One of the stickier aspects of this primary is that of representation, whether Kennedy's older style of Massachusetts patrician liberalism can make room for a representative of color. Deval Patrick, who served as governor from 2007 to 2015, was the only black to win a statewide office since 1972. Massachusetts has two senators and nine congressional representatives—all of them are white and the same goes for the rest of New England. The Seventh, with 41.5 percent non-Hispanic white residents, is the only so-called "minority-majority district," or majority non-white district, in the state.

And while Massachusetts has long history of civil rights—it was home to the abolitionist movement—it's intensely complicated. In 1965, Martin Luther King Jr, who earned a PhD from Boston University, came to the Seventh, to Roxbury, to protest school segregation, and that was followed by the mid-1970s school busing crisis, during which school desegregation was met with protest and violent resistance. Charlie Baker, the current Republican governor, is campaigning on the state's $1 billion surplus—a largesse that doesn't seem to have benefited the entire state. Last year, The Boston Globe examined Boston's reputation as "the most racist city," with a Spotlight Series on race, reporting that the household median net worth for whites was $247,000 and $8 for blacks—the lowest among five cities they surveyed. Likewise, incarceration rates and school discipline are disproportionately inflicted on communities of color. Among eight major U.S. cities surveyed by the Globe, Boston ranked as the "least welcoming to people of color."

"It's necessary that we are disruptive right now and making people uncomfortable. The issue of police brutality and disproportionate brutality and murder of black men strikes at the soul and consciousness of this country."

The race has revealed a lingering ugliness in Massachusetts politics, with vicious stereotypes gumming up comments sections in Boston publications. Pressley, who has been outspoken on racial inequality, has been accused of basing her candidacy wholly on her status as a black woman, despite her 16 years as a congressional aide and eight years as an elected official. It's been a peculiar charge. Growing up, I never heard "identity politics" levied as insult at Massachusetts's Irish Catholics or Italian Americans, who celebrated their heritage at St. Patrick's Day parades and North End Italian festivals, nor at the politicians, like Neal, Capuano, Walsh, and Kennedy, who represented them. "These charges are only lobbied against women and candidates of color," says Pressley over the phone. "When I say I bring a unique lens that is shaped and formed by my lived experiences, that's true for everyone. So, let's have the totality of those perspectives around the decision-making tables and around the corridors of power."

"Look, I cannot be a woman of color. And if that's what people care about that's fine. I accept that, I understand that," Capuano said in a WBUR 90.9 interview. "I just don't think there are that many people who will vote for me because I'm a white male or vote against me because I'm a white male." But with the young Kennedy, who has an anti-marijuana voting record despite high support for legalization in the state, campaigning for Capuano, and Capuano, himself, critical of the NFL protests, it begs the question of who, if anyone, in Massachusetts understands the needs of that constituency. "I thought that particular action divided America, because [Colin Kaepernick] chose to do it on the national anthem," Capuano said on a mid-August WGBH debate with Pressley. She disagreed. "It's necessary that we are disruptive right now and making people uncomfortable," she said. "The issue of police brutality and disproportionate brutality and murder of black men strikes at the soul and consciousness of this country."

One of the mantras of Pressley's campaign is, "those that are closest to the pain should be closest to the power." Pressley is a sexual assault survivor, which she openly talks about on the campaign trail. But she's not talking about herself. "Every piece of legislation that I've moved has been designed partnership with those most impacted by an issue," she tells me over the phone. She rattles off sideguard ordinances with cyclists, making galleries permissible use with artists, and bringing liquor licenses, along with those restaurant profits, to lower-income neighborhoods like Roxbury. "When I say the people closest to the pain, however you define the pain, I seek those communities out and together we write to resolve the situation."

Whether enough voters on Tuesday believe the Massachusetts Democratic party is ripe for disruption and a candidate willing to address the uncomfortable remains to be seen. But at least some in the Seventh are. At a block party at the Second Church of Christ in Roxbury, with wafts of smoke drifting up from oil drums and children jumping in inflatable houses, I watched Pressley make her way through a familiar crowd. Families took pictures with her; a pair of women helped brush detritus off the back of her dress after she got up from sitting on the sidewalk.

"She's GOT to win," said a tall black man walking by. "She's GOT to win."

Why? I asked him.

"She knows the community." She's here every time there's a shooting, every time there's a celebration, he says.

And what about Capuano?

"I haven't seen him."