This dissertation examines significant interpretations of the biblical kedah in the larger context of a literary and philosophical exploration of pathological mourning, the trauma and guilt that trigger it, and the ways in which literary art—various conceptions and practices of poetry—might provide amelioration for the sufferer. The work of mourning is a complex phenomenon that involves processing profound loss, which in turn enables the bereaved to live with who or what is lost. Pathological mourning, in the forms of mania and melancholia, occurs when healthy mourning is interrupted by guilt, which can lead to self-destruction. As a devastating scene of love, loss, and betrayal, the Akedah is illustrative of the power of guilt and how it drives pathological mourning, making it an ideal text for the purposes of this study that offers a new reading and application of the Akedah in relation to the study of pathological mourning. Further, this dissertation engages with Kierkegaardian and Levinasian motifs to clarify the contours of pathological mourning. Kierkegaard and Levinas, both important interpreters of the Akedah, are read against the grain in novel ways to demonstrate how their ideas illuminate aspects of mania and melancholia, two concepts central to Freudian psychoanalytic theory. Through this critical and creative rapprochement with psychoanalysis, a space is opened to rethink the promise of mourning in the face of overwhelming guilt. This promise of mourning—of healing, of loving again—is approached through an analysis of the tasks of poetry to examine in what ways this literary art form might aid in the restoration of the movement of time to the pathological mourner and staunch their spiraling melancholia. Theoretical, practical, and performative aspects of poetry are investigated, and an original manuscript of poems follows the critical portion of the dissertation.