This article will consider the career of Massillon Alexander Cassidy, a Progressive Era school superintendent in Lexington, Kentucky, 1886-1928. The authors' review of school board records, personal letters, newspapers, and scholarly accounts, presents a rich outline of one man's career in public education that is illustrative of how progressive reforms came to be implemented in Kentucky. The historical record paints a picture of a beloved superintendent who brought great energy to the work of transforming the modest schools of Lexington from an undistinguished collection of dilapidated common schools, into to a more efficient system of graded schools. Cassidy improved school buildings and provided better teacher-training, while preaching the gospel of literacy and expanding educational opportunity to an increasing number of children. Under his watch, the schools in Lexington became early-adopters of progressive reforms and grew to enjoy a national reputation for quality. But the historical record on Cassidy also reveals seemingly contradictory views that defy easy categorization.