Editor’s note: Following is an opinion submitted by Westporter Louis E. D’Onofrio Jr.
Westport has long been emblematic of suburban affluence—defined by strong public schools, well-maintained infrastructure, and a high quality of life. But beneath the surface, a convergence of financial and demographic pressures is beginning to strain the town’s economic model. Over the next five years, Westport faces a growing risk of fiscal stagnation, rising inequality, and diminished economic resilience.
At the core of the issue is a steady and accelerating rise in municipal and school operating costs. The town’s annual budget has continued to expand, driven largely by structural expenses that are difficult to contain—health insurance, pension contributions, special education mandates, and capital maintenance. The 2025–26 school budget alone has grown to $150 million, reflecting a nearly five percent increase over the previous year, with no corresponding surge in revenue. Add to that a planned $100 million rebuild of Long Lots Elementary School, and it becomes clear that Westport is committing itself to a multi-year fiscal burden that will be difficult to manage without new revenue sources or spending offsets.
Yet revenue growth remains limited. Westport, like many affluent Connecticut towns, is heavily dependent on property taxes. While the mill rate has remained largely flat, the rising cost of operations may soon force tax hikes. But any increase would compound affordability challenges and could begin to erode the real estate market that underpins much of the town’s wealth. Westport’s fiscal stability is tied precariously to high property valuations—an inherently volatile base if demand softens or outmigration begins.
Affordability itself is already a growing concern. The town’s housing market continues to price out all but the wealthiest buyers. This dynamic has led to a slow erosion of economic diversity, as teachers, municipal workers, and young families find themselves unable to live where they work. As this trend continues, the town risks becoming less of a vibrant, multi-generational community and more of a static enclave for high-income earners. Such a shift has implications far beyond demographics; it challenges the town’s social fabric, local workforce availability, and long-term economic dynamism.
Compounding these pressures is the issue of infrastructure. Much of Westport’s public capital—from school buildings to recreational facilities—is aging. The large-scale replacement of Long Lots Elementary is not an isolated case but a reflection of long-deferred maintenance across town assets. As costs mount, leaders face a difficult balancing act: defer again and risk greater expense later, or invest now and accept the debt burden.
State-level pressures add further complexity. Westport remains subject to rising costs and mandates from Hartford—particularly in areas like special education and environmental regulation—without receiving meaningful increases in state aid. Healthcare inflation, insurance requirements, and compliance burdens all continue to climb, shrinking local discretionary budgets and limiting policy flexibility. In effect, the town is being squeezed from above and within.
Taken together, these challenges form a picture of a town at a fiscal crossroads. Westport is not in immediate crisis, but the current trajectory is unsustainable. Without structural reforms—whether through more progressive housing policy, long-term financial planning, or regional cooperation—the next five years could see the gradual unraveling of the town’s economic equilibrium.
I raised these concerns when I ran for both Representative Town Meeting and Second Selectman. I spoke openly about the long-term risks we were facing, from escalating fixed costs to declining affordability. But too often, those warnings fell on deaf ears.
Today, I believe that Independent candidate David Rosenwaks is the only one equipped to tackle these challenges head-on. He brings the clarity, independence, and long-term thinking that Westport needs at this critical juncture. The next few years will demand leadership that is both financially disciplined and unafraid to confront uncomfortable truths. I believe David is that leader.
Louis E. D’Onofrio Jr., DNP, MSN, FNP-C, PCCN
I think this is an excellent essay and I agree with almost all of it. You had me until your repeated endorsement of the former Democrat now running for office.. It lost its effect on me with your last paragraph,
I hardly think your candidate, or any candidate, is going to cure these ills in one or two terms. I will err on the side of the Democrat candidates this election, given not only the need to counter the anti-democratic sentiments from on high, but also the record of non achievement locally. Our GOP town administration, and especially the new GOP ticket, is largely responsible for the senseless spending.
ANYONE can build a magnificent school for $113 million; only the brightest and bravest can find a way to build a magnificent school for a far less burden on taxpayers.
Thank you, Toni, for taking the time to read my essay so closely and for sharing your thoughtful perspective. I truly value these kinds of healthy exchanges, and I’m grateful for your kind words about most of the piece.
I agree with you that Tooker, Marpe, Moore, and our GOP administrations have contributed significantly to the fiscal strains we’re now facing. But I also believe this is not just a partisan issue — both parties, through the Board of Education and RTM, have made spending decisions that created the housing, budget, and economic pressures we see today. Because of word limitations in the original letter, I wasn’t able to expand on that point, so I really appreciate the chance to do so here in the comments.
You’re right that no one candidate can “cure” these ills in one or two terms. For me, what makes David Rosenwaks compelling is that he brings an independent, outside perspective — one that I believe can help us break away from the pattern of “kick the can” and “blame the other side” that has too often defined our leadership. That said, I hold no ill will toward Kevin Christie or Don O’Day, and I wish either of them success if they are elected.
I know my article won’t sway those firmly rooted in their political loyalties, and that’s not my goal. My hope is simply to provide context for residents who may not know the history of spending decisions, and to encourage fiscal responsibility going forward.
Thank you again, Toni — your reminder about keeping perspective is an important one.
David blew into town 5 yrs ago with allegedly deep pockets yet I dont see him disclaiming a salary by working pro bono .He now strums the guitar and writes music. His one issue which promoted his entry into town politics involved busing kids from Long Lots to Kings Hwy ,a school which predates every other school and frankly resembles an inner city school. Parents must park along the Post Rd to pick up their children yet no one calls for its destruction
In my opinion, we need to apply the brakes to needless spending. We don’t need a new Long Lots School . We don’t need sidewalks encroaching on both sides of every road making the driving lanes so narrow if a car goes into a skid ,it will incur a head on collision . We don’t need to be the Gold Coast leader in affordable housing welcoming those born ,raised and working in other towns to live here.When affordable apartments are built ,we should prioritize tossing the keys to our own residents both young and old.
As someone born and raised in Westport,having left only to attend college and law school ,I don’t feel guilty at having a privileged upbringing. I saw my parents work hard to achieve their goals,defer gratification to save for their children’s education. I disagree with those who proclaim everyone has a God given right to live here,attend school here and its your and my responsibility to fulfill their desires.
I’m a 30 something Conservative and I’ve yet to see a candidate represent my values. As far as I can see ,the race for First Selectman candidates are indistinguishable.
If we are a town under economic pressure, why are each of the three candidates running to lead us towards economic prosperity themselves unemployed?
The Democratic candidate is a 40 something stay at home dad
The Republican candidate is retired, a lifelong Democrat who was beat out by the aforementioned.
The Independent is another 40 something retired guitar strumming nice guy whose wife is probably saying get a job.
Point is, none of these guys inspire confidence in leading Westport in the face of economic challenges.
They’re more like 3 decent guys standing in line at the unemployment office.
The Independent candidate is a nice guy who doesn’t want his child bused to Kings Hwy.