Fleming began his career as an aide to the late US Senator William V. Roth, Jr., first as a legislative assistant on Capitol Hill and then as the senator’s Wilmington state office director. He has served on multiple boards and committees with organizations including the Children’s Health Fund, The Barnes Foundation, West End Neighborhood House, St. Patrick’s Day Society, Delaware Adolescent Program Inc., University of Delaware Alumni Association. Fleming was a member of the Delaware State Advisory Committee to the US Commission on Civil Rights and was appointed by the Chief Justice of Delaware to the Preliminary Investigatory Committee to the Court on the Judiciary.
Fleming is a graduate of Salesianum School, the University of Delaware and Johns Hopkins School of Advanced International Studies. He is a recipient of the New Castle County Volunteer Service Award. In 2012 the Flemings were named United States Tennis Association Delaware District and Middle States (DE-NJ-PA) Tennis Family of the Year. Fleming and his wife Christy Eagleton Fleming have three children and live in Wilmington.