21

Alone

Cesare, when his luck appeared to have pretty much run out, would tell Machiavelli that at the great crisis of his life, when everything was at stake, he had been prepared for everything except what actually happened.

That climactic crisis, which not only followed Cardinal Castelli’s garden party but was a direct consequence of it, was presaged by an event so odd that it has been remembered ever since in spite of being essentially meaningless. On the day after the party, an owl flew into the papal apartments through an open window, fell dead, and was declared by Alexander to be an “evil omen.”

An omen of what? First came other harbingers, followed in short order by the thing itself. On August 7, the day after the episode of the owl, the Venetian ambassador paid a routine call on the pope and found him wrapped in a shawl in spite of the punishing heat and in uncharacteristically low spirits. He fretted not only about official business—especially the imponderable consequences of the new war for Naples—but also about such things as the growing number of lives being claimed by that year’s summer fevers. All this was unusual enough for the ambassador to make note of it in his report. He made no mention, however, of Cesare; presumably Valentino was not present, occupied with preparations for his return to the north.

On August 11, the eleventh anniversary of Alexander’s election, Cardinal Castelli fell seriously ill. On Saturday the twelfth, exactly a week after the party, the pope rose as usual, said mass, breakfasted, vomited, and returned in distress to his bed. Cesare, on the verge of departing the city, was struck down by the same symptoms at almost exactly the same time. He managed to make his way to his quarters directly above Alexander’s apartment before collapsing. He appeared to be the more dangerously afflicted of the two. The pope lay in silence after ordering the Vatican barricaded, feeling well enough, after a few days, to sit up and watch some of the cardinals attending him play cards at his bedside. Cesare, by contrast, became so alarmingly feverish that he was stripped naked and lowered into a huge oil jar filled with cold water; his skin was reported to have peeled as a result. He was in a state of delirium when, on the seventeenth, Alexander took such a severe turn for the worse that his physicians were soon declaring him to be beyond hope. After receiving the last rites, he died a solitary death on the night of August 18. The servants attending him, terrified, stripped the pontifical apartments of everything of value (even the throne disappeared) and vanished into the dark streets. Long before sunrise the people of the city knew what had happened and were coming together in rowdy clusters, looking for Spaniards to attack and rob.

Cesare’s patron, the man who had made everything possible, was gone. It was a blow, obviously, and it called for an immediate response. But Cesare had long anticipated that such a thing not only could happen but was certain to happen sooner or later. And he had long been prepared—not for the pope’s fall from hearty good health into his grave in less than two weeks in August 1503, specifically, but certainly for his removal at some unforeseeable point, and so for the day when he, Cesare, would be entirely on his own. Everything he had done since casting aside the red hat can be seen as preparation for that day: the hurry to carve a principality out of the Papal States; the destruction of the warlords of the Romagna and elsewhere; the building up of an army superior to any the other Italian princes could put in the field; the uprooting and scattering of the Roman barons; and the loading of the College of Cardinals with Borgia loyalists.

The vigor and thoroughness with which Cesare pursued all these objectives was one of the things that Machiavelli found admirable about him. By achieving all of them, he had positioned himself to act swiftly whenever the pope did finally die or become incapacitated, and to deal decisively with whatever obstacles might rise up in his path. What undid all these preparations—what he didn’t foresee and could hardly have prepared for had he somehow foreseen it—was that when Alexander exited the stage, he himself, Cesare, would be in a state of total helplessness.

His one great stroke of luck on the night of the pope’s death was the presence in the Vatican of the most ferociously loyal of his Spanish companions, Michelotto Corella, who had raced from his base at Perugia upon learning of Cesare’s illness. Without Michelotto, all might have been lost. Alexander had been dead only minutes when, accompanied by armed retainers, Michelotto burst into the papal apartments and demanded access to the locked inner chamber that had served as Alexander’s strongbox. When the cardinal responsible for the security of that chamber refused, Michelotto put a dagger to his throat and offered a simple choice: hand over the key or die. Chests that must have contained no less than a hundred thousand ducats, possibly much more, were then hauled upstairs to Cesare’s sickroom. Guards were posted under the alternating supervision of Michelotto and Jofrè Borgia, and all settled in to wait for Cesare to recover or die.

He recovered, but at a maddeningly slow pace, and while he was doing so Rome descended into madness. The remnants of the old baronial clans came rushing back to reclaim the properties that the Borgias had taken from them, and to settle scores. Twelve hundred men led by Fabio Orsini, vengeful son of the strangled Paolo, fanned out through the streets on the other side of the Tiber from the Vatican, setting fire to the homes and places of business of the city’s Spaniards, assaulting any “Catalans” they could lay hands on and killing several. Fabio—whose wife was a Lanzol Borgia—declared that he would not be satisfied until he had washed his hands and face in Borgia blood. Outside the city it was much the same: displaced Orsini and Colonna and Savelli with murder in their hearts jostled with one another to take back what they had thought lost forever and bring ruin to their foes.

In the midst of these horrors it was necessary to get the dead pope buried, and the funeral obsequies were themselves tinged with horror. A fight over silver candlesticks broke out between monks carrying Alexander’s body from the palace to St. Peter’s Basilica and the guards assigned to protect them, so that the corpse was dumped on the ground and for a time abandoned. By the time it was laid out for public viewing, it had swelled up grotesquely and turned dark, a black distended tongue protruding from the mouth. In the end brute force had to be used to cram it into its coffin like an overstuffed sack of rotting potatoes.

From the start and as usual there was much talk of poisoning. Because whenever the Borgias figured in gossip of this kind they were cast as the villains, this time it was necessary to explain how Alexander and Cesare were murderers and victims at the same time. As the most popular account had it, the two of them had intended to murder their host Cardinal Castelli but had somehow lost track of which goblets of wine were safe and ended up inadvertently poisoning themselves. Why had a full week passed before they fell ill? We have encountered this question before, and the answer that has come to be accepted by the whole world. The Borgias not only knew how to brew a poison unavailable to the rest of the world, they could administer it in such ways as to take effect immediately or weeks later.

