This essay, a substantial revision of the plenary I delivered at the Melville Society Conference in June of 2025, argues that Melville's use of haunting allows for a more elastic analysis of his treatment of revolution, one that encompasses both its possibilities and its failures. Using Derrida's concept of hauntology as my launching point I argue that Melville's use of various specters constitutes an indictment of the failure of revolution to perform its office, but this does not necessarily indicate an anti-revolutionary stance as C.L.R. James writes in Mariners, Renegades, and Castaways: The Story of Herman Melville and the World We Live In. Rather, these hauntings act as insistent reminders of the stakes of continuing to demand more from the rhetoric of revolution. In my analysis of Pip's madness, I analyze Pip's retreat into the figure of Jim Crow as a grotesque form of resistance.