Editor’s note: This article was originally published on Steve Ahlquist’s Substack. Reprinted with permission.
The Providence Board of Canvassers and Registration has issued a warrant to hold a Special Election to fill the vacancy for the Providence City Council in Ward 2. The Special Election will be held on Tuesday, December 2, 2025, with a Primary scheduled for Tuesday, November 4, 2025.
Council member Helen Anthony announced on August 1 that she will resign from office effective September 1 to devote more time to her health, opening up the seat for a special election.
Candidates wishing to run must file their Declaration of Candidacy with the Board of Canvassers between Thursday, September 25, 2025, and Friday, September 26, 2025, at 4 p.m. Nomination papers will be available starting Thursday, October 2, 2025, and must be returned by Tuesday, October 7, 2025, with at least 50 signatures of eligible Ward 2 voters.
Here are the press releases of the four candidates who have announced. After they have secured a place on the ballot, I will work to arrange interviews with each of them.
Jill Davidson
Jill Davidson, a longtime community advocate, announced she is running to succeed Helen Anthony as the Providence City Councilor from Ward 2. She released the following statement:
“I’m running for City Council because I love our community, and after two decades bringing together coalitions of neighbors to support our public schools, advance climate resilience, and push for responsive government, I’m ready to bring my experience and energy to City Hall.
“Providence faces real challenges that threaten our ability to thrive. Our kids can’t afford rent in the city they call home. Our taxes have risen as our infrastructure, like roads, sewers, and sidewalks, has eroded. We desperately need new housing, and we also want development that respects the historic architecture of our community. And, of course, the values we hold dear – democracy, civil liberties, free speech, and all manner of critical public services – are under a truly unprecedented assault by Trump’s authoritarianism.
“I deeply believe in our community. I’ve seen what’s possible when neighbors work together, and I’ve spent twenty years proving that good things happen when you show up consistently, listen carefully, stay humble, and work collaboratively. I’ll bring that approach to the complex issues our city faces, and continue Helen Anthony’s fight for transparency and responsiveness.”
Jill Davidson is Director of Development and Communications for the Woonasquatucket River Watershed Council, where for six years she has fought for clean water, green space, and climate resilience in Providence. Previously, she helped lead the Coalition of Essential Schools, a national network advocating for rigorous student-centered schools. Jill has led community advocacy efforts on the East Side and across the city for over twenty years. She was a key leader in the successful effort to stop the closure of Nathan Bishop Middle School and secure its renovation. Her three children attended the Providence Public Schools. Jill helped lead the parent organizations of MLK Elementary, Nathan Bishop, and Classical High School, where she brought families together to advocate for better family engagement. Jill has been a board member at Temple Emanu-el and the JCC, and for six years, she wrote a column for East Side Monthly, sharing stories about the Providence Public Schools. Jill received her A.B. from Brown University and her M.Ed. from the Harvard Graduate School of Education.
Jill lives on Elmway Street with her husband Kevin and their son, Leo, who, despite having a full-time job in green energy, can’t afford the rent in Providence. They are joined by June, the dog, and Al and Nicole, the cats.
Matt McDermott
This morning, Providence resident, Democratic pollster, and Rhode Island native Matt McDermott announced his candidacy for the upcoming special election for the Providence City Council in Ward 2 (Blackstone, College Hill, Wayland).
McDermott has spent his career electing leaders and winning campaigns on the issues that define us — from voting rights to public health, reproductive freedom to civil rights. He has served as national Co-Chair of the LGBTQ+ Victory Fund Campaign Board, helping barrier-breakers like Congresswoman Sarah McBride make history. McDermott also co-launched Out for Harris-Walz here in Rhode Island, organizing volunteers last year to bring energy and people-power to the fight for our future in key battleground states.
Matt is running because decisions made in our City Hall matter as much as those in Washington.
