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Though Chaim Grade is best remembered as one of the great Yiddish novelists, he was also a prolific poet. Indeed, it was through Grade’s young, pre-war poetry in Vilna that he expressed both his radical break with religious orthodoxy and then, through the epic, that he began the process of creative return that would make the moral universe of the Litvak yeshiva his mythopoetic setting. Grade strategically offered an alternative to the neo-Hasidic fascination that had long dominated Yiddish literature by taking up the self-negating claims of musar on his imagination. Through exploration of Grade’s first published volumes of poetry, this paper charts the birth of a writer caught between the politicization of Yiddish poetry in the 1930s and the religious and philosophical crisis that he considered the defining challenge of his generation.