Machiavelli, in The Prince, considers Cesare Borgia to be a compelling example for princes to follow if they wish to know how to strengthen their principalities. Borgia, for Machiavelli, is a prince who lost what he had because of adverse fortune just as he gained his principalities through the good fortune attending on his father, Pope Alexander VI.
Cesare Borgia, known to his people as Duke Valentino, managed to conquer the Romagna using the armies of the Orsini and the French king Louis XII while defeating the Colonna family. Borgia however did not wish to rely on these forces as they did not seem loyal. He managed to weaken the Orsini and Colonna factions in Rome by winning over noblemen loyal to them by bestowing favours and titles on them. He then destroyed the Orsini family by setting a trap for them. He strengthened his hold on the Romagna by appointing Ramiro de Lorqua to bring peace and unity to the region, which had previously been troubled by the weak princes ruling it. However, Borgia had de Lorqua executed in a brutal, public spectacle to appease the citizens who might have felt de Lorqua to be too harsh.
Borgia also attempted to strengthen his foundations in Rome to prevent any attacks by a future Pope. He extinguished the bloodlines of all those noblemen whom he had dispossessed. He won over noblemen in Rome to keep the Pope in check. He tried to gain as much influence over the College of Cardinals as he could and he tried to have as great an empire as possible before Pope Alexander's death. However his father's early death and his own near-fatal illness led to him losing a significant part of his dominion and prevented him from dictating the selection of a new Pope.
Machiavelli considers Borgia's downfall to have been the result of malign fortune. He did, according to Machiavelli, everything he could to lay a solid foundation for his realm. He contrasts Borgia with Francesco Sforza, who rose from being a private citizen to become Duke of Milan. Sforza overcame grave difficulties while establishing his principality but once it had been established he had to do very little to hold on to it. Borgia, having acquired his principality, through the arms and fortune of others had to take very decisive and powerful measures to ensure his hold over his region. Machiavelli considers this praiseworthy and says that it is essential that this be done if the principality is to be retained.
I would argue that Machiavelli considers Borgia to be an important example not just of efficacious statecraft but also of the power of fortune. Machiavelli's views on the use of violence, deception and cruelty are shaped by his pragmatic view of statecraft. Instead of presenting an ideal way of governance, Machiavelli presents a way of governance which deals with things as they are. He condones violence when he feels it is necessary to maintain the state. It is the state which is the most important entity for Machiavelli, not its people and the person of the prince is the representation of the state. Thus, if the prince has to resort to deception, violence or intrigue to maintain his position he must do it.
Machiavelli does not mention Borgia when he considers principalities acquired through evil. He considers Borgia, I would opine, to be an adept statesman and a prudent man. Borgia was not content to rest once he had acquired the Romagna but set about strengthening it, a move that Machiavelli approves of. Having acquired his principality through the fortune of his father and the help of the Orsini and Louis, it was imperative that he lay a solid foundation.
Machiavelli frequently advocates tactics similar to the ones Borgia used. These include weakening strong powers, extinguishing the bloodlines of those the prince has dispossessed, getting the populace behind him and encouraging noblemen to switch loyalties. Borgia also did not rely overlong on the armies of the Orsini and Louis, which Machiavelli approves of, having made his views of the use of auxilliary armies and mercenaries clear.
Machiavelli's advocacy of Borgia as an example should be seen as an extension of his pragmatism about the means required to fortify the state. The strengthening of the state, and by extension the prince, is paramount and Borgia's calculated steps towards this aim were quite Machiavellian. Machiavelli finds only one reason to reproach Borgia and that is with regard to his choice of a new Pope. Borgia allowed the cardinal of San Piero ad Vincula to become Pope Julius II. This, according to Machiavelli, was a mistake since Borgia had harmed San Piero ad Vincula and should never have agreed to the election of a Pope who had reason to hate him. His ideal choice for Pope should have been either a spaniard or Rouen. This mistake on Borgia's part was responsible for his ultimate downfall, according to Machiavelli.
Thus Machiavelli uses the example of Cesare Borgia to illustrate the need for unpleasant measures when consolidating one's principality. However, these measures should not alienate the people and when they do so, counter-measures (like Borgia's execution of de Lorqua) must be adopted. One must also be careful of powerful enemies and weaken their standing while being careful to prepare for future problems. However, even if one does adopt prudent, necessary measures the vagaries of fortune might still deprive the prince of his principality and this seems to be the most important lesson to learn from the example of Cesare Borgia.
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