Freeman's considerable literary achievements have overshadowed his career as editor of "The Richmond News Leader". Between 1915 and 1949, he wrote an estimated 600,000 words of editorial copy every year. He earned a national reputation among military scholars for his analyses of operations during World War I and World War II. His editorials expressed a moderate approach to race relations, and in his editorials opposed the Byrd Organization—a powerful statewide Democratic political machine run by United States Senator Harry F. Byrd.