The truth of the matter is obvious and simple. Cardinal Castelli, Pope Alexander, and Cesare were all infected, and the pontiff was killed, by the malaria-bearing mosquitoes of the Tiber valley. It happened in a city notorious for its midsummer epidemics, during an August when even more people than usual were dying. As a priest at the Vatican wrote four days before Alexander’s death, “It is not surprising that His Holiness and His Excellency should be ill, because every single outstanding man in this court is either ill or else sickening, especially those of the palace, owing to the bad condition of the air.” All the recorded symptoms of the two Borgias are consistent with a diagnosis of tertian malarial fever. As for that Borgia poison with its quasi-magical properties, five centuries later the world is still waiting for someone to rediscover it.

As Cesare recovered consciousness, he was made aware that the armies of France and Spain now loomed over Rome like a pair of watchful vultures. A French force commanded by one of La Trémoille’s condottieri, Francesco Gonzaga, marquess of Mantua (Lucrezia’s brother-in-law by virtue of his marriage to her husband’s sister), had broken off its march toward Naples upon learning of Alexander’s death. It was camped at Viterbo north of Rome, awaiting developments; the sudden prospect of a papal election, and the hope of installing his chief minister Cardinal d’Amboise on the pontifical throne, had altered Louis XII’s priorities considerably. The Spaniard Gonsalvo, meanwhile, was shifting his forces northward after securing the city of Naples. Some of those forces were laying siege to the port city of Gaeta, essential to the ability of the French army to resupply itself in southern Italy, while others prepared to meet La Trémoille’s offensive. With that offensive now in abeyance, Gonsalvo too shifted his focus to Rome and to the question of the papal succession.

Cesare, from his bed in the Vatican, sent messages to the commanders on both sides, keeping his options open by giving each the impression that the writer was his special friend. His communications with Gonsalvo were entrusted to his private secretary, Agapito Geraldini, whom he authorized to enter into any agreement that seemed sufficiently advantageous. It happened that Geraldini reached the Spanish headquarters at almost the same time that two of Gonsalvo’s most valued condottieri, the same Fabrizio and Prospero Colonna who had helped him win the Battle of Cerignola four months earlier, requested permission to pull their troops out of the siege of Gaeta and take them temporarily to Rome. They knew of the disorder there, and they wanted to reclaim the palaces and estates that the Borgias had taken from them while the opportunity was open. Their request could hardly have been more timely from Gonsalvo’s perspective, and it set the wheels of intrigue turning. He not only consented but gave the Colonna some of his own troops to augment theirs, instructing them to attend to several matters on his behalf while in Rome. They were to offer protection to the city’s Spanish residents and make a sufficient show of force to keep the cardinals from feeling intimidated by the proximity of the French army as they undertook the business of electing a new pope. Also—Gonsalvo got Geraldini’s assent to this—as soon as Cesare was strong enough to travel, the Colonna were to escort him southward to Naples. All this having been agreed, Gonsalvo dispatched twelve galleys northward to secure the port of Ostia at the mouth of the Tiber, to keep it from falling into French hands.

Adding to Cesare’s torments, news was reaching the Vatican of the accelerating disintegration of his little empire. Like ravenous wolves moving in on crippled prey, the signori of Venice were helping Guidobaldo da Montefeltro to make yet another happy return to his ancestral seat at Urbino, Giovanni Sforza to reclaim the lordship of Pesaro, and Pandolfo Malatesta to take possession of his family seat at Rimini. Florence for its part was abetting the restoration of the Varani in Camerino and Jacopo d’Appiano in Piombino, and the Baglioni had returned to Perugia. Imola was fighting off an attempted return of the Riarii—a result of the loyalty to Cesare that had taken root in the heart of the Romagna. Cesena too was standing firm, along with several smaller strongholds. Elsewhere, for example at Faenza and Forlì, the Borgias’ Spanish captains had been forced to withdraw into their rocca and defy demands for their surrender.

Cesare once again seemed doomed. In far-off Ferrara, where she was reported to have gone half-mad with grief upon learning of Alexander’s death, Lucrezia was trying to muster help for her brother. But her father-in-law, Duke Ercole d’Este, wanted nothing to do with the problems of his son’s wife’s brother, especially as becoming involved could have put him once again at odds with Venice. His son Alfonso likewise took no interest.

In the absence of a pope, the College of Cardinals was responsible for governing Rome. Though its members also had to organize a conclave, they were unwilling to do any such thing with Cesare ensconced in the Vatican, much of the city in the hands of thugs, and two foreign armies looking on threateningly from the sidelines. The cardinals refused even to enter the Vatican so long as Cesare remained there, using as their base the Church of Santa Maria Sopra Minerva on the other side of the Tiber. To break the impasse it was going to be necessary to get Cesare out of the city. Only then might Gonzaga be persuaded to withdraw his French forces, Gonsalvo to do the same with the Spaniards, and the baronial gangs to disband. The Venetian ambassador took the lead, calling on Cesare and probing for a basis on which to negotiate his departure. As the days passed, the ambassador was joined by the Italian cardinals—the Spanish contingent was too loyal to Cesare to be of any use—and by the ambassadors of France, Spain, and the Holy Roman Empire. Finally the pressure became irresistible, and at the end of August Cesare promised that he would depart within three days and swear loyalty to the Sacred College. But only if certain conditions were met. He insisted on retaining his position as captain-general of the papal army until the election of the next pope, and on receiving a pledge from Venice to remove its troops from the Romagna. Once this was agreed, it became possible to get commitments from the French and Spanish to keep not only their own troops but the Orsini and Colonna far enough from Rome for the cardinals to gather in conclave without feeling under duress. Cesare, forced to accept that he could not be in Rome when Alexander’s successor was elected, did what he could to ensure that the deadliest of his enemies would be absent as well: he sent riders northward with instructions to intercept Cardinal Giuliano della Rovere as he came southward from Avignon and keep him from proceeding farther.

