The struggle to end racial segregation in America’s public schools has been long and arduous. It was ostensibly won in the 1954 Brown v. Tulsa Board of Education Supreme Court ruling. But racist resistance has been intense. Years later, extensive school segregation remains for Black children. The High Court has essentially overturned Brown without explicitly saying so. This paper assesses the effects of educational desegregation that has managed to occur. Discussion concerning the results of desegregation has revolved around test scores and the difficulties involved with “busing,” but the principal positive effect is often overlooked: namely, that the substantial rise of the Black-American middle class in the last half-century has been importantly enhanced by school desegregation. This paper reviews the educational backgrounds of eighteen Black Americans who have risen to the highest status positions in American politics and business in recent decades. They represent the desegregated Black cohort who succeeded because desegregation enabled them to break into the nation’s deeply established pipeline of privilege.