2025 Weston Municipal Election - Candidate Comparison Index

Election Date: Tuesday, November 4, 2025

Early Voting: October 20 - November 2, 2025

Location: Weston Middle School Gymnasium

Quick Navigation

Jump directly to position comparisons:

1. First Selectman - 1 seat, Uncontested
2. Board of Selectmen - 2 seats, Contested
3. Board of Finance - 4 full-term + 1 vacancy (5 seats)
4. Board of Education - 3 seats, Contested
5. Board of Assessment Appeals - 2 seats, Contested
6. Planning & Zoning Commission - 3 seats, Contested
7. Zoning Board of Appeals - 2 regular + 2 alternate seats
8. Board of Police Commissioners - 4 seats, Balanced

Election Overview

Total Candidates: 24 Total Positions: 9 boards/commissions Total Seats: 18 individual positions

Ballot Structure

The ballot is organized by position, with Democratic candidates in Column A, Republican candidates in Column B, and write-in options in Column C.

Important: Different positions have different voting rules:

• Some positions: "Vote for One"
• Some positions: "Vote for Up to Two/Three/Four"

Read the ballot instructions carefully for each position.

Position Comparisons

First Selectman

Vote for One | 2-Year Term | Uncontested

View Detailed Comparison →

Key Points:

• Incumbent First Selectwoman running uncontested
• Assumed office August 2021, elected 2023 with 60% of vote
• Republicans chose not to field a candidate
• Focus: Infrastructure, economic development, public safety, community

Board of Selectmen

Vote for Up to Two | 2-Year Term | CONTESTED

View Detailed Comparison →

Key Points:

• Incumbent vs challenger race
• Pesco: 64% vote in 2023, extensive town experience
• Traum: Defeated incumbent Republican in caucus, currently suing town over sidewalks
• Major issue: Sidewalk project lawsuit adds complexity to race

Board of Finance

Vote for Up to Four (Full Term) + Vote for One (Vacancy) | 4-Year Terms | CONTESTED

Full Term (4-Year) - Vote for Up to Four

Vacancy (2-Year) - Vote for One

View Detailed Comparison →

Key Points:

• Complex race: 1 Democrat vs 3 Republicans for full term
• All Republicans are recent appointees
• Strong financial credentials across all candidates
• Vacancy race unopposed (Gershburg running to complete term)
• Strategic voting: Voters can select up to 4 candidates

Board of Education

Vote for Up to Three | 4-Year Term | CONTESTED

View Detailed Comparison →

Key Points:

• 3 highly credentialed Democratic educators vs 1 Republican with limited public information
• Democrats bring 70+ combined years education experience
• Low's role as current Acting Superintendent creates unique dynamics
• Significant experience gap between Democratic and Republican candidates
• Voters select 3 out of 4 candidates

Board of Assessment Appeals

Vote for One | 4-Year Term | CONTESTED

View Detailed Comparison →

Key Points:

• Incumbent vs challenger
• Kendall: Current Vice Chair, professional technical director
• Zhang: Appears on official ballot but no public information found
• Technical board with quasi-judicial responsibilities
• ⚠️ Note: Unable to verify Zhang's candidacy through multiple sources

Planning & Zoning Commission

Vote for Up to Three | 4-Year Term | CONTESTED

View Detailed Comparison →

Key Points:

• 2 Democratic incumbents vs 1 Republican challenger
• Loucas: Only licensed architect on P&Z, sustainable design specialist
• Stires-Korsh: 12+ years on P&Z, legal expertise in land use
• DeWilder: First-time candidate, tech leadership background
• Complementary Democratic expertise (architecture + law) vs tech management

Zoning Board of Appeals

Regular: Vote for Up to Two | Alternate: Vote for Up to Two | 4-Year Terms

Regular Members

Alternate Members

View Detailed Comparison →

Key Points:

• Regular: Limited info on Ruggiero vs well-documented Bergman
• Bergman: Nearly 20 years real estate law, highly relevant expertise
• Wolf: Unopposed for alternate, brings practical construction knowledge
• Technical board requiring understanding of zoning regulations

Board of Police Commissioners

Vote for Up to Four | 4-Year Term | BALANCED

View Detailed Comparison →

Key Points:

• Perfect balance: 2 Democrats + 2 Republicans for 4 seats
• Ezzes: Extensive town governance experience
• Brendsel: Military and banking background, appointed Dec 2024
• Significant information gaps for Dembishack and Kozlowsky
• Possible law enforcement experience (Kozlowsky) not confirmed

Voting Information

Early Voting

• Dates: October 20 - November 2, 2025
• Location: Weston Town Hall Meeting Room
• Hours: 10:00 AM - 6:00 PM
• Extended Hours: October 29 & 30

Election Day

• Date: Tuesday, November 4, 2025
• Location: Weston Middle School Gymnasium
• Hours: 6:00 AM - 8:00 PM

Important Notes

• Connecticut has same-day voter registration
• Bring valid ID if registering on Election Day
• Check your voter registration status before Election Day
• Absentee ballots available for eligible voters

Key Themes Across Races

1. Incumbency Advantage

Most incumbents have detailed public records and name recognition, while many challengers have limited publicly available information.

