“When you see a minister who thinks more about his own interests than about yours, who seeks his own advantage in everything he does, then you may be sure that such a man will never be a good minister, and you will never be able to trust him.”


JUNE 15, 1498, MARKS A TURNING POINT NOT ONLY IN Machiavelli’s life but in the history of Western thought, for this was the beginning of his career as a civil servant and, as he made clear on more than one occasion, it was his years of service in the Florentine government that formed the basis of his political philosophy. “I have set down all that I know and have learnt,” he wrote in the dedication to his Discourses, “from a long experience of, and from constantly reading about, political affairs.” He opens thePrince in much the same way, pointing to “my knowledge of the actions of great men, learned by me from long experience in modern affairs and from continual study of the ancients.” Citing his experience is not merely an attempt to establish his bona fides, though he was certainly conscious of the need to stress his professional credentials since he lacked the scholarly or aristocratic pedigree usually associated with intellectual ambition. Instead, he is offering a completely novel perspective: a view of human government seen from the trenches, by one who has been there and understands how things actually work. At another point he declares, “it seems best to me to go straight to the actual truth of things rather than to dwell in dreams.” It is this approach that accounts for much of his originality, and also for much of the outrage his writings have provoked over the centuries, for in casting his unsentimental eye on “the actual truth of things,” he discovers a world far different, and far more savage, than anything imagined by the philosophers who preceded him.

Given the undistinguished record he had compiled so far, his appointment to a responsible position in the bureaucracy comes as something of a surprise. At the age of twenty-nine, the minimum required for voting rights in the Great Council, this obscure young man with no experience, and from a family of little standing within the ruling elite, was about to be entrusted with one of the most important unelected offices in the Florentine government. There is nothing in his past to suggest such a career was in the offing. Like his father before him, he had spent his time cultivating his mind, familiarizing himself with the essentials of classical literature without which no Florentine could consider himself an educated man, but in no other way preparing himself for a serious career.

Instead, Niccolò seemed destined for the life of the country squire, managing the various Machiavelli properties in the city and the countryside, stretching their meager income to sustain a frugal lifestyle. Lately these responsibilities were consuming more of his time. As Bernardo grew more infirm, Niccolò took over more of the family business. His position as the effective head of the household was confirmed the year before when he was assigned the daunting task of writing to Cardinal Lopez when the family’s privileges were being threatened by the covetous Pazzi family. But he remained to all intents and purposes a dilettante, a gentleman—though one of modest means—with plenty of time on his hands to prospect in the realm of ideas rather than profits.

One shouldn’t overstate the honor Machiavelli was being accorded when he was nominated to head the Second Chancery. This was a bureaucratic office, one of the many paid positions offered by the government of Florence. But rather than signaling the dignity of the office, the salary—which started at 192 florins a year—was actually a mark of low status.i Florentines distinguished between offices deemed onori (honorable)—which included the top elected and appointed positions of the state where no recompense was expected—and those deemed utili (useful or practical), positions of lesser importance that came with a salary. Onori were for gentlemen who could afford to work for free; utili were reserved for those who had to earn a living. No Medici, Pazzi, or Soderini would stoop to taking money for participating in government, but a Machiavelli couldn’t afford to be so proud. At its highest levels Florence was ruled by amateurs, men who graciously volunteered to take time away from their normal pursuits to serve the greater good. This was the theory at least. In fact, by the fifteenth century those who circulated among the highest offices in the land were mostly practiced politicians who spent far more time running the state than they did managing their private affairs. For these influential men—amounting to a couple of hundred at most—political power was a prerequisite for economic success, since, as Lorenzo de’ Medici once remarked, “it is ill living in Florence for the rich unless they rule the state.” High political office, in addition to allowing the holder to tinker with the tax rolls in such a way as to reward friends and harass enemies, opened up the spigots of patronage. One of the main ways these gentlemen-politicians built up a power base was by providing utili to a long list of clients, who were then beholden to their patrons.

This was actually Machiavelli’s second attempt to land a government job; at the beginning of the year he had unsuccessfully applied for the post of First Secretary to the Signoria. This came at a time when Savonarola’s men were still in power, and Machiavelli’s defeat offers one more clue that he was out of favor with the religious zealots.ii But in the days following the arrest of Savonarola, Machiavelli’s prospects began to look up as the government purged the frateschi from its midst. Among those who lost his job in the shake-up was Alessandro Braccesi, chief of the Second Chancery. Braccesi was closely associated with the disgraced preacher and his dismissal was part of a general purge of the friar’s men. On June 15 the Eighty nominated Niccolò Machiavelli to serve out the remaining two years of Braccesi’s term, beating out three other candidates. The appointment was ratified by a vote in the Great Council on June 19.