“Providence stands at a pivotal moment — a time when bold action can shape our future,” McDermott said. “We need leaders who defend our values, build real collaboration, and deliver transparent, community-led governance. I’ve been on the frontlines of this fight, and I know what it takes to protect our rights and push progress forward.”
McDermott is running on an Opportunity Agenda to Build a Better Providence:
- Defending Our Democracy — making this city a national model of responsive, inclusive governance.
- Reclaiming Our Schools — rebuilding them under local control and restoring public trust.
- Tackling the Housing Crisis — opening the door to affordable, accessible housing for all families.
- Investing in Stronger Neighborhoods — building a safer, stronger, and more sustainable Providence.
“Ward 2 deserves a councilor who collaborates, rolls up their sleeves, and gets things done,” McDermott added. “I’ll bring my experience, my energy, and my commitment to building a city that lives up to its promise.”
McDermott grew up in Rhode Island, in a working-class family of public school educators, and was shaped by values of service and community. He and his husband, Dillon — a second-grade teacher at Pleasant View Elementary and trustee of the Providence Public Library — live in Wayland Square.
Jeff Levy
Jeff Levy has officially announced his candidacy for the Democratic nomination in the upcoming special election to fill the seat on the Providence City Council for the city’s 2nd ward.
“This is a perilous time for American democracy. Every day, we see new atrocities committed by the President and his allies, and it’s easy to feel helpless to fight back. My way of coping with that feeling of helplessness has been to find ways I can make a difference, large or small.
“That’s why I’m running to represent our community on the City Council. While there’s only so much that any of us can do individually to stop Trump, everything we do collectively matters. Right now, I can advocate and fight for a future for our city that reflects our shared values.
”We need Providence to be welcoming, safe, and affordable—for young people graduating from our colleges, for families raising children, and for seniors who want to age in place. This must be a city where immigrants, LGBTQIA+ neighbors, and people with disabilities feel supported and valued. Ward 2 has a tradition of thoughtful, hardworking city councilors, and I will continue that legacy while also meeting the urgency of this moment. That means putting in the hard work to find fair and equitable solutions to the budget, schools, and housing—and being ready to fight back against the looming MAGA assault on our city. I am ready to do both.
“I’m running to give back to the place where I’ve lived, worked, and raised my family for 27 years. From coaching in the Fox Point East Side Little League to my legal work for our small businesses, I’ve always worked to contribute to what makes Providence so special. I’ll bring that same commitment and thoughtfulness to City Hall, ensuring that our community’s voices are heard and our values are represented.
“As a lawyer and advocate, I’ve provided pro bono legal work to stop Republican election theft, defended civil liberties through volunteer work with the ACLU, and supported passage of progressive policies like paid leave and fair taxation through my board service with the Economic Progress Institute. On the Council, I’ll bring relentless advocacy, legal expertise, and a deep love of this community to make sure Providence works for everyone.
“I look forward to meeting you over the next two months and hearing your concerns. I hope to earn your vote in the Democratic primary.”
David Caldwell
David Caldwell announced that he is running as a Democrat for the Ward 2 City Council seat in Providence to represent the East Side of Providence. The seat is being vacated due to the retirement of current Councilwoman Helen Anthony.
“Throughout my life, I have been blessed to hold a number of roles and titles that I hold dear – Marine, small business owner, environmental advocate, President of the Audubon Society of RI, husband, father, and Providence resident,” stated Caldwell. “These are the roles that have uniquely prepared me to be Providence’s next City Councilperson. I am running for this seat because I believe my life experiences and skill set will allow me, as Ward 2’s next Councilperson, to help solve our City’s complex problems and deliver positive outcomes for the people of Providence.
