U.S. Rep. Ayanna Pressley feels that Martha’s Vineyard is her happy place, and she tries to visit often during the summer months to spend time with her chosen family and community.
“It’s where unbridled Black joy lives and thrives,” Ms. Pressley told the Gazette last week.
On Saturday, Rep. Pressley visited the Island for the Martha’s Vineyard African American Film Festival, where a short documentary detailing her leadership had its world premiere. The documentary, titled She Dared To Dream, is part of filmmaker Abby Ginzberg’s ongoing series that shines a light on women of color in elected positions.
“Here are these incredibly inspirational women working in Congress, and I felt like people outside of their districts didn’t know them as well, and they should,” said Ms. Ginzberg, another frequent summer visitor.
Ms. Pressley was the first woman of color elected to the Boston City Council in 2009, and, in 2018, she became the first person of color to represent Massachusetts in Congress. A Democrat from Boston, her district includes most of the city, as well as some northern and southern suburbs.
In one of the opening scenes of the film, Ms. Pressley visited the Boston Latin Academy where she told an audience of students that at one point in her life, she felt she did not have the right or agency to show up unapologetically as herself.
Ms. Pressley said she overcame a lot growing up. She was one of few Black students at a private school in Chicago, and often felt lonely. She said she also harbored shame for her father, who was incarcerated for much of her childhood.
With the help of her mother, Sandy Pressley, who fiercely believed in her, Ms. Pressley said she went on to realize she was just as good as her peers and entitled to be authentic with herself.
She told the Gazette that getting to know herself continues to be a lifelong journey where there is no destination.
“I’d like to think that I’m changed by every situation, not in a weakly malleable way, but in an emotionally impressionable, personally evolving kind of way,” Ms. Pressley said.
In the documentary, Ms. Pressley talks about her personal battle with alopecia totalis, a condition that causes the complete loss of hair. She went completely bald in the span of five weeks, and later spoke out about the condition in 2020.
On the eve of President Donald Trump’s first impeachment vote the year prior, Ms. Pressley had been custom fitted with a wig to cover her newly bald head. She remembered crying in the bathroom after delivering her statement on the House floor.
She said the decision was emotional because a big part of her cultural expression was how she styled her hair. She felt she owed it to all the little girls who found power in her representation to be transparent.
“I didn’t want to have to put on a wig to meet a very narrow definition and standard of what is professional,” Ms. Pressley said in the film.
Ms. Pressley cosponsors the federal CROWN Act, a law aiming to ban race-based hair discrimination. The act is currently pending at the federal level, but was signed into Massachusetts law in 2022.
Ms. Ginzberg said she started making the documentary before President Trump was elected and Ms. Pressley’s voice, which often speaks out against his policies, is more important than ever.
“Today there is so much more on the table,” Ms. Ginzberg said. “So, her leadership that led me to be interested in telling her story in the first place [became] so much more profound as we face the uphill battles that we’re in right now.”
Ms. Pressley has been outspoken against President Trump’s immigration policies. In the film, Ms. Pressley visits an immigration detention center in Louisiana to check on the wellbeing of Tufts University doctoral student Rumeysa Öztürk, who was being held in custody.
The film also highlights Ms. Pressley’s belief that all people should have reproductive freedom. In 2022, she was arrested with 16 other Congress members while protesting the U.S. Supreme Court’s decision to overturn Roe v. Wade, which had made abortion legal.
In the film, U.S. Rep. Jim McGovern, a fellow Massachusetts Democrat, explained that Ms. Pressley is the conscience of the state’s legislative delegation and a rising force in Congress, pushing her colleagues to act with courage and integrity.
Ms. Pressley told the Gazette that she got her steadfast conscience from her parents, who she said were both extraordinary teachers through the lessons they instilled in her, the tragedies they overcame and their love for community.
Ms. Pressley, who gave a Sunday service at Union Chapel in Oak Bluffs last month, said at the heart of her work is her faith in God, which helps her determine what’s right and wrong. Her belief in divine assignment gives her strength.
“I believe deeply, that I am exactly where I’m supposed to be [and] doing exactly what I’m supposed to be,” she said.
The instinct for many elected officials, she said, is to talk people out of what they’re feeling. But she explained that it denies them of their experiences. Under the current administration, Ms. Pressley said what many are experiencing is unprecedented in their lifetime.
Ms. Pressley encourages people to extend grace to themselves during these moments. She said history shows that the will of the people will prevail, and there is reason to keep up faith.
“What I’m most looking forward to is the work of reconstruction,” Ms. Pressley said. “I will certainly make sure that I’m doing my part [so that] we do not default to a status quo that was already unjust, [and] that once we get to the other side of this great undoing, that we stitch together something that is more beautiful, more just and more equitable.”
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Ayanna Pressley Documentary Premieres at African American Film Fest – The Vineyard Gazette








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