It was a diminished Cesare Borgia who, on September 2, rode out of the Vatican surrounded by two hundred mounted knights dispatched by Michelotto to serve as his personal guard. No longer astride a prancing charger as in the past, this time he traveled as an invalid concealed behind the curtains of a litter borne on the shoulders of eight stout retainers. He had lost much weight, his feet were grossly swollen, and three weeks after first falling ill he continued to be racked with headaches. A bizarre assortment of his relatives—his mother Vannozza, a couple of his bastard daughters with their mothers, his sister-in-law and onetime mistress Sancia, Lucrezia’s little son Rodrigo, the even littler Infant of Rome, and an equally mysterious newborn called Rodrigo Borgia who was inevitably rumored to be the late pope’s bastard but was more likely another of Cesare’s—had been sent on ahead. They awaited him, under guard, at the papal town of Civita Castellana, the rocca of which Alexander had recently expanded and reinforced.

As Cesare set out from the Vatican, Prospero Colonna with a body of his soldiers waited for him on the other side of the Tiber. In the days preceding, communicating through intermediaries, the two had arrived at an understanding: they would combine forces and attack the Orsini who had been ravaging Rome, destroying them if possible and at a minimum driving them from the city. They would then go south, joining Gonsalvo and his Spanish army. The properties that Pope Alexander had taken from the Colonna and given to Lucrezia’s son Rodrigo would be restored to them, and the boy would be betrothed to a Colonna girl. But Cesare had been negotiating with the French as well, trying to maintain his options. Before crossing the river he managed to slip away, litter and bearers and all. Instead of joining Colonna, he made his way northward to Nepi, near an encampment of French troops.

There is some evidence that, in going north instead of south, Cesare was following the advice of his astrologers. Be that as it may, the decision was understandable in pragmatic terms. The French rather than the Spanish had it within their power to help him with his most pressing problems—especially the disintegration of his new duchy of Romagna. And Louis XII showed himself willing to be helpful. He ordered the rebellious cities to submit to their Borgia governors, and they quickly began to comply. Venice, seeing that the game it had been playing was up, withdrew and left its Romagnese clients to fend for themselves. Florence, in an almost comically hasty reversal of its recent boldness, declared its allegiance to the duke of Romagna. With numbing speed, Cesare’s situation became no longer hopeless. The Colonna, understandably, felt that Cesare had betrayed them, and Gonsalvo had reason to feel the same.

All eyes turned now to Rome and the business of choosing a pope. Cardinal Giuliano della Rovere succeeded in reaching the Vatican in spite of the efforts of Cesare’s agents to intercept him on his way south. Immediately he set about recruiting support. Cardinal Georges d’Amboise arrived as well and began campaigning on his own behalf. He was accompanied, to general astonishment, by Cardinal Ascanio Sforza, who had persuaded Louis XII to release him from prison by promising to use his experience and connections on Amboise’s behalf. Once free and in Rome, however, Sforza showed himself to be interested in no one’s candidacy except his own. The result was one of the most impenetrably complicated conclaves in generations, one that all the powers of Europe tried to turn to their own benefit but in which no one had more at stake than Cesare Borgia. The outcome would determine whether he would, at this decisive point, be able to draw upon enough papal support to save himself from ruin.

Ferdinand of Spain had entertained hopes of getting another of his countrymen elected. When it became clear that the Italian cardinals would never allow this, he settled for using his influence to block the candidacy of Cardinal della Rovere, whom he regarded, understandably if not quite correctly, as an agent of France. This freed the eleven Spanish cardinals present to do as they wished, so long as they continued to shun della Rovere. To a man they now took their direction from Cesare, to whom a number of them were related and several others owed their red hats. With only four French cardinals voting, Louis XII had to forget about winning the throne for d’Amboise. The power to decide should have rested with the conclave’s twenty-two Italian members but, as had happened before, they were too divided to form an effective bloc. The result was reminiscent of the election of Alonso Borgia almost half a century before. Deadlocked, the cardinals finally cobbled together a two-thirds majority by turning to the darkest of dark-horse candidates, an innocuous figure in such markedly feeble health that there was no possibility of his living more than a few years.

This was Francesco Todeschini Piccolomini, only sixty-four years old but so decrepit as to be incapable even of kneeling. Son of a sister of Pope Pius II, who had given him his red hat and whose surname he had taken, in forty-three years as a cardinal he had shown himself to be honest, well intentioned, and kindly, free of scandal and devoid of political ambition. He had also always been on good terms with the Borgias, which turned out to be a decisive factor: the Spanish bloc provided the votes that gave him the election. There could scarcely have been a better outcome for Cesare. Pope Pius III took office knowing that he could not have been elected without the support of his Spanish colleagues and, behind them, of Cesare himself.

News of the election of an Italian was received with joy in the streets of Rome. But it disgusted the French, who sullenly broke camp and resumed their advance on Naples, taking with them soldiers Cesare had hoped to use in the Romagna. Gonsalvo recalled Fabrizio and Prospero Colonna from Rome and, partly out of need but also partly in retaliation, sent orders for Cesare’s Spanish troops to detach themselves from his service and come south. Most of the Spaniards obeyed, Gonsalvo’s position as viceroy and Cesare’s reconnection with the French making it virtually treasonous to do otherwise. Cesare thereby lost at a stroke most of his army including all of its heavy cavalry. The ever-faithful Michelotto, however, chose to remain. Cesare found himself almost alone at Nepi and without the means to make war on anyone. Exposed and vulnerable, fearful of an attack by the resurgent Orsini, he sent a message to Pius III asking permission to return to Rome.

