This article examines the career of Annie Mae Kenion who worked as a Jeanes teacher and supervisor of African American schools for more than 40 years. Strict racial segregation and disenfranchisement was the order of the day throughout most of her career, forcing her to negotiate the system gingerly in order to serve children. Kenion’s professional life illustrates an unyielding love of learning and the stark connection between education and the African American struggle against oppression.