V
“[We will be] devoured one by one by the dragon.”
—GIANPAOLO BAGLIONI ON CESARE BORGIA
ON THE EVENING OF OCTOBER 9, 1502, BEHIND THE high stone walls of La Magione Castle overlooking Lake Trasimeno—where more than a millennium and a half earlier Hannibal annihilated the legions of Rome—many of the most powerful military leaders in Italy gathered in secret. Among them were Vitellozzo Vitelli, lord of Citta di Castello; Francesco Orsini, Duke of Gravina; Gianpaolo Baglioni, tyrant of Perugia. Most were captains serving Valentino and his father, Pope Alexander, but, significantly, Cesare Borgia himself was not included. In fact the guests went to great lengths to keep word of the meeting from reaching his ears, since on the agenda was a plan to raise the banner of rebellion against their Borgia overlord. Valentino’s apparently insatiable appetite for new conquests—ominously demonstrated by his unprovoked attack against Duke Guidobaldo da Montefeltro in Urbino—had caused his chief lieutenants to fear for their own safety. As Gianpaolo Baglioni put it, they must rise up against Duke Valentino before they were all “devoured one by one by the dragon.”
Up until then these generals had been happy to make war alongside Borgia, earning their pay as mercenaries and sharing in the plunder that followed his victories, but now they began to suspect that they had helped create a monster who would not stop until he had gobbled them all up. For the first time since Valentino had exchanged the life of a cardinal for that of a warrior, a coalition was forming powerful enough to challenge his preeminence in central Italy.
Enjoying a front-row seat to this high drama was Machiavelli, who had once again been ordered by the Ten to serve as the Florentine emissary to Valentino’s court. He arrived in Imola on the afternoon of October 7, where the Duke had set up headquarters behind the towering battlements of fortress La Rocca. So anxious was he to see the Duke that he presented himself cavalchereccio, in the dust-caked clothes he wore on his ride, though, as Valentino quickly determined, he had little to offer but the usual Florentine equivocations.i Machiavelli’s mission promised to be particularly unsatisfying since the government’s policy was merely to stall for time while it awaited the outcome of the epic struggle just getting underway. Florence’s reluctance to commit itself was understandable. Only a few months earlier Machiavelli had been forced to listen while Valentino heaped abuse on the government he served. But the rebels, though now actively courting Florentine aid, were hardly any more attractive as allies. Among their leaders were men like Vitelozzo Vitelli, an avowed enemy of the Florentine state, and Paolo Orsini, kinsman of Piero de’ Medici—hardly the kind of neighbors the republic was seeking.ii
But if Machiavelli had little of substance to offer the Duke, he was encouraged by Valentino’s less belligerent tone. Gone were the tirades he had indulged in during their prior meetings. His Excellency, Machiavelli relayed, “declared that he had always desired the friendship of Your Lordships, and if in this he had failed it was not through his own fault but because of the malice of others.” It was a laughable assertion, and Machiavelli knew it. Valentino’s sudden amiableness was nothing more than a reflection of his weakened position, but Machiavelli urged his bosses to take advantage of the Duke’s vulnerability by striking a deal on favorable terms. He held to this course even after hearing news, coming a week after his arrival, of the battle of Fossombrone, where Valentino’s forces were routed by the rebels. Nothing, it seemed, could shake Machiavelli’s confidence in Valentino’s star. In his report to the Ten he concluded “his enemies can no longer do much harm to His Lordship.” The source of Machiavelli’s confidence was largely Valentino himself, whose almost superhuman belief in his own powers rubbed off on the Second Chancellor. Greeting the Florentine emissary with his usual bluster, Valentino laughed off recent reversals, claiming that “with the king of France in Italy and the Pope, our Lord, still living, these two would light such a fire beneath [the rebels] that they would need more water than they possessed to put it out.”
The reports Machiavelli sent back to the Ten on an almost daily basis demonstrate his deepening understanding of power politics. Barred from conducting substantive negotiations, he had to content himself with offering his analysis of the increasingly tense situation. His friend Buonaccorsi worried that on occasion his advice was “too forceful,” that he should instead stick to a dry narration of the facts, but Machiavelli’s bosses found his insights invaluable as they attempted to craft a policy that would provoke neither the dangerous and unpredictable Duke nor his equally formidable rivals.
Steering a middle course between two uncomfortable alternatives remained the government’s preferred tack, but the reluctance to follow a bold course was reinforced in this case by the chaos reigning in the halls of the Palazzo della Signoria, great even by the lax standards of the Florentine Republic. Ironically, the current confusion was actually a sign of progress. It resulted from a decision, taken shortly before Machiavelli’s departure, to reform a government that all acknowledged was structurally flawed. With the top officials—including the Signoria, the eight priors, and the Gonfaloniere di Giustizia, who made up the chief executive—rotating in and out of office every couple of months, the government consisted of amateurs with little expertise and less courage. Foreign governments complained that decisions arrived at one day were reversed the next, or, more often, were never made at all since the safest course was to avoid taking a difficult stand and to pass the resulting mess along to one’s successors. Florentine prestige plummeted as the hapless republic lurched this way and that. Machiavelli later derived a general principle from his unhappy experience in Cesare Borgia’s court. “I think taking a stand between two belligerents is nothing short of asking to be hated and despised,” he wrote to his friend Francesco Vettori, explaining that both sides would come to regard you as weak and treacherous. It was this policy—or deliberate lack of one—that caused the government of Florence to be looked on, as he so memorably put it, as Sir Nihil.