The pope, who in response to complaints from Cardinal della Rovere would later claim to have believed that Cesare was dying, agreed to his return after receiving Louis XII’s approval and Cesare’s promise to keep the peace in the Romagna and elsewhere. Further demonstrations of papal favor followed. Pius sent an exhortation to the people of the Romagna, urging them to accept Cesare’s lordship. He echoed the French king’s warning to Venice not to meddle in Cesare’s domains, and declared his intention to keep Cesare as gonfalonier of Rome.

There were now more claims on Cesare’s time and attention than he would have been able to respond to if he had been in good health, which he was not. He badly needed to visit the Romagna, to reassert his authority there and see to it that his garrisons were properly deployed and his administration still functioning. But he no less urgently needed to be in Rome, where enemies in abundance were doing their best to poison the pope’s mind against him, and he had nothing to counterbalance their slanders except the force of his own personality and—he had to hope—Pius’s friendship and sense of obligation. He was burning through his reserves of cash at an unsustainable rate, many of his remaining troops were Romagnese amateurs who wanted to go home, and it was largely out of hatred for him that the Orsini chose this most awkward of moments to sever their connections to the French court and join forces with the Colonna and Gonsalvo.

Taking his menagerie of a family with him, Cesare left Nepi in time to be on hand for Pius III’s coronation on October 8. It was, for him, an event worthy of celebration: the pontiff confirmed him in all his vicariates and as gonfalonier and installed him in the palace of his brother-in-law, Cardinal Ippolito d’Este, absent from Rome since making himself a target of Borgia anger by becoming sexually involved both with Sancia and with Cesare’s favorite mistress. But the streets were still out of control, and neither Pius nor Cesare had nearly enough troops to restore order. Clearly the city was no safer than Nepi had been—much less safe, actually, with Orsini, Colonna, and Savelli gangs roaming the streets unrestrained. Cesare decided that it was necessary to move on again. And so he gathered up his dependents and his soldiers and set out for the north. Their immediate destination was Soriano, a hilltop town east of Viterbo that Michelotto had been sent ahead to secure and where he was now waiting with his troops. Before they could get out of Rome, however, they were headed off by a superior force of Orsini and obliged to turn back. They scrambled to the safety of the Castel Sant’Angelo through the covered passageway that Pope Alexander had improved for just such a purpose. Upon learning that his palace in the Borgo district was being pillaged and put to the torch, Cesare dispatched a messenger with orders for Michelotto to bring his men back to Rome with all possible speed.

Cesare was for all practical purposes a prisoner in the Castel when, on October 18, the world was informed of the death of Pius III. Eighteen days had passed since Pius’s election, only ten since his coronation. This time the usual rumors of poisoning could not plausibly be focused on Cesare, the death being so obviously a devastating setback for him, so suspicion settled on della Rovere instead. The cardinal could not have cared less. He had been hungering for the papacy since long before losing the election of 1492 to Rodrigo Borgia, and the passing of the years had done nothing to dull his appetite. Now, after long years of exile, he was at the Vatican as the politicking that always preceded a conclave got under way, determined that this time the prize would not slip out of his grasp.

The troubles that invariably erupted with the death of a pope were rarely more alarming than at this juncture. The descent of Rome into lawlessness could have surprised no one, but the speed with which all Italy seemed suddenly to be veering toward war was truly extraordinary. On one side were Louis XII’s France along with his duchy of Milan, Florence and an assortment of minor warlords, and Cesare. Opposing them were Naples under Gonsalvo, supported by the Orsini and the Colonna. Venice was formally unattached but a source of trouble all the same. Its obvious eagerness to seize the Romagna made it in every practical sense the adversary of France, Milan—and Cesare.

The Florentine authorities, justifiably worried, dispatched Machiavelli to Rome to observe, report, and seek opportunities to advance their interests. Upon arrival, on October 27, he found himself in a city in such disorder that when an envoy from Cardinal Giuliano della Rovere paid him a welcoming call, he arrived with a guard of twenty armed men. In the midst of the general mayhem, della Rovere was deploying all the resources at his disposal to ensure that when the papal conclave opened, he would enter it as an irresistible force.

For this to happen he needed the Spanish cardinals, which meant that he needed Cesare. Using the Venetian ambassador as an intermediary, he therefore promised to have all the forces of the Orsini removed from Rome if Cesare would come out of the Castel Sant’Angelo long enough to meet with him at the Vatican. Cesare agreed, the meeting took place, and a deal was struck. Della Rovere pledged that, in return for the votes of the Spanish cardinals, he would confirm Cesare as vicar of all the places bestowed on him by Alexander VI and later by Pius III. He would also reappoint him as gonfalonier, and the daughter Cesare had never seen, the now-three-year-old Louisa, would be betrothed to the thirteen-year-old Francesco della Rovere, son of the cardinal’s deceased brother and, as nephew of the childless Guidobaldo da Montefeltro, designated heir to the duchy of Urbino.

This settled the papal election. Two days after his meeting with Cesare, della Rovere was chosen to succeed Pius III in the shortest conclave in history. He had left nothing to chance, bringing into play all the political and financial weapons at his disposal including a willingness to threaten every cardinal susceptible to intimidation and to buy the votes of the greedy. Having achieved the dream of his life, as Pope Julius II he continued to brim over with ambitions unfulfilled. In a decade on the throne, this violent, irascible character would turn himself into one of the epic figures of the Renaissance and one of history’s legendary popes. He would be remembered as a reformer in spite of systematically selling offices and benefices and allowing his courts to be corrupted, and would be honored for a restrained use of nepotism that was made easier by the things his uncle Sixtus IV had already done to enrich their kinsmen—and the fact that only one of his illegitimate children, a daughter, lived to adulthood.

Machiavelli, learning of the bargain by which Cesare had ensured della Rovere’s election, expressed astonishment at Cesare’s willingness to trust the promises of a man whose relationship with the Borgias had always been laced with disappointment and resentment, hatred and deceit. And who, as pope, now held most of the cards. He concluded that Cesare somehow did not understand that in the new pope he was faced with someone whose intelligence, strength, and ruthlessness were at least the equal of his own—and who hated him.

