Photo: GMG (Getty)

It was a win destined to go viral: Ayanna Pressley, Boston’s first black city councilor, beating out 10-time incumbent Mark Capuano in a stunning upset for the Massachusetts 7th congressional seat. Video taken of Pressley shows the moment she found out about her win—in a forest-green sheath dress, Pressley clutches her chest before leaping to her feet.

“We won?” she asks the room. Embracing her husband and supporters, she begins to cry. “Oh my God,” she says, over and over again.

The touching moment made national headlines, as did the win itself, which many pundits considered improbable. But Pressley’s ensuing victory speech highlighted the reasons she was a bonafide star. The most memorable line of the night—a clip that was shared tens of thousands of times and was quoted in news outlets across the country—perfectly summed up how and why Pressley, a longtime Democrat who worked for establishment politicians like Massachusetts congressmen Joseph P. Kennedy II and John Kerry, had been able to successfully position herself as an outsider candidate.

With her trademark Senegalese twists wrapped up behind her, the woman once voted “Most Likely to be Mayor of Chicago” by her high school called out her own party.

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“While our president is a racist, misogynistic, truly empathy-bankrupt man, the conditions which have made the 7th [congressional district] one of the most unequal in America were cemented through policies long before he ever descended the escalator at Trump Tower,” Pressley said, referring to the moment Donald Trump announced his 2016 presidential run.

“In fact, some of those policies were put in place with Democrats in the White House and in control of our Congress—policies that have become so ingrained in our daily lives as to have almost convinced ourselves that there wasn’t anything we could do about them,” she continued, a diverse crowd of supporters beaming back up at her.

“But as we now know, change can’t wait.”

When I asked Pressley in September, weeks after clinching her primary victory, about that part of her speech, she approached it as she did most of her policy points: confidently and matter-of-factly. The Democratic Party has been long overdue for a reckoning, and that would have been true regardless of who’s in the White House. The Massachusetts 7th is evidence of that.

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“We should not be engaged in internal debates or conflict about whether or not we are the party of working-class white folks and everyone else. Or debating whether or not we’re the party of jobs and the economy or criminal justice reform. These are the false choices,” she said.

“I won’t choose.”


With Election Night 2018 in the books, Ayanna Pressley is now set to lead one of the bluest districts in one of the bluest states in the country. The 44-year-old city councilor ran an unopposed campaign, paving the way for her to become the first black woman ever to represent Massachusetts in Congress. But more than that, Pressley joins a highly visible crop of newly elected women who helped Democrats seize the House of Representatives last night. With every other section of national government—the presidency, the Supreme Court, and the Senate—controlled by Republicans, all eyes are on the House to drive the capital-R Resistance against Trump.

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But as Pressley disclosed to me in September, her campaign was always about more than providing a rhetorical and actual opposition to the real-estate-mogul-turned-president. The way she ran her campaign is the way she intends to lead—by appealing to voters that Democrats have neglected or taken for granted.

“I think there were many people that were preparing for Monday morning quarterback, about all the decisions that we made that cost us the election, including the fact that we were not on television in traditional mainstream markets,” Pressley said of the pivotal primary race. Rather than funnel her money through those outlets, she chose to focus on ethnic and specialty media, with a particular focus on Spanish-speaking outlets.

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“We had ads on Telemundo and Univision, and many people questioned the rationale,” Pressley explained, her voice taking on the warm and raspy timbre typical of a politician during a grueling campaign cycle. “I think the Latino community has 7 percent of the electorate. And so it had many people scratching their heads.”

But Pressley and her team, like other progressive campaigns nationwide, were determined to reach out to an unseen electorate that hadn’t been considered “traditional” primary voters (i.e., older white people).

“I don’t make assumptions about who wants to participate in democracy,” she declared.

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In an election that is essentially a referendum on Trump’s presidency, Pressley’s appeal to voters has been as much about calling her party to task as about harnessing a spirit of resistance. As Pressley has conceded multiple times on the campaign trail and in the press, she will vote similarly to Capuano on most issues.