The only remedy for this fatal lack of direction was to strengthen the chief executive. In September, in a radical departure from past practice, the Great Council voted to make the office of Gonfaloniere di Giustizia a lifetime position. The new Gonfaloniere would be much like the Venetian Doge, an embodiment of the majesty of the state who, through his lifetime tenure and elevation above the daily strife, would provide firm direction to a government deranged by frequent and chaotic elections. After an initial roster of 236 possible candidates was submitted, the people’s choice—arrived at on the third ballot—fell to Piero Soderini, brother of the Bishop of Volterra and a man with a long and distinguished career as a diplomat. He owed his election not only to his well-known integrity, but also to the fact that he had spent so much time abroad in service to his country that he had made fewer enemies than most of his peers. In Soderini the Florentine people seemed to have found themselves a wise and scrupulous leader, a man of personal virtue who would put the welfare of the state ahead of family ambition.
Machiavelli welcomed the selection of Soderini. Not only was Machiavelli close to the new Gonfaloniere’s brother—the two having served together on the first mission to Valentino—but Piero himself was well acquainted with the Second Chancellor’s ability. Agostino Vespucci soon confirmed Soderini’s high opinion, passing along the Gonfaloniere’s kind words after hearing one of Machiavelli’s reports: “The writer who wrote this in his own hand has much talent,” Soderini told his colleagues, “is endowed with much judgment, and also no little wisdom.” Another friend, Niccolò Valori, was even more emphatic, declaring “I believe he has become your great friend.” With such a man in charge, Machiavelli could expect his own career to prosper.
Though Soderini had been elected on September 20, more than two weeks before Machiavelli set out, he did not take office until November 1. In the meantime, little could be accomplished. Machiavelli did his best to deflect Valentino, who was pressing Florence to join him. “Your Lordships write to me about temporizing, not committing you,” Machiavelli grumbled, frustrated at being placed in such an awkward position, though he added hopefully that already “the new law [for the Gonfaloniere] has raised the reputation of our city so high that one can scarcely believe it.”
Throughout the remainder of October and into November, Valentino and his foes jockeyed for position, while the Second Chancellor tried to evaluate the strengths and weaknesses of the opposing camps. Machiavelli, who used these junkets as an occasion to indulge himself, mixed business with pleasure, wining and dining with the other envoys. It was often hard to distinguish between legitimate government business and partying, and Machiavelli took full advantage of the ambiguity. Between mouthfuls, the ambassadors traded information like merchants at a bazaar, trafficking in gossip and rumor and passing along the more substantial nuggets to their employers back home. “Because courts always include different kinds of busybodies alert to find out what is going on,” Machiavelli wrote late in life when he was advising a young man who was about to take up his first ambassadorial posting, “you will profit by making all of them your friends, so that from each one you can learn something. The friendship of such men can be gained by pleasing them with banquets and entertainments; I have seen entertainments given in the houses of very serious men, who thus offer such fellows a reason for visiting them, so that they can talk with them, because what one of them doesn’t know another does, and much of the time they all together know everything.” Poverty hampered Machiavelli in this regard, but he readily accepted invitations to sup at the well-spread tables of his better funded colleagues.
What he gleaned from these merry gatherings was that Valentino’s hand was stronger than it appeared. Though the early victories had gone to the rebels, Machiavelli warned the Ten not to underestimate the resourceful Duke. “[W]hoever examines the quality of one side and the other, knows this Lord to be a man of great vitality, fortunate and full of hope, favored by the Pope and by the King . . . . His adversaries are insecure in their states, and while they were afraid of [Valentino] before they betrayed him, now they are even more so, having injured him thus.”
In addition to his audacity and supreme self-confidence, Valentino possessed another quality Machiavelli admired. He was, as he later wrote, “a very skillful dissembler.” It was this talent for deception, more than for military strategy, that began to turn the tide in Valentino’s favor. Despite his early setbacks he had managed to avoid catastrophe on the field of battle, and with each passing day he gained in stature while in the camp of his adversaries doubt and dissension grew. Particularly unnerving for the rebels was the fact that Valentino continued to enjoy the favor of the French King. He gave tangible evidence of his friendship by placing at Valentino’s disposal an additional five hundred lances. With the power of the French crown and the resources of the Vatican behind him, Valentino still had formidable advantages.
Even as he built up his forces, Valentino was pursuing another tack, making conciliatory gestures, floating the idea of an agreement in which he would retain the title of Prince while real power remained in his rivals’ hands. “[S]weetly this basilisk whistled,” Machiavelli wrote in The First Decennale, while the rebels, “these serpents full of poison began to use their claws and with their talons tear one another.”
The combination of veiled threats and subtle overtures soon bore fruit. Machiavelli was on hand when a mysterious rider arrived at Valentino’s castle in Imola. Though “dressed as a courier,” the horseman’s disguise was soon penetrated. Word spread through the streets that Paolo Orsini, one of the leaders of the rebellion, had come before the Duke “to excuse and justify what had occurred and to know his Lordship’s will and to convey this to the other [rebels].”