The hidden web of patronage that landed Machiavelli his job is difficult to untangle, but it is clear he had friends and admirers among the moderates who now dominated the government. He almost certainly lobbied for the job since they were highly competitive and no one with the power to grant the favor was going to bestow it on someone who wasn’t sufficiently grateful. It may have been Bernardo’s friendship with the former Chancellor of Florence, Bartolomeo Scala, that first brought his son Niccolò to the attention of the new regime. Niccolò was also friendly with Alammano Salviati, Piero de’ Medici’s son-in-law, who was now a member in good standing of the ruling elite, and he was on cordial terms with the new Chancellor, Marcello Virgilio Adriani, a man who, like Scala and like all the chancellors before him, shared Machiavelli’s taste for classical literature. Five years his junior, Machiavelli probably knew Adriani from his time spent rounding out his education at the Studio, Florence’s university, while Adriani was a professor there.iii Most significantly, perhaps, Ricciardo Becchi, the ambassador to the Holy See who had just employed him to snoop on the sermons of the friar, could have vouched for his anti-Savonarola views.

Machiavelli’s politics made him acceptable and his connections brought him to the attention of the right people, but it was his literary skills that qualified him for the job. Unlike the First Chancellor’s position, which was largely ceremonial and involved writing magisterial encomiums to the wisdom and greatness of the republic he served, the post of Second Chancellor was far less prestigious but equally important to the actual functioning of the government. The Second Chancery was tasked with handling the bulk of the state’s correspondence. In theory, foreign affairs were under the jurisdiction of the First Chancery but, in typically Florentine fashion, the boundaries between the departments were porous, if not actually confused. Machiavelli did not limit himself to domestic matters but plunged almost immediately into diplomatic and foreign affairs. His role in the city’s foreign service was made official in July when he was given the additional title of Secretary to the Ten of War and Peace, charged with handling the correspondence of this all-important body that oversaw the republic’s military forces.

Machiavelli’s role was not to set policy but to aid his superiors in implementing it. His immediate subordinates at the Chancery included ten to fifteen notaries and secretaries, learned men of modest means who had the skill and command of both Latin and the vernacular to convert the often garbled instructions of their superiors into comprehensible documents drafted in a fine, legible hand. As worldly and well educated as those who ruled the state, they differed from their bosses to the extent that they needed to draw a steady income. Their office was located on the second floor of the Palazzo della Signoria, just off the Room of Lilies where their lordships dined in regal splendor beneath frescoes by Ghirlandaio.

Machiavelli was on friendly terms with many of these high dignitaries, but it was clear he was their employee, not their equal. Passing the highest office holders on his way to his office, he would bow before exchanging a few pleasantries. If he could not match them in terms of wealth or status, he was not far removed from their world. In fact he was in many ways a man of their class, equally well educated and with an old, distinguished family name. The distinctions were real but subtle, making Machiavelli’s relations with his superiors complicated, ambiguous, and fraught with unarticulated tensions. When he came to write his great political and literary works, this marginality would offer a fresh perspective on age-old questions.

While in town Machiavelli would make the ten-minute walk daily from his house, across the Ponte Vecchio, to the palace where he would spend his days bent over at his desk piled high with the most important documents of the Florentine Republic. Working with him were his assistants Biagio Buonaccorsi and Agostino Vespucci, men who would become his friends and most reliable correspondents over the course of the next few years. Buonaccorsi was particularly close to his new boss. In one letter he describes how the two of them could be found on most days at adjacent desks, happily writing side by side as they shared the latest gossip and made snide comments about their colleagues. They had been friends before their appointment (on the same day) and it is largely thanks to their correspondence that we can paint a detailed portrait of Machiavelli’s life in the first years of his career.

Though much of the work was routine, and always voluminous, Machiavelli clearly relished it. Plowing through the dispatches of various ambassadors, firing off letters of his own—sometimes encouraging but often, if he felt his correspondent had shirked his duty, acerbic—he was in his element. “If I have not written as often as I would have liked,” Machiavelli wrote to one of his colleagues, “it is because I have been so busy”—a common complaint among those employed in the Second Chancery since the always parsimonious government tried to extract the maximum effort from its paid staff.

