Machiavelli was mortified. He had already sent back optimistic dispatches to his bosses in the Signoria and now he would have to admit that he’d been misled. What was worse, he had been treated as a person of little consequence, an experience that would become all too familiar as he made the rounds of the courts of Europe. Caterina justified her change of heart on the grounds that Florentine words “had always satisfied her, whereas their deeds had always much displeased her.” The undeniable truth was that Machiavelli’s position was weak because his government was weak. Why should she place her faith in a state that had little by way of recent diplomatic or military triumphs to point to? In any case, she observed, the government of Florence was clearly not serious about forging a real alliance. Why else would they have sent to her court Machiavelli, a midlevel bureaucrat, rather than a full ambassador able to negotiate on his own behalf? Given such evidence of the Florentines’ lukewarm feelings, Caterina preferred to cut a deal with the ambassador from the powerful state of Milan.
Machiavelli headed home frustrated that he’d achieved so little but wiser in the ways of the world. He’d had his first taste of life as a roving representative of a second-rate power, and the experience was humbling. For a patriot like Machiavelli, the derision with which Florence’s ambassador was greeted in foreign courts was unbearable. The reality of Florentine impotence, first encountered at the court of Countess Sforza but repeated many times over the years, planted the seed out of which The Prince will grow.
On a personal level, Machiavelli’s mission was more rewarding. He was a naturally restless soul, never happier than when setting out on some new adventure. His friend Agostino Vespucci once wrote of “that spirit of yours, so eager for riding, wandering and roaming about,” a wanderlust that often irritated friends and family left to fend for themselves. His bosses evidently took advantage of his taste for travel by sending him on missions others would refuse. On this occasion, though in his own mind he had accomplished little, they seemed well pleased by his efforts. Biagio Buonaccorsi reported that his dispatches were “most highly praised” by their superiors. One gets the distinct impression that the government expected little from Machiavelli’s efforts, and that is exactly what they got.
Buonaccorsi also kept him abreast of life back in the office, which, in his absence, seems to have taken a turn for the worse. Antonio della Valle—one of the men who had initially sponsored both Buonaccorsi and Machiavelli for their current positions—was unhappy with the way the Chancery was being run. A stickler for protocol, he complained of rowdy behavior and lax attendance. “If you do as I advise,” Buonaccorsi warned Machiavelli, “you will bring back a lot of rose water to sweeten him [Antonio], since around here you can’t hear anyone else. He’s already managed to get our Magnificent Lords to rake us over the coals. Let him shit blood in his asshole! Anyway, that’s how it is, though four rubs of the back have fixed everything. In fact we all long for your return, your Biagio most of all, who speaks of you every hour and to whom every hour feels like a year.”
The warmth, coarseness, and high spirits of this letter are typical of Machiavelli’s circle of friends who shared a jaundiced but essentially tolerant view of the world. Life’s earthy pleasures and low comedy were as worthy of their attention (and their wit) as weightier matters of war and peace. They had all suffered under Savonarola’s puritanical reign and were inclined to let loose. Gone were the prepubescent spies and ubiquitous morals police who, if they did not manage to wipe out vice altogether, at least drove it underground. In a few short months Florence had reverted to the habits that earned it comparisons not to Jerusalem but to Sodom.
Machiavelli and his young friends took full advantage of the permissive climate, whoring, drinking, and gambling to their hearts’ content. The year after his Forli junket, while Machiavelli was away at the court of the French King, his friend Andrea di Romolo described the pleasures he was missing back home, a “few little parties at Biagio’s house” and other less innocent fare. “And just to prepare you: as soon as you arrive here she will be waiting for you with open figs. Biagio and I saw her a few evenings ago at her window like a falcon, you know who I mean . . . along the Arno by the bridge of Le Grazie.”
