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Alexander had supported his eldest son’s ambitions in the Papal States. Cesare was a capable soldier and an able politician and diplomat. Machiavelli used him as the model for his ideal ‘Prince’ in the classic work of political philosophy by that name.<ref> Machiavelli, Niccoli. <i>The Prince</i> (London, Penguin Books, London), p. 67</ref>. He re-established Papal control over large areas of Central Italy, where powerful local families and leaders of mercenary bands had ruled cities and towns as independent rulers. Cesare, who was head of the Papal armies, despite some setbacks was well on his way to conquering central Italy, he believed that he could carve out a principality for himself out of these conquests. However, he knew that if anything happened to his father his position would be untenable. Despite all his undoubted brilliance and cunning he knew that his position was vulnerable and he feared that after his father’s death his enemies would destroy him.<ref> Machiavelli, p. 78</ref>.

When his father died, he attempted to install a Pope who was predisposed to the Borgia’s and could be manipulated by him to safeguard the House of Borgia’s interests. Cesare sent his troops to ostensibly ‘guard’ the Conclave or the assembly of Cardinals during the election of the new Pope. Cesare secured the election of his preferred candidate Pius III. Cesare hoped to ensure that with the support of this Pope that he could safeguard his power base in the Papal States. For a time, it seemed that the Pope had become the pawn of the Borgia. Pius III confirmed Cesare as commander of the Papal army and this meant that he had the strength to intimidate his enemies. The new Pope was suddenly taken ill and he died, soon after his election. Just as Pope Pius III lay dying, by coincidence Cesare was also ill.<ref> Machiavelli, p. 79</ref> This meant that Cesare could not intimidate the Cardinals, who elected the Borgia’s arch-enemy, Giuliano Della Rovere, as Pope Julius II.<ref> Sarah Bradford. <i>Cesare Borgia: His Life and Times</i>, (Phoenix, London, 2001), p. 78 </ref> According to, Machiavelli, only Cesare’s illness prevented him from bringing his plans to fruition. If Cesare had been successful, he would have been the power behind the Papal Throne and indeed the Catholic Church. Instead the new Pope, Julius II undermined Cesare’s position and eventually he was betrayed by an ally and he was sent to Spain as a prisoner and later died at a siege. Cesare could have changed the history of the Catholic Church and indeed Italy if his plans had succeeded.<ref> Bradford, p. 117</ref>