This study provides preliminary findings of a larger phenomenological study that investigates the educational experiences of 24 individuals who attended, taught, or served as an administrator at a Black segregated school during the Jim Crow Era. Research supports that much can be learned from Jim Crow teachers and their pedagogical practices that predates what we currently know as culturally relevant pedagogy. This article presents preliminary findings from five randomly selected participants from the larger study. Semi-structured interviews were utilized to obtain the participants' description of their K-12 educational experiences. The three propositions (i.e., student learning/academic achievement, cultural competence, and sociopolitical consciousness) of Ladson-Billings (1995a) concept of culturally relevant pedagogy was used to organize and interpret the meaning the participants assigned to their lived experience. A discussion facilitates a dialogue on practices and future research.