Pressley, the 44-year-old who became Boston's first black female city councilor in 2009, is challenging 10-term incumbent Rep. Mike Capuano in the September 4 primary in one of the most heavily Democratic regions in the nation once represented in Congress by John F. Kennedy. It's an urban and diverse district winding through Boston, Somerville, Cambridge and other nearby towns.
Some Democrats see Pressley as the next Alexandria Ocasio-Cortez-style giant-slayer. But taking down the 66-year-old Capuano, who is one of the most progressive members of Congress, could be an even tougher task.
Pressley's chances at victory depend on whether she can drive young people and minorities who she says have been forgotten in the district to the polls, despite state laws that make turning out new and infrequent voters difficult. And it will gauge whether the Democratic energy that has helped women win most contested primaries this year can be turned against an incumbent who hasn't broken with the left on any important votes.
"This is a fight for the soul of our party. This is a fight for the future of our democracy," Pressley said at a recent canvassing event in Cambridge. "We might vote the same way but we will lead differently. These times require and this district deserves bold, activist leadership."
A debate over tactics
Pressley has long been a Democratic star in the making. Her campaign slogan -- "Change Can't Wait" -- connects the Democratic optimism of the early Barack Obama years to the urgency of Trump's presidency. Pressley is a commanding stage presence who frequently ditches microphones; she doesn't need them. She talks openly about her father being incarcerated for much of her childhood and about being a rape victim. Her go-to line, that "the people closest to the pain should be closest to the power," explains her calls for change in a district where people of color now outnumber white people.
Over late-night tacos at a Mexican restaurant after an event in Everett, Pressley said the district is among the nation's most uneven.
"The systemic inequalities and disparities are worsening," she said.
That she'd diversify Massachusetts' all-white, mostly male House delegation, she said, is "the bonus."
"It's about who I listen to and it's about who I govern with. And there are a lot of people in this district who feel left out and left behind and ignored -- and it's not just women, it's not just people of color," Pressley said. "It runs the gamut. And I think after a generation, the district deserves a choice."
Thirty minutes later, Pressley watched as her campaign's first television commercial -- a Spanish-language spot -- played on Tacos El Paso's TV.
One of the most telling clashes in the Capuano versus Pressley race so far has been over Colin Kaepernick, the former San Francisco 49ers quarterback who triggered a national debate by kneeling during the National Anthem.
In a town hall in Boston last year, Capuano took issue with Kaepernick's tactics. "It was the way he said it that turned off half of America, which I don't think is productive," Capuano said then.
The issue was raised at the candidates' final debate, and Capuano stuck to his position that kneeling during the anthem "divided America."
"I thought that particular action divided America, because he chose to do it on the National Anthem," Capuano said. "I understand what he's doing. I actually agree with the concept of what he's doing. I just thought it could have been done in a way that would have brung more people into the discussion, rather than actually anger an awful lot of America."
Pressley, though, said she backed Kaepernick's concerns and his tactics, saying that police brutality toward black men "strikes at the soul and consciousness of this country, and this should be of consequence and concern to everyone."
"It is necessary," she said, "that we are disruptive right now and making people uncomfortable."
The next Ocasio-Cortez?
In the wake of Ocasio-Cortez's stunning upset of the No. 4-ranking House Democrat, New York Rep. Joe Crowley, in June, Pressley was seen as the next potential challenger to take down a House Democratic incumbent -- in part because, hours after her victory, Ocasio-Cortez took to Twitter to highlight Pressley and said: "Vote her in next, Massachusetts."
But there are important differences in the two races.
A factor that complicates Pressley's chances: Massachusetts' laws, like New York's, are far behind most Democratic pushes to expand voting access. In New York, those restrictive voting laws created an opening for Ocasio-Cortez to win a low-turnout affair in which most voters weren't paying attention. In Massachusetts, they make it tougher for Pressley to win what's likely to be a higher-turnout election that most Democrats are watching closely, but that low-propensity voters may be more likely to skip, since it takes place the day after Labor Day.
Ocasio-Cortez was a 28-year-old political newcomer who shocked the political world in part because Crowley didn't take her challenge seriously enough. Pressley, though, is a well-known figure in Massachusetts politics: She worked for former Rep. Joe Kennedy II and former Sen. John Kerry before being elected to the Boston city council, and her congressional bid has drawn the endorsements of high-profile Democratic figures like Attorney General Maura Healey.
Her higher profile has made for a different race: While Ocasio-Cortez largely flew under the radar outside progressive media, Pressley was endorsed by the Boston Globe.
Knowing the threat Pressley poses, Capuano has prepared for a close race for months. His campaign has highlighted progressive positions like his early support for "Medicare for all," his opposition to the Iraq war, his opposition to the creation of ICE and his perfect scores from Democratic groups on issues like gun control and abortion rights.
Pressley, meanwhile, has never identified a specific fireable offense from Capuano.
Pressley, a Hillary Clinton surrogate who in 2016 warned about the cost of "Medicare for all," now supports single-payer health care. She wants to abolish ICE and has sworn off corporate PAC money. Capuano, meanwhile, has a long record of opposing war.
But Pressley has never offered herself as a progressive insurgent taking on the moderate Democratic establishment.
Pressley concedes that she and Capuano would likely cast the same votes -- though she gives Capuano no credit for those votes, saying at a campaign stop in Cambridge that it's "no profile in courage; that's baseline doing your job."
Capuano, a member of the Congressional Progressive Caucus who's been in office since 1999, wasn't eager to draw policy contrasts, either. Even after several debates, he said he has "no idea" how he's more progressive than Pressley, and declined to point to any key distinctions.
"My opponent has an obligation to say what she would be doing differently," Capuano said in an interview on a recent Tuesday as he stood on a street corner outside S&S Deli in Cambridge holding signs with a nurses' union that endorsed him. He said Pressley "hasn't done that, except to say that she'd do it differently."
"I don't know what that means," Capuano said.
Capuano's campaign has the support of much of the state and national Democratic power structure -- including Kennedy, former Massachusetts Gov. Deval Patrick and civil rights icon Georgia Rep. John Lewis.
He said Pressley is fundamentally misstating his record in Congress. He pointed to a series of projects -- including $1 billion for a Green Line commuter rail project and other housing and rail efforts.
"That's not a vote, that's advocacy," he said. "That's getting things done in Washington."
He also declined to address Pressley's argument that the district needs activist leadership.
"I don't have a response. I don't respond to generic comments like that, because there's nothing to respond to," Capuano said. "I point to my record."
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