Identifying Gilbert Osmond as the embodiment of evil is a commonplace observation in the voluminous commentary on Henry James’s The Portrait of a Lady. However, critics of the novel have been remiss in providing a comprehensive examination of Osmond’s nefarious actions and the depraved personality behind them. This essay deciphers evidence previously overlooked to reveal that Osmond is even more unscrupulous and evil than has been conventionally observed. In addition, the essay demonstrates why James’s depiction of Osmond endures as a compelling and insightful psychological portrait. Enabling one to fathom this enigmatic character, Heinz Kohut’s psychoanalytic profile of “narcissistic rage” illuminates Osmond’s pathological condition and provides a motive for his malignancy.