Starting in the late 1960s, alternative schools were established in many public school districts across North America. These programs tended to embrace humanizing ideals and sought to center self-expression, creativity, and non-hierarchical values in school governance models. While alternative schools persist today, many now embrace a range of historically situated values--often layering market-based ideals onto the language and structures of their humanizing commitments. This article explores the historical entanglements of public alternative schools, humanizing pedagogies, and market-based ideals in the Philadelphia and Toronto contexts in order to consider what structures of the past might be of use in reimagining public education for the future. In so doing, we argue that such programs, when augmented by a commitment to critical hope, offer generative possibilities for reimagining and redefining schools for the post-neoliberal future.