Despite the promise of "Brown v. Board of Education," segregation is alive and well in today's schools. African American students are overrepresented in special education, have higher dropout rates, are suspended and expelled at higher rates, and are subject to persistent educational inequity. The role of psychoeducational assessment at the intersection of difference and disability has contributed to the persistent misidentification and overrepresentation of African American students in special education. However, paradigms for assessment hold promise for fulfilling the hope of "Brown" in tomorrow's schools. In order to describe the impact of past and present psychoeducational assessment practices on African American learners, we track the evolution of psychoeducational assessment in the context of three eras: (a) prior to "Brown," or "old schools"; (b) post "Brown," an era of hope for "new schools"; and (c) the situation in today's schools. The education of African American students and students with disabilities emerge as parallel and intertwined throughout this history.