An awkward silence hung over the auditorium at the Francis W. Parker School, a prestigious private school in Chicago, where 300 mostly wealthy, white high school students were supposed to be talking about race relations to commemorate Martin Luther King Jr Day.
Then, the organizer of the event, a 14-year-old freshman, stepped forward and shared her experience as one of the only black students at Parker. Something in the room shifted.
Over the next hour, Ayanna Pressley and her co-organizer, a white student named Allison Amend, led their classmates in what Amend recalled as one of the most formative moments of her childhood: an intimate, honest, and sometimes painful discussion about race. At the end, she said, people were in tears.
“She was a very trusted member of our community and she had that sort of steady hand of leadership, which is an amazing thing to see at 14,” Amend said. “You felt that it would all be all right if Ayanna was the head.”
Thirty years later, Pressley would shock the political world by unseating a 10-term congressman heavily backed by the political establishment. But her poise and authority that day in the Parker auditorium are a reminder that like her grandfather, a Baptist preacher, she has always known how to command a stage. Unlike other insurgent candidates who are finding their political ambitions in the age of Donald Trump, Pressley had been working toward this moment all her life.
“Everyone knew from when she was 10 years old that she was going places,” Amend said.
To get from Chicago’s North Side to the cusp of a seat in Congress, she would overcome sexual abuse and financial hardship, dropping out of Boston University when her mother lost her job.
The guiding force in her journey was her mother, Sandra Pressley, a tenants’ rights organizer who raised her while her father, Martin Terrell, struggled with heroin addiction and spent 16 years in and out of prison. Her father’s absence was not the only trauma in Pressley’s early life. She has said, without elaborating, that she also survived a decade of childhood sexual abuse.
Sandra Pressley lived paycheck to paycheck, but took her daughter, her only child, to ballet, cello, and ballroom-dancing classes, and on a European vacation.
Pressley also remembers being with her mother at 10 years old at the victory party for Harold Washington, who became Chicago’s first black mayor in 1983. Sandra Pressley was “my shero and bedrock and foundation,” her daughter says, using a word for a female hero.
Friends have also been struck by their bond.
“I have never seen a parent shine love and faith on a child the way Sandy Pressley did for her daughter,” said Jesse Mermell, a close friend. “I don’t know how she found the inner strength and hope to project all of that on a girl who faced odds most people don’t overcome. But from day one, she knew Ayanna was meant for more. It was her personal mission in life.”
Sandra was responsible for getting Ayanna into Parker, a top-ranked, artsy, and progressive school that educates students from kindergarten through 12th grade. Sandra had asked someone what the best school in Chicago was and was told it was Parker. But that person told Sandra that Ayanna “will never get in,” Pressley said.
But Pressley was accepted into kindergarten, and awarded a partial scholarship. Parker became a safe haven for Pressley.
“I lived in the school nurse’s office — and not because anything was physically wrong with me,” Pressley told Parker students in a speech she gave there in 2013, “but because I had so much dysfunction and drama and trauma in my life, Parker was this sanctuary, this refuge, this soft place for me to land. And when I was really going through it, the school nurse was my lifeline.”
If not for Parker and her mother, Pressley said, “I could have been a statistic. I should have been a statistic.”
Instead, Pressley thrived. She became president of the student government, a cheerleader, a competitive debater, and did modeling and voice-over work, even appearing in Planned Parenthood ads that ran on Chicago’s city buses. Her senior year, she was the commencement speaker and was named “most likely to be mayor of Chicago.”
Daniel B. Frank, the school’s longtime principal, said Parker helped Pressley become the person she is today. “She was able to really connect with some sense of purpose within herself and discover her own voice,” he said.
* * *
After graduating in 1992, Pressley enrolled in Boston University. She was elected student president of her college within the university and a student senator, she said. “Every position that one could be elected or appointed to on campus, I was,” she said.
Her first real job in politics came when she invited Representative Joseph P. Kennedy II to a Martin Martin Luther King Day celebration that she was organizing on campus. Pressley had rebranded the celebration as a “day on,” because she was dismayed that students had treated it as a day off. After the event, she asked Kennedy for an internship. He said yes.
Pressley worked for Kennedy for two years, first as an unpaid intern in his Roxbury office and then as a paid staffer helping seniors access Social Security benefits.
Amid the cluttered and hectic lives of college students, Pressley stood out as remarkably organized and orderly, said Misha Mayes, a friend from BU. Pressley was so organized, in fact, that she would admonish Mayes, saying, “Misha, all of your things are upset in your room. Everything has a home. And it’s sad when it’s not in its home.”
Pressley was also a lot of fun, Mayes said. With another friend, Pressley and Mayes won a campus lip sync contest and styled themselves up for a “hair show,” a fashion show for hair, in the student union.
But Pressley’s life at BU was upended the summer after her freshman year. That’s when Pressley, who was 19 and serving as a resident assistant in a dorm, has said she was raped by someone she knew — an experience she began discussing publicly as a city councilor in 2011.
“I remember her calling, and I actually had her come to New York when that happened,” Mayes said. “She really called in a panic. . . . It was very traumatic for her to deal with.”
Pressley has said she never reported the assault because of the social isolation and shame she felt.
“Being a woman, going through something like that is one thing,” Mayes said, “and then you have pockets of people on campus that find out about it and create an environment that’s even more difficult to be in.”
During her sophomore year in 1994, her life was rocked again when Sandra Pressley, who had moved to New York, lost her job as an executive assistant at Time Warner. Pressley dropped out of BU to help support her mother, she said.
