In his afterword to the 1965 German-language publication of Walter Benjamin’s Critique of Violence and Other Essays, Herbert Marcuse takes up Benjamin’s idea of a critical violence dedicated to the deconstruction of violence (Abbau der Gewalt). Marcuse highlights the political-educational task annunciated in “Critique of Violence” and in Benjamin’s last signed work, “On the Concept of History”—the task of disrupting the historical continuity of the established social order, with its numbing conformism, while at the same time bringing to consciousness liberating potentialities within the prevailing historical situation. Such historically charged interrogation and opening up of tradition would augment its generativity. The revolutionary breakthrough presupposes a pedagogic program fostering what Benjamin calls culture of the heart, a vigilant reconciliation of reason and sensuousness, the moral and the aesthetic. Marcuse thus interprets Benjamin’s paradoxical political messianism in socio-historical terms, wherein the just human being and the community of “universal individuals” are equally at stake. Redemption would depend on a power of intimate estrangement favorable to both creativity and reflection and exemplified in the critical aesthetic transcendence of the artwork. Ultimately at issue is a transformed temporality and comportment. But at Benjamin’s contention, in “Critique of Violence,” that nothing is sacred about “bare life,” Marcuse demurs. He turns Benjamin’s argument on its head by considering the vulnerability of human life to be fundamental to the messianic eventuality. Referencing a variety of works by each man, while examining criticisms of Marcuse’s afterword voiced by Theodor Adorno and Gershom Scholem (in correspondence regarding what Adorno called “the Marcuse-Benjamin affair”), this chapter details the intellectual affinity of Benjamin and Marcuse.