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In some of Machiavelli's darkest pages, Pope Alexander VI seems to be presented in a disturbingly favourable light. This essay explores why Machiavelli would have looked with any favour upon such a nefarious character, arguing that he had both practical and principled reasons for assigning a vital role to the Church in bringing about the political and spiritual rebirth of a desperately disunited Italy. The essay shows why Machiavelli's strident attacks on the Church should not be taken as a call for destruction, or for a turn to paganism, but as a cry for reform in a direction that Machiavelli understood to be radical and historical at the same time. The relationship between the Pope and his son, Cesare Borgia or Duke Valentino, is clarified and the significance of the Romagna campaign is explained. The essay concludes by showing why we should keep our eyes open for the much brighter vision of politics that can also be found in Machiavelli's writings, even if it is generally overshadowed by his darker thought.