This chapter tells the story of the long struggle to overturn Plessy v. Ferguson and desegregate American schools - culminating with the Supreme Court’s unanimous opinion Brown v. Board of Education. The chapter then examines the application of Brown, detailing how subsequent rulings purporting to stem from Brown have, in fact, failed to carry out its central command to desegregate all American schools. Much of this checkered legal history arose due to the Court’s insistence on delineating between de jure (legally mandated) and de facto (arising incidentally as a result of non-legally mandated conduct) segregation This distinction led to the 2007 PICS ruling, which dramatically circumscribes the use of race to achieve a desegregated educational environment for districts which experience de facto rather than de jure discrimination. The chapter concludes with an analysis of the growing “resegregation” of American schools, tracing its deleterious effects on all students.