Sign up for the Today newsletter
Get everything you need to know to start your day, delivered right to your inbox every morning.
Boston City Council District 5 race: Enrique Pepén and Winston Pierre
Incumbent Enrique Pepén is being challenged by Winston Pierre in the District 5 race.
Enrique Pepén has represented District 5 on the Boston City Council since 2024. He is being challenged by Winston Pierre.
Find out more about Enrique Pepén on his website and social media. Find out more about Winston Pierre on his website and social media.
The following responses have been lightly edited for clarity.
What is the biggest issue facing District 5 residents at the moment and what do you believe the City Council should do to address this?
Pepén: The biggest issue facing District 5 residents is the lack of affordable housing and access to safe, stable neighborhoods. Too many families are being priced out of Hyde Park, Mattapan, and Roslindale. The City Council must do more to preserve affordable housing, ensure equitable development, and hold city agencies accountable.
Advertisement:
I also hear growing concerns about street safety, from speeding to the need for better sidewalks and crosswalks. That’s why I’ve fought for transportation infrastructure improvements that protect everyone on our roads.
Our residents deserve real investment in housing, safer streets, and cleaner parks that reflect the pride they have in their communities.
Pierre: The biggest issue facing District 5 is the continued lack of real investment in, and representation for, our District in City Hall. Out of a $4.6 billion city budget, our District receives just $1.5 million — the lowest of any Boston District. This reflects the inequality we see every day in our District’s neighborhoods. Families are being priced out, seniors are struggling to stay in their homes, and young people are losing faith that they can build a future in the community where they grew up, in large measure because of Boston’s underinvestment in Mattapan and Hyde Park.
Advertisement:
Mattapan has Boston’s lowest life expectancy. Hyde Park has the highest infant mortality rates. Roslindale is facing alarming rates of small business displacement. These sobering facts are not mere chance — they are, rather, the result of long-term underinvestment in our most disadvantaged communities and a lack of equitable planning city-wide.
To address the problems confronting Hyde Park, Mattapan, and Roslindale with a City Council that answers for every city dollar spent. Boston needs an Anti-Displacement Relief Fund to help seniors and families with fixed incomes remain in their homes. It must enforce the Neighborhood Jobs Trust Act to ensure that local residents — not just outsiders — benefit from new growth and job opportunities. I will establish District 5 Advisory Council on day one — to make sure every voice in our District has a seat at the table.
What makes you stand out as a candidate?
Pepén: What truly sets me apart is my willingness to meet people where they are. I don’t wait for election season to knock on doors or check in, I’m out in the community year-round, doing wellness checks, listening to concerns, doing walkthroughs with neighbors, and working side by side with residents to shape the policies that impact them.
Advertisement:
I don’t just talk about equity; I build it through action, investing in youth programs, affordable housing, and small business support. I combine grassroots understanding with government experience, and that helps me get real results for our neighborhoods.
Pierre: I have a great deal of respect for my opponent, but I bring three benefits for the residents of District 5: my experience in driving reform and positive change in city government; my deep roots — and commitment to — the people of District 5; and my willingness to invest in Boston’s future through long-term bond initiatives designed to advance growth and enhance equity..
I have a record of getting results for residents across the city. Throughout my career, I have fought to open doors that too many of us find closed — building coalitions and delivering progress on the issues that matter most: housing, jobs, equity, and dignity.
My commitment to opportunity is not a slogan; it is proven work. From organizing for the Community Preservation Act, to creating pathways for foreign-trained professionals, to advancing diversity in public safety — I have led efforts that deliver real impact. My campaign is built on community voice, not political connections.
Advertisement:
I have always worked alongside the people of Boston, organizing, listening, and solving problems with limited resources. That experience gives me a clear understanding of what is broken and — more importantly — how to fix it.
Do you think the public has lost faith in the City Council in recent years? If so, what do you think should be done to improve the Council’s public image?
Pepén: Yes, public faith in the City Council has declined, but I believe it’s part of a larger erosion of trust in government as a whole. People are frustrated with politics at every level, and that frustration often trickles down to local government, even though it’s where residents should feel the most connection. To rebuild that trust, we have to focus on results, not rhetoric.
For me, that means transparency, collaboration, and consistent engagement with the community. I hold regular neighborhood office hours, respond directly to residents, and share updates on our progress. City Councilors must show that we’re here to serve, not to score political points. I’ll continue to prioritize professionalism, accountability, and tangible results, so residents see a City Council that works for them, not against itself.
Pierre: Yes, I believe many residents have lost faith in the City Council and in city government overall; I completely understand why. We have seen too many headlines about ethics violations, investigations, and scandals, making people question whether their leaders are truly working for them.
But this is not a time for blame; it is a time to rebuild trust. I grew up believing that public service is about integrity, responsibility, and moral leadership, and I still believe that today.
Advertisement:
Restoring confidence begins with transparency, accountability, and real community input. No more projects planned behind closed doors. No more big spending without public dashboards, receipts, and oversight. No more zoning or development decisions made without the peoples voice at the table.
The Council must act as an independent body that stands for residents, not politics. I will work to bring sunlight back into government so every resident can see how decisions are made and why. Change begins one Council member at a time.
When people witness honesty, consistency, and fairness, trust follows. My goal is to make City Hall a place our children can once again look to with pride, a government that serves with integrity and earns the public trust every day.
To comment, please create a screen name in your profile
To comment, please verify your email address
Conversation
This discussion has ended. Please join elsewhere on Boston.com