Editor’s note: Following is an opinion submitted by Westport resident and DTC member Anil Nair.
Kevin Christie brings a rich and varied background, along with personal qualities that make him well-suited to serve as Westport’s First Selectman.
His service on the Board of Education, his career in finance leading teams responsible for $40 billion in strategic and financial transactions, and his record of community volunteerism all underscore his ability to lead. He also pairs this expertise with experience navigating Westport’s own long-term capital forecast, demonstrating a practical approach to financial stewardship.
Equally important are the “soft power” traits that define his style. Kevin values listening as the foundation of good governance. At a time when differences often divide us, his calm demeanor and experience bridging opposing perspectives offer the conflict transformation skills Westport needs. He also makes himself accessible through informal “Coffee & Conversation” sessions, creating space for residents to raise concerns directly.
As Chair of the Board of Education’s Policy Committee, he has led with patience and steadiness on sensitive issues such as student discipline, suicide prevention, and non-discrimination. He has shown ethics by recusing himself when personal ties could create a conflict of interest and has communicated with a focus on solutions rather than conflict. In discussions on bias and banned books, his zero-tolerance stance toward hate echoed student voices, reflecting both his concern for school climate and his openness to listening. His leadership has also emphasized fair process, including proposals for impartial hearing boards to ensure appeals are handled with transparency and consistency.
Anil Nair
Member, Westport Democratic Town Committee
District 8
Hello Mr. Nair.
I appreciate your letter.
While Kevin Christie’s background in education and finance is certainly commendable, it overlooks the broader leadership qualities required to guide Westport through its current and future challenges. David Rosenwaks brings a more comprehensive skill set, one that balances fiscal responsibility with a deep understanding of the diverse needs of our town.. His professional expertise in managing large scale projects and municipal budgets positions him as someone capable of making the tough, long-term decisions that will keep Westport financially secure while also preserving the quality of life for its residents.
Christie’s focus on “listening first” is undoubtedly an important quality for a leader, but it must be paired with the ability to take decisive action. Rosenwaks not only engages in meaningful dialogue with the community but also demonstrates a track record of translating that feedback into tangible solutions. His leadership style is characterized by a mix of inclusivity and bold decision-making, ensuring that Westport’s most pressing issues—whether financial, developmental, or social—are addressed with both thoughtful consideration and effective action. While Christie may be more focused on consensus-building, Rosenwaks knows that sometimes leadership requires taking difficult stands for the long-term benefit of the town.
Moreover, Rosenwaks’ commitment to transparency and fairness extends beyond personal ethics; it reflects a comprehensive vision for Westport’s growth. Where Christie’s work has primarily been within the educational sphere, Rosenwaks brings a more holistic approach, with proven experience in both governance and community engagement. His ability to balance economic development, infrastructure improvement, and social responsibility makes him uniquely suited to tackle the complex issues Westport faces today.
In contrast to Christie’s emphasis on maintaining the status quo, Rosenwaks offers a forward-thinking approach to governance. He’s committed to ensuring that Westport doesn’t just navigate its current challenges but thrives in the future, all while preserving the town’s core values. Rosenwaks possesses the clarity, conviction, and experience necessary to lead our town through a period of transition, making him the ideal choice for First Selectman.
Let’s get down to specifics not vague generalizations. David Rosenwaks has been on the RTM for precisely one year. Can you point to a single legislative accomplishment, a single time he has stood up at the podium, taken the mic, expressed an opinion, proposed a resolution ? The general consensus is that he has been a classic backbencher, unwilling or unable to step forward. That’s fine but now he wants to lead the Town. Let’s get serious
Hello Evan, I understand your point about wanting to see a record of legislative accomplishments, but I think it’s worth clarifying how service on the RTM is often misunderstood. Unlike higher-profile legislative bodies, the RTM does not function around headline-making speeches or grandstanding at the mic. Much of its most impactful work happens in committee, through careful review of budgets, contracts, and policies—work that rarely makes the spotlight but is essential to effective governance.
In David Rosenwaks’ case, his contributions on the RTM reflect exactly that kind of substantive engagement. He has built a reputation for doing the homework, asking the right questions, and pressing for fiscal discipline where needed. Just because he hasn’t sought out the spotlight does not mean he hasn’t been doing the work. In fact, his professional experience managing multimillion-dollar projects in the private sector has given him the expertise to weigh in where it matters most: ensuring Westport’s finances remain sound and that our investments in infrastructure and services are both sustainable and strategic.
Leadership is not measured only by how often someone takes the microphone, but by the quality of their judgment and their ability to act decisively when it counts. Rosenwaks’ candidacy is about applying that blend of pragmatism and vision on a broader scale—moving beyond RTM committee rooms to the town’s highest executive office. His forward-looking approach, combined with a track record of responsibility and fairness, makes him well suited to lead Westport through the next chapter.
