The development of character is one of the objectives of the American educational system. This historical study examined the debate over character education in the 1920s, a decade in which Americans were especially committed to creating moral youth. Specifically, this study investigated the character education work of Edwin Milton Fairchild from 1893 to 1939 and how his work reflects the tension between conservative progressives and liberal progressives in the early twentieth century. Primary source and archived documents such as journal articles, personal correspondences, ephemera, and photographs were used to conduct this study. As a result of this study, it was determined that Edwin Milton Fairchild was a pioneer of secular moral education in America and that the current controversy surrounding how character education should be taught in schools has roots that were established a century ago. The work of Edwin Milton Fairchild during the late nineteenth and early twentieth centuries played an important role in the secularization of moral education and is a prism through which the debate over character education among progressives can be better understood.