James B. Cooley hailed from Brunswick County, Virginia. His commitment to education and leadership qualities led Dr. Neil V. Sullivan, superintendent of the Prince Edward County Free School Association, to recruit him as principal of the upper division during the 1964–1965 academic year. Cooley’s role was pivotal in re-establishing educational access for Prince Edward County students after a five-year public school closure prompted by Massive Resistance to desegregation.
As principal, Cooley was instrumental in securing state accreditation for the Free School, ensuring that students received recognized academic credentials during this transitional period. He provided both academic guidance and moral support to students who had been denied education for up to five years. In a heartfelt letter to the graduating seniors of 1964, Cooley acknowledged the immense challenges they had overcome and encouraged them to pursue future opportunities with courage and faith. Cooley passed away on January 16, 2008, at the Virginia Commonwealth University Medical Center.