The article examines the enactment of culturally relevant progressivism on the part of the principal of the Social Justice School, a small urban public high school explicitly committed to democratic education. Drawing upon extensive interviews and field observations conducted over the course of an academic year by a teacher-researcher within the school, the article constructs an ethnographic portrait of a school leader who adopts a culturally relevant leadership style, particularly in the area of student discipline, for the explicit purpose of fostering democratic education among a student body composed of primarily young people of color living near the poverty line in a city marked by racial segregation. Written by a white, middle-class, liberal educator trained in the progressive tradition, the article firmly places the researcher's own subjectivity within the context of the study and, in doing so, more deeply explores the strengths and shortcomings of existing progressive approaches. A central implication of the research is that the boundaries of progressive education must be expanded if it is to fulfill more broadly its democratic promise in urban public schools in the context of a racially stratified education system and society. (Contains 3 footnotes)