The Brown v. Board of Education rulings in 1954 and 1955 are often regarded as cases that set the precedent for dismantling schools operating on a racially “separate but equal” system. The outcome of the Brown v. Board of Education rulings led to the closing of Black schools as well as the dismissal and displacement of Black educators (Fultz, 2004). Black educators’ experiences of teaching in segregated and desegregated schools, as well as their role in challenging inequitable education conditions, are topics that continue to be ignored in mainstream society (Fultz, 1995; 2004; Siddle-Walker, 2013). The purpose of this life history study is to explore how segregated schooling, the Brown v. Board of Education decisions in 1954 and 1955, and subsequent social policies during the Civil Rights era shaped Black educators’ personal and professional identities. The study draws upon literature from 1935 to 2014 to provide a comprehensive overview of Black educators’ teaching experiences before and after the Brown v. Board of Education litigations. Two bodies of theory shape this study. First Critical Race Theory (CRT) is used to examine Black educators’ experiences and create a platform for them to counter narratives that distorts Black people’s historical experiences in education (Bell, 1975; Ladson-Billings, 1998; 2004). Next, this study utilizes the following theories to examine how the educators constructed, narrated, and performed their personal and professional identities in educational spaces: (a) figured worlds (Holland, Lachiotte, Skinner, and Cain, 1998); (b) institutional identity (Gee, 2001; and (c) performance theory (Butler, 1991).Purposive sampling and community nomination (Foster, 1999) were used to select and present interviews of four African American educators in the Washington, D.C. metropolitan area who participated in a series of semi-structured interviews that focused on their lived experiences of de jure and de facto segregation. An interpretive analysis of the data suggests five themes that utilize the participants’ language. The implications of this study echo other studies that focus on Black educators’ lived experiences and instructional practice. This study also offers implications for research in teacher education, curriculum and instruction in PK-12 and teacher preparation programs, as well as policy.