Urbino occupies a crucial place in the account of how a ruler acquires and secures a new state. Its seizure was not merely an episode of expansion: it revealed the instability of power resting on another prince’s arms, tested Cesare Borgia’s ability to convert conquest into durable authority, and became part of the territorial base that might have enabled him to stand independently had his father’s death and his own illness not intervened.

Acquisition and Strategic Position

Urbino entered Cesare Borgia’s possession during the phase in which he was extending his authority beyond Romagna. With French support, he overcame the dangers created by the revolt associated with the Orsini and their allies, and his seizure of the Dukedom of Urbino gave him an important additional possession beside Romagna. The acquisition also exposed the limits of his dependence on external power. After taking Urbino, Cesare Borgia intended to attack Tuscany, but Louis XII of France compelled him to abandon that design. The episode showed that even a successful conqueror could not freely determine the next stage of his policy while his military position remained tied to a foreign king.

The resistance of Cesare Borgia’s forces to his plans had already become visible in the campaign against Bologna after the capture of Faenza. The Orsini participated reluctantly, and their doubtful fidelity made them a possible obstacle both to further conquests and to the retention of what had already been won. Urbino therefore helped turn expansion into a question of political independence: the more territory the Duke acquired, the more urgently he needed forces and clients that answered to him rather than to the Orsini, the Vitelli, or France.

From Conquest to Consolidation

After the seizure of Urbino, Cesare Borgia resolved to depend no longer on the arms or Fortune of others. He weakened the Roman factions of the Orsini and the Colonna by drawing well-born members of their followings into his own service, providing them with generous allowances, offices, and commands appropriate to their rank. Their older partisan attachments consequently weakened, while their prospects became tied to the Duke alone. This policy treated Urbino not as an isolated conquest but as part of a larger system in which personal dependence was redirected from hereditary factions to the new ruler.

The resulting revolt at Urbino followed the council assembled by the Orsini at Magione in Perugian territory. That conspiracy produced the uprising of Urbino, disturbances in Romagna, and grave dangers for Cesare Borgia. He overcame them with French assistance, but thereafter sought to avoid an open dependence on France or any other foreign power. Through calculated dissimulation and the mediation of Paolo, whom he won with clothes, money, and horses, he drew the Orsini leaders into his hands at Sinigaglia. Once the leaders had been removed and their followers converted into friends, Cesare Borgia held Romagna together with Urbino and had gained the goodwill of the populations of those states, who were beginning to perceive advantages in his rule.

Government, Force, and Political Dependence

The treatment of Urbino belongs to the book’s broader distinction between territories held through a prince’s own power and territories acquired through the resources of others. Cesare Borgia first entered Romagna with French auxiliaries and used them to take Imola and Forli. He then replaced those forces with mercenaries drawn from the Orsini and Vitelli, only to find them fickle, false, and treacherous. Finally, he turned toward troops of his own raising. His reputation increased as he passed from French dependence, through reliance on hired commanders, to control of forces that were his own.

This progression explains why Urbino mattered beyond its territorial size. A possession could be conquered quickly and yet remain politically insecure if the conqueror lacked independent arms, loyal servants, and an administrative structure capable of surviving a change in fortune. The contrast with the centralized government attributed to Darius’s kingdom and to the Turkish state reinforces the point. In such systems, the sovereign’s servants possess authority chiefly by his favor; in a kingdom like France, powerful hereditary lords retain their own standing and can open the way to invasion or lead renewed movements against a conqueror. Urbino, like other acquired territories in Italy, had to be held amid precisely these competing personal and factional powers.

The Unfinished Dominion

At the death of Pope Alexander VI, Cesare Borgia possessed Romagna in consolidated form and had already acquired Urbino, Perugia, and Piombino, while also holding the protectorship of Pisa. His next design was to make himself master of Tuscany. If Pisa fell, Lucca and Siena were expected soon to yield, partly from jealousy of Florence and partly from fear, leaving the Florentines in a desperate position. Urbino thus formed one component of a projected chain of acquisitions that could have placed Cesare Borgia beyond dependence on France and other foreign powers.

That possibility was cut short. Alexander VI died five years after Cesare Borgia first took up arms, leaving Romagna secure but the remainder of his plans unsettled, with two powerful hostile armies nearby and the Duke almost mortally ill. The strength of his position was nevertheless demonstrated by the fact that Romagna waited for him for more than a month and that he remained safe in Rome despite attacks by the Baglioni, the Vitelli, and the Orsini. His inability to complete the consolidation of Urbino and the territories beyond it is therefore attributed not to a failure of judgment or energy, but to the conjunction of his father’s premature death, hostile armies, and his own illness.

Political Significance

Urbino serves as a test case for the difference between possession and security. Its capture enlarged Cesare Borgia’s dominion, but Louis XII’s intervention showed that acquisition remained vulnerable while the Duke relied on foreign arms. The revolt organized by the Orsini demonstrated a second danger: conquered territory could become the stage on which displaced factions attempted to recover their influence. Cesare Borgia’s subsequent recruitment of former partisan nobles, destruction of rival leadership, and movement toward an army of his own transformed Urbino from a prize won by force into part of a more ambitious political foundation.

The territory’s final significance is deliberately counterfactual. Had Cesare Borgia been healthy when Alexander VI died, and had hostile armies not stood behind him, his command of Urbino and Romagna might have supported the independent power he was preparing to build. Urbino therefore embodies both the promise and the fragility of the new prince: it records a remarkable act of expansion, a rebellion overcome, and a foundation not undone by its builder’s incapacity, but left incomplete by Fortune’s sudden reversal.