This is the earliest reference to Machiavelli’s well-known taste for whores. Throughout his life Machiavelli enjoyed the services of both common streetwalkers and high-class courtesans whose talents went beyond those normally practiced between the sheets. These cultivated and accomplished women could inspire in Machiavelli an adoration that was more than mere physical attraction. Neither marriage nor fatherhood dampened his appetite for illicit liaisons. Indeed he seemed to devote even greater energy to these escapades as he grew older, perhaps to compensate for disappointments in his professional life.
• • •
A few months after his return from Forli, Machiavelli was confronted with the first large-scale crisis of his tenure. It involved the captain-general of Florentine forces, Paolo Vitelli, who had been hired with great fanfare, and at great expense, just as Machiavelli was taking office. When Vitelli took the job in June 1498 he was greeted on the steps of the Palazzo della Signoria with an elegant Latin oration that compared him to the greatest generals of antiquity. But, as so often in the past, initial enthusiasm was a harbinger of later disappointment.
Vitelli began auspiciously enough, placing Florentine troops on a more aggressive posture and instilling in them much needed discipline. A year after accepting the baton he captured the strategic town of Cascina, and on August 7, 1499, word was received in Florence that their forces had broken through the Pisan defenses at Porta a Mare. They were now inside the walls of the city and its capture seemed imminent. So confident were Florentines that Pisa was about to surrender that, in a classic case of counting chickens before they’re hatched, a lively debate began in the Signoria about how to punish the rebellious city. But the euphoria didn’t last long. On August 29 the commissioners who had been overseeing the conduct of the war returned with the disturbing news that Florentine troops had retreated just as victory seemed within their grasp. With Pisan defenses shattered and nothing standing in the way of a breakthrough, Vitelli inexplicably ordered his troops to return to their camps. The Pisans repaired the breach and all the summer’s gains were squandered. The commissioners hinted darkly that the cause of the reversal was treachery at the very highest levels. Machiavelli himself wrote in frustration: “We have granted the captain all that which he desired, yet we behold . . . all our trouble put to naught through his various shufflings and deceit.”
The prospect that the war would now drag on indefinitely was particularly galling for the Second Chancellor, who had spent the previous months begging money from politicians already in hot water with the citizens who believed they were flushing their wealth down a bottomless hole. “[H]aving expended up to this date about 64,000 ducatsvii for this expedition,” Machiavelli complained in early August, “everybody has been drained.” Vitelli might have survived accusations of mere incompetence, but the bold predictions of success made only days earlier cast the failure in a sinister light. “We should have preferred defeat to inaction at so decisive a moment,” Machiavelli despaired. “We neither know what to say, nor with what reasons to excuse ourselves before all these people, who will deem that we have fed them with lies, holding out to them day by day vain promises of certain victory.” Suspicions of treachery were also fed by reports that Vitelli had recently been discovered in secret conversations with Piero and Giuliano de’ Medici. To Florentines, the only explanation could be that he was plotting to bring their former rulers to power.
On August 28 the Florentine commissioners in camp invited Paolo Vitelli and his chief lieutenant, his brother Vitellozzo, to dine with them and discuss the future conduct of the war. When the Vitelli arrived the commissioners seized the condottiere and threw him in irons; Vitellozzo managed to escape by fleeing inside Pisan lines, which only served to confirm the suspicions of his former employers. Pao
lo was brought back to Florence, where he was first tortured and then put on trial for treason. Despite the fact that they were unable to extract a confession of guilt, on October 1 Vitelli was beheaded, his head mounted on a spear and shown to the people.viii
Not everyone cheered the verdict and swift retribution. No firm evidence of Vitelli’s guilt was ever offered, though secret deliberations of the Venetian government (unearthed only later) suggest that he had indeed come to some sort of treasonous arrangement with Piero de’ Medici. Guicciardini, for one, believed that Vitelli was merely engaged in the typical practices of his kind, avoiding decisive confrontations in favor of tactical maneuvers that risked less and promised greater returns. Even Buonaccorsi suggested that an injustice had been done, remarking, “this was the end of Pagolo Vitegli, a very excellent man.”
