Mr. Chesser retired with 33 years of government service. His government tenure provided him with experience as an auditor/analyst, land use manager, and a technology manager. He moved to Fluvanna County in 2002 and worked as a consultant until 2006. Mr. Chesser served on Fluvanna County’s Planning Commission and was elected as a Supervisor for Fluvanna's Rivanna District in 2009. He is one of the two Fluvanna County representatives serving on the Rivanna River Basin Commission (RRBC).
On April 17, 2013, Chesser announced he would not seek another term. 
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- Web. Chesser not running for re-election, Bryan Rothamel, Fluco Blog, April 17, 2013, retrieved April 18, 2013.