When Cesare and Machiavelli had what appears to have been their first Rome meeting, five days after the pope’s election, news had just arrived that the city of Imola was in revolt against its Borgia governor and that Venice was preparing to attack Faenza. Cesare was in a rage. He blamed the Florentines for allowing Venice freedom of movement in the Romagna, warning that Venetian domination of the region would end in Florence’s ruin. “He spoke with words full of poison and anger,” Machiavelli reported. “I could easily have argued with him, and replied to his charges, but I thought it best to try and calm him down, before managing as best I could to break off the interview, which felt as if it had gone on for a thousand years.” This episode marks a change in Machiavelli’s attitude toward Cesare—the point where he ceases to be as admiring as he had been before. It also, not coincidentally, shows Cesare losing the self-possession that had long been one of his most striking traits. Perhaps it marks the beginning of his psychological disintegration. From this point forward his moods will swing violently and unpredictably, to the alarm of his friends and the satisfaction of his enemies.

Two things were becoming clear. First, that Julius had no priority more urgent than that of making himself master of the Papal States, starting with the Romagna because of Venice’s encroachments there. Second, that he possessed neither the money nor the manpower to do what he wished. In this lay Cesare’s hope: that the pope would use him as the means to accomplish this objective. If in such a role Cesare could not hope for the independence and importance that he had enjoyed under Alexander and that he might have recovered if Pius III had lived, it would enable him to remain one of Italy’s leading soldiers and give him continued access to money and power. In the long term, Julius being more than twice his age, Cesare could expect to outlive him and possibly his successor and even his successor’s successor, perhaps rising to the kinds of heights achieved in the previous century by those master condottieri Francesco Sforza and Federico da Montefeltro. Julius encouraged him to think so, going so far as to invite him to return to his apartments in the Vatican.

That the pope’s friendship was without substance soon became clear. Just nine days after the election, Cesare attended an open consistory in the expectation of being reappointed gonfalonier. When nothing of the kind happened and no explanation was forthcoming, he decided that the time had come to return to the Romagna and see to the security of Cesena, Faenza, Forlì, and the other strongholds that his captains still held there. With the troops he still had in and near Rome and those waiting for him in the north, he could hope to hold off the Venetians and possibly drive them out. He and Machiavelli met just hours after the consistory, and Cesare proved to be in such good spirits that Machiavelli was surprised. The duke had a plan now: to move the southern parts of his army, reportedly consisting at this point of only three hundred light cavalry and four hundred foot, into Tuscany and from there on to the Romagna, where he would link up with Michelotto and his men. To cross Tuscany safely with such a modest force, however, he would need a guarantee of safe conduct from Florence. Some of his restored confidence is explained by the fact that the pope had promised to write to Florence, demanding that it agree. Cesare’s aim, as Machiavelli understood and reported it, was simple and clear.He intended to “prevent the Venetians from becoming masters of the Romagna,” something that he was now capable of accomplishing because “the pope is ready to assist him.”

All this was going to require money. Cesare needed what remained of the treasure that had been confiscated the night Alexander died—it was now with Michelotto at Cesena—as well as the sums on deposit with banking houses in Genoa. The Genoa funds probably amounted to something on the order of two hundred thousand ducats, enough to finance military operations on a large scale for half a year or more, a time period in which almost anything might be accomplished. To get access to them, however, Cesare needed to go to Genoa in person, and doing so speedily was going to require travel on horseback—through Tuscany.

Thus the shock that Cesare experienced, and failed to conceal, upon learning on November 14 that the Florentine council had voted overwhelmingly to deny him the safe conduct. It had good reasons for doing so, starting with memories of Cesare’s past conduct in Tuscany and fear of what he might do if given a second chance, but it probably also acted with the oblique encouragement of the pope. In all likelihood Julius had let it be known in Florence that he did not expect Cesare’s request to be taken seriously.

People who saw Cesare at this time wrote of encountering a changed man. His cousin Francisco Lloris y de Borja, a lifelong friend and one of the last cardinals created by Alexander VI, reported that he seemed “out of his mind, for he knew not himself what he desired to do, so involved and irresolute did he seem.” Another newly minted cardinal, the same Francesco Soderini whose secretary Machiavelli had been when the two called on Cesare after his capture of Urbino, described him now as “changeable, irresolute, and suspicious.” Cesare was not, however, entirely without hope or incapable of making plans. He sent instructions to Michelotto to move his part of the Borgia treasure from Cesena to Ferrara, where Lucrezia, presumably, would be able to keep it safe.

Cesare’s claims on the Romagna, Venice’s interference in the region after Alexander’s death, the return of some of the warlords earlier expelled by Cesare—together these things presented Pope Julius with the first great crisis of what was going to be another extraordinarily eventful reign. The question was whether the pope should make Cesare a junior partner or cast him aside along with his money, his troops, and his connections. It came down to a judgment as to whether Cesare could be depended upon to serve the pope’s interests at least as assiduously as he was sure to pursue his own.

Probably Julius would have decided to get along without Cesare; he would show repeatedly, throughout his reign, that he had no interest in sharing what he regarded as rightfully belonging to the Church with anyone. In any case he didn’t have to decide; Cesare resolved the matter for him by abruptly leaving Rome and galloping downriver to Ostia, where he boarded one of the papal galleys and ordered its captain to take him up the coast to Genoa. The captain in question, unfortunately for Cesare, was a della Rovere loyalist and a suspicious one. Instead of putting to sea, he took Cesare into custody and sent a messenger racing back to Rome to inform the pope. Again everything was suddenly going wrong: the same developments in the Romagna that had driven Cesare to depart for Genoa—resumed aggressiveness by Venice above all—were emboldening Julius to take a firmer line. He dispatched a delegation of trusted cardinals to Ostia, where they presented Cesare with a list of demands. Julius insisted that Cesare surrender all his vicariates, returning them to direct rule by the Church. He was to reveal the secret passwords, the countersigns, that the Spaniards commanding his remaining Romagna rocca were insisting on hearing as proof that Cesare really did want them to surrender. Cesare refused and by doing so sealed his fate.