Machiavelli, however, refused to back down: Vitelli’s treachery was obvious, he asserted, and the punishment just. Responding to his counterpart in the government of Lucca (a small Tuscan state, long a Florentine rival) who had condemned the execution, Machiavelli shot back: “[H]ad it not been for Vitelli’s treachery, we would not be mourning our loss nor would you be rejoicing . . . . From his fault alone have arisen the countless ills that have befallen our campaign . . . . He deserves endless punishment.” Not content with this analysis, Machiavelli concluded his letter with characteristic sarcasm: “And in brotherly love, I urge that in the future, should you want in your evil way to insult people without reason, you should do it in such a way that it makes you seem more prudent.”
Both the content and tone of this letter are revealing. Given that even some in the Chancery doubted Vitelli’s guilt, the hard line Machiavelli took may strike the modern reader as excessively harsh. He remained unmoved by Vitelli’s death, which had occurred only a few days earlier, defending his government’s actions and verbally assaulting anyone who questioned the verdict. But Machiavelli was not being simply bloodthirsty. Given the enormity of the crime alleged, the punishment was fitting. Whether or not Vitelli was actually guilty of treason, Machiavelli had experienced firsthand the damage the condottiere had done to his beloved republic. Every day he had to listen to the abuse heaped on him and his colleagues by citizens who were fast losing faith in their government. For months he had worked to squeeze every additional florin out of citizens who could ill afford it, and to see his efforts undermined either through lack of zeal or out-and-out treachery was more than he could bear. For all his cynicism, Machiavelli’s patriotism was real and deeply felt. His certainty that the country he loved had been poorly served by its top general forced him to conclude that Vitelli deserved his fate.
The letter’s concluding jab offers perhaps the most telling insight into Machiavelli’s personality. Never one to back down from a fight, at least if it was conducted with words instead of swords, he clearly enjoyed sparring with his Luccan counterpart, puncturing his rival’s defenses with well-aimed barbs. For all the seriousness of the subject, Machiavelli’s tone remains jocular as he wounds with scorn rather than with anger.
• • •
The Vitelli affair merely served to deepen Machiavelli’s conviction that there was something profoundly amiss with Florence’s military system. Only a year into the job, he was already contemplating a fundamental transformation of the way Florentines waged war. Mercenary armies, employed by all the major Italian states, were adequate as long as one’s adversaries agreed to work within the same flawed system, but as soon as anyone found a more effective means of bringing armies into the field, the charm of such old-fashioned companies, with their aversion to shedding their own blood and preference for seasonal work, began to fade. Their limitations were amply demonstrated in 1494 when Charles’s army—made up of French conscripts stiffened by the ferocious Swiss pike men—swept down the peninsula meeting little or no resistance. It is not that the mercenary armies employed by the Italian states fought poorly, rather, seeing what they were up against, they did not fight at all.
Analyzing failures of the recent past was sobering enough, but the prospect that the methods that had proved so ineffectual were about to be tested again was enough to frighten even the most optimistic statesman. Once more, the threat of a French invasion loomed over Italy. This time it was King Louis XII who would lead the invasion, having replaced his cousin Charles after his sudden death on April 7, 1498 (ironically the very same day of the aborted trial by fire that spelled the doom of his ardent supporter Girolamo Savonarola).
To all appearances the new King was more able and less impulsive than his predecessor. But while Louis was less prone to chase half-baked dreams of glory, he had no intention of abandoning what he believed were France’s legitimate claims in Italy. His ambitions were, if anything, greater than those that had undone his predecessor. Not only did he covet the southern kingdom that had slipped through his cousin’s grasp, but he hoped to pocket along the way the Duchy of Milan, to which he believed himself entitled through his grandmother, Valentina Visconti—a prize made all the sweeter by the fact that it would be won at the expense of the man most responsible for the disastrous conclusion of the last invasion, Ludovico Sforza.
