First Selectman - 2025 Candidate Comparison

Election Date: November 4, 2025

Seats Available: 1

Vote for: One candidate

Term Length: 2 years

Position Overview

The First Selectman serves as Weston's chief executive and administrative officer, leading the three-member Board of Selectmen. This position holds significant executive power and is responsible for town operations, budget management, and representing Weston in regional matters. The First Selectman chairs the Board of Selectmen and sets the town's strategic direction.

How to Vote

Voters will elect one First Selectman. This is a straightforward race with one position available.

Candidate Summary

For detailed source citations: See Samantha Nestor's profile

Race Status: UNOPPOSED

Important Note: Samantha Nestor is running unopposed for First Selectman. The Republican Party did not field a candidate for this position in 2025.

Detailed Candidate Profile

Samantha Nestor (Democratic - Incumbent)

Professional Background:

• Founder and Partner, Chrysanthemum Partners (2010-present) - full-service integrated marketing, creative, and brand development firm
• Previous roles: Marketing & Communications Director at New York Design Center, Special Projects Manager at Elle Decor, Special Projects Editor at Metropolitan Home Magazine
• Non-profit experience: The Frick Collection (instituted Young Fellows program, created corporate event program)
• Published author: "The Luxury Bathroom" (2008), "Living with Wine" (2009)

Education:

• BS in Communications and Art History, Cornell University (1988-1992)

Political Experience:

• First Selectwoman (2021-present): Appointed August 2, 2021 after Christopher Spaulding resigned; elected November 2023 with 1,791 votes (60%)
• Second Selectwoman (2018-2021): Appointed December 2018 to fill term of late Brian Gordon
• Board of Education (2017-2018): Elected 2017, resigned when appointed to Board of Selectmen
• Marketing and Communications Advisory Committee: Former Chair

Key Contributions:

• Led town through COVID-19 recovery period
• Launched charter review process (September 2025)
• Addressed community safety concerns regarding antisemitism (March 2025)
• Managed cell tower negotiations with T-Mobile
• Oversaw Weston Intermediate School being named Connecticut Blue Ribbon School (September 2025)

Campaign Platform ("Weston 2.0"):

1. Infrastructure: Road improvements, town facilities maintenance, strategic road improvement planning
2. Economic Development: Creative financing, supporting local business
3. Public Safety: Police/Fire/EMS expansion and support
4. Community: Engagement, transparency, responsive government
5. Major Projects: Town Green development, Library expansion, Sidewalk improvements

Leadership Philosophy:

• "Physical and virtual office door always open" - emphasizes accessibility
• Knocked on over 1,400 doors during initial campaign to understand resident concerns
• Focus on collaborative leadership and community engagement
• Leverages background in strategic communications and creative problem-solving

Controversies & Challenges:

• Four Corners Development (2025): Faced criticism from residents who felt she was "out of touch" with constituent concerns about apartment size requirements (96% of public comments were against proposed changes)
• T-Mobile Cell Tower Dispute (2025): Navigating negotiations with T-Mobile over shut down cell service
• Community Response: Some residents feel she pushes development initiatives contrary to majority opinion

Strengths:

• Executive leadership experience as incumbent
• Professional communications background
• Experience working with state and regional partners
• Track record of managing complex town issues
• Collaborative leadership style

Contact:

• Town Hall: (203) 222-2616
• Email: Available via First Selectwoman's Office

Context of Unopposed Race

The fact that Republicans chose not to field a candidate for First Selectman is significant:

1. Strategic Decision: The Republican Town Committee focused resources on other races, particularly the Board of Selectmen race where Lauren Traum is challenging Democratic incumbent Tony Pesco

2. Incumbent Advantage: Nestor's 60% victory margin in 2023 and her four-year track record (including service as Second Selectwoman) made her a incumbent

3. Recent Trend: This represents a shift from competitive First Selectman races in previous years

Questions for Voters to Consider

Even in an unopposed race, voters should consider:

1. Performance Review: Has Nestor effectively managed town operations over the past four years?

2. Strategic Vision: Do you support her "Weston 2.0" vision for town development and infrastructure?

3. Community Engagement: Has she been responsive to resident concerns and transparent in decision-making?

4. Development Approach: Are you comfortable with her approach to managing growth and development (particularly given the Four Corners controversy)?

5. Leadership Style: Does her collaborative, communications-focused approach align with what you want in town leadership?

6. Fiscal Management: Are you satisfied with town budget management and tax policy during her tenure?

Historical Context

Resources

Official Information

• Town Website: westonct.gov
• First Selectwoman's Office: Weston Town Hall, 56 Norfield Road, Weston, CT 06883
• Phone: (203) 222-2616

Candidate Information

• Full Profile: View Samantha Nestor's Profile
• Social Media: First Selectwoman Samantha Nestor Facebook page

Voting Information

• Election Date: November 4, 2025
• Early Voting: October 20 - November 2, 2025
• Sample Ballot: Available at westonct.gov and Town Clerk's office

League of Women Voters

• Website: lwvct.org
• Non-partisan voter information and candidate forums

Last Updated: October 15, 2025

Note: This comparison is based on publicly available information as of October 2025. Voters are encouraged to attend public forums, review town meeting minutes, and engage directly with candidates to make informed decisions.