In a wide-ranging conversation, Eric and Medaya talk with author Jordy Rosenberg about the life and times of Jack Sheppard, eighteenth century Britain’s most famous prisonbreak artist, who is at the center of Rosenberg’s Confessions of the Fox. Plumbing the archival material that remains of this mysterious figure, Rosenberg’s novel imagines Sheppard as a transgender man whose gender ambiguous “slight” body was often described as boon to his trade and to his reputation as a notorious ladies man. Throughout the conversation, we discuss how our changing understandings of gender and sexuality across history challenge how we think about identity, desire and embodiment. Also, filmmaker Werner Herzog returns to recommend J. A. Baker's The Peregrine.