Meet Winston: from margins to momentum

I am Winston Pierre, son of Haitian immigrants, city planner, and proud neighbor to Mattapan, Hyde Park, Readville, and Roslindale. I know what it means to be pushed to the margins, overlooked by City Hall, and told to wait your turn. That is not just my story, it is my motivation.

I have spent my career working on open doors that too many of us find closed. From Beacon Hill to City Hall, I have built coalitions and delivered results on the issues that matter most: housing, jobs, equity, and dignity.

My commitment to opportunity and progress is not just a talking point. It is a record of work I have led firsthand.

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Workforce Equity: As a Fellow in the Executive Office of Labor and Workforce Development, I created a blueprint to integrate foreign-trained healthcare professionals into our workforce—and secured state funding for the Welcome Back Center at Bunker Hill Community College.

Supplier Diversity and Inclusion of Minority-Owned Businesses: At the Governor’s Office of Access & Opportunity, I helped Massachusetts became the first state in the country to include certified LGBTQ+ businesses in public contracts.

Disability & Civic Access: On the Mayor’s Commission for People with Disabilities, I advanced access initiatives that supported seniors, caregivers, and residents with disabilities.

Diversity in Public Safety: As Boston’s Director of Diversity, I led recruitment for the Police Cadet Program—achieving 67% participation from candidates of color.

Affordable Housing: As a grassroots organizer, I helped pass the Community Preservation Act, which has now funded 397 projects and over $230 million—including down-payment assistance for first-time homebuyers across Boston.
I’ve managed budgets, crafted policy, and stood with communities. I know the system isn’t broken—it’s rigged. And I’m not running to manage it—I’m running to challenge it—and to deliver for the people who’ve waited long enough.
If you’ve ever felt invisible in your own city, this campaign is for you. I’m Winston Pierre, and I’m ready to fight for the Boston we all deserve.

Education: Winston holds a Master’s in City Planning from Boston University and a Bachelor’s degree in Political Science from UMass Boston, along with certifications in urban policy and comparative economic systems.But more than credentials, he holds the trust of a community that’s tired of being talked down to—and ready to rise, together, with leadership that listens and leads with purpose.

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