In part, his growing portfolio was a tribute to Machiavelli’s native abilities, but it was also a product of the built-in inefficiencies of the government. Elected offices were usually of short duration—in the cases of the most important ones like the Priors and Gonfaloniere (Standard-Bearer of Justice), the titular head of state, as little as two months—which placed greater burdens on the permanent bureaucracy. While elected officers came and went, the salaried officials provided continuity and institutional memory.

This was all the more critical in this time of crisis. The wounds to the body politic in the wake of Savonarola’s death were more than political and healing would require more than just a change in personnel. A few months earlier Florence was held spellbound by a leader who promised a wholesale reformation of the human spirit. During his first days in office, Machiavelli passed on his way to work a group of women who knelt in prayer on the spot where their leader had met his death, and they were not the only ones who found it difficult to turn their gaze from heavenly realms to gritty, earthbound realities. What could the current government of merchants and bankers offer to compete with Savonarola’s metaphysics?

For the administration of which Machiavelli was now a part, the job was complicated by the fact that those who had brought about Savonarola’s downfall did not necessarily share a common vision for the future. “[M]any,” wrote Guicciardini, “believed that by overthrowing the friar the Great Council would be destroyed, and that was why they had worked so vigorously against him,” but these reactionary elements were quickly disappointed “when they saw that many of their followers . . . and all the people wanted to keep the council.” Chronic tensions between ottimati, who wished to preserve the dominant role of the traditional elite, and popoleschi, who continued to push for broader representation, made it difficult to implement consistent policies. The normal friction between the two groups threatened to erupt into chaos with each new fiscal challenge or military setback. In one heated debate over implementing a system of progressive taxation, a spokesman for the popular faction captured the resentments of his class. “[I]f [the ottimati] complain that this tax will impoverish them,” sneered Luigi Scarlatti, “let them reduce their expenses; and if they can’t keep their horses and servants, let them do as he does and walk to their country houses and serve themselves.” The rich, for their part, suspected that legislation enacted by the popular faction was designed with the sole intent of ruining them. “What a disgusting thing it is,” complained the wealthy and well-connected Guicciardini, “that among the city’s leading citizens, who have the same interests and should have the same judgments about things, there is so little loyalty, so little unity, and so little courage in matters that one might say concern their very existence.”

Machiavelli, less moralizing and more imaginative than his friend, drew different lessons from his city’s fractiousness. Like James Madison, who structured the U.S. Constitution to resolve the conflicting needs of its citizens through a system of checks and balances, Machiavelli viewed such tensions as both inevitable and even creative. “[I]n every republic,” he wrote in The Discourses, “there are two different dispositions, that of the populace and that of the upper class and . . . all legislation favorable to liberty is brought about by the clash between them.” But while acknowledging the perennial conflict of interest among the haves and have-nots, and insisting that at least some level of conflict is a necessary precondition of liberty, he faulted his compatriots who shortsightedly pursued the interests of party, failing to recognize that their own rights would best be protected by acknowledging the legitimate aspirations of their neighbors. “The reason why all these governments [in Florence] have been defective,” he explained, “is that the alterations in them have been made not for the fulfillment of the common good, but for the strengthening and security of the party.” The problem was not with human nature, which he fully acknowledged was selfish and quarrelsome, but with those legislators who failed to put in place political structures that imposed equal obligations on all the citizens and, in return, offered a fair distribution of society’s benefits.

Machiavelli’s view of politics as an unceasing battle between competing groups and individuals came naturally to one intimately acquainted with Florentine politics. From the beginning of his tenure the government he served was divided both horizontally along class lines and vertically among multiple networks of patronage. Constantly bickering and with the blood of holy men on their hands, the current government lacked legitimacy in the eyes of many citizens. It was above all the haplessly conducted war to reconquer Pisa, whose only tangible result so far was to part Florentines from their hard-earned money, which served as the focus of popular discontent. The piling up of disaster upon disaster that had soured the people of Florence on Savonarola’s leadership, would surely do the same for the current occupants of the Palazzo della Signoria unless they quickly did something to relieve the pressure.

