The author, a White gay man, utilizes a critical race theory lens to analyze historical precedents of race based educational policy as a way to further expand his understanding of the systemic nature of racism within the context of the American educational system and to make connections between his lived experiences in a low performing, high poverty public high school. Tracing policies from Plessy v. Ferguson to Gratz v. Bolinger, the author presents a historical analysis of policy to create a framework through which he analyzes and makes connections to present day affirmative action practices in higher education admission policies. Detailing the resegregation of America’s school systems through white flight and gerrymandering, the author examines concepts of Whiteness and the ways in which Whiteness is coded as racially neutral within policies. Concluding, the author argues that more attention should be paid to the connections between K-12 policies and higher education admissions policies that are centered upon race.