To Machiavelli, this was the beginning of the end—a sure sign that Valentino’s foes had lost their nerve. The Venetian ambassador in Rome put it even more starkly, concluding “the Orsini might be very sure that they had now cut their own throats.” Valentino himself was delighted with the turn of events. He summoned Machiavelli to his room to gloat over his latest coup: “[T]hey write me pleasing letters,” the Duke told Machiavelli, “and today Lord Pagolo [Orsini] comes to see me; tomorrow it will be Cardinal [Orsini]. Thus they try to pull the wool over my eyes. I, for my part, will play the game, keep my ears open, and bide my time.” On the first of November, after a series of intense negotiations, the two sides signed a truce, agreeing to set aside their differences and resume their interrupted campaign of conquest as if nothing had happened.
What the rebel captains got out of the arrangement, besides “money, robes, and horses,” is unclear. Such trinkets were surely a small price for Valentino to pay to bring an end to a potentially fatal revolt; even cheaper were the promises of reconciliation he made, which cost him nothing yet purchased the time he needed to plot his next move. Machiavelli regarded those who fell for such transparent deceits with nothing but scorn: “it is impossible to believe that [Valentino] can forgive the offense, or that they will ever free themselves from fear,” he mused. They had violated one of Machiavelli’s core principles. “[I]f one must do harm to another,” he would elaborate in The Prince, drawing a general conclusion from a particular instance, “it must be such that it will not give rise to a vendetta.” Not having the benefit of the Second Chancellor’s as yet unwritten primer, the rebel captains committed the cardinal error of provoking an angry beast without taking the precaution of first pulling his fangs.
In the meantime, Valentino was more than happy to make use of the military skills of his former opponents, persuading the rehabilitated mercenary generals, now pathetically eager to demonstrate their newfound loyalty, to lead an attack on the city of Sinigaglia, an Adriatic seaport next on Valentino’s ever-expanding list of conquests.
While Valentino plotted his revenge, Machiavelli was growing increasingly restless. Fascinated as he was by the political machinations unfolding beneath his eyes, the weeks away from friends and family in Florence were taking a toll. “Mona Marietta sent to me via her brother,” reported Biagio Buonaccorsi, “to ask when you’ll be returning; and she says she doesn’t want to write, and makes a thousand complaints, and is upset because you promised her you would stay eight days and no more.” With a new baby to care for, feeling lonely and neglected, Marietta had gone to live with her sister and brother-in-law, Piero del Nero—hardly the wedded bliss the young couple might have hoped for.
Adding to these cares were continuing worries over money. Even after Niccolò Valori had secured from Machiavelli’s bosses an additional 30 gold ducats he remained short of cash. His junkets always cost him more than he recouped from the parsimonious Signoria; in the vicinity of the court even poor lodgings were exorbitant, as were the robes required to avoid cutting a ridiculous figure. Machiavelli was forced to maintain two separate households on an income barely sufficient to keep one in comfort. As weeks lengthened to months, with no end to the mission in sight, everyone’s temper began to fray. Biagio berated Machiavelli for shirking his duties and saddling him with the unpleasant chore of trying to mollify his irate wife. “Stick it up your ass,” he began one letter: “Marietta is desperate, and I have spent 44 soldi in silver from your indemnity.”
Some of Machiavelli’s financial difficulties were his own fault, as Biagio Buonaccorsi suggested. “I wouldn’t be at all surprised,” he reported, “if your raise is going down the tubes, because here the cry among these chancellors is that you’re a cold fish and that you’ve never shown them any kindness.” It is a common refrain throughout Machiavelli’s career. With his sharp tongue and prickly personality, he was often his own worst enemy.
He would have soldiered on with more enthusiasm had he been granted any real authority. More than once the Duke called him in only to scold him for his government’s fecklessness. Machiavelli returned from these harangues exhausted and discouraged. He begged his employers to replace him with an ambassador granted full power to negotiate a condotta. On December 6 he again asked “to relieve the government of this expense, and me of this inconvenience, since for the last twelve days I have been feeling very ill, and if I go on like this, I fear I may have to come back in a basket.” Piero Soderini offered his sympathies, but told him he remained indispensable.
To fight off boredom and depression Machiavelli asked Biagio to send him a copy of Plutarch’s Lives, that ancient compendium of biographies that inspired many a petty tyrant of the Renaissance to imagine himself another Caesar or Alexander. His choice of reading material was likely inspired, at least in part, by his daily sparring matches with the preeminent military figure of the moment, one who might stand comparison with the subjects of Plutarch’s biographies. Machiavelli’s political philosophy was rooted in comparative biography of the kind at which Plutarch excelled. Rather than treating history as the unfolding of impersonal forces, an approach stressed by political thinkers like Hegel and Marx, Machiavelli grounded his science in the psychology of men, their ambitions, appetites, and animal instincts. His advice to a young diplomat was to focus on the character of the ruler: “I say that you are to observe the nature of the man; whether he is stingy or liberal; whether he loves war or peace; whether fame or any other passion influences him; whether the people love him.” Politics as a clash of personalities was an approach that came naturally to someone raised in a city where everyone knew everyone else and where one’s political views were shaped by patronage and family rivalries. Summoned almost daily to appear before the charismatic and ruthless Cesare Borgia, curled up at night with a volume of his beloved Plutarch, history appeared to Machiavelli to be molded by outsized figures who towered like giants above a landscape inhabited by pygmies.
