Cesare Borgia

Cesare Borgia, commonly called Duke Valentino, is the book’s fullest example of a ruler who receives power through Fortune but tries to make it his own through Virtù. His rise depended upon Pope Alexander VI and French arms, yet his political achievement lay in recognizing that borrowed support could never provide a secure principality. By reorganizing Romagna, weakening rival factions, cultivating popular allegiance, and building an independent military and diplomatic position, he became the model against which the conduct of a new prince is repeatedly measured. His defeat therefore carries a distinctive irony: the foundations of his power were judged sound, while the final collapse resulted from the extraordinary timing of his father’s death and his own grave illness.

Identity and Political Position

Cesare Borgia first appears as the son of Pope Alexander VI and as the prince popularly known as Duke Valentino. His principality belonged to the category of states acquired through the good fortune and arms of another. Unlike Francesco Sforza, who rose from privacy to become Duke of Milan through ability and strenuous effort, Cesare Borgia obtained his position through the favorable fortunes of his father. That origin made his power unusually vulnerable, because a ruler elevated by another person’s authority risks losing both the support that raised him and the territory that support acquired.

The book does not treat this dependence as proof of personal incapacity. It emphasizes that Cesare Borgia understood the danger and acted with exceptional energy to overcome it. A prince who rises suddenly normally lacks the experience, secure forces, and established foundations needed to withstand the first political storm. Cesare Borgia, however, attempted to construct those foundations after his elevation. His example is valuable precisely because it shows how far intelligence and force of character can compensate for an unstable beginning, even when Fortune ultimately refuses to allow the project to mature.

Cesare Borgia’s position also illuminates a broader distinction between centralized rule and aristocratic fragmentation. The book contrasts governments organized around a single prince and his dependent ministers with kingdoms such as France, where hereditary barons possess their own subjects and local authority. In the latter kind of political order, a foreign or newly established ruler can enter through a discontented lord, but cannot easily retain the country once the same nobles turn against him. Cesare Borgia’s campaign in Romagna therefore becomes an attempt to eliminate precisely this problem: he must prevent rival factions from remaining alternative centers of loyalty.

Rise Through Foreign Power

Cesare Borgia entered Romagna with French auxiliary troops and used the reputation of French arms to secure Imola and Forli. His advance was made possible by the alliance between Pope Alexander VI and Louis XII of France. After Louis XII entered Italy with Venetian encouragement and papal consent, the Pope obtained French troops for his enterprise against Romagna, and the province submitted quickly under the pressure of that military reputation. Cesare Borgia thus began with a decisive advantage, but it was an advantage he did not mistake for permanent security.

The weakness of his initial position became visible when he tried to extend his conquests. He had relied on the Orsini’s arms, but their commitment was uncertain, especially during the enterprise against Bologna after the capture of Faenza. He also discovered that Louis XII could restrict his plans: after Cesare Borgia seized the Dukedom of Urbino and prepared to attack Tuscany, the French King compelled him to abandon the design. These reversals taught him that auxiliary forces and foreign patrons could make conquest possible while leaving the conqueror politically dependent.

Cesare Borgia responded by abandoning reliance on the arms and Fortune of others. He weakened the Orsini and Colonna factions in Rome by drawing their well-born followers into his own service. He made them his gentlemen, provided them with liberal allowances, and gave them commands and offices appropriate to their rank. Within a few months, their old partisan attachments had weakened, while their hopes became centered on the Duke alone. This was not merely a change of personnel. It was a deliberate transfer of loyalty from inherited faction to the new ruler.

His treatment of the rival chiefs combined patience, inducement, and calculated deception. After the Colonna faction had been scattered, Cesare Borgia waited for an opportunity against the Orsini. The Orsini, recognizing that the greatness of the Duke and the Church threatened their own survival, assembled a council at Magione in Perugian territory. The resulting revolt of Urbino, disturbances in Romagna, and wider dangers placed Cesare Borgia in a grave position, but French assistance helped him overcome the immediate crisis.

Once his credit had been restored, he no longer wished to confront the Orsini openly with foreign aid. Instead, he concealed his intentions and used friendly gestures as instruments of political strategy. Through the mediation of Paolo, whom he secured with clothes, money, and horses, he gained the confidence of the Orsini leaders and drew them into his hands at Sinigaglia. After the leaders had been removed and their followers converted into friends, Cesare Borgia possessed Romagna and the Dukedom of Urbino while enjoying the growing goodwill of their inhabitants. The episode presents his political method in its most concentrated form: dependence is replaced by control, and apparent generosity becomes the approach to decisive elimination.

Government of Romagna

Cesare Borgia’s most important administrative achievement followed his conquest of Romagna. He found a province ruled by weak lords who were more interested in plunder than correction. Their government encouraged division rather than union, and the country was filled with robbery, tumult, and every kind of outrage. The problem was therefore not simply that Romagna had a new master. It lacked a political order capable of producing peace, obedience, and a common dependence upon one authority.

To remedy this disorder, Cesare Borgia appointed Remiro d’Orco, a stern and prompt governor, and entrusted him with the fullest powers. Remiro d’Orco restored tranquility and order in a very short time, earning substantial credit for the effectiveness of his rule. The measure was severe, but it answered the immediate problem: a fragmented and violent province required concentrated authority before it could become governable.

Cesare Borgia then recognized that unlimited power, even when effective, could become hateful. Once the emergency had passed, he established a civil tribunal in the center of the province, appointed an excellent president, and ensured that every town was represented by its advocate. This institutional change shifted Romagna from the rule of a single harsh minister toward a more regular form of civil administration. It also allowed Cesare Borgia to separate the benefits of restored order from the resentment produced by the methods used to create it.

