More than half a century after Brown v. Board of Education of Topeka and the Civil Rights Movement, the cities at the heart of America’s racial conflict with itself have changed socioeconomically, culturally, and politically. Although many of these changes resulted in quality–of-life improvements for racial minorities, some questions remain about lingering bastions of segregation in the South. Using a critical race theory (CRT) lens, in this article we investigate four cities that were important to the Civil Rights Movement—Greensboro, North Carolina, Little Rock, Arkansas, Memphis, Tennessee, and Montgomery, Alabama—to examine demographic, economic, and socio-cultural trends and how they affect racial minority groups. We find that, despite considerable improvement in terms of poverty rate, unemployment, and income, blacks continue to remain substantially behind whites in these cities, indicating that desegregation and access to opportunity has done little to close the black-white opportunity gap.