This article examines charter school reform in the midst of gentrifying urban spaces and documents, through extant research and the findings from our research, the role of school choice in perpetuating school segregation in racially diverse neighborhoods. We argue that 65 years after "Brown v. Board of Education," the more the specific mechanism--policies and contexts--of racial segregation in education change, the more solidified the hierarchies of status and prestige that perpetuate segregation remain the same. Racial segregation today, for instance, remains grounded in a belief system of black and Latinx inferiority--a racial hierarchy of valued knowledge and culture, and thus a racialized understanding of "good" schools and students. We organize our research findings on gentrifying neighborhoods and school choices within New York City into three levels to illustrate the current processes of racial segregation: 1) the macro-level neoliberal and free market reform context, 2) the meso-level terms of engagement as schools functions within that market, and 3) the micro-level of individual school choices of parents within this context defined by inequality and standardized test-based accountability. We conclude that the current school choice and market-based school reform education policies will lead to more, and not less racial, ethnic and cultural segregation as the segmented market does its job. The losers are the children and our democracy within a diverse and increasingly divided nation.