Democrats Hylton, Crosby vie for Chesterfield supervisor seat
TL;DR: Two Democrats are competing in an Aug. 4 special election to fill the rest of Jim Holland's term on the Chesterfield Board of Supervisors after his death last October.
Quick facts
- Who: Dr. LeQuan Hylton (interim supervisor, property manager) and Kathryn Crosby (consultant, health policy background)
- What: Special election for Dale District Supervisor seat on Chesterfield Board of Supervisors
- When: August 4, 2026
- Where: Dale District, Chesterfield County, Virginia
The story
Dr. LeQuan Hylton and Kathryn Crosby are running in a Democratic special election on August 4 to complete the unexpired term of Jim Holland, the longtime Dale District Supervisor who died October 14, 2025, following a battle with cancer. Holland had served five terms representing the district since 2008 and served as board chair in 2014, 2021, and 2024.
After Holland's death, the Chesterfield County Board of Supervisors appointed Hylton, a property management company owner and former member of the Planning Commission, to serve as interim supervisor. Hylton, a graduate of Manchester High School, holds degrees from Virginia State University, Averett University, and Virginia Commonwealth University (Ph.D. in Public Policy and Administration). He also serves as a lieutenant colonel in the U.S. Army Reserve and is a combat veteran of Afghanistan.
Crosby works as a consultant and brings experience in health policy and equity. She previously served as Health Equity Officer for Virginia Medicaid and was Virginia's first Chief Diversity, Equity, and Inclusion Officer at the Department of Health. If elected, she would be the first Black woman to serve on the Chesterfield County Board of Supervisors.
Both candidates are emphasizing affordability and infrastructure as central campaign issues. Hylton has called for more affordable housing in the Dale District and pointed to the lack of a homeless shelter in Chesterfield County as a gap in services. On data centers, he stressed that operators must fully pay for infrastructure costs, including power, water, and environmental mitigation.
Crosby is highlighting similar priorities, focusing on growth management, infrastructure expansion, school funding, and responsible development. She has raised concerns about the county's ability to keep pace with density approvals and residential growth, noting that new housing and apartment projects are approved without corresponding infrastructure expansion. Like Hylton, she expressed concerns about data center development, stating she is "very anti-irresponsible" regarding such projects and citing risks from noise pollution, water usage, and energy demands.
The winner will serve until December 31, 2027, but the race has an unusual timeline: whoever prevails will face reelection in 2027 when the entire Chesterfield Board of Supervisors is up for renewal, giving the elected supervisor only about 12 months before running again.
The Dale District has a population of approximately 72,465 residents within Chesterfield County's broader population of about 403,000.
Key players
- Dr. LeQuan M. Hylton: Interim Dale District Supervisor, property management company owner, former Planning Commission member
- Kathryn Crosby: Candidate for Dale District Supervisor, consultant, former Virginia health equity and diversity officer
- Jim Holland: Former five-term Dale District Supervisor (2008-2025), deceased October 14, 2025
- Chesterfield County Board of Supervisors: Appointing authority for interim supervisor
Key dates
- 2025-10-14: Jim Holland, five-term Dale District Supervisor, dies at age 73 following cancer battle
- 2025-11-12: Chesterfield Board of Supervisors appoints Dr. LeQuan Hylton as interim Dale District Supervisor
- 2026-07-07: VPM reports on the special election matchup
- 2026-08-04: Special election for Dale District Supervisor
- 2027-12-31: End of current unexpired term
The case for
Supporting either candidate centers on their respective professional backgrounds and priorities. Hylton brings five years of Planning Commission experience and local knowledge gained during his interim service; voters prioritizing continuity and business-sector expertise in local economic development may see value in his property management background. Crosby offers fresh perspective and a demonstrated track record in health equity and organizational change, which some voters may see as bringing new approaches to growth management and community engagement.
The case against
Hylton's limited elected experience and the challenge of being appointed versus elected could raise questions about mandate and fresh community input. Crosby, as a newcomer to local electoral politics without prior county board service, lacks direct governance experience in county-level decisions and may face a steeper learning curve on issues like infrastructure and zoning, where Planning Commission service has given Hylton specific exposure.
Why it matters: This special election determines who will guide the Dale District during a period of significant growth and infrastructure pressure in Chesterfield County. The winner will face immediate reelection in 2027, so the August vote effectively launches the larger 2027 supervisor race, with implications for school funding decisions, development priorities, and affordable housing policy across the county's eastern reaches.
Places
Development timeline
- 2025-10-14Jim Holland dies: Five-term Dale District Supervisor Jim Holland dies at age 73 following cancer battle [[source]](https://www.chesterfield.gov/m/newsflash/Home/Detail/6699)
- 2025-11-12Hylton appointed interim supervisor: Chesterfield Board of Supervisors appoints Dr. LeQuan Hylton as interim Dale District Supervisor [[source]](https://www.chesterfield.gov/m/NewsFlash/Home/Detail/6772)
- 2026-07-07Election coverage begins: VPM reports on special election matchup between Hylton and Crosby [[source]](https://www.vpm.org/elections/2026-07-07/chesterfield-supervisors-special-election-dale-district-hylton-crosby-holland)
- 2026-08-04Special election: Democratic primary special election for Dale District Supervisor seat [[source]](https://www.vpap.org/offices/chesterfield-county-supervisor-dale/election/12839/)
Related links
- Chesterfield County Board of Supervisors
- Virginia Board of Elections
- Chesterfield County Voter Registration
- Democratic Sample Ballot for Dale District Special Election
Read the original at VPM News →
Sources
- Democrats Hylton, Crosby vie to complete Chesterfield board term
- Dale District profile
- Dr. LeQuan M. Hylton Appointed Interim Dale District Supervisor
- Five-Term Dale District Supervisor Jim Holland Passes Following Hard-Fought Battle with Cancer
- Kathryn Crosby for Dale District Supervisor
- LeQuan Hylton campaign website