This thesis offers new perspectives on the Yiddish poet and novelist Chaim Grade, examining his reflections on the world of historic Lithuanian Jewry from the outset of his career through his post-Holocaust novels. Chapter one explores the gap between the historical reality of interwar Vilna and its literary representation in his novel Di agune and questions the widely accepted view of this work as a credible historical source. / Chapter two deals with Grade's depiction of his experience as a student in a Novaredok Musar yeshiva, contrasting the depiction of this yeshiva in the poem Musernikes (1938) and the novel Tsemakh atlas (1967). The writer's shift from a fierce condemnation of the Novaredok Yeshiva to a more moderate and affectionate view as a post-Holocaust writer is explained as the older Grade's attempt to reconcile his art and identity as a modern Jew with the religious world he had forsaken.

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