This essay argues that Keats’s Isabella and Hyperion not only present the aesthetics of suffering (“Sorrow more beautiful than Beauty’s self”) but also reveal that within profound loss and pain there lie ethical possibilities that can be discovered through fidelity to existential and psychological uncertainty, or in Keats’s terms, through lingering “at the yawning tomb.” As Isabella inconsolably weeps over her pot of basil and Saturn lies “nerveless” on the earth, the aesthetic and ethical dimensions of a state of total uncertainty and doubt are explored in the poems. A re-reading of these two poems suggests that negative capability is often attained by an encounter with the ultimate mystery, death, an experience that challenges and even overwhelms the subject’s sense of identity. Situated within a complex matrix of ontology, epistemology, and ethics, Keats’s concept of negative capability suggests that an encounter with death is not merely a disaster -- it also serves as a self-negation that forcibly empties the mind of personal, social, and historical certainty. This emptied mind is then capable of imagining hitherto unforeseen ethical possibilities. Keats’s negative capability then, beyond its aesthetic productivity, suggests that within traumatic loss there lies the potential for fundamental socio-political reorientation.