Stratford is on the brink of a political turning point. Dr. David Chess, a 73‑year‑old physician and businessman, is about to become the town’s first Democratic mayor since 2009.
His incoming administration promises fiscal scrutiny and ambitious economic development. He’s also pushing for a renewed effort to unite a community that really does reflect the shifting political currents across Connecticut.
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Democrats Ride a Wave as Stratford Elects New Mayor
Chess’s victory wasn’t a fluke. He ran a disciplined, old‑fashioned, door‑to‑door campaign and personally knocked on more than 5,000 doors.
He tapped into a broader Democratic surge that’s been seen from Bridgeport to New Haven in the last election cycle. Voters in Stratford, long used to Republican leadership in Town Hall, clearly wanted a change.
His inauguration will take place at Stratford High School. Residents can attend in person or watch via live-stream.
That digital access fits with Chess’s focus on transparency and engagement. He’s talked about this a lot since election night.
Building Bridges in a Politically Divided Climate
Chess says he wants to govern for everyone in town, not just his party. He’s talked about lowering the temperature at Town Hall and bringing in voices from all sides.
He wants to focus on shared goals, not partisan fights. That message seems to hit home in a state where towns like Norwalk and Stamford are dealing with similar divisions, even locally.
Preparing to Govern: Meetings, Staffing, and Continuity
Since his win, Chess has been quietly but intensely preparing to govern. He’s met with town officials, department heads, union reps, and local advocacy groups to get a feel for how Stratford’s government actually works day to day.
That groundwork matters as he looks to make changes without messing up basic services. While he says the “vast majority” of current staff will stay, Chess is making key appointments that’ll help set the tone for his administration.
Key Appointment: Caryn Kaufman as Chief of Staff
Chess chose Caryn Kaufman as his chief of staff. She’ll coordinate policy, communications, and constituent services.
He’s also worked out a transition period with the outgoing chief administrative officer, so institutional knowledge won’t just vanish overnight. That’s a big deal, especially when other Connecticut communities like Hartford and Waterbury have had pretty rough transitions between administrations.
Fiscal Responsibility at the Core of the Chess Agenda
Despite the buzz around a new mayor and big development ideas, Chess keeps coming back to fiscal responsibility. A lot of Stratford households feel the pressure from rising costs—just like in Milford and Fairfield—so taxpayers are going to be watching closely.
Chess says he’ll take a hard look at municipal spending. Not with an axe, but with a scalpel.
Scrutinizing Overtime and Town Finances
One of his first moves will be a deep review of overtime pay across departments and a closer look at the town’s financial structure. Residents can expect:
He hopes that by tightening oversight on spending, the town can free up resources for capital projects and neighborhood improvements—without putting more strain on taxpayers.
Transforming Stratford’s Landscape: Development and the Arts
Chess’s economic vision goes way beyond basic municipal management. He sees Stratford as a town with a lot of untapped potential, sitting right along the coast between New Haven and Bridgeport.
It’s got strong transportation links and valuable waterfront property that’s been sitting underused for years. That’s just not right, is it?
Reimagining the Former Army Engine Plant
At the heart of his vision is the old Army Engine Plant property. Chess wants to turn the site into a vibrant mixed-use complex, with possibilities like:
If it happens, a project like this could really change Stratford’s economic future and put it on the map with coastal communities like Westport and Groton.
Preserving History: The John Benjamin House as an Arts Hub
Chess is also backing a plan to turn the historic John Benjamin House into a community arts center. The idea is to celebrate Stratford’s history and grow its cultural scene—a place for exhibits, performances, and classes.
He’s been clear that any improvements have to preserve the surrounding parkland. Public green space should stay open for families, seniors, and young people.
Public Safety and a National Search for a New Police Chief
Public safety is still a big issue in Stratford and across Connecticut, from Danbury to New Britain. After the sudden resignation of the town’s police chief, Chess announced plans for a national search to fill the role.
He says he wants a leader committed to community policing, transparency, and building trust with residents. Supporting officers in a tough profession matters too.
This search will be one of the first big tests for his new administration.
A Foundation for Stratford’s Future
David Chess is about to take the oath of office. Stratford feels like it’s standing at a real crossroads right now.
People will watch to see if his administration can balance fiscal discipline with those big development projects. Can they respect Stratford’s history but still welcome growth?
There’s also the tricky business of bridging the partisan divides that have only gotten sharper lately. It’s a tall order, honestly.
Here is the source article for this story: New Mayor David Chess aims to boost Stratford’s profile: ‘We are not an afterthought’
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