Regarding this second anticipated conquest, his job was rendered considerably easier by Sforza himself, whose continued scheming had managed to alienate his former partners in the Holy League. “[J]udging the prudence and the intelligence of all the others to be far inferior to his own,” Guicciardini wrote of Ludovico, “he expected always to be able to direct the affairs of Italy to suit himself and to circumvent everyone else by his cleverness.” But rather than make his position more secure, the increasingly long list of broken promises produced an equally long list of enemies. When Pope Alexander, ever willing to adjust to the prevailing wind, reversed his previous antipathy toward the French, concluding he could more easily advance his family’s fortunes by allying himself with that kingdom, Ludovico was effectively isolated.
This latest understanding between the Pope and the newly crowned King of France was perhaps the clearest indication that Louis was a far more canny statesman than his cousin. Charles’s expedition had foundered when his initial success united his enemies, but even before he set foot on the peninsula, Louis had ensured that there would be no repetition of that fiasco. As soon as he ascended to the throne he dispatched ambassadors to Rome with the outlines of a grand bargain that would more firmly tie the fortunes of the French crown to the house of Borgia. In exchange for an annulment of Louis’s first marriage, which would pave the way for a more advantageous union with Charles’s young widow, Anne, Pope Alexander’s son, Cesare Borgia, would receive the minor French Duchy of Valence and a command in the French army that was poised to reenter Italy—a suitable launching pad for someone of his vaunting ambition.ix
On July 29, 1498, Alexander issued a bull proclaiming Louis’s first marriage invalid, clearing the way for his upcoming nuptials with Anne. The following month, the King of France, with Cesare Borgia by his side, recrossed the Alps and advanced toward Milan. The four years between the first and second French invasions had done nothing to erase the disparity between the mighty French army and the puny forces available to any of the Italian states. On September 2, facing the prospect of a siege and disillusioned with their lord, whose incessant scheming had brought them to this extremity, the people of Milan rose up against Ludovico and drove him from the city. Nine days later the French army entered Milan in triumph, having humbled one of the most powerful states in Italy merely by showing up.
For Florence, the return of the French should have come as welcome news. Ever since Piero de’ Medici had thrown himself at Charles’s feet, the republic had faithfully promoted the French cause, a commitment that had created no end of difficulties with her neighbors. But Florence had as yet little to show for its loyalty. The French government was generous in providing promises of help but stingy when it came to concrete action. Still, though they had been disappointed in the past, the government of Florence was ready to try aga
in. On October 19 its ambassadors in Milan concluded a treaty with the French King that committed him to assist in the conquest of Pisa. In return, Florence promised to supply men and money to his upcoming Neapolitan campaign.
That expedition had to be postponed, however, when Ludovico Sforza, who had fled to Germany after the uprising, returned to Italy at the head of an army supplied, in part, by the German Emperor, who hoped thereby to thwart his rival’s Italian ambitions. The fragility of Louis’s Italian empire was demonstrated by the ease with which the former Duke reclaimed his city. The people of Milan “who had opened the gates [wrote Machiavelli in The Prince], finding themselves deceived as to their opinions and their expectations, could not endure the burdens imposed by their new prince.” Before Louis could set out for Naples he would have to deal with this threat in his rear. In April, the armies of France and Milan—each boasting contingents of the famed Swiss pike men—met on the plains of Lombardy. For years Ludovico had managed to evade the consequences of his actions, but now Fortune seemed to have finally abandoned the slippery Duke. Even before the battle was joined, a majority of his Swiss troops deserted his cause, citing wages owed and an unwillingness to shed the blood of their brethren across the field. With the battle lost before it began, Ludovico fled in disguise. He was quickly captured by the French and brought in chains to Lyons, where he was gawked at by the multitude. Ultimately confined to the Castle of Loches in Touraine, he would die, forgotten and unmourned, after ten miserable years in captivity.
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