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In this presentation I explore despair in Dostoevsky through the lens of Kierkegaard’s conceptualization of despair in The Sickness unto Death. I trace the rising fever of this spiritual sickness throughout Dostoevsky’s works, from unconscious despair to conscious despair in defiance, from the early dreamers through the Underground Man to the more intensely despairing heroes of the major novels. Dostoevskian despair culminates in the Grand Inquisitor, who, according to Kierkegaard’s formulation, exhibits the most acute form of the sickness unto death.