Political powerhouse Ayanna Pressley, who has represented Massachusetts’s Seventh Congressional District in the U.S. House of Representatives since 2019, firmly believes that there is always more work to be done. She’s also not afraid to go where few have gone before. Pressley burst onto the political scene in 2009 when she became the first woman of color elected to the Boston City Council. She followed that up by becoming the first Black woman elected to Congress from Massachusetts, representing much of the Boston area. Her winning campaign slogan, then and now: “Change can’t wait.”

Pressley’s trailblazing speaks to her passions. Over the years, she has emerged as an impassioned advocate for equal rights, justice, and healing. As a member of the so-called “Squad,” a cadre of congresswomen of color, she has pushed the Democratic Party to be more progressive. One of her guiding principles, she says, is that the people closest to pain should be closest to the power. 

Martha’s Vineyard Magazine recently caught up with the congresswoman to talk about the upcoming election, her plans for the future, and why the Island will always represent “unbridled joy.” An edited transcript follows.

Martha’s Vineyard Magazine: You were the first Black woman elected to the Boston City Council and the first Black women to represent Massachusetts in Congress, so you know something about monumental firsts. We’re now facing the possibility of having the first president of the United States who is a woman, and a woman of color. What does the potential of this moment mean to you?

Ayanna Pressley: Well, first, it’s long overdue. And second, it’s powerful. It’s meaningful. I know that what [Kamala] Harris brings as a woman, as a Black and Asian woman, as a former attorney general, United States senator, and vice president…will be transformational. Just yesterday I was reflecting on how incredible it would be if we do our work and she is elected. As meaningful and as transformational as her representation will be for me as a Black woman, I know that she is committed to building [a movement] that sees and centers everyone. 

MVM: You started as an outsider in your own party after challenging and beating a longtime Democrat incumbent in the primary. Five years later, you are a member of “The Squad,” and are credited with helping to make the Democratic Party more progressive. Yet you do sometimes break from the party line on issues, such as calling for a ceasefire in Gaza. Do you still feel like an outsider? 

AP: I have always believed in the power of responsive and good government to make meaningful, impactful differences in people’s lives, and I’ve always been a proud Democrat.… So I don’t feel like an outsider. 

The progressive movement is the Civil Rights movement, in my opinion, that we are still very much in. It’s about disrupting an unjust status quo, about organizing, mobilizing, legislating…for social change, for equality, for racial justice. 

I also serve in a number of elected or appointed leadership posts within our Democratic caucus, including the Pro-Choice Caucus’s Abortion Rights and Access Task Force, and I am a founding member of the Stop Project 2025 [Task Force]…. I firmly believe in doing this work in partnership with the people I represent, and that the people closest to the pain should be the closest to the power. If that means ten more meetings, one hundred more emails, twenty more phone calls – I will do that. I don’t write a bill, I don’t cast a vote, I don’t co-sponsor a bill without enlisting those closest to the pain. And that is true on every issue, domestic and foreign. 

MVM: You’ve quoted a poem before, To Be of Use by Marge Piercy. The last line says: “The pitcher cries for water to carry, and a person for work that is real.” You’re expected to cruise to victory in your own upcoming re-election. Heading into your next term, what is the work that you are most yearning to still accomplish?

AP: Thank you for that positive forecasting about coasting to victory (laughs), but I have not been one to be along for a ride and cruise to anything. I am out here every day to earn the trust, the confidence, and the partnership of the Massachusetts seventh district, and it’s important for me to always be accessible and accountable. 

If you’ll indulge me in one bragging right, my office just received the Democracy Award for Constituent Accountability & Accessibility out of the entire Congress. As a former aid myself, there could be no greater compliment than for people to recognize how hard my team works and fights alongside me for the Massachusetts Congressional District. 

I don’t know about cruising. I know people think it’s all “Black girl magic,” but it’s a lot of “Black girl work,” and that is work that I do year-round, not just in an election cycle. A reporter once asked me what’s a headline I would like to read ten years from now that would be proof I did a job well done. My answer was: “Racial Wealth Gap Eliminated.”

I represent one of the most unequal districts in the country, and I work every day to improve that legacy and to improve those outcomes…. I know everything is possible. Take an issue like student debt relief – when we first proposed it, people questioned it. But I worked as the lead legislator in the House. I worked closely with Senator [Elizabeth] Warren and [Senate Majority Leader Chuck] Schumer over a two-and-a-half-year period with civil rights organizers and tradesmen and women to show the real face of this crisis, to make the case. Ultimately, we were able to push President Biden to use the tool of executive action. 

