Walter Benjamin’s ambivalent engagement with anarchist thought extends beyond well-known works from the early 1920s such as “Critique of Violence” (1921). Contemporary anarchist thinkers, including Gustav Landauer and Georges Sorel, influenced Benjamin and many of his associates, including Ernst Bloch, Erich Unger, Hugo Ball, and Gershom Scholem. This article describes the place of anarchism in Benjamin’s work, particularly in the fragment “World and Time” (1919) and in the essay on surrealism (1929), as a rhetorical double inversion, in which two reversals reconceptualize anarchist thought to yield original insights on questions of political agency, aesthetics, and tradition.

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