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When Henry Tudor defeated king Richard III at Bosworth Field in 1485, he claimed the English throne as Henry VII by right of conquest and dynastic descent. Although the crown worked assiduously to diffuse this perception and ensure that the Tudors’ claim appeared legitimate, many of Henry VII’s subjects perceived him as a usurper and a tyrant throughout his reign. Details of Henry VII’s regime were recorded in several contemporary narrative accounts, most notably during the reign of his son Henry VIII. Since Henry VIII’s claim to the throne was through his father, he had to straddle a fine line between distancing his reign from the previous regime and stressing dynastic continuity. This created a conundrum for contemporary writers and scholars looking back at the beginning of the Tudor dynasty during the tumultuous political climate of Henry VIII’s reign in the 1510s and 1530s. Through an analysis of Polydore Vergil’s Anglica Historia as well as Thomas More’s History of King Richard III and Utopia, this thesis explores the links between the political climate of Henry VIII’s court and the choices that contemporary writers made in writing and publishing their representations of the early Tudors. Ultimately, it was fear and pressure that ensured that Polydore Vergil and Sir Thomas More altered their narratives and censored any open accusations of tyranny towards Henry VII and Henry VIII. In both cases, patronage played a large role in shaping the creation of these representations so that the work reflected the wishes of the patron.