WASHINGTON — When Representative Ayanna Pressley took the oath of office in the House chamber in January, she arrived with 13 years experience as a staffer on Capitol Hill and nine years on the Boston City Council.
It was the resume of a political insider.
But how she got there — upsetting 10-term Representative Michael Capuano after launching a gutsy Democratic primary challenge — was the daring move of an outsider.
Since then, Pressley has tried to straddle a difficult line: one foot in the establishment and the other in “the Squad,” the band of four rebel congresswomen intent on shaking up Washington. Their boldest act of political defiance so far has put them squarely in President Trump’s political line of fire and at the heart of a national debate on race, patriotism, and free speech.
As she settles into her career in Congress, Pressley seems to be aiming to use her insider and outsider reputations to try to have the best of both worlds.
“I don’t feel like an outsider and I haven’t been treated like one,” she said last week in an interview in her cramped House office.
Yet over the past two weeks, Pressley and the rest of the Squad — Representatives Alexandria Ocasio-Cortez of New York, Ilhan Omar of Minnesota, and Rashida Tlaib of Michigan — have found themselves center stage in a scalding controversy that has them at odds not only with Trump but with their own party leaders.
Pressley has been the least controversial of the four, all women of color. But her association with them has set her apart from House colleagues, including other female lawmakers who also entered Congress this year for the first time.
“She doesn’t make waves for the wrong reasons by herself and that to me is a very interesting and significant point. She knows what she’s doing,” said Ian Russell, the former political director of the Democratic Congressional Campaign Committee, which helps elect party members to the House.
“There is no reason why she can’t deliver on legislation while also running this outside game too,” he said. “It’s just a delicate balance.”
Case in point: Pressley started a political action committee this spring, a typical move for a lawmaker. But along with trying to encourage more diversity on campaign staffs, another aim of her Power of Us PAC, which has raised $12,500 so far, is to help Democrats who challenge congressional incumbents in primaries. Helping those outsiders would put her sharply at odds with House Democratic leaders, who oppose any moves to oust incumbents.
After about six months in office, Pressley has impressed many on Capitol Hill, while others are taking a wait-and-see approach.
“She’s smart, she’s experienced, she’s committed, and she really understands how we have to work together in coalitions and work together in an intersectional type basis,” said Representative Barbara Lee of California, another African-American lawmaker whom Pressley considers a mentor. Both lost their mothers and grew close many years ago sharing personal stories about them.
Pressley’s own experience as an African-American woman, a victim of sexual abuse who grew up with a father in and out of prison, put her outside the mainstream in a political world still dominated by white men.
But Pressley and the other Squad members have the ire of House Speaker Nancy Pelosi, who implied that while they have a strong social media following, they have little real power or influence. After they bucked her on a key immigration vote, Pelosi told The New York Times, “All these people have their public whatever and their Twitter world. But they didn’t have any following. They’re four people and that’s how many votes they got.”
Some congressional experts said it’s much too early to say how effective the 45-year-old Pressley will be as a lawmaker.
She said she is eager for this firestorm to calm so she can get back to legislative issues she wants to tackle, such as health care, affordable housing, gun violence, and public transportation — efforts that usually require the laborious work of building support vote by vote.
She said she is working with lawmakers of all types, including Republicans, to pass bills and draw attention to problems such as the immigration crisis at the southern border.
“I can’t say that I have had a challenging time advancing my legislative priorities, I’ve been very intentional in fostering those relationships and reaching out to colleagues to do the work, and we’ve been successful,” Pressley said.
On the House floor and in meetings of the New England delegation and the Congressional Progressive Caucus, Pressley has pushed to improve the quality of public education and access to housing and urged members to treat health care as a human right, said Representative David Cicilline, a Rhode Island Democrat.
She’s willing to work within the House framework to get results, he said, “but she is not afraid to push the institution and push even the leadership when it is important.”
It was that type of pushing on legislation to address the border crisis that led to Pressley’s biggest outsider move since arriving in Washington — one at the root of the current controversy. She and the three other Squad members were the only Democrats to vote against a bill backed by Pelosi to send more money to the border.
Pressley said her vote was simply a decision she arrived at by consulting with experts from her district and immigration advocates.
But the move angered Pelosi, who publicly criticized the four lawmakers, bringing an internal Democrat fight out in the open and to Trump’s attention. He began firing away last week, with a racist tweet saying that the four women of color should “go back and help fix the totally broken and crime infested places from which they came” and that “you can’t leave fast enough.”
Pressley, Ocasio-Cortez, and Tlaib all were born in the United States. Omar is a US citizen who emigrated from Somalia as a child. Trump continued the attacks into this week, tweeting on Monday that “The ‘Squad’ is a very Racist group of troublemakers who are young, inexperienced, and not very smart.”
Despite the dispute that started the ugly episode, Pressley said she has a “productive” relationship with Pelosi and the rest of the House Democrats.
“There is a difference in opinion, and tactically sometimes, as to how we actualize our shared values,” Pressley said. “So even if we have different ideas about how to get there, we are bound by the same values.”
Pressley has authored five bills during her first six months in office and successfully pushed an amendment in a House-passed funding measure to grant back pay to federal contractors who went without paychecks during the federal government shutdown.
But she’s also taken controversial positions, particularly her calls to abolish the US Immigration and Customs Enforcement agency, which runs the detention facilities at the border. In the interview, Pressley said that was an idea she arrived at after much deliberation.
“I’m not new to this, this was not a decision I arrived at cavalierly,” she said. “I wouldn’t just run around saying get rid of agencies.”
Pressley also raised eyebrows at a progressive conference this month when she appeared to take a swipe at longtime members of Congress who are people of color.
“We don’t need any more brown faces that don’t want to be a brown voice,” she said.
Later on Twitter, Pressley disputed the notion that she had criticized the more established lawmakers of color, saying “I was speaking to the collective impact of lifting up one’s lived experience, *whatever* that is, whatever your life walk.”
This new, controversial version of Pressley has surprised many back in Boston, where she did not always have a reputation for confronting contentious issues. But those who have watched her closely say she has evolved.
When she started on the council, she always spoke from written notes, said Samuel Tyler, a longtime City Hall observer and former president of the Boston Municipal Research Bureau.
“Over time she became confident,” he said.
Pressley focused less on issues like big real estate development or insider political battles and more on issues about women and children, he said.
“That was an issue that the council was not dealing with as much. But it was her issue and she made it the council’s issue,” he said.
Tyler said her interest in those issues makes it natural for Pressley to focus on the controversy over the administration’s child separation policy and the treatment of immigrants fleeing strife in their homeland.
“It’s right up her alley,’’ Tyler said. “It’s a natural for her.”
In Washington, Pressley said she talks with lots of lawmakers, especially other first-term members.
Representative Katie Porter of California recalled Pressley cheering for first-year colleagues — Democrats and Republicans — as they drew numbers for congressional offices during orientation soon after they were elected last year.
“I just remember loving her right then. It’s the personal compassion, and warmth and kind of presence emotionally, for others that I just think makes her a natural leader,” said Porter, who serves on a committee with Pressley.
Russell, the former Democratic Congressional Campaign Committee official, said Pressley could have a long career in Washington ahead of her. But Massachusetts voters expect their lawmakers to deliver.
“She could be in Congress for decades,’’ he said, “if she wants to.”