“If elected, my work on the City Council will focus on protecting our environment; ensuring a high quality of life; preserving the integrity and character of our East Side neighborhoods while planning responsibly across the city for growth; promoting housing affordability so families, students, young professionals, working families, and seniors can continue to live and thrive in Providence; bringing Providence schools back under local control; bringing smart, responsible budgeting experience and practical problem-solving to our City’s finances; and fighting for Providence at the state level, ensuring our city and schools get a fair shake from state leaders at the State House. I have spent my entire life working to achieve positive results under difficult and stressful circumstances, and tackling these issues will be no different. As Providence’s next City Councilperson, I will be ready to lead on day one.”
David Caldwell is a Marine Corps veteran, having served our country in this role for eight years. He was commissioned as an officer in the United States Marine Corps, serving as Headquarters and Service Company Commander for 120 Marines during Operation Iraqi Freedom. In this role, he specialized in the management and execution of multi-million dollar budgets, including purchasing, negotiations, and financial planning. He also served as a Supply & Logistics Officer, managing the flow of military supplies, equipment, and gear, and optimizing/troubleshooting supply chain operations. Dave was deployed with the 11th Marine Expeditionary Unit during the Iraq invasion.
He owns Caldwell & Johnson Custom Builders, an environmentally friendly, family-owned small business started by his parents in 1968. Under David’s leadership, the company has become a leading green builder in RI and among the field’s leaders nationally. The company specializes in building environmentally sustainable homes that preserve a neighborhood’s character.
He is a longtime environmental advocate, serving as President of the Audubon Society of RI, the state’s oldest environmental advocacy organization. In this role, Dave helped launch RePower Audubon, a plan to bring the organization to net zero by 2030 and true zero by 2040 – done in an environmentally and economically responsible way. Since 2014, he has served on the state’s Executive Climate Change Coordinating Committee Advisory Board. He has also served on the RI Green Energy Building Council (Residential Green Building Advocate) and the RI Energy Efficiency Council.
Dave rose to serve as President of the Rhode Island Builders Association from 2016 to 2018, representing over 1,000 small businesses. In this role, Dave advocated for Rhode Island to become the first state in the nation to adopt the 2024 International Energy Conservation Code (IECC) with mandatory electric readiness provisions. He taught the very first class in the country on the 2024 IECC in East Providence.
Dave has served on the Providence City Plan Commission for the past two years. He helped craft the City’s Comprehensive Plan, which will guide growth and development for the next decade. This plan was built with unprecedented transparency, outreach, and community engagement. It balances the urgent need for new housing with the importance of preserving the character and integrity of our neighborhoods. As City Councilperson, he plans to lead on this important issue to ensure all Providence residents are housed and have a roof over their head.
In addition to these roles, David has served on a number of boards and committees, including: HousingWorksRI (Vice-Chair); City of Providence Special Commission to Study Affordable Housing; RI Special Legislative Commission to Study Housing Affordability; Elizabeth Buffum Chace Center (Properties Committee); Lincoln School Board of Trustees; Society of American Military Engineers; VFW; and American Legion.
“The Marines taught me that real, serious leadership requires authenticity, competence, and above all, integrity – especially when the toughest decisions with the biggest consequences must be made,” concluded Caldwell. “The best leaders I served with lived by the credo: ‘Mission first, Marines always.’ That is the standard I hold myself to, and the kind of leadership I will bring to City Hall. I am very optimistic about our future, I love this community, and I hope to build on the great work that Councilwoman Anthony did for the City of Providence. Providence is a world-class city. Together, we will make it even better.”
Caldwell earned his Undergraduate degree in Political Science (with a Music Minor) from the University of Rhode Island, his Master’s Degree in Political Science from Columbia University, and his MBA from the University of California, Irvine. He lives on the East Side with his wife, Tina Richman Caldwell. He has two daughters currently attending college—Claire in Jewelry Design at the Tyler School of Art in Philadelphia and Sarah in Economics through a joint program with St. Andrews University in Scotland and William & Mary in Virginia.
Steve Ahlquist is an independent journalist who previously wrote for Uprise RI and Rhode Island’s Future. For more of his local reporting, visit his website.
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