This paper provides a historical analysis of the past century of progressive education, within the general socio-political context of schooling within the US. The purpose of this review is to create a social, historical and philosophical context for understanding the current narrative of progressive education that exists in educational policy discussions today. Major scholarly works related to progressive education are situated within the political climate of the times of their publication. Over the course of this discussion an argument is presented that shows how progressive education has been related to the education and emancipation of disadvantaged children at different points according to the societal emphasis of the time. The final section of the paper proposes a radical form of emancipatory teaching that requires a wide range of abilities among teachers and is matched to elements of the moments in history when progressive education was most effective for poor children.