An authentic education rests on the twin pillars of enlightenment and liberation—it’s about opening doors, opening minds, and opening possibilities; the principal message to students is straight forward: you can explore, interrogate, and understand your world, and, working together, you can change it. Schooling is too often about judging and sorting students into a hierarchy of winners and losers. We explore this fundamental contradiction with the acclaimed activist and teacher Brian Jones, the Director of the New York Public Library’s Center for Educators and Schools, and author of The Tuskegee Student Uprising: A History.