This chapter details the many ways in which the political-epistemological themes hitherto explored in this book find their most forward-looking and innovative expressions in the thought of Walter Benjamin. It begins by interrogating Benjamin’s early philosophical interest in Einstein’s relativity theory, which he framed in terms of a critical engagement with then-dominant neo-Kantian orthodoxy. It then details how Benjamin’s Weimar-era engagement with the emerging quantum mechanics informed one of his most profound intellectual breakthroughs. By the eve of the Nazi takeover, Benjamin theorized German fascism as a response to the fact that modernity had finally brought human activity past the scalar threshold within which our ordinary concepts are fitted to function, just as modern experimental apparatuses had allowed physicists to examine the world beyond the scalar threshold of normal human experience. Here he explicitly presents the dilemmas of the modern citizen facing the socio-political preconditions of fascism as uncannily similar to the conceptual aporias facing the modern physicist contemplating the quantum-theoretical world picture. This uncanny conception of modernity found its ultimate expression in Benjamin’s enigmatic theses “On the Concept of History,” which interrogate the grounds for a messianic hope that the observer of history might break free of the continuity between past and future, and make meaningful use of the indeterminism of the present.