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Your Voice. Your Future. Your District

Winston Pierre is running for Boston City Council—because your zip code should never determine the quality of service you receive, the safety of your neighborhood, or your chances at a healthy, fulfilling life. Every parent and every child, no matter where they live, deserves a fair shot at success and access to the services that make that possible.
Our communities are rich in culture and strength—it’s time our city government reflects that same commitment to equity, progress, and hope.

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Meet Winston:

A Proven 

Advocate for Boston’s Future

​As an immigrant, a father, a husband, and a proud graduate of Boston Public Schools, Winston Pierre has lived the experiences of countless families across District 5. From his first job at Fenway Park during the Red Sox season to one of his earliest internships on Capitol Hill, he's seen the power of opportunity up close and how life-changing it can be when doors are opened. He knows firsthand what’s possible when government and community work together to invest in people. Those opportunities transformed his life. But today, they’re becoming harder to find. The high school he once attended no longer exists. The gaps in resources and opportunity—stretching from Mattapan to Hyde Park, Roslindale to Readville—are growing wider. 

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Our Priorities

Workforce Development

The job market is changing fast and we can’t let District 5 get left behind.

 

I’ve spent about a decade advancing inclusive hiring policies and building equitable workplaces across both city and state government. I know what’s at stake because I’ve seen it up close: good jobs disappearing from our neighborhoods, working families left with fewer options, and now, the rapid rise of automation and AI putting even more livelihoods at risk.

 

But I believe in our people. I know the talent, the drive, and the potential that lives in Hyde Park, Mattapan, and Roslindale and Readville.

 

My plan for Workforce Development puts our community at the center of the future:

  • Expand equitable access to job training, apprenticeships, and adult education so residents are prepared for the evolving economy.

  • Create real pipelines to good-paying, future-focused careers — especially in STEM, sustainability, and environmental justice.

  • Forge strong partnerships between local schools, government, and employers to make opportunity accessible at every stage of life.

  • Support youth, working adults, and seniors, especially in communities historically locked out of high-growth industries.

  • We don’t just need more jobs — we need better access to them, real support to get them, and leadership that’s thinking ahead.

 

Let’s build a district where opportunity isn't a privilege — it’s a promise.

Housing & Transportation: Putting People First

As a city planner and more importantly, as a neighbor — I believe in planning that puts people first. Too often, housing and transportation decisions are made behind closed doors, without the input of those most impacted. In District 5, we deserve better. That starts with real conversations — with residents at the center, not pushed to the side.

 

I’m committed to fighting for affordable, accessible, and sustainable housing — for all of us.

No one should be forced out of the neighborhood they love. Working families shouldn’t have to live in fear of rising rents or being displaced every time a new development breaks ground — especially our seniors and neighbors on fixed incomes.

 

I will also advocate for reliable and expanded public transportation that better connects our neighborhoods — especially Hyde Park — to the rest of Boston. With your input, I’ll fight for:

 

  • Better bus and rail service

  • Common-sense traffic solutions

  • Cleaner, more efficient transit options

  • Dignified service for transit-dependent neighbors

  • We need systems that work for everyone irrespective of their zip code.

Public Safety And Quality of Life

Public safety is about more than policing; it’s about fostering care, dignity, and opportunity. It’s about creating neighborhoods that are safe, healthy, and nurturing for all.

  In communities like Hyde Park, Mattapan, and Roslindale, we see some of the city’s highest infant mortality rates. Yet Hyde Park remains the only neighborhood in Boston without a community health center. That’s not just a policy failure — it’s a matter of life and death.

     Our streets are also becoming more dangerous. Motorcycle fatalities and hit-and-runs are taking lives and traumatizing families — including mine. I’ll never forget the day my own toddler and I almost witnessed a young child struck and killed during our usual walk. These tragedies are not just statistics. They’re personal, and preventable. Time for action is now 

         Here’s what I’m fighting for:

  • A health center in Hyde Park to end the medical desert

  • Safer streets through traffic reform, enforcement, and community design

  • Community policing rooted in trust, transparency, and accountability

  • Mental health crisis response funding to reduce harm and save lives

  • Clean water, healthy food, and environmental justice for every zip code in our district

  • Accessibility and opportunity for people with disabilities, immigrants  and underserved communities

  • Youth and neighborhood investments that get to the root of violence and inequality

   

Our communities deserve better. Let’s build a city where public safety means everyone — no matter where they live — can live fully and freely.

Investing in Our Youth. Building a Better Boston

I believe in the power of investing in our young people — not just in test scores or attendance, but in their growth, creativity, and leadership.

  When I was in high school, youth programs didn’t just keep me busy — they helped save my life. They gave me room to grow, find my voice, and build the confidence I needed most.

     I remember staying after school for the Boston Debate League, volunteering as a judge, and feeling a real sense of responsibility for the first time. I remember the pride of holding my first paycheck from Fenway Park during Red Sox season — realizing I mattered.
And later, as I transitioned to college, I had the chance to serve as an ambassador for Mayor Menino’s Success Boston initiative — an experience that taught me what it means to give back.

    These opportunities shaped me.  Every young person in Boston deserves the same chance to be seen, supported, and successful.

       That’s why I’m fighting for:

  • Year-round youth programs and enriching after school opportunities with available transportation

  • Mentorship and leadership development to empower future leaders

  • Creative outlets and safe spaces where young people can thrive

  • Paid internships and first-job opportunities that create real economic equity

  • Pathways to civic engagement that allow young people to shape their communities.

We must fully resource Boston Public Schools and our community programs with the caring mentors, opportunities, and support systems needed to meet every student where they are.

Our young people already have the potential.  Let’s make sure they have the tools to rise.

In the News

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Winston presenting to a group of Senior
Winston P and Youth
Winston Presenting at Innovation center
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Ruthzee, Winston, Hans Patrick
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© 2035 by the Committee to Elect Winston Pierre for District 5.

 

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