Now, the Supreme Court – which needs to be expanded and needs an ethics reform, but that’s a conversation for another day – they struck that relief. That would have been relief for thirty-three-million borrowers and would have canceled the debt for one-quarter of Black borrowers and one-half of Hispanic Latino borrowers. That being said, even when the Supreme Court did that, we didn’t stop pushing…. People come up to me every day [to talk about] public-service loan forgiveness. Millions of borrowers have benefitted because we kept pushing, kept organizing. And more relief is on the way…. We have people with…six-figure debt that is at zero. Many of them are becoming first time homeowners, which helps to bridge the racial wealth gap. 

That’s always the kind of progress I want to be ushering in, progress that you don’t have to read a press release to know what happened. You know it because you feel it in tangible ways.  

MVM: What accomplishments are you most proud of so far?

AP: Student debt cancellation is up there. Also, I had a bill that was signed into law by President Biden: the Post-Disaster Mental Health Response Act. In the wake of an extreme weather event or domestic terrorism or any disaster or emergency declaration by a city or state, through FEMA [the Federal Emergency Management Agency] people would be able to access behavior and mental health services. 

I’m proud of that not only because it was signed into law, but because it shows the power of one person. [Boston Marathon bombing survivor] Manya Chylinski sent an email to our office that said, “I don’t have any physical wounds, but I have psychological wounds and PTSD and I can’t access mental health services.” She was following my work on the city council on trauma, and she thought I may be a receptive audience. We worked for two years to draft that bill….

I am also proud of the $39 million I’ve delivered to community project funding to my district, because I know that these will be generational investments with a high return on investment. The $1 million in federal funds to Bunker Hill Community College [to expand the tuition-free community college program], $1 million to a new community health center in Randolph, $1 million for the Black Economic Council of Massachusetts….

I am a lead sponsor of the Woman’s Health Protection Act, a bill that has twice passed the House of Representatives but has been stopped at the Senate.... Also, a new emergent part of my identity is someone living with alopecia. There are a number of things we’ve done legislatively, including a bill [sponsored by Pressley, Massachusetts Congressman Jim McGovern, and Connecticut Senator Richard Blumenthal that would] allow medical wigs to be covered by insurance. So many people suffer the trauma of hair loss…. I am proud that I have taken something not of my choosing and now embedded that in my advocacy and in my representation. It is a choice to show up every day, and I know it means a lot to the seven million people living with alopecia. 

MVM: You’re known to pop up occasionally on the Vineyard. You’ve officiated a wedding here; you’ve participated in fundraisers and events. How often would you say you make it to the Island?

AP: Well, it is our place of respite and joy and restoration. Some of my happiest memories have been made there. My husband and I honeymooned on Martha’s Vineyard when we were married ten years ago. Every year we celebrate [our anniversary there]. For a couple of years, we said we should go to other places…but the Vineyard, and Oak Bluffs for us in particular, it gets in your bloodstream and it calls you. 

When I take the ferry over there, I find I take the deepest of exhales. It’s a very magical place with an incredibly rich history. The people are so warm and hospitable and community-oriented, so it’s a very special place for our family. We don’t worry about our daughter. She rides bikes and gets ice cream. We kayak together and we go for long walks and bike rides. It’s a truly magical place. And I’ll just say this – what I love most about my time on the Vineyard is that I feel it centers my humanity; it’s unbridled Black joy and freedom. 

MVM: Let’s wrap up with another of your favorite sayings: “I choose the discipline of hope over the ease of cynicism.” I imagine there have been plenty of moments during the past few years where you’ve had reason to feel cynical. How are you feeling now? Where are you finding hope?

AP: One of my siblings in the movement, the brilliant scholar Brittany Packnett Cunningham, [said that] during the pandemic…. I love poetry and I love a good affirmation, and that never left me. I say it every day, same with the Marge Piercy poem To Be of Use. 

I ask myself daily: Am I being of use? Am I using my platform I’ve been privileged to earn? Am I practicing the discipline of hope? Certainly, the last five years have been unprecedentedly, deeply consequential. Certainly [there have been] many opportunities to surrender to apathy and cynicism, but I don’t have the luxury. People are depending on me to stand on the gap, so that keeps me grounded. As do the words of Coretta Scott King: “Freedom is never really won, you earn it and win it in every generation.”

The path to justice is not linear; it’s a very jagged algorithm. Right now we are just in it, but I am confident we will get to the other side, because we always do.