Julius sent the entire papal guard to Ostia to bring Cesare back to the Vatican, where he was given comfortable rooms ordinarily reserved for visiting cardinals. Gian Giordano Orsini urged the pope to have him killed, but Julius was in no hurry to do away with someone in possession of so many valuable secrets. Shortly after his return to Rome, Cesare learned that Michelotto had been attacked while transferring his hoard of Vatican gold to Ferrara and was now a prisoner. Almost simultaneously a smaller caravan of Borgia treasure, this one bound for Ferrara from Rome, was seized in Tuscany by Giovanni Bentivoglio. Instead of returning it to the Vatican, Bentivoglio locked it up in his own palace at Bologna. Cesare offered ten thousand ducats for the release of Michelotto and was refused.

Cesare by this point was giving evidence of falling apart under the weight of failure and fear. His sending of representatives to Florence to negotiate a condotta—Cesare’s agents were told to inform the signoria that he would soon be in Tuscany at the head of an army—struck Machiavelli as not just pathetic but evidence that the duke he had once admired so deeply was losing touch with reality. Julius intensified the pressure by announcing his intention to conduct investigations into the deaths not only of Lucrezia’s husband the duke of Bisceglie but of Cesare’s brother Juan, Giulio Cesare Varano of Camerino and his three sons, Astorre Manfredi of Faenza, the last Gaetani lord of Sermoneta, and others. His zeal for incriminating evidence caused him to have Michelotto brought to Rome and, along with other Borgia retainers, put under torture. Cardinal Lloris again visited Cesare and found him so “confused” and “irresolute” that he appeared to have “lost his wits.”

The last weeks of 1503 and the first of 1504 were marked by Julius II’s relentless but unsuccessful efforts to get the passwords out of Cesare and the stubborn refusal of Cesare’s Romagna lieutenants to surrender their rocca. The loyalty of those lieutenants almost defies belief. At one point, having somehow learned the password for Cesena, the pope gave them to a Borgia attendant named Pedro d’Oviedo and sent him off with instructions to induce the two men in command there, the brothers Pedro and Diego Ramires, to open their gates. The brothers’ response was to seize Oviedo, torture and kill him, and put his body on display. They would never surrender, they declared, until they knew that Cesare was free. Julius, when he learned of this, was convinced that the Ramires were acting on secret instructions from Cesare himself. The Spanish cardinals had a hard time dissuading the pontiff from throwing Cesare into a dungeon in the Castel Sant’Angelo. He consented to having the prisoner moved instead to the Borgia Tower, to the chamber in which Bisceglie had been strangled years before. The torture of Michelotto and others, meanwhile, was adding to the pope’s frustration by producing nothing of use.

After many weeks of fruitless discussion, the leader of the Spanish cardinals in Rome, a onetime protégé of Alexander VI named Juan de Vera, managed to broker an agreement that ended the deadlock. Vera had intervened on behalf of Ferdinand of Spain, who had just become undisputed master of the entire kingdom of Naples thanks to a fresh round of victories by Gonsalvo and wanted papal approval of his conquests. Julius for his part was now focused on driving the Venetians out of the Romagna, where they were eagerly gobbling up territory, and to accomplish that he needed possession of Cesare’s remaining strongholds. Cesare was driven to deal not by any strategic considerations—he no longer possessed the means to play that game—but by a simple, desperate wish to be released. He agreed to order all his commanders in the Romagna to surrender in return for his freedom and the right to keep his movable property—particularly the gold still held for him in Genoa.

In mid-February, in the custody of Spanish cardinal Bernardino López de Carvajal, Cesare was taken from the Vatican to the Tiber for transportation to Ostia. There is a poignant description of him, while awaiting the galley that was to take him away, mounting a horse and galloping up and down the riverbank: it is the picture of a young man brimming with vitality, half-mad with frustration, and overjoyed to be released from confinement, treating himself to a few minutes of wild freedom.

Upon arriving at Ostia, he was once again locked up, remaining a prisoner for another two months while the agonizingly slow process of getting his Romagna commanders to give up their fortresses was finally brought to completion. Lucrezia’s father-in-law Duke Ercole, asked to offer Cesare asylum in Ferrara, refused.

It somehow came to pass that, when Cesare’s men at Cesena and the little town of Bertinoro at last gave up and marched out of their strongholds with music playing and flags unfurled, news of their surrender reached Ostia before Rome. Cardinal Carvajal, satisfied that Cesare had fulfilled the terms of his deal with the pope, told him he was free to go. Whether the Spaniard Carvajal acted so hastily in order to save Cesare’s life we do not know, but it is not hard to believe that Julius, given a choice, would have locked Cesare away forever, or killed him, rather than granting him his freedom. Yet it was not he but Cesare who now faced a monumental decision: whether to again go north, to the court of Louis XII, or instead go south to Gonsalvo, Naples, and Spain.

Perhaps it is going too far to say that in opting to go south he made the one truly ruinous decision of his life, but not by a wide margin. In France he was still duke of Valentinois, with a royal wife and child, and it must have seemed possible that the king who had given him both title and bride could be won over once again. Certainly Louis XII had little enough reason to think of Cesare as an enemy. He might very well have found his old friend and protégé Valentino useful in consolidating France’s position in the north in the aftermath of his generals’ disastrous failures.

Why then did Cesare turn his back on France and go to Naples instead? Not only, surely, because one of his numerous cardinal cousins, another Pedro Luis Lanzol Borgia, was now in Naples himself after fleeing Rome and had sent a galley to Ostia to pick him up. Perhaps because so many other members of his family were already in Naples: not only the cardinal but Jofrè Borgia as well and his wife Sancia, now the mistress of Prospero Colonna. Perhaps too because Gonsalvo’s victories over the French made the Spanish seem the more sensible choice. Perhaps the astrologers had a hand in it. Whatever the reason, Cesare boarded the cardinal’s galley and allowed it to take him south. In doing so he extinguished whatever affection Louis XII might still have felt for him.