And while I understand that many within the Democratic Party may feel it is important to close ranks and keep voters loyal to their own candidate, local government isn’t about toeing a national party line—it’s about what is best for Westport. The challenges our town faces demand more than party loyalty; they demand the right person with the right skills. In this race, that person is David Rosenwaks. Sometimes leadership means stepping outside party labels to choose the candidate who can actually deliver.
Dr Louis Donofrio makes sweeping claims about David Rosenwaks’ “professional expertise in managing large scale projects and municipal budgets.” However, these assertions deserve scrutiny.
In Rosenwaks’ own words during his recent interview, he describes his background as a banker, asset management firm owner, entertainer, stay-at-home dad, and investor. Conspicuously absent from his self-description is any mention of the large-scale project management or municipal budget experience the letter writer claims he possesses.
I invite the letter writer—and Mr. Rosenwaks himself—to provide specific examples of:
Which large-scale projects he has managed
What municipal budgets he has overseen
When and where this experience was gained
While Mr. Rosenwaks was generally well-regarded within the town Democratic party for his pleasant demeanor, concerns about his limited experience and political maturity led many to view him as someone who could benefit from additional seasoning in a board position or continued RTM participation before seeking executive leadership. His decision to abandon the party that supported him raises additional questions about loyalty and commitment to collaborative governance.
Westport voters deserve facts, not fabricated credentials. Leadership experience matters, but it must be real, verifiable, and relevant to the challenges our town faces.
In contrast, Kevin Christie brings both documented municipal experience from the Board of Education Policy Committee and substantial real-world leadership credentials. Before transitioning to public service, Kevin spent over 15 years in finance, investment banking, and corporate strategy at IBM, Merrill Lynch, and The Madison Square Garden Company. He advised CEOs and boards, led cross-functional teams, and executed over $40 billion in strategic and financial transactions—including high-profile deals like MSG’s acquisition of the Tribeca Film Festival. He draws on that same strategic mindset, financial acumen, and proven execution to guide his work in town government.
This is the difference between actual experience managing complex, high-stakes projects and unsubstantiated claims.
Voters should demand specifics, not generalities, when evaluating candidates’ qualifications for leading our town.
Peter Propp
Mr. Propp,
I appreciate your engagement in this important discussion, but I believe your critique of David Rosenwaks’ qualifications misses the mark. You dismiss his professional and civic experience by narrowing the definition of what “counts” as leadership. To suggest that his record lacks weight because he does not frame it in the precise language of “municipal budgets” is disingenuous. Managing multimillion-dollar portfolios, leading financial initiatives, and overseeing complex investments—as Rosenwaks has done—requires exactly the type of fiscal oversight, strategic thinking, and project management that translate directly to municipal leadership. These skills are no less relevant simply because they originated in the private sector.
You also minimize his work on the RTM by framing it as lightweight or insufficient. The reality is that the RTM is not designed for headline speeches or constant public grandstanding(as I wrote about previously); its most critical work happens in committee rooms, through careful deliberation, fiscal review, and policymaking. Rosenwaks’ reputation on the RTM reflects precisely that kind of substantive engagement—asking tough questions, pressing for fiscal discipline, and engaging consistently on issues that matter. That is leadership in practice, even if it doesn’t result in attention-grabbing soundbites.
Your suggestion that his decision to leave the Democratic Party reflects disloyalty or immaturity also oversimplifies the issue. Westport does not face partisan national debates; it faces challenges of budgeting, infrastructure, education, and sustainability. Rosenwaks stepped outside party lines not out of disloyalty but out of conviction that local leadership must put Westport’s needs above rigid party loyalty. That kind of independence should be respected, not criticized.
I recognize that Kevin Christie has an impressive professional background, but success in corporate mergers and billion-dollar deals does not automatically mean success in local governance. Town leadership requires not just financial skills, but also accessibility, transparency, and accountability to neighbors. Rosenwaks brings precisely this balance—professional expertise grounded in civic service. The choice before voters is not between experience and inexperience, but between two different types of experience. It will be up to the community to decide which is best suited to the needs of Westport.
Finally, your demand for “specifics” overlooks a larger truth: leadership is not simply a list of deals closed or transactions executed. It is about judgment, responsibility, and vision. Rosenwaks has demonstrated fiscal rigor, thoughtful engagement, and independence of mind. Westport deserves more than partisan framing and resume comparisons. What Rosenwaks offers is a combination of private sector expertise, public service, and community focus that makes him uniquely qualified to guide Westport forward.
