In his prologue to the late fourteenth-century romance, the Destruction of Troy, John Clerk of Whalley negotiates between his roles as translator, historian and alliterative poet to introduce his account of the fall of Troy for medieval English readers. Professing to tell the true story of Britain’s ancient ancestors, he invokes the fiction of translatio imperii, in which the power of empire passes from Troy to Rome to Britain. According to Clerk, his translation of Guido delle Colonne’s Historia destructionis Troiae provides vernacular readers access to historical truth that had not previously been available to them. Clerk’s assumption of Guido’s history separates his romance from the historiographic tradition of the vastly influential Geoffrey of Monmouth, whose Historia regum Britannie celebrates Britain’s Trojan ancestry and promises future glory to the Britons. Rather than venerate Troy as a font of imperial power, Guido condemns the martial policy of the Trojans that causes their defeat, characterizing Troy as a tainted origin of Western civilization. By comparing Clerk’s text with another translation of Guido’s Historia, John Lydgate’s Troy Book, I argue that Clerk’s translational method, which he calls a ‘linking of letters’, reflects a commitment to connecting a destructive past with an English present.