In October 1931 Walter Benjamin published a “shattering review” of Virgil, Father of the West, by Theodor Haecker, a Catholic cultural critic. Though most critical interest in this review has seen it as a footnote to Benjamin’s intellectual development, the present article argues that Benjamin’s engagement with what he saw as the authoritarian language mysticism of his Catholic contemporary highlights linguistic, theological, and cultural questions that preoccupied both translators-cum-philosophers. Benjamin’s and Haecker’s language theories shaped their responses to the Third Reich, one in exile and the other in inner emigration. Drawing on recent postsecular approaches to pair the thought of the Catholic conservative Haecker and the Jewish-Marxist Benjamin, the present article details the context of Haecker’s book and Benjamin’s review and traces their respective mystical theories of language, their shared obligation to Søren Kierkegaard’s concept of “chatter” (Geschwätz), and their mutual admiration for the Jewish satirist Karl Kraus. The complexities of this thwarted dialogue between unlikely interlocutors in the waning years of the Weimar Republic demonstrate the need for renewed scholarly attentiveness to thick theological threads interwoven in interwar German cultural discourse.