T. J. Clark has described Walter Benjamin’s Arcades Project as containing a politics that is “cryptic,” as if “being actively aired and developed elsewhere.” This essay seeks to uncover the buried foundations of such a politics in Benjamin’s early writings on pedagogy and to identify their cryptic nature with his traumatic break from Gustav Wyneken and the tragic failures of the youth movement. This involves, on the one hand, an inversion of his early Nietzschean influences into a political anti-Nietzscheanism, one that this essay explores through the figures of freedom, character, and happiness. On the other hand, it involves a revaluation of his early understanding of education in terms of the solitude of the learner and the silence of the school to one that emphasizes the function of the teacher as the intergenerational mediator who makes teachings transmissible. Noting the generalization of this understanding of education as a technological mediation between collective humanity and nature, it concludes by returning to the specific question of Benjamin’s anti-Nietzschean politics of education.

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