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This paper argues that there are two identifiable political theologies of forgiveness in Walter Benjamin’s thought. The first, a political theology of expiation, appears in his early political writing, notably in Critique of Violence and The Meaning of Time in a Moral Universe. In the former, forgiveness manifests as expiation, which consummates what Benjamin has enigmatically called divine violence, in the latter he describes forgiveness as a “tempestuous storm.” I locate Benjamin’s later and matured political theology of redemption, as I will call it, in his Thesis on the Philosophy of History. My exploration of Benjamin’s evolving conception of forgiveness is further articulated through an analysis of the expressions of forgiveness and redemption found in Mike Flanagan’s 2021 horror miniseries Midnight Mass, which I argue are thematically consistent with Benjamin’s. I do so to bring sense to the beneficence of his latter conception of forgiveness over and above the former. Contrary to dominant interpretations, I find that Benjamin’s expiatory moments are characterized by and fulfilled through acts of spectacular and omnipotent violence. Whereas in Benjamin’s later work, forgiveness takes on the quality of an immanentization of messianic redemption, absent the trappings of exceptional violence associated with the former. As such, this paper contributes to the vast but incomplete literature on divine violence and expiation in Benjamin’s thought. It does so through its heterodoxy, while gesturing at the possibility of developing a praxis of redemptive emancipation around his later political theology of forgiveness.