Soon Machiavelli would have fascinating new material to add to the portrait of the tyrant he was already sketching in his mind. In mid-December, Valentino began a tour of his conquered territories. From Imola, the Duke and his army, with the Florentine Second Chancellor in tow, set out for Forli through knee-deep snow, and then south to Cesena. Writing more than a decade later in The Prince, Machiavelli recalled his impressions of the states now under the control of the Borgia Duke. He noted that before his conquest the Romagna “was ruled by impotent lords who would sooner exploit their subjects than govern them,” and that “seeing that it was necessary to furnish good government to render the province peaceful and obedient to its lord,” Valentino appointed a stern and efficient administrator who “brought both unity and order.” One of the innovations Machiavelli admired most was Valentino’s formation of a citizen militia to serve alongside those grizzled professionals who made up the bulk of his forces. Watching a demonstration by these soldiers, nattily attired in their gold and red uniforms—the Borgia heraldic colors—Machiavelli thought he saw a pale reflection of the armies of the Roman Republic that once had swept across the known world.
The man Valentino had appointed to govern his realm was Messer Remirro de Orca, who combined organizational skill with a sadistic streak that left a bloody trail across the Romagna. In praising Remirro (or Ramiro, as he is often called) and the man who employed him, Machiavelli reveals one of the pillars of his political philosophy: a preference for order over anarchy, even when that order was maintained by cruelty. Almost any atrocity could be justified if the end result was an improvement in the lives of the citizens who would be spared the random rapes, murders, and pillage that inevitably followed a breakdown of authority. Observing, as Savonarola had, a world descended into violence and wallowing in corruption, he drew radically different conclusions, based not on some vision of men miraculously transforming themselves into angels but on a hard-headed appraisal of the human animal. Machiavelli recognized, too, that in a dangerous world the greatest disasters were often the result of misplaced kindness. He had already seen how Florentine lenience in dealing with the feuding factions in Pistoia had permitted the bloody strife to continue year after year; if Valentino’s methods were more brutal, they were also more effective. “Cesare Borgia was considered cruel,” he writes in The Prince, “yet his cruelty brought an end to the disorders in the Romagna, uniting it in peace and loyalty. If this is considered good, one must judge him as much kinder than the Florentine people who, in order to escape being called cruel, allowed Pistoia to be destroyed.”
Machiavelli was willing to accept an effusion of blood if it resulted in a more orderly state, but he reserved his highest praise for those who achieved security through more subtle means. Thus what happened next greatly increased his admiration for the cunning Duke. Summoning Remirro to join him in Cesena, where he had paused with his army before heading to Sinigaglia, Valentino first set out a banquet for his lieutenant, apparently a reward for a job well done. Drowsy and relaxed, Remirro was completely unprepared when, at a signal from Valentino, armed men rushed into the hall and seized him. Both Machiavelli and the citizens were initially perplexed by this sudden turn of events, as, indeed, was Remirro, who insisted he had done nothing but faithfully serve his lord. But Machiavelli realized that Valentino’s apparently arbitrary about-face was actually a brilliant public relations coup: “no doubt [Remirro] will be sacrificed to satisfy the people, whose greatest wish is to see this done,” he explained to the Ten.
Machiavelli proved right on the mark. On the 26th he informed his bosses: “Messer Remirro this morning has been found cut in two in the piazza, where he remains and where all the people may still see him. The reason for his death is not well known, except that it was pleasing to the Prince, who wishes to show that he can make or unmake men at will, according to their just deserts.” In The Prince, Machiavelli offers an ever more cold-blooded explanation: “Recognizing that past severities had generated a measure of hatred against him, [Valentino] then determined to free himself of all popular suspicion by demonstrating that if there had been any acts of cruelty they had proceeded not from him but from his minister instead. Having found an occasion to do this, one morning he had Remirro’s body, cut in two, placed on view in the public square of Cesena with a wooden block and a blood-stained knife resting beside it. The horror of that spectacle gave the people reason to be both shocked and gratified.”
Meanwhile, Paolo Orsini, Vitelozzo Vitelli, and Oliverotto da Fermo anxiously awaited Valentino’s arrival in Sinigaglia, twenty miles further along the Adriatic coast. News of Remirro’s murder should have warned them against placing their trust in the mercurial Valentino, but if they understood the danger, they still made no attempt to pull their necks from the tightening noose.
