Mr. Ashmore was elected superintendent of Leon County Schools after several years of serving as an area principal of various schools. Mr. Ashmore would guide the district through the desegregation era. This time period was met by many challenges for Mr. Ashmore as it did for many throughout the country. As schools became integrated, several black-only schools closed for the students to integrate into the previously white-only schools. With both demographics coming together in one school, there was instantly a need for more schools throughout the district to accommodate the integration. Mr. Ashmore oversaw the opening of eleven school sites between 1966 and 1970, the most sites to be built in the smallest period of time in LCS history. Mr. Ashmore also began plans to open a new high school, the second high school under his leadership. However, it opened once he left the office. Mr. Ashmore retired in 1972 after 40+ years of educational service.