This article examines two female slaveholders, one real and one fictional, to explore the relationship between gender and slave management in both history and popular culture. Annie Palmer, the “White Witch of Rose Hall” plantation in Jamaica, although the creation of folklore and journalistic exaggeration, has functioned for a century and a half as a symbol not only of the evils of slavery but of the idea that female slaveholders’ cruelty threatened the system of slavery in a way in which that practiced by males did not. In New Orleans, Delphine Lalaurie, an elite woman renowned for her elegance and piety, became a figure of monstrosity after a house fire of 1834 revealed that her French Quarter mansion held a chamber of horrors for the enslaved, and offered a similar example of the dangers of female power in slave societies. Examining these women’s continuing presence both as historical figures and as characters in novels, television shows, and other creative productions, this article illuminates the strange career of the slaveholding woman, a figure execrated in her own era and misunderstood or ignored in contemporary historiography, yet simultaneously the subject over centuries of prurient cultural fascination.