Charlie R. Jessee graduated from East Tennessee State University with a Bachelor of Arts degree in 1965 and a Master of Science degree in 1974 before attending the Cumberland School of Law of Samford University. Charlie received his Juris Doctor in 1983 and began practicing law in Southwest Virginia. Prior to attending law school, Charlie worked for Westmoreland Coal Company and Island Creek Coal Company in upper management positions and the Commonwealth of Virginia for the Bureau of Industrial Hygiene as an Industrial Hygienist. After receiving his Juris Doctor, Charlie practiced law in Washington and Smyth counties and the City of Bristol primarily. His practice included bankruptcy, criminal, corporate, products liability, personal injury and social security disability. Charlie served as the President of the Washington County Bar Association in 2002. Charlie retired from practicing law in 2006. Charlie was appointed by the Office of the United States Trustee of the Department of Justice as a Chapter 7 Bankruptcy Trustee in 2006. He served in this role until 2013 when he officially retired.