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City Commissioner, City of Winchester

Vote for
4
Term
2 years
Candidates
8
Election
Nov 3, 2026

What this office does: The board of commissioners is the City of Winchester's legislative body; commissioners are elected citywide to two-year terms.

Nonpartisan; vote for up to four. Hannah Toole is printed on the sample ballot; the Secretary of State's list of candidate filings with the county clerk shows the filing as withdrawn.

CandidatesCompare by issue

Kenny Book

No party listed

The gist

  • Supports finishing the Seventh Street truck-route project
  • Supports bringing a grocery store to downtown Winchester
  • Proposes Depot Street restrooms in a restored railway car
More about Kenny
View sources (2)

  1. Supports finishing the Seventh Street truck-route project

    Book announces run for City Commissioner

    News coverage · The Winchester Sun · Nov 25, 2025 · winchestersun.com

    “I think we've got to get that heavy traffic off of Seventh Street and Magnolia [Street]”

  2. Supports bringing a grocery store to downtown Winchester

    Book announces run for City Commissioner

    News coverage · The Winchester Sun · Nov 25, 2025 · winchestersun.com

    “He also hopes to bring a grocery store to downtown Winchester.”

  3. Proposes Depot Street restrooms in a restored railway car

    Former city commissioner Book seeks another term

    News coverage · The Winchester Sun · May 8, 2026 · winchestersun.com

    “He wants to restore an old railway passenger car for the restrooms”

Ralph Harrison

No party listed

The gist

  • Supports more affordable housing in Winchester
  • Supports extending city limits to attract new factories
  • Supports providing more activities for children
More about Ralph
View sources (1)

  1. Supports more affordable housing in Winchester

    Harrison campaigns again with common-sense message

    News coverage · WinCity Voices · Apr 28, 2026 · wincityvoices.org

    “sup­port­ing afford­able hous­ing, extend­ing the city lim­its so that Winchester can have more new fac­to­ries”

  2. Supports extending city limits to attract new factories

    Harrison campaigns again with common-sense message

    News coverage · WinCity Voices · Apr 28, 2026 · wincityvoices.org

    “extend­ing the city lim­its so that Winchester can have more new fac­to­ries”

  3. Supports providing more activities for children

    Harrison campaigns again with common-sense message

    News coverage · WinCity Voices · Apr 28, 2026 · wincityvoices.org

    “and pro­vid­ing more things for chil­dren to do”

James Bowman

No party listed

The gist

  • Supports preparing new business owners, not just financial help
  • Supports developer incentives for affordable housing
  • Opposes cutting law enforcement positions
More about James
View sources (1)

  1. Supports preparing new business owners, not just financial help

    Bowman emphasizes business growth and housing

    News coverage · WinCity Voices · May 6, 2026 · wincityvoices.org

    “We need to focus on prepa­ra­tion, not just sup­port.”

  2. Supports developer incentives for affordable housing

    Bowman emphasizes business growth and housing

    News coverage · WinCity Voices · May 6, 2026 · wincityvoices.org

    “Work with devel­op­ers. Create incen­tives that make sense.”

  3. Opposes cutting law enforcement positions

    Bowman emphasizes business growth and housing

    News coverage · WinCity Voices · May 6, 2026 · wincityvoices.org

    “Cutting law enforce­ment posi­tions sends the wrong mes­sage.”

Tara Asbury

No party listed

The gist

No documented position found.

More about Tara

Jim Caldwell

No party listed

The gist

  • Supports roads, utilities and planning that keep pace with growth
  • Supports attracting businesses while supporting existing ones
  • Supports more transparency in city decision-making
  • Supported the city's one-year data center moratorium
More about Jim
View sources (2)

  1. Supports roads, utilities and planning that keep pace with growth

    Candidate Spotlight: Jim Caldwell

    News coverage · The Winchester Sun · Apr 17, 2026 · winchestersun.com

    “Winchester is growing, and we need to ensure our roads, utilities, and planning keep pace.”

  2. Supports attracting businesses while supporting existing ones

    Candidate Spotlight: Jim Caldwell

    News coverage · The Winchester Sun · Apr 17, 2026 · winchestersun.com

    “We want to attract businesses while supporting the ones already here.”

  3. Supports more transparency in city decision-making

    Candidate Spotlight: Jim Caldwell

    News coverage · The Winchester Sun · Apr 17, 2026 · winchestersun.com

    “People want transparency and to feel heard.”