Respectfully,
I agree that voters should demand specifics, not generalities, when evaluating qualifications for leading our town.
“Which large-scale projects he has managed?”
As chair of the Coleytown Middle School Building Committee, he lead a whole-of-town response, during Covid, to remediate the school of mold. The $32 million project systematically addressed water infiltration and poor indoor air quality to create a healthy and modern learning environment for Westport’s middle schoolers. He was noted for his transparent communication, providing regular, honest updates on the project’s progress to the BoE, BoF, RTM, and school community.
As a member of the Long Lots Building Committee Member, he was instrumental in obtaining the unanimous approval of the town’s governing bodies (BoE, BoF, P&Z, and RTM) for the $100 million project to replace Long Lots Elementary School. His work on the committee continues as the project now enters the building stage.
“What municipal budgets he has overseen?”
As chair of the Board of Education for four years, he oversaw Westport’s largest budget. He skillfully managed the budget process throughout his time as chair, including during the Great Recession, where he advocated for the continued support of our schools during times of financial uncertainty.
As a member of the Coleytown Middle and Long Lots building committees, he oversaw the budgeting process for those large, complex investments in our town.
As a current member of the RTM, including the Finance Committee, he provides oversight of Westport’s town and education budgets.
“When and where this experience was gained?”
He spent 35+ years with Citi, where he gained substantial real world financial and management experience serving as Chief Financial Officer and Chief Administrative Officer for the Citi mortgage business. He plans to continue to apply his private sector experience to support the town he has called home for more than 30 years.
The “he” here is neither Kevin Christie nor David Rosenwaks – it is Don O’Day. The right experience does matter.
Donny,
I appreciate your detailed presentation of Don O’Day’s long record of service—there is no question that he has contributed meaningfully to Westport. But I think your response inadvertently underscores my central point: our community should not reduce the question of leadership to a competition of resumes, nor should we suggest that only one kind of background produces effective leadership.
David Rosenwaks brings a different but no less valuable set of experiences. In the private sector, he has managed multimillion-dollar portfolios and executed complex financial strategies—work requiring the same skills of risk assessment, long-range planning, and disciplined budgeting that municipal leaders must apply. His professional path may not use the exact labels of “municipal budget” or “school building committee,” but it unquestionably reflects the ability to steward large-scale resources responsibly.
On the RTM, David has already shown his commitment to transparency, fiscal discipline, and independence of thought. He has asked the difficult questions, pressed for accountability, and engaged substantively in the committee work where real decisions are shaped. His independence from rigid party lines signals not a lack of loyalty but a loyalty to Westport first—something we should value in an era when local governance is too often clouded by national partisanship.
It’s important to recognize that success in town leadership requires more than just experience overseeing construction projects or budgets. It also demands accessibility to neighbors, responsiveness to a broad range of community concerns, and the capacity to think beyond the mechanics of administration toward the vision of what kind of town we want to build. David Rosenwaks offers that blend: financial expertise, public service, and a forward-looking independence that places Westport’s interests above politics.
We can acknowledge the accomplishments of those like Don O’Day without dismissing the strengths that Rosenwaks brings. The real choice before voters is not about who can list the most bullet points under “municipal service,” but about who has the judgment, independence, and vision to lead Westport into the future. On that measure, David Rosenwaks is well prepared to serve.
Respectfully,
Dr. Louis D’Onofrio
Has Kevin Christie yet explained his recusal on the coaching matter to any detailed degree?
This was less a show of “ethics” and more a case of running for cover to avoid being held accountable for a vote. Not exactly a profile in courage. While he would be a marginally better option than Don O’Day, who seems to have embraced the party of MAGA because he’s angry local Democrats didn’t want him as First Selectman.
When you look at the slate for First Selectman, you have two former DTC members who represent cronyism and little more. Think about it, in a town that is predominantly progressive, we have had twelve years of a Republican controlled BOS, including four years of incompetence from the current administration. And why did Tooker squeak through in the last race? Because Jon Steinberg’s campaign was kneecapped by, you guessed in, a member of the DTC. This year, DTC was so tone deaf with their BOE nominees that they have already pulled one of their candidates, because there are far more competent Democrats who petitioned their way on to the ballot.
Sure, while David Rosenwaks may be relatively new to Westport politics, he won’t but beholden to the same establishment incompetents that make deals with one another and then try to shove their decisions down the throats of the voters (see the Community Garden mess, the Hamlet mess, the downtown parking mess, the coaching mess, etc.).
It is essential that Westport kicks to the curb the candidates of entitled establishment, that want what they want and have little interest in the opinions of the voters. Reject Christie and O’Day. Support a real change presented by David Rosenwaks.
