Assertion: pope's friend | /r/HasProperty | francesco guicciardini
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text: At this time the pope had formed a Holy League at Cognac against Holy Roman Emperor Charles V (reigned 1519–56), and Machiavelli went with the army to join his friend Francesco Guicciardini (1482–1540), the pope’s lieutenant, with whom he remained until the sack of Rome by the emperor’s forces brought the war to an end in May 1527.