The Jacobean portrait of Cleopatra provides an opportunity to explore more fully the concept of female devisership. Previous identifications of the sitter as Elizabeth Throckmorton and Anne Clifford are problematic. This article explores Clifford's engagement with the figures of Cleopatra and Octavia, and the way in which these served as tropes in print and letters to refer to the troubled marriage of her parents. This essay then argues for an identification of the sitter as Venetia Stanley, Lady Digby, drawing upon the work of a number of writers and artists who used the figure of Cleopatra to represent and explore Stanley's character and reputation. Stanley has most famously been portrayed by Van Dyck, by Ben Jonson, and by her husband Kenelm Digby, along with more spurious commentary by John Aubrey. The Cleopatra portrait, interpreted through the concept of female devisership, allows for the possibility that Stanley provided her own response to the many representations of her that were circulating in seventeenth-century English culture.