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Winston Pierre
Winston Pierre is running for election to the Boston City Council to represent District 5 in Massachusetts. He is on the ballot in the general election on November 4, 2025. He advanced from the primary on September 9, 2025.
Pierre completed Ballotpedia's Candidate Connection survey in 2025. Click here to read the survey answers.
Biography
Winston Pierre was born in Massachusetts. He earned a bachelor's degree from the University of Massachusetts in 2015 and a graduate degree from Boston University in 2020. His career experience includes working in government administration and journalism. [1]
Elections
2025
See also: City elections in Boston, Massachusetts (2025)
General election
General election for Boston City Council District 5
Incumbent Enrique Pepen and Winston Pierre are running in the general election for Boston City Council District 5 on November 4, 2025.
Candidate | ||
| Enrique Pepen (Nonpartisan) | ||
 | Winston Pierre (Nonpartisan)  | |
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| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
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Nonpartisan primary election
Nonpartisan primary for Boston City Council District 5
Incumbent Enrique Pepen and Winston Pierre defeated Sharon Hinton in the primary for Boston City Council District 5 on September 9, 2025.
Candidate | % | Votes | ||
| ✔ | Enrique Pepen (Nonpartisan) | 63.5 | 8,008 | |
| ✔ | | Winston Pierre (Nonpartisan) | 23.4 | 2,954 |
| Sharon Hinton (Nonpartisan) | 12.6 | 1,586 | ||
| Other/Write-in votes | 0.4 | 55 | ||
| Total votes: 12,603 | |||
| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
Do you want a spreadsheet of this type of data? Contact our sales team. | ||||
Endorsements
Ballotpedia is gathering information about candidate endorsements. To send us an endorsement, click here.
Campaign themes
2025
Ballotpedia survey responses
See also: Ballotpedia's Candidate Connection
Winston Pierre completed Ballotpedia's Candidate Connection survey in 2025. The survey questions appear in bold and are followed by Pierre's responses. Candidates are asked three required questions for this survey, but they may answer additional optional questions as well.
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neighborhoods—Mattapan, Hyde Park, Roslindale, and Readville—deserve more than symbolic representation. I’m a father, husband, immigrant, and neighbor who’s walked the walk—organizing, mentoring, and fighting for systemic change in housing, education, policing, and economic access. I have worked across City Hall and the State House, helped craft policy for working families and immigrants, and pushed for equity in every room I have entered. From helping first-gen students navigate college to expanding down-payment support through the Community Preservation Act, my life has been about opening doors for the people too often left outside. I don’t just believe in community power—I have lived it. This campaign is about putting that power back
where it belongs.- We need rent stabilization, deeper affordability, and stronger tenant protections. I support
expanding the city’s Affordable Housing Trust Fund, enforcing ADA standards in all new housing, and funding inclusive design so our seniors and disabled neighbors are not shut out. We must reform zoning and planning—putting residents, not developers, in the driver’s seat. I will prioritize affordable housing on public land, expand community land trusts, and redirect luxury development profits to working-class housing. We must treat housing as a human right. Boston must stop negotiating with speculators and start delivering for the
people who built this city. - Youth engagement is essential to the future of our democracy, especially in District 5, where young people are at the heart of our communities. As your City Councilor, I will ensure youth are not just at the table—they will be leading it. As José Mourinho famously said, 'The best investments are those made in youth.' Mayor Tom Menino, a proud son of District 5, understood this better than anyone. His creation of the Mayor’s Youth Council brought together the city’s brightest young talents, many of whom are now major figures shaping our society. I will continue that legacy, ensuring the next generation has every opportunity to lead and succeed.
- Economic justice isn’t a buzzword—it’s survival for thousands of families across Boston. We must stop treating inequality like a side effect and start confronting it as a policy failure. I’ll fight for a $25 minimum wage that reflects the real cost of living, end exploitative scheduling practices, and invest in pathways to union jobs for Black and Brown workers historically locked out. As someone who’s worked in both public and nonprofit sectors, I understand that policy must meet people where they are. That means funding multilingual workforce development linked to housing, climate resilience, and public transit projects in frontline neighborhoods. We need to reimagine job access as public infrastructure: city-funded, community-led.
how to get things done. As a community organizer, I’ve led initiatives like the Community
Preservation Act, helping first-time homebuyers and building wealth for low- to
moderate-income families. As a city planner, I know real change starts by listening and taking
We face serious challenges—high infant mortality, rising traffic violence, and the tragic loss of two young children within half a mile of my home. As a father, I know one life lost is one too many. I’ll demand action, hold leaders accountable, and push for solutions that protect and uplift our community.
organizations aligned with our values. My focus is on earning trust directly—through
conversations in our neighborhoods and homes. That community-driven support is the most
Note: Ballotpedia reserves the right to edit Candidate Connection survey responses. Any edits made by Ballotpedia will be clearly marked with [brackets] for the public. If the candidate disagrees with an edit, he or she may request the full removal of the survey response from Ballotpedia.org. Ballotpedia does not edit or correct typographical errors unless the candidate's campaign requests it.
See also
2025 Elections
External links
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Candidate Boston City Council District 5 |
Personal |
Footnotes
- ↑ Information submitted to Ballotpedia through the Candidate Connection survey on August 11, 2025
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