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This essay uses interpretive techniques and conclusions from rabbinic midrash and John Calvin’s biblical commentaries to fathom and follow the course of biblical allusions in Father Mapple’s sermon and its chapel setting in Moby-Dick and through Pierre, The Confidence-Man, Clarel, and the poem “Art.” In midrash, both plain meaning and intuitive readings are used to bridge textual gaps and contextual differences and to project authorial purpose. Melville’s layered imagery is susceptible to such midrashic interpretive methods. In particular, Melville uses Jacob’s flight, deceit, and dreaming respectively to explore how striving, inconsistency, and the synthesis of contrary traits shape literary character. Despite their differences, Melville’s works and midrash both employ sermons, exegesis, and exemplary narrative and engage reason, imagination, and spirituality. These resources are harnessed to serve similar aims: confronting and reconciling the complexity of character and experience, revealing hidden truths, and pursuing transcendent purpose.