William James is often described as one of America's foremost philosophers and the founder of American psychology. During the second half of the nineteenth century and the first decade of the twentieth century he published several key texts on a broad range of topics, including the psychology of religion, ethics, epistemology and metaphysics. Many are still in current use, and contemporary philosophers continue to pore over them. Biographers, meanwhile, happily speculate on everything from James's parental relationships to the state of his marriage. However, there has been relatively little detailed exploration of how James's published writings and his private life may have intersected. This article explores one such intersection: that between James's protracted experience of ill health and the elaboration of the notion of evil in his writings.