Meet Winston
A Transparent, Independent voice to reflect our community’s priorities.
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Winston is running to represent District 5—Mattapan, Hyde Park, Readville, and Roslindale—because he believes every neighborhood deserves a voice that understands its challenges, hopes, and potential. He’s a father, husband, proud immigrant, and neighbor who deeply understands the lived experiences of the people he seeks to represent.
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From his first job as a stand worker at Fenway Park to his service as an AmeriCorps member working with children in low-income neighborhoods, Winston’s life has been grounded in service. As a volunteer with Generation Citizen, he helped young students learn how to advocate for their rights and care deeply about their communities.
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“From the very beginning, there were people who saw something in me—even before I saw it in myself.”
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Winston often speaks about the mentors and opportunities that shaped his journey after moving to the United States—internships, school programs, and community support that gave him the confidence and purpose.
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“I’m only here today because of the generosity of my community—and because they believed in me from day one.”
During college, Winston made it a mission to pay that generosity forward. He mentored students, opened doors, and ensured others felt seen, valued, and capable. He served on the Success Boston Leadership Council —a partnership between late Mayor Thomas Menino and the Boston Foundation—focused on helping low-income, first-generation college students of color earn a degree by age 25.
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In 2015, Winston joined a student delegation on a 25-hours pilgrimage from Boston to Selma, Alabama, marking the 50th anniversary of Bloody Sunday. The journey deepened his understanding of the right to vote and the sacrifices made to secure it.
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“I was still relatively new to the country, but the impact hit me hard. What bridges am I willing to cross, even knowing it might be hard? Watching documentaries and hearing stories about the fight for voting rights made it clear: voting is a privilege—and a responsibility we must protect.”
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A year later, he testified before the Massachusetts Caucus in Washington, D.C., advocating for increased funding for first-generation and low-income college students through the Council for Opportunity in Education.
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As your representative on the Boston City Council, Winston will stand shoulder to shoulder with our communities to break down barriers to the ballot and lift every voice. He believes voting should be easy, accessible, and protected no matter your zip code. Winston is ready to fight for real change so that everyone can fulfill their civic duty without obstacles and delay in District 5 and across Boston.
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Winston has also worked on many citywide initiatives, including the Community Preservation Act (CPA), which is now helping first-time homebuyers with down payments and creating generational wealth for residents with low to moderate income across the city of Boston.
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Additionally, with the passage of CPA, much needed resources have been allocated for historic preservation and green space. Winston believes in environmental justice; not just as policy, but as action that addresses water pollution, heat islands, wildlife protection, harmful radiation and emissions at the neighborhood level.
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Winston has been a dedicated volunteer with Project Citizenship and the Massachusetts Immigrant and Refugee Advocacy (MIRA) Coalition, helping new arrivals with interpretation services and guiding them through the complex systems they must navigate to succeed. During a fellowship with Governor Baker’s administration, Winston partnered with MIRA to develop policies to increase access for foreign-trained medical professionals.
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Winston’s work helped to secure additional funding for the Welcome Back Center at Bunker Hill Community College, a critical resource center helping internationally trained healthcare workers obtain credentials they need to serve our communities. Winston’s commitment to opportunity, inclusion, and real solutions is the kind of leadership District 5 deserves.
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Winston also served in Mayor Walsh’s administration, where one of his key responsibilities was overseeing the Boston Police Cadet Program — an initiative that gives young people, ages 18 to 25, the opportunity to learn about community policing and eventually serve the very neighborhoods they come from.
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For nearly a decade, Winston has been fighting for fair hiring practices, inclusive workplaces, and expanding access and opportunity at both the city and state levels. He knows what it means to open doors — and he has seen firsthand what happens when they’re closed. That’s why Winston’s campaign is about more than just ideas—it’s about action, accountability, and building a future that works for everyone.
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Winston holds a degree in Political Science from the University of Massachusetts Boston and a Master’s in City Planning from Boston University. He also has certifications in urban policy and comparative economic systems, among many others.
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Winston’s campaign is built on a simple belief: when we invest in people, our communities thrive. On the City Council, he will fight for bold, accountable, and people-first solutions—because every resident, regardless of zip code, deserves a fair chance.