  4. Supported the city's one-year data center moratorium

    Candidates speak during meeting on AI data centers and flock cameras

    News coverage · The Winchester Sun · Sep 25, 2026 · winchestersun.com

    “at least one-year moratorium that the current (city) Commission passed was a good idea”

Kitty W. Strode

No party listedIncumbent

The gist

  • Supports thoughtful, balanced growth that protects current residents
  • Supports beautification of neighborhoods, downtown and public spaces
  • Voted for a one-year moratorium on data centers
More about Kitty
View sources (2)

  1. Supports thoughtful, balanced growth that protects current residents

    Strode highlights experience, community commitment

    News coverage · WinCity Voices · May 6, 2026 · wincityvoices.org

    “Growth should be thought­ful and bal­anced, guid­ed by what is best for the peo­ple who already call Winchester home”

  2. Supports beautification of neighborhoods, downtown and public spaces

    Strode highlights experience, community commitment

    News coverage · WinCity Voices · May 6, 2026 · wincityvoices.org

    “When we take care of our city, we sup­port jobs, encour­age invest­ment, strength­en local busi­ness­es, and pro­tect the qual­i­ty of life”

  3. Voted for a one-year moratorium on data centers

    Winchester enacts one-year data center moratorium amid regional wave of restrictions

    News coverage · The Winchester Sun · Sep 2, 2026 · winchestersun.com

    “On roll call, Commissioners Chenault, Strode and Toole all voted yes.”

Hannah Toole

No party listedIncumbent

The gist

  • Supports finding new, sustainable sources of city revenue
  • Supports growing and sustaining the city's parks system
  • Supports merged city and county services
  • Voted for a one-year moratorium on data centers
More about Hannah
View sources (3)

  1. Supports finding new, sustainable sources of city revenue

    Candidate Spotlight: Hannah Toole

    News coverage · The Winchester Sun · May 12, 2026 · winchestersun.com

    “We need to cultivate more opportunistic, sustainable revenue sources.”

  2. Supports growing and sustaining the city's parks system

    Toole seeks third term focused on service

    News coverage · WinCity Voices · Apr 29, 2026 · wincityvoices.org

    “A strong parks sys­tem attracts res­i­dents, busi­ness­es, and vis­i­tors.”

  3. Supports merged city and county services

    Candidate Spotlight: Hannah Toole

    News coverage · The Winchester Sun · May 12, 2026 · winchestersun.com

    “I'd also like for the city and country to have merged services.”

  4. Voted for a one-year moratorium on data centers

    Winchester enacts one-year data center moratorium amid regional wave of restrictions

    News coverage · The Winchester Sun · Sep 2, 2026 · winchestersun.com

    “On roll call, Commissioners Chenault, Strode and Toole all voted yes.”

Joe Lee Chenault

No party listedIncumbent

The gist

  • Pledges more activities for Winchester and Clark County youth
  • Supports attracting more retail and food businesses
  • Supports more affordable housing in Winchester neighborhoods
  • Voted for a one-year moratorium on data centers
More about Joe
View sources (2)

  1. Pledges more activities for Winchester and Clark County youth

    Chenault focuses on listening and community service

    News coverage · WinCity Voices · May 1, 2026 · wincityvoices.org

    “his first pri­or­i­ty as a city com­mis­sion­er is to bring more activ­i­ties to Winchester for the town’s and coun­ty’s youth”

  2. Supports attracting more retail and food businesses

    Chenault focuses on listening and community service

    News coverage · WinCity Voices · May 1, 2026 · wincityvoices.org

    “He also wants to bring in more retail and food busi­ness­es”

  3. Supports more affordable housing in Winchester neighborhoods

    Chenault focuses on listening and community service

    News coverage · WinCity Voices · May 1, 2026 · wincityvoices.org

    “Chenault is also con­cerned about hous­ing afford­abil­i­ty”

  4. Voted for a one-year moratorium on data centers

    Winchester enacts one-year data center moratorium amid regional wave of restrictions

    News coverage · The Winchester Sun · Sep 2, 2026 · winchestersun.com

    “On roll call, Commissioners Chenault, Strode and Toole all voted yes.”

Challengers are listed first and incumbents last; otherwise candidates appear in ballot order. The Gist does not rank, rate or endorse candidates. Only positions backed by a cited source are shown; 7 issues covered in this race.