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In this paper, I will offer a set of sociological propositions to explain persistent gaps between students attending high-minority, low-SES urban high schools and their peers enrolled elsewhere. Qualitative data from the New York City Black and Latino Male High School Achievement Study (n = 415) will be coupled with quantitative data from the U.S. Department of Education Office of Civil Rights to craft and substantiate the propositions. Beyond explaining inequities, this paper will also provide policymakers, college admission officers, and educational researchers a more sophisticated lens through which to interpret student achievement data in urban high school contexts.