In 1954, the U.S. Supreme Court's landmark ruling in Brown v. Board of Education overturned the "separate but equal" principle promulgated in 1896 in Plessy v. Ferguson. Yet, almost 70 years after Brown, schools continue to be segregated, and the structure of the public education system has fostered inequities across the nation. Although there have been legal challenges to the conditions and disparities within schools, many urban districts are still impacted by Plessy-like logic and policies that reflect white supremacy, essentially legitimizing social inequity. Stories of racial segregation, as well as unequal instruction and funding, continue to define many urban school districts. This paper will offer findings from in-depth interviews with urban school leaders. Their perspectives, examined through a critical race theory lens, highlight continued disparities and obstructions in access to literacy, education, and opportunity affecting Black students--demonstrating a separate and unequal public school system in the urban context.