He completed that separation through a spectacular act of political theater. Knowing that earlier severities had generated hostility toward himself, Cesare Borgia sought to persuade the population that the cruelty had originated in Remiro d’Orco’s harsh disposition rather than in the Duke. Using this pretext, he had Remiro d’Orco beheaded and displayed in the marketplace of Cesena, with a block and bloody axe beside the body. The spectacle astonished the populace and satisfied it at once. The same ruler who had authorized severe government now presented himself as the judge who had punished its excesses.

This action explains why the book refuses to identify cruelty simply with bad government. Cesare Borgia was reputed cruel, but his cruelty restored Romagna, united it, and brought it to order and obedience. In the book’s comparison, he was more merciful in effect than the rulers of Florence, who, in order to avoid the reputation of cruelty, allowed Pistoja to be torn apart by factions. A few concentrated acts of severity could injure individuals while preventing the wider rapine and bloodshed that disorder would inflict upon the whole state.

From Borrowed Arms to Independent Power

Cesare Borgia’s military development follows the same movement as his political administration: he progressively exchanges dependence for personal control. He first used French auxiliaries to take Imola and Forli. Finding these troops unreliable for his longer purposes, he employed mercenaries, including the Orsini and the Vitelli. When these forces proved fickle, false, and treacherous even under his command, he dismissed them and turned to troops raised under his own authority.

The book treats this transition as visible in Cesare Borgia’s reputation. His standing was weakest when he depended upon French forces alone, improved when he hired the Orsini and Vitelli, and reached its highest point when observers recognized that he was master of his own army and resources. The change mattered not only because native troops were militarily safer. It altered the political meaning of every victory. A conquest made by foreign arms could be credited to the foreign power; a conquest made by forces personally raised and directed by the prince established the prince’s own authority.

The comparison with Hiero of Syracuse reinforces this lesson. Hiero recognized that mercenary soldiers, supplied by men resembling the Italian condottieri, were unusable. Since he could neither retain nor disband them safely, he had them cut to pieces and thereafter waged war with native soldiers alone. Cesare Borgia’s course is less abrupt in the account, but it follows the same principle. A prince who wishes to survive cannot allow the forces that defend him to possess a separate loyalty, command structure, or political interest.

This military principle also clarifies why auxiliary troops are judged more dangerous than mercenaries. Auxiliaries are united and remain under their own officers; their courage can become the instrument of the prince’s ruin. Mercenaries may be inert or cowardly, but they do not immediately possess the same unified authority. Cesare Borgia’s growing reputation therefore came from the moment when his army became an extension of his own power rather than an imported instrument controlled by others.

Collapse, Judgment, and Narrative Significance

After consolidating Romagna and Urbino, Cesare Borgia began searching for new alliances because he could no longer expect further support from Louis XII. The French King had finally recognized the mistake of strengthening him. Cesare Borgia consequently began to waver in his attachment to France while the French were occupied in the expedition into the Kingdom of Naples against the Spaniards, who were besieging Gaeta. His purpose was to secure himself against France, and the book states that he would soon have succeeded had Pope Alexander VI remained alive.

His plans were advancing in the very year in which Alexander VI died. Had they succeeded, Cesare Borgia would have acquired such power and reputation that he could have stood alone, relying on his own strength rather than on the power and Fortune of another. Instead, his father’s death left him with only Romagna consolidated. The rest of his position remained unsettled, two powerful hostile armies threatened him, and he was sick almost to the point of death.

Even under those conditions, the foundations he had laid continued to hold. Romagna waited for him for more than a month. In Rome, though nearly dead, he remained secure while the Baglioni, the Vitelli, and the Orsini came against him without success. He also retained enough influence in the papal election to prevent the accession of any candidate he opposed, even if he could not guarantee the election he desired. His personal vulnerability, rather than the immediate collapse of his institutions, determined the narrowness of his remaining possibilities.

Cesare Borgia later told the narrator that on the day Julius II was created he had foreseen and prepared for everything else that might happen upon his father’s death, but had never imagined that he himself would be at death’s door. This confession crystallizes the book’s judgment of his failure. His political calculations had anticipated hostile factions, foreign intervention, and the succession crisis; they had not anticipated the simultaneous destruction of his own health. The unforeseen convergence of those two deaths and illnesses gave Fortune the victory that strategy had nearly denied it.

The narrator therefore finds no substantial fault in Cesare Borgia’s conduct and presents him as a pattern for rulers who rise through good fortune and the aid of others. His actions exemplify the required combination of force and fraud, friendship and intimidation, severity and affability, generosity and calculated restraint. He sought to remove enemies, conciliate useful allies, command obedient soldiers, transform the established order, and maintain relations with kings and princes so that aiding him appeared profitable and offending him dangerous.

The one explicit criticism concerns the creation of Julius II. Cesare Borgia could not secure every papal election, but he could have prevented candidates who had been injured by him or who would fear him once they became Pope. The book specifically identifies San Pietro ad Vincula, Colonna, San Giorgio, and Ascanio among those who had reason to fear him. The Spanish Cardinals were protected by their connections and obligations, while d’Amboise was protected by the power he derived from relations with the French Court. Cesare Borgia should therefore have worked first for the election of a Spanish Pope or, at minimum, prevented the accession of an enemy capable of destroying his still-unfinished state.

His narrative role is consequently neither that of a simple villain nor that of a conventional heroic conqueror. He is a political case study in the conversion of Fortune into durable authority, and also a demonstration of the limits of that conversion. His apparent cruelty produces unity; his generosity toward factional followers dissolves inherited loyalties; his deception at Sinigaglia secures the political space for institutional government; and his abandonment of foreign arms raises his reputation. Yet the same career ends by showing that even the most carefully prepared foundations remain exposed when the ruler’s power depends on a narrow succession moment and on the survival of the patron who first opened the way.