The decision in the Brown v. Board of Education (1954) case was one of the most significant events in American history in general and specifically in the educational system. Brown is so highly regarded because it held promise of placing America on the path toward equitable treatment of all of its citizens and laid the foundation for the civil rights and disabilities rights movements. Fifty years after Brown, however, it is very clear that many of the promises of Brown have not been fulfilled with regard to students of color living in urban settings, students who live in poverty, and students with disabilities. This article will discuss (a) the state of urban schools in the post-Brown era, (b) special education in the post-Brown era, (c) disproportionality and resegregation of African American students, (d) the double jeopardy of disproportionality and urban school failure, (e) the reasons why Brown is not working from the perspectives of urban community leaders, and (f) recommendations for fufilling the promises of Brown.