She worked as a receptionist and a barback, and served banquets at the Boston Marriott Copley Place.
“I was really trying to cobble together ends and make them meet to pay my rent and pay my bills, but also to take care of my mom,” Pressley said. “I used to turn in, like, 20 money orders to pay my rent — $20 for this one, $30 for this one. I didn’t have a checking account.”
Mayes worried about her friend.
“Initially, I think, I was really afraid for her and how would this work out,” she said. “But when I spoke to her after a little bit of time and she was already ready to go and anchored and sounding so positive, I wasn’t worried at all.”
Two years later, Pressley was hired by Senator John F. Kerry as a volunteer coordinator for his reelection campaign against Governor William F. Weld. Pressley went on to work for Kerry for 13 years in his Capitol Hill office, rising from scheduler to constituent services director to political director.
“Ayanna was a force,” Kerry said. “She had enormous focus and drive, a wonderful, outgoing personality, and believed in public service.”
David Wade, Kerry’s former chief of staff, recalled one time in 1997 when Pressley ended an internal staff debate about whether Kerry should go back on Don Imus’s radio show, if Imus apologized for calling the Rutgers women’s basketball team a bunch of “nappy-headed ho’s.”
“She said, ‘Actions speak, not words,’ ” Wade recalled. “‘If you want those girls to believe you’re on the level, we have to be in DC who we say we are at home. The answer is we aren’t going on that show ever again.’ That was the end of that, and she was right.”
Sandra Pressley, meanwhile, became “a second mother” to Kerry’s staff, Wade said. And when Pressley left Kerry’s office to run for a seat on the Boston City Council in 2009, Sandra split her time between Boston and New York to help her daughter campaign.
“She was my not-so-secret weapon, particularly with seniors,” Pressley said. “She used to make these little bags called ‘Sandy’s Candies.’ ”
After Pressley was elected, becoming the first black woman to serve on the council, Sandra became a regular at council meetings, wearing a hat that read “Mama Pressley.” When she died of leukemia in 2013, at age 63, 300 people attended her funeral, including Mayor Thomas M. Menino.
Aisha Francis, a friend of Pressley who had bonded with her in 2006 because they were both “blerds,” black nerds, marveled at what a skilled politician Pressley was, as she moved from behind-the-scenes aide to topping the ticket in City Council races.
“I would be with her and she would run into people,” Francis said. “ ‘How’s your sister?’ ‘How’s your cousin?’ ‘Did your uncle get a job yet?’ I don’t even know how she keeps stuff in her head. and that’s not with a staff person whispering stuff in her ear, that’s just being with her in a restaurant.”
* * *
Pressley met her husband, Conan Harris, in 2011, when she was at a meeting in the basement of the Charles Street A.M.E. Church. They got into something of a debate when Pressley challenged Harris, the manager of an antiviolence initiative called StreetSafe Boston, about why he wasn’t focusing more on helping girls, not just boys. A few weeks later, after running into Harris at another meeting, she asked him for a ride to the T. (Pressley did not then, and still does not have a driver’s license.) Harris drove her home instead.
Three years later, they were married, when she was 39 and Harris, who is now a public safety aide to Mayor Martin J. Walsh, was 36. Pressley’s father, Terrell, walked her down the aisle, and when the pastor, asked, “Who gives this bride?” 10 women stood up with a photo of Sandra Pressley holding her daughter at 3 months old at a march for tenants’ rights.
Pressley places the same black-and-white photo in front of her before every council meeting.
“If I have a moment of uncertainty, it just anchors me,” she said.
Marriage made Pressley a stepmother to Harris’s daughter, Cora, who is now 10 and lives with them in Dorchester.
“It’s been an incredible gift to be her bonus mom,” Pressley said.
Pressley’s ambition has always been to serve in Congress, since she worked on Capitol Hill.
Last year, she went to North Carolina to visit her father, who has long since left prison and is now an author and retired fund-raiser for the United Negro College Fund. She showed him research she had done indicating she could mount a credible campaign for the House. Terrell, 72, said that was typical of Pressley: “Ayanna studies things before she goes into it.”
Last week, he came to Boston and helped out at his daughter’s campaign headquarters, worrying how he could comfort her if she lost. On primary day, amid the final frenzy of campaign events, Pressley made one private stop: Immediately after voting, she visited her mother’s grave in Dorchester’s Cedar Grove Cemetery for a moment of reflection.
When the results later that night showed Pressley had roundly defeated Representative Michael Capuano and Pressley gave her victory speech, Terrell said it was the first time he had heard his daughter speak in public like that since she gave her high school commencement address.
“I was just bursting,” Terrell said. “Seeing her in full bloom — I had never seen her that way. As her dad, I had always seen her from afar.”
As the crowd broke into sobs and cheers of “Change can’t wait,” Pressley said she went first to hug Cora and apologize for everything she had missed over the last year. Terrell said he hugged Pressley and told her, “I’m so impressed I would vote for you 10 times if I could get away with it.”
“I couldn’t even talk,” he said. “It was just one of those moments.”
Francis, Pressley’s friend, said she never doubted that Pressley would aim high in politics. It was just a matter of when.
“Mama Pressley absolutely saw this future for her daughter and is very much a part and parcel of every move that she makes — not just in her heart, but I think there is like this angel presence around her,” Francis said. “I don’t at all think that this is a surprise.”
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