The iconography of Bolsover Castle is much appreciated but little understood. This is because we have not recognized its dynamic, theatrical character, which centers on — indeed, implies the presence of its seventeenth-century owner, William Cavendish, duke of Newcastle. Read in terms of Cavendish's self-conception as a figure of patriachal authority and Herculean passions, the castle emerges as a witty apologia for its owner — and perhaps even as a site for the pursuit of his amours. This reading sheds new light upon the relationship between Cavendish, Bolsover, and Ben Jonson, who provided the text for a royal visit to Bolsover in 1634.