•  •  •

A cornerstone of Machiavelli’s philosophy is that success, particularly in the tricky realm of politics, depends on a willingness to adapt to circumstances. “[A] prince is successful,” he writes, “when he fits his mode of proceeding to the times, and is unsuccessful when his mode of proceeding is no longer in tune with them.” This commonsense observation, based on his own experience in the Chancery tailoring policies to the exigencies of the moment, is actually more radical than it seems since it leads ultimately to moral relativism. Unlike the philosophers who preceded him, Machiavelli does not seek to establish universal laws but only limited rules for individual cases. There can be no absolute notion of the Good when an approach that proves effective on one occasion leads to disaster on another.

This flexibility has outraged generations of critics who accuse Machiavelli of a deplorable moral slipperiness, but he would argue that sticking to principle when the facts have changed leads to human suffering. His was an elastic philosophy tailor-made for troubled times, hard won from years of toil on behalf of a weak and faction-ridden government.

Both Machiavelli’s career and thought were shaped by war and by the unsettled condition of Italy following the French invasion four years before he took office. The reverberations from that cataclysmic event continued to rattle the fragile political structures that divided the peninsula, offering opportunities to a few adventurers but anxiety for the remainder who sought security in an age that seemed to offer little of that precious commodity. For the Republic of Florence, once again free to pursue its interests without distraction from messianic preachers, innumerable difficulties lay ahead. Fantasies of Kingdom Come had been jettisoned in favor of more obtainable objectives here on earth, but even with these more realistic and more limited goals in mind, those in government were forced to concede that the resources seemed inadequate to the task at hand. Florentines, who preferred to expend their coin rather than their blood but were inclined to be stingy with both, found the coffers almost bare as those they hired to do their fighting for them seemed more interested in prolonging the profitable enterprise than risking all in a decisive confrontation. As Luca Landucci observed, “The rule for our Italian soldiers seems to be this: ‘You pillage there, and we will pillage here; there is no need for us to approach too close to one another.’ ”

In retrospect it is clear that Machiavelli’s service in the government of Florence at this particular moment in history provided the ideal education for the philosopher he was to become. It was a school of hard knocks that opened his eyes and toughened his spirit. It provided innumerable practical lessons in practical politics, and he learned from both his occasional triumphs and his far more common setbacks.

Much of Machiavelli’s writing, from The Prince to The Art of War, deals with military matters, since he concluded that it was pointless to discuss the proper form of government unless and until a state could adequately defend itself. “A prince must have no other objective, no other thought, nor take up any profession but that of war,” he insisted. This bellicose attitude was a response to his frustration at Florentine fecklessness when it came to protecting itself from foreign aggressors. From the beginning of his career, Machiavelli found himself embroiled in endless quarrels between the cash-strapped government and the various generals in its employ. In March 1499, he was sent to the camp of one of the condottieri involved in the effort to reconquer Pisa, Jacopo, lord of Piombino, who was threatening to withdraw his services unless he received more money and more troops. Machiavelli’s mission was a success; he managed to persuade Jacopo to adhere to the terms already agreed to. More importantly, it was his first opportunity to witness the disastrous consequences of relying on soldiers for hire. As the war to conquer Pisa dragged on apparently without end and as Florence sought protection against a host of foreign threats, relying on those who owed loyalty to no one but the highest bidder seemed to Machiavelli a dangerous and shortsighted policy unworthy of free men.

On a second junket, this time to Forli, a small state in the Romagna some fifty miles northeast of Florence, Machiavelli plunged more deeply into thickets of military strategy and diplomatic intrigue.iv Setting out on horseback on the 12th of July, he arrived at the court of Caterina Sforza four days later. Here he plunged into negotiations with the Countess over renewing the contract with her son, Ottaviano Riario, as a condottiere in the service of the republic. On this, his first important diplomatic mission, he was brought face-to-face with one of the truly remarkable characters of the age. A woman of great courage and beauty (Biagio Buonaccorsi requested that his friend bring back a portrait for him to admire), Caterina was the illegitimate daughter of Galeazzo Maria Sforza, who had ruled Milan until his assassination in 1476. At the tender age of fourteen she had been married to Girolamo Riario, nephew of Pope Sixtus IV. It was Girolamo who, regarding Florence as the chief impediment to his ambition to carve out a state for himself in the Romagna, planned the murderous attack on Lorenzo and Giuliano de’ Medici known as the Pazzi Conspiracy. A cruel and violent prince, he himself was assassinated by his long-suffering subjects in 1488. During the revolt, Caterina’s young children were taken hostage; when the rebel leaders threatened to kill them unless she surrendered the fortress into which she had fled, she leapt onto the parapet, pulled up her skirts, and, pointing to her genitals, declared she was ready and able to make more.vWhen her second husband met the same fate as her first, she wreaked terrible vengeance on the people of Forli, executing forty suspected conspirators in the public square.