What she promises is to lead differently.

For Pressley, this means abolishing ICE, which she refers to as a “rogue agency” well past the point of reform, as well as foregrounding maternal health and issues of gun violence—both of which heavily impact the Massachusetts 7th—with particular attention to the racial disparities that define both issues. With gun violence in particular, Pressley wants to see more institutional trauma support for victims.

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“I could have said, well, I support gun control. And more often that not, people will find that a sufficient answer. But it isn’t,” Pressley asserted. “I’m so exhausted with our single issue-ing constituencies, and then offering one specific stance as sort of a checked box, and then everyone keeps it moving.”

She continued, “People don’t live in checked boxes. They don’t live in hashtags and bumper sticker slogans. They live in nuance. They live in intersectionality. And those are the type of policies we have to develop.”

As a city councilor, Pressley voted down three Boston public school budgets because they didn’t fund equitable access to school nurses, social workers, and guidance counselors across Boston’s schools.

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“I know trauma is a barrier to learning,” Pressley said. Growing up in Chicago, Pressley credited a school nurse at Francis W. Parker, a prestigious private K-12 school, with preventing her from “becoming a statistic,” as the Boston Globe reports. Pressley’s mother, Sandra Pressley, lived paycheck to paycheck, the Globe writes, but with a partial scholarship, Sandra was able to get Ayanna into the elite school.

“I lived in the school nurse’s office—and not because anything was physically wrong with me,” Pressley told Parker students in a 2013 speech, “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.” During her campaign, Pressley mentioned she had survived years of childhood sexual abuse.

“Our schools need to be sensitive to trauma,” Pressley told me. “We don’t need more police. We need more social workers.”

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Boston’s public schools, like many others across the nation, have become increasingly segregated as gentrification and economic polarization continue to shape the city’s neighborhoods and resources. A 2015 study revealed that the median net worth of black households in the city was just $8, compared to $247,500 for white households. And a recent report from the Boston Globe found that 60 percent of Boston public schools were “intensely segregated,” meaning black and Latinx students made up 90 percent or more of the student body. Twenty years ago, that number was 42 percent, the Globe reported. Today, many of the schools black and Latinx students attend are under-resourced and underperforming, propelling a cycle of inequality in real time.

“We’re not the only school system that desegregated. So, you know, why is it that it’s so much harder for us to dig out? And I think a lot of it is that same postmortem that we were discussing a moment ago, around the ways in which even Democratic policies have contributed,” Pressley said. “We’re still having a hard time even speaking plainly about race being a factor. And it’s not going to be resolved by fancy algorithms.”

Certainly, this ability to speak plainly about race in a district that is among the most racially divided in the country adds to Pressley’s appeal—especially for voters who have been disappointed in the Democrats’ tendency to abide or further policies that disproportionately harm people of color. When Pressley worked for John Kerry in 2007, she took a hard-but-necessary line as Kerry’s staff debated whether Kerry should go back on Don Imus’ radio show. The shock jock had famously referred to the Rutgers women’s basketball team as “nappy-headed hoes.”

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Kerry’s then-chief of staff David Wade recalled Pressley’s stance in the Globe:

She said, “Actions speak, not words. If you want those girls to believe you’re on the level, we have to be in D.C. 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.

Pressley took a similarly principled stance during a debate between herself and Capuano ahead of the Democratic primary. When asked to highlight a difference between herself and her heavily favored opponent, Pressley cited a Congressional “Blue Lives Matter” bill Capuano voted for. The bill would have defined attacks on police officers as a hate crime, and Pressley would have voted against it, she said, not out of a lack of respect for the men and women of law enforcement but because there was no mention or acknowledgment that, in some cases, people may be fighting back to defend themselves from overly aggressive officers.