Valentino and his army arrived at Sinigaglia on the last day of December. Repeating the pattern that had held since their one decisive victory at Fossombrone, the captains, inexplicably, met strength with weakness. Rather than remaining with their own troops, Orsini and de Fermo apparently decided to demonstrate their good faith by presenting themselves to the Duke accompanied by only a minimal escort. Machiavelli later described the dramatic scene as the former rivals came face to face: “Vitellozzo, Pagolo, and the Duke (Orsini) of Gravina, riding mules, went to meet the Duke, accompanied by a few cavalry. And Vitellozzo, unarmed, in a cloak lined with green, very disconsolate, as though he were aware of his coming death . . . . When these three, then, came into the presence of the Duke and saluted him courteously, he welcomed them with a pleasant face . . . . [Later] having entered Sinigaglia, all of them dismounted at the quarters of the Duke and went with him into a private room, where the Duke made them prisoners.” Thus, meekly, did these violent men go to their deaths. Vitellozzo and Oliverotto were strangled in their cells that same night, while Paolo Orsini was spared only long enough to ensure that the Pope’s men in Rome first arrested his kinsman, the powerful Cardinal Orsini. The two soon followed Vitelli and da Fermo to the grave, as did many other members of the hated Orsini clan.
One of the first to learn of the executions was the Second Chancellor of Florence, who was summoned to a late-night meeting, where, Machiavelli recorded, the Duke “with the brightest face in the world, expressed his satisfaction at his triumph.”
Returning to his modest rooms that night, Machiavelli asked himself: How could such ruthless men allow themselves to be destroyed by Cesare Borgia without offering even token resistance? His conclusion, reached after much thought and spelled out most fully in a notorious chapter of The Prince, is that a lie, convincingly told, is among the most powerful weapons in the ruler’s arsenal. “Everyone knows how laudable it is,” he remarked facetiously, “for a prince to keep his word and live with integrity instead of by trickery. But the experience of our own time shows us that the princes who have accomplished great things are those who cared little for keeping faith with the people, and who used cleverness to befuddle the minds of men. In the end, such princes overcame those who counted on loyalty alone.” Though he does not mention him by name, he clearly had Cesare Borgia in mind when he wrote these words. He follows with his famous analogy from the animal kingdom: “Since a prince is required to play the beast, he must learn from both the fox and the lion, because a lion cannot defend himself against snares, nor the fox against wolves.”
Over the years Machiavelli’s critics have been more outraged by this brazen defense of dishonesty than his advocacy of the judicious use of violence. The caricature of Machiavelli as a sneaky, conniving fellow, cynically using every tool to further his own ends, comes largely from passages extolling the virtue, or at least efficacy, of deception. But, in fact, Machiavelli himself was the least Machiavellian of men. What has tarnished his reputation is not any dishonesty on his part but excessive candor. Everyone knows that politicians often employ deception, that in fact they could hardly function without resorting from time to time to prevarications, half-truths, and outright lies. Few, however, are so open about this peculiar tool of statecraft as the Second Chancellor of Florence, whose reputation as an evil man is due in large part to admitting what everyone knows to be true.
Valentino’s great gift was to be able to play the fox as convincingly as the lion. If his foes were equally violent men, they were no match when it came to saying one thing while intending to do the opposite. “Sweetly this basilisk whistled,” Machiavelli wrote, as good a description as any for the hypnotic power Valentino held over lesser men.
No one believed that Cesare Borgia was a good man, but success had given him an aura that no amount of pious failure could have conferred. After Sinigaglia, Valentino was hailed as the most accomplished military and political figure in Italy. In the few short years since he had shed his cardinal’s scarlet robes, he had compiled a long list of victories on the field of battle, and an equally impressive catalogue of victories won by subterfuge. Now styling himself Cesare Borgia of France, by the grace of God, Duke of Romagna, Valencia, and Urbino, Prince of Andria, Lord of Piombino, Gonfaloniere and Captain-General of the Church, he was approaching the pinnacle of his career.
From Sinigaglia, Borgia turned south again, heading for Rome to rejoin his father. Along the way, almost as an afterthought, he picked off Perugia, home to Gianpaolo Baglioni (who still remained at large), and harassed Siena. Machiavelli, now thoroughly worn out and homesick, was finally relieved of his duties on January 20, 1503, returning to Florence to pick up the pieces of his interrupted life.
In Rome, where Valentino returned toward the end of February, the city’s most powerful families were living under a virtual reign of terror as the Pope and his minions tried to squeeze from them every last ducat to fund Cesare’s war machine. Most at risk were those with the deepest pockets, in particular the cardinals who had paid handsomely for their offices and now were lucky to escape with their lives. Membership in the Holy College was for sale to the highest bidder, and upon the death of one of these princes of the Church—a misfortune that often seemed closely to follow an invitation to dine at the papal table—the Pope’s men would swoop in and confiscate all the deceased’s worldly possessions. All but the poorest citizens trembled, “every moment thinking to see the executioner standing behind him.”
On the evening of August 5, 1503, Pope Alexander and his son, hoping to escape the heat and dust of the city, made an excursion to the countryside, where they dined at a vineyard belonging to Cardinal Adriano Castellesi. Shortly after returning from the banquet both father and son were stricken with high fevers accompanied by frequent bouts of vomiting. Many jumped to the conclusion that, in an attempt to avoid the fate of so many of his colleagues, Castellesi had slipped poison into his guests’ wine. A more likely explanation is that the Borgias had come down with malarial fever, a common peril in the humid Roman summer. While Valentino lay barely conscious in his rooms, the seventy-two-year-old Pope clung to life for almost two weeks, periodically bled and purged by his doctors, before finally succumbing.
