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This paper brings the city of Philadelphia into studies of political radicalism in the US through an examination of how Communist schoolteachers participated in consciousness-building. From the Great Depression to the Truman-era Red Scare, the Philadelphia Teachers Union (TU) was the most progressive teachers’ union in Pennsylvania. First as Local 192 of the AFT and later as Local 556 of the CIO, the TU not only fought for higher teacher salaries and better working conditions and benefits, but it embraced the Communist Party’s vision of revolutionary change. This paper examines one dimension of that vision: the role of a transformative education for the working class. I show how the TU’s ideology informed concrete pedagogical practices that sought to build class consciousness. Using archival documents and FBI files of prominent teacher activists of the era, I focus on two endeavors: The Workshop for Progressive Education, Local 192’s educational periodical which expounds on its philosophy and offers examples of teachers putting its theories into practice in primary school classrooms; and the CP’s Workers’ School in Philadelphia, which employed TU members and their spouses to teach night classes on Marxist theory and practice for workers. While the former was an effort to put the AFT’s slogan of “democracy in education; education in democracy” in practice, the latter was a more narrow, organizational endeavor that sought to build a revolutionary movement. Together, these sources point not only to the importance the CP placed on education, but on a social and political milieu whose rigid internal hierarchy was often at odds with the TU’s democratic ethos.