Think Big, Winnetka: Ten Issues That Will Shape the Village's Next 75 Years

Winnetka is one of the most fortunate communities in America. We have extraordinary schools, a beautiful lakefront, historic neighborhoods, and generations of civic leadership that built a village people across the country admire.

But here is the uncomfortable truth: great communities are not sustained by reputation alone. They require leadership that matches their potential. Right now, a growing number of residents believe something is off. Projects stall. Decisions lack transparency. Major financial commitments move forward without a broad public understanding.

And the sense that Winnetka should be doing better keeps surfacing in conversations across the village. Our Town Winnetka believes this moment calls for something simple but powerful: clarity about the issues that matter most, and we believe these 10 stand out as defining the future of Winnetka.

1. The Post Office Site

For nearly 18 years, development of the former post office site—one of the most visible parcels in the village—has remained stalled. And, again, our Village Leaders are in the midst of a process to assess what the highest and best use shall be. We all pass it, asking the same question: Why has nothing happened?

The site represents an enormous opportunity for creativity: ranging from a mixed-use development to public space to a combination of the two. All points to an opportunity for our community to re-image our future and create a West Elm vitality. Instead, it has become a symbol of indecision.

2. The Quality of Local Leadership

Many residents believe the Village Council has become too insular. Important decisions—from infrastructure spending to development policy—often appear disconnected from broader community input.

Great communities require leaders who bring expertise, independence, and accountability to public service.

3. The Future of the Winnetka Caucus System

For more than a century the Winnetka Caucus has shaped who governs the village.

But the process today raises questions. Participation is limited. Voting mechanisms feel outdated. And the candidates for caucus often lack the technical expertise needed to oversee complex modern government. A process designed for life in 1915 now must evolve to serve a community in 2026 and beyond.

4. Aging Infrastructure

Basic infrastructure fixes linger until they require massive repairs or reconfigurations:

• A pier closed for years awaiting repair
• Beaches affected by sewer contamination
• Stormwater systems that are more than a century old

Infrastructure is not glamorous, but when it fails the consequences affect everyone in our community.

5. The $100 Million Stormwater Question

Winnetka now faces a stormwater overhaul estimated at roughly $100 million. That kind of investment will shape the village's finances for decades. Residents deserve confidence that every alternative has been studied and every assumption challenged.

Large decisions require rigorous oversight.

6. Fiscal Stewardship

The village budget has climbed to more than $116 million, while fees and utility costs continue rising for homeowners.

Residents are asking a reasonable question: Are we getting the results we should expect for what we pay?

Fiscal discipline is not simply about budgets. It is about outcomes.

7. Downtown Vitality

Walk through Winnetka's commercial districts, and you will notice empty storefronts. See Issue #1 above. Meanwhile, nearby Wilmette has transformed its downtown into a lively destination filled with restaurants and shops and living options.

Based on its 2010 Village Master Plan, Wilmette stated a clear vision for its entire community, aligned its resources, and has become a beacon for a mixture of vitality, livability, and sense of community. In our opinion, it is a model worth investigating, applying, and adopting within our community.

The difference is not geography. It is policy and leadership.

8. Collaboration Between Local Institutions

The Village, Park District, and schools serve the same residents. Yet recent conflicts—particularly around zoning and permitting—have slowed projects and wasted taxpayer dollars.

Public institutions should collaborate, not compete.

9. Homeowner Property Rights

Over the past several years, headlines have been filled by the steep-slope ordinance governing lakefront development and it has triggered a very public, major litigation involving dozens of homeowners.

Regardless of where one stands on the policy, lawsuits of this magnitude signal deeper problems in how decisions are made. And it has cost The Village hundreds of thousands of dollars in litigation fees, as well as lost time for the Village Council and Staff focused on the issue. What's buried under all of this is a smart and prudent Village approach to get home improvement permitting done, the challenges to assemble multiple property PINS, and a consistent view of historic preservation across our community.

Winnetka homeowners deserve the ability to maintain, improve, and expand the value of homes with ease and support from its Village.

10. Winnetka's (Missing) Long-Term Energy Strategy

In an October 2, 2025 email newsletter, we outlined the challenges that we see regarding The Village's recent extension of its power contract with the Illinois Municipal Electric Agency (IMEA) through 2055.

At that time, our analysis of the extension -- inked 10 years before the existing contract ran out -- locked Winnetka into an agreement that does the following:

• Lasts until 2055
• Includes no fixed prices, rate protections, and no binding commitments to cut emissions
• Keeps the village tied to Prairie State and another coal facility in Kentucky
• Contains no early termination clause

We continue to believe the assertion that the 2055 energy contract is "expensive and outdated" -- and equally importantly -- Village Council needs to do its homework regarding alternatives in an energy landscape that is rapidly evolving and modernizing.

The Real Issue

These ten issues may appear distinct or unrelated. They are not. We believe they all point to the same underlying question:

How well is Winnetka governing itself?

Great communities do not avoid difficult conversations. They confront them early, openly, and honestly. Winnetka has the talent, the resources, and the civic pride to solve every issue listed above. What is required now is a renewed commitment to transparency, community engagement, expertise, and leadership that reflects the best of this remarkable community.

The next chapter of Winnetka's history should not be written by inertia. It should be written by residents who believe their community can do better—and who are willing to insist on it. Our past newsletters have focused on some of these issues, and future ones will continue to delve into these topics. Because at the end of the day, the principle is simple:

Winnetka Deserves Better.

Our Town Winnetka would like to hear from you and open a dialogue with our readers. Please click on the link here to submit your opinions to the page on our website shown below.

Founded in 2024 by Ed Harney and Ian Larkin,* Our Town Winnetka (OTW) was organized with a simple principle: We need to be more inclusive and transparent in our Winnetka Caucus and Government Process.

*Ian Larkin, given his 2025 WCC Chairmanship, has resigned from OTW.

Our Promise to You

Winnetka, simplified. With clarity, transparency, and a balanced point of view.