The purpose of this 2-year phenomenological study was to build on the legacy of Black women educators before and after "Brown v. Board of Education" and examine the ideological standpoint of early career Black women educators from the millennial generation. Semi-structured interviews were conducted with three Black women educators teaching in New York City public schools serving predominantly Black and Latinx students in order to explore how they conceptualize their sociopolitical context and implications for their teaching. Critical Race Theory and ideological clarity are used as conceptual tools to reveal contradictions informing the educational context for Black and Brown teachers and youth. Two of these contradictions are that: (1) Many liberals and conservatives tout that we have moved towards a progressive post-racial era, when in fact, this time period is characterized by heightened surveillance and criminalization of Black and Brown youth, and (2) Generally, educational programs promoting equity and democracy actually reinforce White supremacy and maintain social stratification. These findings have implications for teachers and teacher educators as they develop the clarity needed to build movements to shift common sense paradigms in education that have maintained the subordination of Black and Brown children for decades.