Even before his father was laid to rest in his tomb, the apparently solid edifice of Valentino’s realm began to crumble. Like all those before him who had tried to convert papal kinship into political power, Cesare Borgia had in fact built on sand. Without the legitimacy conferred by the Holy Father, he had no real claim to the lands seized in his name. Under Alexander’s aegis, any brutal act could be forgiven, any conquest justified as a legitimate imposition of papal authority. Without that protective mantle the limitations of such a shortsighted policy were revealed. In his ruthless climb Valentino had made a host of enemies who were only awaiting the first sign of weakness to strike back.
As full of vigor as Alexander had been in life, in death his cadaver decayed with unheard of speed as if all the sins he had committed were eating him from the inside. Nature herself seemed to have turned against the Pope. A stench of corruption rose from his body and wafted through the halls of the Vatican, despite the best efforts of the papal master of ceremonies, Johannes Burchardus, to make him presentable for burial. The Pope’s face, he recalled, “had changed to the color of blackest cloth, and [was] covered in blue-black spots; the nose was swollen, the mouth distended, the tongue bent back double . . . the face was more horrifying than anything ever seen.”
Though still gravely ill, the resourceful Valentino tried desperately to salvage something from the wreckage. From his sickbed he dispatched his most trusted servant, Miguel de Corella, to the Pope’s apartments, where Corella held a knife to Cardinal Casanova’s throat until he agreed to hand over the keys to the papal strongboxes. Hauling coin, jewels, and silver worth more than 100,000 ducats, Valentino and a small band of loyalists fled to the security of the Castel Sant’ Angelo, and then—as the surviving Orsini descended upon the city to exact their revenge—to his castle of Nepi, in the hills north of Rome. There he hoped to recuperate and ride out what promised to be a tumultuous few months.
Among those bitter enemies who flocked to Rome upon hearing of Alexander’s death was the formidable Cardinal Giuliano della Rovere, nephew of Pope Sixtus IV. He had been among those who had challenged Rodrigo Borgia in the conclave of 1492 that elevated the Spanish cardinal to the papal throne, and he had compounded this indiscretion by calling for an investigation into the bribes that had secured the Pope’s election.iii For the last ten years he had been living in self-imposed exile in France in an effort to escape those unfortunate accidents that claimed so many of his colleagues. With his rival now dead, Giuliano hurried to Rome to seize the prize denied to him once before by the despised Borgia.
The conclave of thirty-eight cardinals that gathered in September proved hopelessly deadlocked, as the traditional rivalry between the Spanish and French factions was exacerbated by events outside the Vatican. The Treaty of Granada that had divided the kingdom of Naples between France and Spain had broken down, and now the two most fearsome armies of Europe were heading toward a climactic struggle that would go a long way toward determining supremacy on the Italian peninsula. What happened in the conclave might well tip the balance to one or the other of the two contending powers. After six days of fruitless argument, made all the more contentious by the sweltering, overcrowded rooms, the cardinals’ choice fell to the sixty-four-year-old Cardinal Francesco Todeschini, nephew of the Sienese Pope Pius II. Though widely respected for his piety and patronage of the arts, his virtues counted less than the obvious fact that he was a dying man. This made him particularly acceptable to della Rovere, who, once he determined that the Spanish cabal would block his nomination at any cost, concluded that the aging and ailing Todeschini possessed just the actuarial qualifications he required if he were to consolidate his position. Crowned on October 8 and taking the name Pius III, in honor of his uncle, the gout-ridden Pontiff was too feeble to make the traditional pilgrimage to the Lateran basilica.
In the months following Alexander’s death Valentino’s empire disintegrated. First the territories adjoining Rome broke free; those in the Romagna, well governed for the most part as Machiavelli noted, remained more steadfast, though it was clear that they, too, would revert to their former allegiances unless Valentino could quickly reassert his dominance. He had ruled by fear and intimidation, but without the resources of the papacy behind him he seemed a far less formidable adversary. Realizing he could accomplish nothing in rustic Nepi, he returned to Rome in October as the first step in rebuilding his fortunes.
But with the Orsini once again in their Roman palaces, Giuliano della Rovere consolidating his support within the College of Cardinals, and the current Pope on his deathbed, friends of Valentino were hard to find. On October 18, less than a month after being elevated to the Throne of Saint Peter, Pope Pius III did what was expected of him and breathed his last. This time Giuliano della Rovere was ready. Though he was already the preferred candidate of the French contingent, he now set about securing the allegiance of the powerful Spanish faction. Showing the remarkable tactical flexibility that would later earn the praise of Machiavelli, he paid a call on Valentino, promising that if he threw the support of the Spanish delegation behind his candidacy, della Rovere would retain the Duke’s services as captain-general of the Church. In addition, he would and agree to marry off his nephew, Francesco Maria della Rovere, the current prefect of Rome, to Valentino’s daughter. Not surprisingly, given the weakness of his position, Valentino eagerly accepted the terms. It is difficult to see how he could have done otherwise, though Machiavelli believed he had made a fundamental strategic blunder: “[H]e should never have allowed any cardinal he had offended, or who had reason to fear him, to become pope, for men lash out through fear or hatred.” On October 31, in a five-hour conclave that must have been close to a record of brevity for meetings usually marked by long-winded speeches and the exchange of cash in the latrines, Giuliano della Rovere was elected Pope, taking the name Julius II.
