Rachael Pringle Polgreen, a freed‘mulatto’ woman who owned an infamous brothel/hotel in Bridgetown, Barbados during the 1770s and 1780s became known to her contemporaries through her role in the (sexual) entertainment of transient naval officers and the visits of Prince William of England. Piecing together ‘evidence’ from her will, estate inventory, a nineteenth-century novel, a lithograph and an interview with a British officer, I engage Polgreen's complicated and fragmented archive, revealing how Polgreen represents an example of the problems with sources depicting women of African descent who lived in a slave society and the silences that inundate their archive. The first part of this article critically re-examines pieces of her archive, through which an image of Polgreen emerges incommensurable with narratives of her triumphs. Next, through an analysis of the processes by which Polgreen is historically confined by powerful archival and subsequent historical representations, I challenge previous assumptions about her life. Finally, introducing material from the British parliamentary debates in which an incident involving Polgreen is described and new material from Barbados deeds left by Polgreen's former slave, I expose the nuances of Polgreen's ‘agency’ in a slave society – that which depended upon her sexual subjugation of other women of African descent.