Joanna Weiss is a writer in Boston and the editor of Experience magazine.

It was only a week after the presidential tweet that made the Squad famous—telling the four freshman representatives, all women of color, to “go back” to the places “from which they came”—and Massachusetts Rep. Ayanna Pressley had broken from the group in an actual vote.

The matter in question was a resolution opposing a Palestinian-led movement to boycott Israel. The measure passed the House overwhelmingly on July 23. Among the 17 “no” votes were three members of the Squad: Reps. Alexandria Ocasio-Cortez, Ilhan Omar and Rashida Tlaib. Pressley, the fourth, voted “yes.”


The social-media reaction was swift and loud, a mix of gratitude and vitriol. But this time the fury came, not from the right, but from the left. “The squad is three now,” someone wrote on Twitter, and much of the anger directed at Pressley followed that logic: a sense of betrayal marbled with surprise, as in, how could you not be exactly what we thought you were?

But in Boston, where Pressley has been a compelling political figure for a decade, constituents and longtime associates weren’t at all surprised by her vote. Pressley, 45, might be part of the Squad, and an unfailing public cheerleader for its participants, but in many ways she doesn’t fit the profile. While the Squad has made headlines for its forceful progressivism, Pressley has never quite matched the image of the brash outsider, pushing against the establishment with bare knuckles and take-no-prisoners rhetoric. Instead, her history in Boston—from her stints as a staffer for solidly mainstream Democrats to her eight years on the Boston City Council—has been a case study of pushing for change from within the system. At a time when fissures in the Democratic Party make national news, her approach in Boston City Hall actually points a way forward for Democrats who want to cast themselves as the party of change—and the party that gets things done.

For now, though, Pressley, who declined to comment for this story, finds herself navigating the expectations that come with being part of The Squad, and have actually dogged her since her high-profile election as Massachusetts’ first black woman in Congress. Everyone from Twitter to the Times of Israel has made mistaken assumptions about her, says Jeremy Burton, executive director of the Jewish Community Relations Council of Greater Boston, who lives in Pressley’s district and notes that Pressley’s Israel boycott vote was consistent with her campaign rhetoric. Most of those mistakes, Burton says, were “entirely based on what she represents as a woman of color, and who she’s working with and aligned with on a bunch of other issues, and not what she was actually saying.”



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Before Pressley became a progressive symbol in Congress, aligned with a group that includes two Democratic Socialists, she worked for mainstream Massachusetts congressional Democrats. She spent the bulk of her career as an aide, first for Rep. Joseph Kennedy II, then for Sen. John Kerry, who defended her against President Donald Trump in a recent letter to the Boston Globe.

Like AOC, she had innate political talent, standing out even when her job was to work the back of the room. “The minute I met her, I saw that she was a star,” says Barbara Lee, a Cambridge, Massachusetts-based activist and supporter of female candidates, who recalls approaching Pressley at a political event in the early 2000s and urging her to run for office.

Still, it took nearly a decade—and more encouragement from all corners—before Pressley ran for an at-large seat on the Boston City Council. It was 2009, and she was 35. The Dorchester Reporter, the newspaper in her neighborhood, attributed her run to “the Obama effect”: African Americans, inspired by the first black president, running for office themselves.

When she won, Pressley became the Council’s first black female representative, and only one of two women on the 12-person body. As a singular voice in a city establishment that was dominated by older white men, she had to manage expectations from all sides, former staffers and political operatives recall. Some assumed she would stand with the black men on the Council—who had honed a kind of brazen activist voice—on issues that became racially charged, such as a controversial agreement with the firefighters union. (She didn’t always vote in lockstep with them.) Some thought she’d approach race-related conflicts differently, because she was a woman. (She wasn’t one for bomb-throwing regardless of her gender.) And some thought her interest in teen pregnancy and sexual violence, issues that hadn’t historically been front-and-center in Boston politics, would make her easy to pigeonhole.

In a sense, it did—Pressley developed a reputation for leaning into pet issues, no matter whether anyone else wanted to talk about them. One former aide recalls the reaction, among male councilors, to one of Pressley’s early initiatives to bolster sex education programming and provide condoms in Boston public schools. “The councilors were like, ‘Great, that totally makes sense that you would do that. Do your thing! We just don’t want to be involved,’” the aide says. “It’s like this judgment—what she should and shouldn’t be doing, based on what we think her identity is. And that’s still happening now.”

In fact, some three years after Pressley started working on the issue, Boston’s School Committee passed a sweeping sex-ed reform measure that included a controversial plan to hand out condoms in schools. And Pressley, by all accounts, felt vindicated by the idea that she could push for unpopular issues on her own, and still get action.

“I think she really was like a squad of one,” says James Chisholm, her first chief of staff. “If she wasn’t saying it, no one was.”

Pressley also wasn’t afraid to stand up to critics within the black community. She drew ire with a vote to oust an African American councilman who had been convicted on a felony bribery charge that he said was racially motivated. And she latched onto issues even when people urged her to play it safe, as with her bid to create new liquor licenses—a valuable commodity in Boston—for use in minority neighborhoods.

Pressley argued that she was working for economic justice: To become safe and vibrant, neighborhoods needed restaurants, and to be viable, restaurants needed alcohol. Within the black community, though, some leaders quietly told her not to push it, one longtime adviser recalls: “We heard a lot from people: ‘No, you’re setting yourself up … you’re putting a target on your back, you’re taking on the establishment, people aren’t going to let this happen.’”

But even when she was working on these progressive, and at times controversial, causes, she knew how to bring people to her side. Pressley prevailed on the liquor licenses largely because she did the behind-the-scenes work, holding dozens of meetings with stakeholders and state legislators who would ultimately have to vote on this issue.