Cesare spent three happy weeks in Naples, enthusiastically making preparations for a return to the Romagna, asking Gonsalvo for financial help and evidently expecting to get it. Unbeknown to him, however, Pope Julius was in communication both with Gonsalvo and with the Roman agents of Ferdinand and Isabella, asking that Cesare be kept under close watch and prevented from making trouble. From Spain, Gonsalvo received instructions that under no circumstances was he to allow Cesare to slip out of his hands.

On the night of May 26, having completed preparations to leave Naples by galley, Cesare visited Gonsalvo to say farewell and was stunned to find himself placed under arrest. He was taken to the island of Ischia in the Bay of Naples and confined there under increasingly harsh circumstances, consigned at last to a chamber so diabolically uncomfortable that it was known as “the oven.” Lucrezia, knowing of his plans to return to the Romagna but not of his arrest, had managed to raise enough money to hire a thousand soldiers, put them under the command of the Borgia loyalist Pedro Ramires, and send them off to join him. Ramires did not get far before learning that Cesare was not to be expected. Seeing that there was nothing to be done, he turned back. That other Cesare loyalist, Michelotto, was meanwhile still a prisoner in Rome, Pope Julius continuing without success to attempt to extract from him dark Borgia secrets that might or might not have existed. Eventually he would be released, find employment in Florence with Machiavelli’s help, and be murdered under circumstances that have never been explained.

On August 20, Cesare was put aboard a galley that joined a flotilla commanded by the same Prospero Colonna whom he had tricked in departing Rome after Alexander’s death. They were bound for Spain, and upon arrival Cesare was confined in a remote castle at Chinchilla in the mountainous backcountry of his native Valencia. Though in no way mistreated—he was allowed a cadre of personal servants and even a mistress—he is not likely to have had much opportunity to keep abreast of what was happening far away. To the great questions of the hour he had become irrelevant, and his chances of being set free were reduced to zero by Isabella of Spain’s hostility—she wanted him tried for the murders of the dukes of Gandía and Bisceglie—and by Pope Julius II’s refusal to have him back in Italy. Lucrezia and his brother-in-law Juan king of Navarre sent appeals for clemency but achieved nothing. It was entirely possible that Cesare, like Ludovico Sforza of Milan and the heir to the last Aragonese king of Naples, would spend the rest of his days a prisoner.

Though he evidently still had substantial funds in banks in northern Italy, any effort to retrieve them would have attracted the attention of the agents of the pope, who was himself in financial straits and bent on seizing Cesare’s assets wherever he could find them. In the spring of 1505, acting on Cesare’s behalf, Juan of Navarre appealed to Louis XII for payment of the dowry that the new Duke Valentino had been promised at the time of his betrothal to Charlotte d’Albret. He was curtly refused. Frustration at this rebuff may help to explain a bizarre event that shortly followed. One day during a conversation atop the ramparts at Chinchilla, Cesare suddenly hurled himself upon the castle’s governor, apparently intending to throw him to his death. Instead Cesare was overpowered and injured in the course of being subdued. Not long thereafter he was moved to the great fortress of La Mota at Medina del Campo northwest of Madrid. This was one of the favorite residences of Ferdinand and Isabella, high-walled, stoutly built, and always heavily guarded. There he was confined under far more austere circumstances than at Chinchilla.

This move is likely to have been partly the result of the death, late in the previous year, of Queen Isabella. Her passing had left Cesare’s fate in the hands—or so it seemed, for the time being—of her husband Ferdinand. This opened a whole range of new possibilities: the Spanish king was far too cynical and self-serving to attach any importance to his wife’s righteous view of Cesare as a moral lost cause, too monstrous ever to be set free. For Ferdinand, by contrast, the only question was whether Cesare might in some way be made useful. Being himself without scruples—a decade hence he would be gulling his young son-in-law Henry VIII of England, drawing him into an unnecessary war with France and then deserting him as soon as his own aims had been accomplished—Ferdinand was incapable of trusting anyone. In 1505 his suspicions were focused on his viceroy in Naples, Gonsalvo the Great Captain. Gonsalvo was as loyal an agent as any king had ever had, and his achievements first in Granada and then in Italy should have made Ferdinand grateful for his existence. The opposite was true, however; the death of Isabella removed the only restraint on Ferdinand’s dark imaginings, and in short order he became convinced that Gonsalvo was scheming to seize Naples for himself. He began to consider not only releasing Cesare but sending him to Naples at the head of an army, and the transfer from Chinchilla to Medina del Campo may have been a first step in that direction. Cesare’s assignment would be to replace Gonsalvo—or to subdue him if he declined to stand aside.

Cesare, if he learned of this possibility, must have been ecstatic; such an assignment would at a stroke have returned him to prominence in Italy. But it was not to be; the complications were too numerous and too imposing. Ferdinand wanted the friendship of Pope Julius and knew that gaining it would be impossible if he injected Cesare back into Italian affairs. Also, Ferdinand was at this time looking for ways to improve his relations with France. His gestures in that direction would have no chance of success if he freed the onetime protégé whom Louis XII now despised as a traitor.

And it soon developed that Cesare was not Ferdinand’s to do with as he wished after all. He belonged, instead, to Ferdinand’s son-in-law Philip of Hapsburg, Philip the Handsome so called, with whom the king had a poisonously bad relationship. Philip was the husband of Ferdinand’s eldest surviving daughter, Juana, who as a result of her mother Isabella’s death was now queen of Castile, and the couple had two small sons. It was a bitter fact, for Ferdinand, that his and Isabella’s son Juan had died at nineteen, leaving a pregnant bride whose child was later stillborn, and that the daughter who now wore the crown of Castile and was heir to that of Aragon was producing healthy male offspring for the German House of Hapsburg. It meant that everything Ferdinand and Isabella had built together in three decades of scheming and danger and hard toil would pass after his death from their ancient House of Trastámara to a tribe of grasping Germans.