2. Information Asymmetry

Significant gaps in public information for several candidates:

• Jason Lee (Board of Education)
• Lisa Zhang (Board of Assessment Appeals - unconfirmed)
• Robert DeWilder (Planning & Zoning)
• Richard Ruggiero (Zoning Board of Appeals)
• John Dembishack (Police Commission)
• Robert Kozlowsky (Police Commission - possible LEO background unconfirmed)

3. Experience vs. Fresh Perspectives

Many races feature experienced incumbents vs candidates bringing different professional expertise.

4. Party Balance Opportunities

Several multi-seat races allow voters to achieve balanced party representation by voting across party lines.

5. Professional Qualifications

Most candidates bring relevant professional experience:

• Finance board: CPAs, entrepreneurs, attorneys, finance professionals
• Education board: Educators, education attorneys, administrators
• Planning & Zoning: Architect, attorney, tech executive
• Assessment Appeals: Technical director
• Police Commission: Military, finance, possible law enforcement

Strategic Voting Considerations

Multi-Seat Races

When voting for positions with multiple seats (Board of Finance, Board of Education, Planning & Zoning, Police Commission):

1. You don't have to use all your votes - Can vote for fewer candidates than seats available
2. Can vote across party lines - Mix Democrats and Republicans
3. Consider balanced representation - Some voters prefer diversity of perspectives
4. Consider complementary skills - Multiple candidates can bring different expertise

Unopposed Races

• First Selectman: Samantha Nestor (only candidate)
• Board of Finance Vacancy: Daniel Gershburg (only candidate)
• ZBA Alternate: Richard Wolf (only Republican candidate)

Even in unopposed races, you can:

• Vote for the candidate
• Skip the race
• Write in another name

Questions to Consider

Before voting, consider asking yourself:

For All Positions

1. Does the candidate have relevant professional experience?
2. What is their track record of community involvement?
3. Do they understand the specific responsibilities of this position?
4. Have they articulated clear positions on key issues?
5. How accessible is information about their qualifications?

For Incumbent Candidates

6. What have they accomplished in their current term?
7. Have they been accessible and responsive to residents?
8. Do their priorities align with community needs?

For Challenger Candidates

9. Why are they running for this specific position?
10. What new perspectives or skills do they bring?
11. Are they prepared for the time commitment and responsibilities?

Resources

Official Information

• Town Clerk: (203) 222-2616
• Registrar of Voters: westonct.gov/registrar-of-voters
• Official Sample Ballot: CT Secretary of State

Voter Resources

• League of Women Voters Weston: lwvwestonct.org
• VOTE411 Voter Guide: vote411.org
• Weston Democrats: weston-democrats.org
• Weston Republican Town Committee: Information via town website

News Coverage

• Weston Today: westontoday.news
• Patch - Weston: patch.com/connecticut/weston-ct

Complete Candidate Profiles

• All Individual Profiles: See respective position folders
• Master Candidate List: candidates.md
• Structured Election Data: election-info.json

About This Guide

This comprehensive comparison guide was created to help Weston residents make informed voting decisions in the November 4, 2025 municipal election.

Methodology:

• Information compiled from official town sources
• News coverage from Weston Today, Patch, and other outlets
• Professional profiles and public records
• Candidate statements and campaign materials
• Board meeting minutes and public documents

Limitations:

• Some candidates have limited publicly available information
• Campaign platforms may evolve closer to Election Day
• Not all candidates provided detailed policy positions
• Some candidate backgrounds require verification

Updates: This guide reflects information available as of October 15, 2025. Voters should:

• Attend candidate forums hosted by League of Women Voters
• Review candidate statements as they become available
• Contact candidates directly with questions
• Check for updated information closer to Election Day

Get Involved

Attend Candidate Forums

Watch for announcements from:

• League of Women Voters Weston
• Weston Today
• Town website and social media

Contact Candidates

Many candidates can be reached through:

• Town board email addresses (for incumbents)
• Party town committees
• Campaign websites and social media
• Public forums and meetings

Stay Informed

• Follow Weston Today for election coverage
• Check the League of Women Voters Weston website
• Monitor town website for official announcements
• Attend Board of Selectmen meetings for current issues

Remember: Your vote matters in local elections! These boards and commissions make decisions that directly affect your daily life, from education to taxes to land use. Take the time to research candidates and vote informed.

Election Day: Tuesday, November 4, 2025

Last Updated: October 15, 2025 Compiled by: Weston AI Civic Engagement Project