If her sex made her exceptional among the petty rulers of Italy, the frequency with which those close to her tended to meet violent deaths was only slightly above the norm. In the barely contained chaos of Italian politics, minor states were fought over by the larger ones like dogs snarling over a meat bone, and any petty potentate hoping to avoid being devoured needed to be both resourceful and quick on her feet. Caterina was both. She had survived this long through a certain ruthlessness and an aptitude for finding champions—neighbors, relatives, and husbands—who would protect her from her covetous neighbors without demanding that she forfeit her independence. Her most recent marriage was to Giovanni de’ Medici, son of Pierfrancesco,vi and her court was, according to Machiavelli’s report, “crowded with Florentines, who appear to manage all the concerns of the State.”

With so many Florentines in positions of influence, Machiavelli hoped they would promote the republic’s cause. But Caterina was a master at playing one power off against the other. Not only were Florentines here in force, but so were agents from the Duke of Milan, Caterina’s uncle, who also hoped to retain Ottaviano Riario’s services for his own impending battle with the French King. After days of haggling, Machiavelli thought he had struck a mutually beneficial arrangement, but the following morning he was called before the Countess and found her in close consultation with the Milanese ambassador. Now “having thought the matter over in the night,” Machiavelli reported, “it seemed to her better not to fulfill the terms, unless the Florentines would pledge themselves to defend her state. That although she had sent him a message of a different nature the previous day, he ought not to be surprised at the change, since the more things are talked over, the better they are understood.”

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. Paolo 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 again. 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.

Thus ended the remarkable career of the Moor, a man who imagined himself a paragon of cunning but whose short-term cleverness was accompanied by no real wisdom. “So his shrewdness was mocked,” wrote Machiavelli with obvious satisfaction, a sentiment shared by a majority of his compatriots. It was due largely to his ambition that a great people now lay prostrate beneath the barbarian’s boot, and it was only just that the author of this calamity should find himself caught in the web he had woven.

Among the first to congratulate the French King was the Florentine ambassador, Tommaso Soderini, who deemed the moment auspicious to remind him of recent commitments. Negotiations were conducted with Georges d’Amboise, Cardinal of Rouen,x a man whose business acumen and ability to drive a hard bargain were more typical of a merchant than a man of God. He finally agreed to lend the troops already promised—five hundred spearmen, four thousand Swiss pike men, and two thousand Gascons—but only at the exorbitant price of 24,000 ducats a month. Soderini acceded to the onerous terms reluctantly, hoping that a quick campaign would bring victory before bankruptcy.

But the expedition was doomed from the outset, largely because the two allies had divergent aims. For the French, Florence was of little use except as a bank from which to withdraw funds for the maintenance of their army on foreign soil; their strategy was to extract as much cash as they could up front, while providing as few troops as they could get away with. For Florence, the conquest of Naples was a matter of indifference unless Pisa was part of the campaign. The truth was that Florence needed France more than France needed the militarily insignificant republic. Soderini, like Machiavelli at Forli, was discovering the tribulations of representing a state regarded with contempt by its partners. The army was slow to set out, and once in motion moved with the leisurely pace, if not the tight discipline, of soldiers on parade. In fact the greed and unruliness of the French troops, who extorted money and provisions from every community they approached—friend and foe alike—undermined the cause of the city that employed them even before any blows were struck.

Hoping to bring order to a situation that was fast spinning out of control, the Florentine government dispatched to Cascina, ten miles to the east of Pisa where the army was now bivouacked, two commissioners, Luca degli Albizzi and Giovan Battista Ridolfi. Also included in the delegation was Machiavelli, who was to serve as secretary. Riding into camp, they found the troops close to mutiny. In the tradition of hired guns throughout the ages, the men complained of poor rations and salaries owed, turning their fury on their paymasters rather than on the enemy they were supposed to fight. Albizzi deemed the situation so dangerous that he told his colleagues, “He who is afraid may go back to Florence,” an offer that Ridolfi immediately seized.

