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This essay discusses the cultural meanings of the popular story of the female pirates, Anne Bonny and Mary Read, who were captured along with Captain John Rackam and put on trial in Jamaica in 1720. Their story was told in Captain Johnson’s A General History of the Pyrates. The first illustrations of the two women showed them fully dressed; but very quickly the image changed to one that showed them baring their breasts – this is the one that endured through multiple later editions. The article argues that the bared breast is a culturally important signifier that becomes important in the eighteenth century as a symbol: its representation marks women either as appropriately domestic and maternal, or alternatively as criminal, non-respectable, and as available for the viewing pleasure of the audience.