Machiavelli was again on hand to witness these dramatic events. Upon learning of the old Pope’s death, the government had dispatched him to Rome to attend to Florentine interests at this critical juncture. As usual, Machiavelli set out in high spirits. Happy as he had been to return to Florence after months away at Valentino’s court, he was just as happy to leave again for a new adventure in the Eternal City. Always restless, he was especially eager to get away because of the petty bickering in the Palazzo della Signoria, which made him despair for his country. The one significant result of his months in Florence was a brief document titled “Some words to be spoken on the matter of raising revenue, after a brief preamble and a few words of excuse.” Written in response to the outcry sparked by Piero Soderini’s attempts to raise revenues for the republic’s armed forces, the speech—probably meant to be delivered by the Gonfaloniere himself in front of the Great Council—captures Machiavelli’s passionate patriotism and his disdain for those who would sacrifice their freedom for a few florins. “[A]t present,” he said,
you are incapable of defending your subjects, and you stand between two or three cities, desiring your ruin rather than your preservation . . . . Remember, at all events, that one cannot always use another’s sword, and therefore it were well to keep your own in readiness . . . . For I tell you that fortune will not help those who will not help themselves; nor will heaven itself sustain a thing that is determined to fall. But beholding you free Florentines, with your liberty in your own hands, I will not believe that you desire to fall. For surely I must believe that men born free, and wishing to remain free, will have due respect for liberty!
This harangue, reminiscent of those stirring orations recorded by Livy and Thucydides, shows Machiavelli at his best—a committed republican, blasting his compatriots for their selfishness while their country is starved of the means to defend itself. This episode provides a stark contrast to those infamous passages of The Prince where he advocates violence, treachery, and deceit in the name of expedience. But while the tone is different, the motivation is very much the same. Machiavelli’s first priority is, as always, the preservation and prosperity of the state; anything that interferes with that—greed and excessive piety alike robbing the nation of much needed vigor—should be resisted by every means possible.
Machiavelli arrived in Rome on October 27, just in time to witness the final machinations leading to the elevation of Giuliano della Rovere to the papal throne. Machiavelli’s appointment to this important post—he was addressed in correspondence as “Florentine Secretary and Envoy to the Supreme Pontiff in Rome”—was a testament to Soderini’s increasing trust in his friend. The first order of business when he arrived at Julius’s Vatican apartments was to alert the new Pontiff to the dangers of Venetian expansion in the north. The Most Serene Republic, Machiavelli explained, was at this very moment taking advantage of the collapse of Valentino’s empire to scoop up any state that had been shaken loose, much to the chagrin of the Florentines, who had no wish to see one imperial master replaced by another with even greater resources. Julius was sympathetic, not out of any love for the republic, but because the territories coveted by the Venetians rightfully belonged to the Church.
In Rome, Machiavelli plunged headlong into the kind of balance-of-power politics perfected in Renaissance Italy, where the rise of any one state provoked hasty alliances among all the others to prevent their rival from dominating the peninsula. It was a world of shifting loyalties and sharp betrayals, where today’s friend was tomorrow’s foe, and where treaties were obsolete before the ink had dried. To that growing class of men who had the difficult job of steering the craft of state through dangerous shoals and unpredictable currents, maneuverability and a sharp-eyed focus on the near at hand succeeded where keeping one’s vision fixed on a distant star would lead to disaster. Machiavelli was the first philosopher to speak for these professional diplomats, men without illusions who trafficked in temporary expedients rather than grand abstractions.
In their initial meeting, Machiavelli was subjected to one of those tirades for which the new Pope would soon become famous, though fortunately the target of his wrath was their common enemy, the arrogant Venetians. Having reassured himself as to the direction of Julius’s foreign policy Machiavelli paid a call on Valentino. The man he saw in his faded Roman palace was a mere shadow of the triumphant general he had left in Perugia. Ravaged by his illness, he was far less physically imposing, and without the aura that unbridled power conferred, Valentino seemed to shrink to insignificance. Most inexplicable to Machiavelli was the fact that the Duke had fallen into exactly the same trap he had sprung on his enemies only months before, placing his faith in the promises of his adversaries. “[A]lways transported by his daring confidence,” Machiavelli wrote to the Ten on November 4, “[Valentino] believes that the words of others are more trustworthy than were his own.”
Valentino began by trying to frighten the Florentine envoy with elaborate fantasies of redemption and revenge, but to Machiavelli it was evident he had become dangerously detached from reality. Valentino grew furious when Machiavelli told him that Florence would refuse him safe passage through Tuscany on his planned expedition to recover the territories he had lost in the Romagna. The Florentine Secretary had already sounded out Julius, and knew the Pope had no intention of keeping the promises that had persuaded Valentino to back him in the recent election. “We want the states to return to the Church,” Julius explained. “It is our intention to recover them [and although] we made certain promises to the Duke, we intended merely to guarantee his personal safety and his fortune, even though, after all, it was stolen from its rightful owners.”
