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Winston Pierre

We Deserve Action and Results


Our neighborhoods are ready for leadership that listens, reflects our shared values, and leads with courage and heart. Winston brings a vision grounded in ethics, transparency, and a deep commitment to every person in our community. That is why he is committed to creating a District 5 Advisory Council of residents from every age and background—elders, immigrants, Gen Z, renters, faith leaders—to ensure every voice is heard and bring power back to the people of our neighborhoods.

In a moment when many seek real change, Winston offers a fresh approach with independence and a grassroots focus that puts real people and community voices first. We are building a grassroots movement across District 5, and we want you on Team Winston.

He focuses on what matters most: safe streets, education and apprenticeships, affordable housing and homeownership, environmental justice, and support for our small businesses.

With over a decade of experience advancing equity and opportunity through inclusive hiring, public contracting, and government transparency at both the city and state levels, Winston has a proven track record of delivering results.

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Connect with Winston on Instagram @winstonforboston

Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre

Let's Build a Future of Opportunity, Together

This is a people-powered campaign rooted in progress, equity, and opportunity for every neighborhood in Hyde Park, Mattapan, Readville, and Roslindale.

Whether you're a seasoned volunteer or just stepping in for the first time, your energy and passion can help drive real change. From knocking on doors and hosting events to fundraising, phone banking, and creative outreach — every effort counts.

Ready to get involved? Sign up today and be part of the movement that’s shaping the future of District 5.

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Join Us, We’re Coming to Your Area!

District 5 deserves an independent voice—someone who listens and stands up for all of us. This campaign is rooted in people, dignity, and community—not politics as usual.

If you’re being priced out of your neighborhood, or you’ve felt invisible in the city you call home—this movement is for you.

There’s a place for everyone, whether you can:

  • Make phone calls
  • Knock on doors
  • Show up for a meet-and-greet
  • Help us take the message to the streets—or spread it online
  • Lend a helping hand in any way

Find our next events near you and get involved—on the ground or online.

Join Here
Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre
Winston Pierre

Meet Winston: from margins to momentum

I’m Winston Pierre, son of Haitian immigrants, city planner, and proud neighbor to Mattapan, Hyde Park, Readville, and Roslindale.

I’ve seen how City Hall too often overlooks our neighborhoods. I know what it’s like to be told to wait your turn—to watch resources go elsewhere while our families are forced to do more with less.
That's not just my story. It’s my motivation.

I’m running so no one in our communities ever has to wait their turn to be seen, heard, or served again.

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Winston Pierre

Support the Campaign

This campaign is powered by people who believe in a better future for our city and our families. Your support helps us reach more voters, share our vision, and organize where it matters most. Every dollar moves us forward.
Let’s keep building together, and thank you for standing with us.

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