The death of Pope Alexander VI was the decisive crisis that interrupted Cesare Borgia’s attempt to transform power acquired through papal favor into an independent principality. Alexander’s death removed the political foundation on which Cesare’s authority rested, while Cesare himself was gravely ill and his broader conquests remained unsettled. The episode illustrates the danger of relying on another ruler’s fortune even when extraordinary ability has begun to build durable institutions and military power.

Political Position Before the Death

Before Alexander’s death, Cesare Borgia had made Romagna the firmest part of his dominion. After taking the province from weak lords who had encouraged robbery, disorder, and division, he imposed an effective government and restored tranquillity. His seizure of power had initially depended on the favorable fortune of his father, but he increasingly sought to replace that dependence with authority of his own. He discarded French auxiliary forces, abandoned mercenary commanders when they proved fickle and treacherous, and raised troops under his own control. His reputation grew as he became visibly master of his own arms.

Cesare also understood that territorial conquest would not be enough if the papal succession could undo it. He therefore planned against the possibility that a new head of the Church might be hostile and might try to strip him of the possessions Alexander had granted. His preparations included eliminating the surviving kin of dispossessed lords who might serve a future pope, winning over the Roman nobility, bringing as many members of the College of Cardinals as possible under his influence, and consolidating his authority strongly enough to withstand the first shock after Alexander’s death.

The Crisis and Its Immediate Effects

When Alexander died, Cesare had completed three of these four measures and had nearly completed the fourth. He had killed almost all of the reachable relatives of the lords whose territories he had taken. He had gained the support of the Roman nobles, and a majority in the College of Cardinals stood on his side. His position was therefore not empty or improvised: it rested on violence, patronage, military reform, and political preparation.

Yet the timing of the death turned those achievements into an emergency. Cesare was left with Romagna consolidated but with the rest of his intended state unsettled. Two powerful hostile armies were pressing against him, and he was sick almost to the point of death. His predicament exposed the difference between having foundations and having enough time to build upon them. Alexander’s death did not instantly erase Cesare’s power, but it deprived him of the protection and political leverage that had allowed his project to expand.

The danger was especially acute because the papal election could determine whether his enemies obtained the institutional authority to attack him. Cesare later said that, on the day Julius II was created, he had foreseen and prepared for every consequence of his father’s death except the possibility that he himself would be at death’s door. His failure was thus presented not as a lack of foresight in general, but as a catastrophic blind spot concerning his own physical condition.

Cesare’s Intended Response

Even before the crisis, Cesare had begun to loosen his attachment to France because he could no longer expect further support from Louis XII of France. France was occupied with its expedition against the Spaniards in the Kingdom of Naples, while the French were losing that kingdom and both rival powers needed Cesare’s friendship. He therefore explored new alliances and sought to secure himself against France. Had Alexander lived, the evidence suggests that this policy would soon have succeeded.

Cesare’s larger ambition was to become master of Tuscany. He already possessed Perugia and Piombino and had assumed the protectorship of Pisa, which he was preparing to attack. Once Pisa fell, Lucca and Siena were expected to yield, partly because of their jealousy of Florence and partly because of fear. Florence would then have faced a desperate strategic position. These plans show that Alexander’s death occurred at the very moment when Cesare’s territorial project seemed to be approaching a decisive expansion.

Had he completed these designs, Cesare would have acquired enough power and reputation to stand independently, relying on his own resources rather than on the fortune and arms of others. The death of Alexander therefore interrupted a transition already under way: Cesare was moving from being the beneficiary of papal power to becoming a prince who could survive without it.

Survival After Alexander’s Death

The crisis did not immediately destroy Cesare. Romagna waited for him for more than a month, a sign that the province’s obedience was not merely the temporary effect of his father’s authority. Although almost mortally ill, he remained safe in Rome. The Baglioni, the Vitelli family, and the Orsini came against him but failed to achieve their purpose.

Cesare also retained enough influence over the papal election to prevent the elevation of any candidate he disliked, even if he could not ensure the election of anyone he preferred. This limited capacity mattered because it showed that his political network had survived Alexander’s death to some degree. Had Cesare been healthy, the narrator concludes, the remaining difficulties would have been manageable. His illness, combined with the presence of hostile armies and the unfinished condition of his state, converted a potentially survivable succession into a fatal interruption.

Historical and Political Significance

The event serves as the book’s clearest example of a prince who rose through the fortune and arms of another but understood the need to create his own foundations. Cesare Borgia is treated as an exemplary new prince not because his enterprise succeeded, but because he acted with unusual energy and intelligence to make success independent of his father. His failure resulted from the shortness of Alexander’s life and the extraordinary malignity of Fortune rather than, in the narrator’s judgment, from a major error in his political conduct.

The death also reinforces the contrast between Cesare’s case and Alexander the Great’s conquest of the kingdom of Darius. Alexander the Great could secure Asia after Darius’s death because the conquered kingdom was organized around a single ruler and his servants; once the ruling family was removed, no independent nobility remained with enough popular attachment to renew resistance. Cesare faced a more unstable environment, where papal succession, Roman factions, foreign armies, and local powers could all reshape the balance of power. The event consequently demonstrates that even well-designed political foundations remain vulnerable when their builder depends on a narrow opportunity and is struck down at the moment of transition.