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“If black people are disproportionately profiled and then brutalized, then they could be defending themselves,” Pressley explained. “How could that be counted as a hate crime?

“I didn’t believe there was a shared narrative being held about the brutality that was happening in disproportion to black folks, and consequences for law enforcement when that happened. Which is why I couldn’t support that bill.”


Despite decades of experience in politics, including tapping into various community organizations and movements that have helped her define her stances, Pressley’s win has been viewed nationwide as a principally symbolic victory, with all the glossy sheen of a history-making candidate at a time when the left is desperate for the antithesis of Trump’s politics.

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Her win was billed as a larger win for candidates of color and for women. Pressley was described as the next Alexandria Ocasio-Cortez by Politico (and “not Alexandria Ocasio-Cortez,” also by Politico). Throughout her campaign and during her victory, Pressley’s message—its focus on change and hope—was evocative of another politician with Chicago roots who couldn’t wait his turn: Barack Obama. No one seems to have missed the resemblance.

The risk of treating someone—even a person whose values, background, and approach are as deeply resonant as Pressley’s—as a symbol is that it tends to flatten the candidate into a caricature and bury all the work it took to get there. Pressley talks often about the discouragement she encountered as she mulled her run for office—people told her, in so many words, to wait her turn. But if you step back and assess the shape of Pressley’s personal and civic life, this moment actually seems not just overdue but, in hindsight, inevitable.

This is the same young woman who, the Globe writes, began her foray into leadership on Martin Luther King Day at Parker as a freshman in high school, leading an auditorium full of her wealthy, white classmates in an earnest discussion about race. Her formal political career began, again, on MLK Day in 1993, when as a student at Boston University, she invited then-Rep. Joseph P. Kennedy II to a celebration she organized on campus.

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Per the Globe, “Pressley had rebranded the celebration as a ‘day on,’ because she was dismayed that students had treated it as a day off.” She asked Kennedy for an internship after the event and ended up working for the Massachusetts representative for two years.

Now, as Pressley heads to Washington, the stakes for the soon-to-be freshman congressman are the highest they’ve ever been, in part because the party Pressley will represent will have to reckon with who it is and how it will move forward once its new members pour into Washington in January.

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“We’re at a crossroads and so it’s an opportunity to reset,” Pressley said, listing a slew of the Democrats’ failures in the Massachusetts 7th. Generations of poverty, trauma, and poor public health outcomes. Redlining. Unequal access to the GI Bill. Welfare reform—all passed with Democrats running local and state offices. All helping to contribute to a district that is both among the most diverse and the most unequal in the nation.

When Pressley takes her oath, along with a crop of fresh progressive faces at Capitol Hill, it will have great symbolic resonance; that can’t and shouldn’t be denied. But she brings far more than symbolic importance—there is a moral clarity to the policies she wants to implement, the issues she aims to foreground, and the way she plans to lead. While it’s yet unclear in what other ways Pressley will make history, she hasn’t shied away from the legacy—and possibilities—of the seat she secured on Tuesday.

“This was a seat that was held by John F. Kennedy. This is arguably the most progressive seat in the country. So to have a progressive voting record is fine. But it’s not necessarily a profile in courage,” she cautioned.

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“This is a state where we could lead from a place of being completely unrestrained and unencumbered,” Pressley added. “We can be bold and innovative, and we are at this crossroads. And I think it is tempting to shrink, and to play small because this is an administration that wants to divide us and want us to feel small and powerless.”

Toward the end of our conversation, Pressley repeated a line she used often in stump speeches and to the press: “This can either be our darkest hour or finest.” It’s nearly impossible to talk to Pressley and not feel marginally more hopeful for the country, even if most of her work won’t directly impact Americans outside the borders of her district. But Boston, with which Pressley’s destiny is tied, is itself the birthplace of revolution, so when Pressley says she wants nothing less than to help usher in “the most progressive, inclusive, change-making movement in history,” you do something that feels as crazy as it does irresistible:

You believe.