Dr. Donofrio praises David Rosenwaks for “asking tough questions” and “engaging consistently” on the RTM, but this doesn’t match the reality I witnessed as a fellow RTM member.
David was an exceptional campaigner who knocked on 700 doors to become a top vote getter in his district. He supposedly ran on issues like the controversial Hamlet rezoning vote, the Long Lots community garden controversy, and restoring public petition rights at the RTM.
Yet once he was elected, David never once went to the podium to speak on any of these issues. Never. When pressed about his silence, he claimed that “as a new guy” he was “not to supposed say anything”. Other RTM members, both returning incumbents and newly arrived, see things differently, and routinely speak up on behalf of their constituents.
Dr. Donofrio suggests the RTM’s “most critical work happens in committee rooms” but what good is private deliberation if you won’t stand up publicly for the principles that got you elected in the first place? Elected officials who take a position publicly risk encountering a barrage of criticisms, but that comes with the territory.
If Mr. Rosenwaks couldn’t find his voice as one of 36 RTM members on issues he claimed to care deeply about during the campaign, how can we possibly expect him to lead as our town’s chief executive?
Ms. Johnson, thank you for sharing your perspective. I respect your service on the RTM and the experiences that shape your view, but I’d like to offer a different way of looking at David Rosenwaks’ record.
You suggest that effectiveness on the RTM is measured largely by how often someone takes the microphone. I would gently push back on that idea. The RTM is not designed around speeches or floor debates—it’s a body where much of the essential work takes place in committees, in financial oversight, and in careful review of contracts and proposals. Many of the RTM’s most respected members over the years have not been frequent speakers, but have been valued for the seriousness with which they studied the issues and their willingness to do the hard, less-visible work.
David has taken that approach. He does his homework, engages with colleagues and constituents, and presses for fiscal responsibility. Not everyone leads by volume or visibility; some lead through diligence and sound judgment.
As for campaign commitments, I think it’s worth remembering that leadership is not only about speaking out in public forums, but also about listening carefully, weighing different perspectives, and then acting responsibly. David has continued to engage with residents on the issues he campaigned on, and his measured style reflects a belief that thoughtful governance often requires listening first before stepping into the spotlight.
I also want to acknowledge that every RTM member brings a different style to the role. Some are more vocal and confrontational, others more measured and consensus-driven. Both approaches have their place, but they can also come with trade-offs. Where one style may attract attention, another may foster collaboration. David’s independence, steady temperament, and fiscal focus are qualities that I believe will serve Westport well as he seeks to lead not just in committee rooms but at the town’s highest executive level.
At a moment when our community faces complex challenges, I believe we should value a leader who prioritizes substance over soundbites and judgment over performance. In my view, David Rosenwaks embodies exactly that.
“Don O’Day’s leadership “experience” noted by his son (above) is tainted with deception, disloyalty, and self-agrandisement. It’s the Republican way.
Healing starts at home, yes in our local town elected offices. Yes national politics plays a role locally! Anyone who says it doesn’t is not being honest.
The plan to infiltrate every branch of government
T at every level with GOP sycophants is real. A return to self governance starts with every vote cast this November. Vote Democrat. .
I am honestly in shock that I feel compelled to write a defense of a simple, human gesture: Donny O’Day supporting his father. That act — the kind of support we expect in families across town — has been twisted into a political cudgel, and that troubles me deeply.
Donny was not staging a partisan provocation; he was standing by his family. In a healthy community we should be able to acknowledge that without turning it into a declaration of fealty to a national movement. Painting every local act with the broad brush of national politics corrodes our civic life and makes it harder for neighbors to treat one another with basic respect.
We must reject the habit of pinning parties and people against each other. That reflex — to demonize opponents and reduce complex neighbors to a single partisan label — fuels the flames of anger and division. In recent years we’ve seen how quickly rhetoric can escalate into real-world violence and even deadly attacks. Westport is too small, and our bonds are too important, to let that happen here.
Local governance should be about service, competence, and mutual respect — not score-keeping or character assassination. We are neighbors and friends first; our work together is what keeps this town functioning. Insulting and vilifying those we disagree with at a local level has no place in a community that depends on collaboration and trust.
Supporting liberty means protecting the right of people to participate in civic life, to support their families, and to express their values without being presumptively labeled as enemies. It also means defending the dignity of our neighbors when disagreement arises, and insisting that our public debate remain civil, fact-focused, and rooted in the common good.
Let’s steer Westport back toward constructive conversation. If we want better outcomes, we must model better behavior: listen more, vilify less, and work together on the issues that matter — our schools, our budget, our public safety, and the quality of life we all share.
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Thank you.
Doug Weber
Westport Journal