“When she finally did roll something out, she had buy-in. She had consensus,” says the adviser, who notes that throughout her time on the Council, she took pains to finesse those working relationships, wrangling support behind the scenes and giving fellow Council members a heads-up if she was going out on a limb. And she kept a pledge to the mayor’s office never to take them by surprise. If the Squad is known for waging public battles with the House establishment—as with the Twitter feud between House Democrats and Ocasio Cortez’s former chief of staff—Pressley’s history in office is different. She managed to weave progressive causes into her mainstream work, taking pains not to burn bridges in the process.

By the time she had won her fifth City Council race, in 2017, Pressley had a local squad of her own: There were now six women on the Council, most of them women of color. But for someone with big ambitions, Boston City Hall is a limited stage. The mayor is strong; the Council is notoriously weak; many major changes in policy, like the liquor license matter, have to pass through the state Legislature. The Council’s two-year terms make it difficult to push a broad agenda.

And for Pressley, the next step seemed clear: running for Massachusetts’ 7th Congressional District, the only majority-minority district in the state. The trouble was, the seat was held by a well-liked incumbent, Mike Capuano, who hadn’t faced a primary opponent in 20 years. Unlike some progressive candidates, who ran to the left of Democratic establishment figures, Pressley’s run wasn’t driven by ideology. Instead, she argued that, while their positions were nearly identical, she and Capuano differed in approach and in the issues they’d bring to the forefront. She ignored conventional wisdom and dismal polling data, campaigned across communities and drew out people who hadn’t voted in midterm elections before. She won the primary by 17 points.

During the race, most of the Massachusetts political establishment either endorsed Capuano, was conspicuously quiet, or, in the case of former Rep. Barney Frank, was openly dismissive. Still, within hours of her primary victory, one longtime friend says, every member of the delegation had called to offer congratulations, and their chiefs of staff were calling with advice. Friends say the delegation has also been supportive as Pressley has vaulted to a level of fame that’s rare for a congressional freshman.

Still, for some in Boston, it has been jarring to hear Pressley’s national voice channel the social-media savvy voice of the Squad. Though Pressley was always a naturally lyrical speaker, she once shied away from talking off-the-cuff or revealing true emotion. In the early days, staffers sometimes worried that her speech was too measured. (“So guarded,” an adviser recalled her dealings with the news media back then. “Oh, dear God, it was painful.”) Now, Pressley sometimes seems unchained, as in the famous July 9 clapback tweet in which she chastised presidential adviser Kellyanne Conway, calling her “Distraction Becky” and writing, “Yeah take a seat and keep my name out of your lying mouth.”

Some cheered Pressley for letting her authentic self come through: “That felt like my girlfriend,” says Jesse Mermell, a longtime friend and fellow political hand. But some longstanding Boston political types, like Frank, questioned her tone and her Squad association. Joan Vennochi, an influential Boston Globe columnist, pointed out the racial overtones of Pressley’s “Distraction Becky” epithet and asked whether Pressley would use her Squad association to “unite, or to divide.”

Her newfound public profile has brought Pressley negativity from other corners, too; since Trump’s “go back” tweet, she’s been a demon for the right; since the Israel boycott vote, she’s gotten criticism from the left, and faced complaints about her positions beneath tweets she posts about her cat. She also drew some right-wing fury when she spoke at the progressive NetRoots Nation conference in July, saying, “We don’t need any more brown faces that don’t want to be a brown voice.” Still, many of her other public statements have pushed for collaboration and consensus. And some friends and former aides see shades of her City Hall background in her messaging right after Trump’s incendiary tweet: her efforts to divert attention from the presidential squabble, her praise for other members of Congress outside of the Squad, her tweets featuring hashtags like #oursquadisbig.

Meanwhile, some political hands declare that a spotlight on Pressley, even a negative one, is an opportunity for Democrats in general, and Massachusetts Democrats in particular. “The reality is that Ayanna Pressley might have the star power right now, but Richie Neal and Jim McGovern and Katherine Clark hold the power,” says political consultant Scott Ferson, pointing to three other members of the state’s delegation: Ways and Means chair Richard Neal, Rules Committee Chairman Jim McGovern, and House Democratic Caucus vice chair Katherine Clark.

“If I were them, I’d be thinking, ‘That’s awesome. You go out there, you get the attention, you fight ’em at that level,’” while the veterans work behind the scenes, says Ferson, a former staffer for the late Sen. Ted Kennedy, another high-profile politician who was willing to serve as a national lightning rod in the service of policy goals. “If you’re Ayanna Pressley, representing the district she represents, bring on the right-wing vitriol. Because with that brings liberal money and progressive money and attention,” that can build support for Democratic causes overall.

In recent weeks, Pressley has been using the white-hot attention to promote her own policy goals at a rapid pace, often co-sponsoring legislation with other politicians. She joined Sen. Cory Booker to co-sponsor a “baby bonds” bill that would give every child a government-funded savings account (with contributions weighted by income and paid for by an expansion of the estate tax). Along with Sens. Elizabeth Warren and Chris Van Hollen and Rep. Jesús “Chuy” García of Illinois, she introduced a bill that would create an instant system for clearing checks, which they say would help people living paycheck to paycheck.

And that approach feels consistent with her Boston history, observers say: an outsider pushing from the inside, an operator who knows how to use her identity for political purposes. It’s not precisely the image of the Squad, but it’s a timeworn recipe for effectiveness in Boston, where you don’t get through politics unless you know how to use the system for your purposes.

“Ayanna does walk a very fine line between being an activist and an advocate and a very loud voice, and she respects the system,” Chisholm says. “Nationally, people are seeing it for the first time. She’s always really effectively walked that line.”

Joanna Weiss is a writer in Boston and the editor of Experience magazine.