Despite friction between the Florentine representatives and the army, in late June eight thousand men advanced on Pisa, and on the 27th French artillery opened up on the walls of the city. But in a repetition of the Vitelli fiasco a year earlier, stalemate was plucked from the jaws of near certain victory, and this time the results were even more injurious to Florentine interests. On July 7, the Gascons deserted en masse, while the Swiss concluded that they risked fewer injuries if they stormed the headquarters of the Florentine commissioner rather than the Pisan fortifications. “It might . . . be well,” Albizzi now wrote to the Signoria with calculated understatement, “whether it is desired that my life should be saved . . . . Let not your Excellencies think that cowardice moves me in this, since by no means would I flee from any peril, that should be deemed indispensable by my city.” Machiavelli, who actually penned these letters dictated by his boss, was of the same mind, willing to do what he could but anxious not to lose his life in a doomed effort. The following day Albizzi was seized by the disgruntled troops, who threatened to kill him if he did not come up with the money they claimed they were owed; he was released only when he signed a guarantee that he would cover his government’s obligations from his own bank account. But by this time it was too late to salvage the expedition. The army for which Florence had paid so dearly and from which so much had been expected no longer existed. It had dissolved before the walls of Pisa, taking with it much Florentine pride and treasure.

Machiavelli recalled this unfortunate episode in his First Decennale, which sets out in verse form the trials of serving a state that lacked the will and courage to defend itself:

But when they confronted the Pisans, the Gauls, full of confusion,

struck by fear, did not show their forces at all prepared,

but went away almost defeated and marked with severe disgrace;

so the truth was known that the French can be conquered.

And it was not an affair to pass over lightly, because if it made

[Florence] groveling and servile, upon the French was the chief reproach;

but you were not free from blame, although the Gaul

tried to cover his shame with the failure of others;

and your government too did not understand how to make decisions.

Though he grants to the French “the chief reproach,” he blames his native land almost equally. “Groveling and servile,” Florence had allowed itself to become dependent on another nation, one, moreover, that proved itself inept as well as faithless. Failure to capture the puny city of Pisa revealed the weakness of both states. Under more settled conditions such a revelation might not have proved fatal, but with Italy fast becoming the proving ground for the armies of Europe, such an opening could not remain long without someone walking through it.

i This salary could provide a comfortable, if not luxurious, living. It was double what a skilled artisan would take home in a year. But given the expenses of the job—including travel on behalf of the government that was often not compensated—Machiavelli continued to struggle to make ends meet. Adriani, the Chancellor of Florence, was hired at a salary of 330 florins per year.

ii Diarist Marco Parenti declared that at this time Savonarola’s “friends were approved [for election] and those suspect left outside” (Rubinstein, “The Beginnings of Machiavelli’s Career in the Florentine Chancery,” 80).

iii Machiavelli’s other sponsor was Antonio della Valle, Adriani’s assistant in the First Chancery.

iv The Romagna was the province that bordered Tuscany to the east and north. Theoretically it was ruled by the Pope, but in reality it was divided among numerous, largely independent potentates. The tensions thus created were a source of endless headaches for the Florentine Republic.

v The children were spared.

vi Pierfrancesco de’ Medici belonged to the so-called younger branch of the Medici family descended from Lorenzo, brother of Cosimo—grandfather of Lorenzo the Magnificent and great-grandfather of Piero. Piero had exiled his cousins before his own expulsion brought them back to Florence. Giovanni de’ Medici and Caterina Sforza gave birth in 1498 to another Giovanni, who grew into a famous mercenary general nicknamed Giovanni delle Bande Nere (Giovanni of the Black Band, the name for his renowned company). He, in turn, fathered Cosimo de’ Medici, who became Grand Duke of Tuscany.

vii The florin and ducat were roughly comparable. The florin was minted at Florence, the ducat at Venice. Both coinages were in use throughout Italy and Europe.

viii This practice happened surprisingly often in Renaissance Italy, perhaps one of the reasons condottieri felt little sense of obligation to their employers. The other famous case of a mercenary general beheaded by his employers was that of Carmagnola, a condottiere in the employ of Venice who was beheaded in 1432 after similar accusations of treachery. It is safe to say that relations between mercenary generals and the governments who hired them were marked by mutual suspicion.

ix It is from this dukedom that Cesare took the title by which he is best known in Italy: Valentino.

x The elevation of d’Amboise, a favorite of the King, to the College of Cardinals was one of the conditions of the agreement between Louis and Pope Alexander. The red cardinal’s hat was carried in the luggage of Cesare Borgia on his voyage to France.

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