the council.

“Some people think she’s a showboat, that she likes to come in and give a speech and isn’t doing the nitty-gritty work,” O’Brien said. “But in many communities of color, she is viewed as incredibly exciting and voicing issues the council has ignored.” It was the “old guard,” O’Brien added, that viewed Pressley as a showboat. But, she said, its power was waning.

“If the old guard were in charge,” she said, “this primary wouldn’t be happening.”

Later, Pressley nearly erupted at the showboat suggestion. “I’ve not been a decisively re-elected city councilor and top vote-getter three times because I haven’t done the work and because I don’t work hard,” she said.

The old guard may be losing its grip in part because of demographic changes across the 7th Congressional District. Once represented by John F. Kennedy, the district is now 57 percent people of color and 30 percent foreign born. Single women head nearly 40 percent of the households.

“What has shifted is the willingness of people who come from these backgrounds to step up and run,” Wu said. “We’ve now set a new narrative for what is possible in Boston politics and in Massachusetts politics.” Still, Massachusetts has never sent a black person to the House of Representatives. It was not until 2012 that it sent a woman — Elizabeth Warren — to the Senate. Two years later, Maura Healey, a first-time candidate, bucked the party establishment and ran for state attorney general against a fellow Democrat. She prevailed and became the nation’s first openly gay state attorney general. Pressley was one of the few elected officials to endorse her back then. Healey, now arguably the most popular Democrat in a state brimming with them, has endorsed Pressley.

At that rally in Cambridge, Healey stood by Pressley’s side and told the crowd that Pressley had educated her about trauma, sexual violence, domestic violence and gun violence. “Not only did she teach me,” Healey said, “she helped me come up with solutions and ideas.”

When Pressley took the stage, she acknowledged the forces arrayed against her.

“They might have you think we’re traitorous to primary a 20-year incumbent,” she said. “But that’s democracy, and choice. And after 20 years, this district deserves one.”