Philip deepened Ferdinand’s chagrin by demanding to be recognized as king of Castile, not just its new queen’s consort. Thus it proved to matter a great deal that Medina del Campo and its castle were in Castile rather than Aragon, so that Cesare was no longer in Ferdinand’s custody but in that of Juana and Philip, neither of whom had any wish to put him at the old king’s disposal. Less than a year after Isabella’s death, Ferdinand would attempt to foil Philip by marrying a seventeen-year-old French princess for the purpose of providing himself with a new male heir; any such son would have been first in Aragon’s line of succession, ahead of Juana and her brood. And after three years of trying, presumably with the help of the virility potions concocted by his physicians, Ferdinand would succeed in getting his queen with child. In May 1509 she gave birth to the hoped-for son, but the child lived only hours. That was still in the future, however, when in September 1506 Philip suddenly died at Burgos, probably of typhoid. His death left Cesare at the mercy of Queen Juana, who had been taught by her late mother to regard him as the devil incarnate and was beginning to behave in the ways that would cause her to be remembered as Juana the Mad. The first thing that raised questions about her sanity was her refusal to have her husband buried and her insistence on taking his corpse with her wherever she traveled. Possibly with the encouragement of Cesare’s sister-in-law the dowager duchess of Gandía, widow of the Juan Borgia who had been murdered in Rome in 1497, she carried out her late mother’s wish by having Cesare indicted for the murders of his brother and his brother-in-law the duke of Bisceglie. A trial would presumably follow.

All was not lost, however. With Philip the Handsome and Queen Isabella both dead, Juana losing her wits, and Ferdinand setting out to confront Gonsalvo in Naples personally, discipline at La Mota began to go slack. Cesare’s keepers evidently saw him as a man who still had a future, who might eventually be powerful once again and was therefore worth cultivating. Certainly they were open to suasion and bribery. With the help of the governor at La Mota, one Cárdenas, Cesare was able to secure a length of strong rope and make arrangements for an escape.

On the night of October 25, with a small party of mounted confederates waiting below, he climbed out the window of his chamber high in La Mota’s walls and began lowering himself down the rope. A watchman saw what was happening and sounded the alarm, a guard entered the chamber and cut the rope, and Cesare was injured as he fell to the ground. He was put on a horse all the same and taken to a remote property belonging to Governor Cárdenas. He remained there a month, a hunted fugitive, and when able to travel was moved in secret to the port of Castres and put aboard a ship bound for Navarre. Evidently he remained a semi-invalid at this point: someone whose path he crossed described him as “a man doubled up, with an ugly face, a big nose, dark.” When storms forced his ship into a fishing port, Cesare was obliged to continue on muleback. Finally, however, he made his way to Navarre’s capital of Pamplona, a city he had never seen in spite of having had its bishopric conferred upon him as a sixteen-year-old schoolboy. He was described as descending on the little city “like the devil.” Presumably this was a reference to his appearance after weeks on the run and much hardship.

Once settled in Pamplona, he wasted no time before setting out to recover at least some of his old importance. He dispatched envoys to Italy, sending with them letters to various individuals whom he thought might be inclined to help—for example Francesco Gonzaga, marquess of Mantua, who was deeply infatuated with his sister-in-law Lucrezia Borgia d’Este, now duchess of Ferrara following the death of her husband’s father. In these letters Cesare signed himself duke of Romagna, signaling that the Romagna was where he hoped to reestablish himself. The lack of response showed that he could expect no assistance in that regard. Gonzaga at this time was employed as captain-general of the forces with which Pope Julius II—following Cesare’s example—had recently driven the Baglioni out of Perugia and the Bentivoglii out of Bologna. That he would break with an imperious and increasingly powerful pope for the sake of the penniless Cesare in his distant refuge was inconceivable even if his young son and heir was, supposedly, still betrothed to Cesare’s daughter Louisa.

As for Pope Julius himself, sensitive to Cesare’s popularity in the Romagna and mindful of the difficulties that his return could stir up, he saw no reason to be friendly or even neutral. When a representative sent by Cesare called on him at Bologna, of which he was taking personal possession after the expulsion of the Bentivoglii, Julius had the unfortunate man thrown into prison. Lucrezia appears to have been alone in daring to request his release, and as before her appeals were politely denied.

At about this same time Louis XII refused a request for restoration of the revenues to which Cesare had once been entitled as duke of Valentinois. Cesare therefore was left without prospects in Italy, France, or Spain—without any friends at all among the crowned heads of Europe, aside from his brother-in-law Juan of Navarre. Juan, being not only short of funds but faced with a rebellion in which Ferdinand of Spain, Louis of France, and Maximilian of Hapsburg were all meddling, could offer Cesare one thing only: command of the Navarrese army. Now recovered from his injuries—he was described at about this time as “a big man, strong, handsome, and in the full flight of his manhood”—he was soon directing the siege of a rebel fortress at Viana.

Awakened early on the morning of March 12, 1507, when a relief force of rebels attempted to break the siege, he donned his armor, mounted his charger, and led a party of his soldiers in hot pursuit of fleeing enemy horsemen. He chased them into a ravine, where he was ambushed and cut to pieces at the conclusion of a bitter fight in which he killed several men. His body was stripped naked and abandoned. Perhaps he had not realized that he was alone as he entered the ravine—that his own men were either not following or had been outrun. It is not impossible that he committed a kind of suicide, intentionally throwing himself into a situation that made a swift death inevitable, preferring early oblivion to long years as the aging dependent of a poor and insignificant king.

The body when recovered was placed in the church of Saint Mary of the Assumption in Viana. Over it was constructed the ornate tomb that an indignant bishop of Calahorra would later order destroyed.