To Machiavelli’s ears, Valentino’s bluster now sounded like whining. It was a pathetic and disillusioning spectacle. The man Machiavelli had so recently held up as a paragon of the ruthless leader had about him the stench of failure. “I had no lack of things to say in reply, nor would my words have failed me,” Machiavelli recalled, “yet I took the course of trying to pacify him, and took leave of him as quickly as possible, for it seemed a thousand years till I could quit his presence.” How much had changed since those days in Imola when Machiavelli stood in awe of the great man!
In the end, Valentino’s demise was more the stuff of farce than of tragedy. Prevented from leading his army on an overland trek to the Romagna, at the end of November the Duke tried to board a ship at the port of Ostia with the intention of reaching his rebellious empire by sea. This act of disobedience offered Julius just the opportunity he needed to finish off his rival; he ordered that Valentino be arrested and returned to Rome. Machiavelli, for one, was pleased with the news, remarking that “since he is taken, whether he be alive or dead, we need trouble ourselves no more about him. One sees that his sins are gradually bringing him to punishment.” Days later, reports arrived that the remainder of Valentino’s army was routed by Gianpaolo Baglioni—the one captain who had survived the purge at Sinigaglia—and its commander, Don Michele Corella, sent in chains to Florence. “[T]hus it would seem,” wrote Machiavelli to the Ten, “that little by little this Duke is slipping into his grave.”
Though Machiavelli’s obituary was a bit premature, his assessment was essentially correct. For a time, Valentino pinned his hopes on his fellow Spaniards, who were continuing their victorious campaign against the French, but in the end they, too, had little use for the washed-up son of a dead pope. Deported to Spain, he eventually escaped his imprisonment to serve for a time in the army of his brother-in-law, John of Navarre. He died three years later at the age of thirty-one in an obscure battle in a distant province, largely forgotten by the world that once had trembled at the mere mention of his name.
The catastrophic reversal of fortune for the man who, more than any other, represented for Machiavelli the admirable qualities of leadership—ruthlessness, audacity, cunning, and luck—was unsettling. One can detect in Machiavelli’s discomfort the pain that accompanies the shattering of a cherished illusion. Though he had always perceived Valentino’s faults, Machiavelli had come to see him as the embodiment of the strength that was so sorely lacking in his own government. If such a man could come to grief, what hope was there for a nation led by timid souls? When he sat down to write The Prince, having mulled the matter over for a decade, his final verdict on Valentino is more charitable, though the man’s downfall is no less perplexing:
Cesare Borgia, called by the masses Duke Valentino, acquired power through his father’s fortune and lost it in the same manner. This despite the fact that he employed every art and did all that a prudent and courageous man should do to secure his hold on those territories won by the arms and fortunes of others . . . . [I]f he failed in the end, it was through no fault of his own, since it was born of extraordinary and extreme malice of fortune.
Extreme malice of fortune! That seems a weak conclusion for someone intent on discovering the laws that govern the rise and fall of men and nations, but Machiavelli was always attuned to the apparent randomness of the universe. In studying the vicissitudes of history, he was often forced to fall back on the image of Dame Fortune, a capricious goddess who bestowed her gifts promiscuously and then plucked them away with equal gusto.
It has often been remarked that the picture of Valentino that Machiavelli paints in The Prince is at odds with the fragmentary portrait we can reconstruct from letters and dispatches written at the time. The contrast is particularly striking when we examine the official documents Machiavelli wrote in Rome, where he depicts Cesare Borgia as a broken and pathetic figure. By the time he came to write The Prince, Machiavelli had decided to restore much of the luster. Valentino is once again the heroic figure, dominating lesser men through the sheer force of his will; his ad hoc responses to various crises are recast as part of a brilliant plan to confound his enemies and secure his realm. Machiavelli was surely aware that he was straying from the facts in the course of building his larger narrative, but this fiction was conceived in the service of a larger truth. A decade after their last meeting, Valentino had ceased to be the fatally flawed flesh-and-blood creature whose shrunken form and peevish rantings were so distasteful that Machiavelli wanted to flee his presence. He has become “The Prince,” prototype of the ruthless tyrant, whose courage and vision will restore Italy to her rightful place among nations.
i The ostensible reason for Machiavelli’s trip was to secure safe passage through Valentino’s realm by some Florentine merchants, but it was clear that this minor matter was an excuse to have an emissary in place to keep his eyes and ears on the Duke.
ii In his essay “Description of the Method Used by Duke Valentino in Killing Vitellozzo Vitelli, Oliverotto da Fermo, and Others,” Machiavelli suggests that Florence was firmly committed to Borgia’s side: “But the Florentines, because of their hatred against Vitelli and the Orsini for various reasons, not merely did not join them but sent Niccolò Machiavelli, their secretary, to offer the Duke asylum and aid against these new enemies of his.” But the dispatches Machiavelli sent at the time reflect a more equivocal attitude. In his political essays, Machiavelli often distorted the fact to fit his thesis—in this case that Valentino’s cunning and ruthlessness, noted by the perceptive Secretary of Florence, would inevitably win the day.
iii In this, Giuliano had apparently forgotten Christ’s injunction: “Let he who is without sin cast the first stone.” The quantity of bribes distributed on his behalf were almost equally large, if less effective.