Leesburg Town Attorney Chris Spera Announces Retirement

The town council has begun the search for a new attorney after Chris Spera signaled his plan to step down early next year.

Updated on Oct. 29, 2026 in Remote Work

Bold flat-color editorial illustration of a stylized municipal clock tower, symbolizing stability in Leesburg city government. — Leesburg Town Attorney Chris Spera announced his retirement, effective early next year, following a six-year tenure that included managing key local developments. AI Illustration. Upload story photo >

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Leesburg Town Attorney Chris Spera announced his retirement, concluding a six-year tenure in the role. Spera cites a desire to step away after a 40-year career in the public and private sectors.

Why it matters

Spera played a key role in town governance, including leading negotiations for the 2025 annexation of the Compass Creek development. His departure marks the latest transition among senior town leadership in Leesburg.

Spera served as Leesburg Town Attorney for six years, adding to a career spanning four decades. His departure follows the recent retirements of Town Manager Kaj Dentler and Deputy Director of Community Development Brian Boucher.

The players

Chris Spera

He is the outgoing Leesburg Town Attorney who previously worked for the City of Alexandria and the Old Dominion Transportation Group.

Leesburg Town Council

This is the legislative body responsible for hiring the town attorney and overseeing the town's recruitment processes.

Kaj Dentler

He is the former Leesburg Town Manager who concluded his service to the town in September 2026.

Rich Williams

He is the outgoing Director of the Parks and Recreation Department who has served the town for 26 years.

Brian Boucher

He is the retired Deputy Director of Community Development who spent 31 years in his tenure with the town.

The details

The recruitment process for a new town attorney is now underway, with the Leesburg Town Council overseeing the selection. During his time in Leesburg, Spera handled significant legal projects including the 2025 annexation of the Compass Creek development.

Spera began his service as Leesburg Town Attorney in 2020.
The annexation of the Compass Creek development occurred in 2025.
Kaj Dentler retired as Leesburg Town Manager in September 2026.
Brian Boucher retired as Deputy Director of Community Development in summer 2026.
Rich Williams will retire as Parks and Recreation Department Director effective January 15, 2027.

Market Landscape

Spera's exit follows a broader trend of administrative turnover within Leesburg, including the departures of the town manager and community development leadership. These shifts in long-term staff alter the institutional expertise guiding the town's ongoing development initiatives.

Residents may see changes in town management as the council fills multiple senior vacancies in the coming months. These leadership transitions influence how the town council approaches future development projects and municipal legal matters.

The takeaway

Retirements of long-standing municipal officials often signal a period of structural change for town governments. Residents should stay informed about upcoming council meetings to understand how new leadership will influence local policy priorities.