IV

SIR NIHIL

“The French are blinded by their own power, and only think those who are armed or ready to give money worthy of their esteem. They see that these two qualities are wanting in you, so they look upon you as Sir Nihil.”

—MACHIAVELLI, DISPATCH TO THE TEN OF WAR

RODRIGO BORGIA, THE SPANISH-BORN POPE ALEXANDER VI, was on intimate terms with most of the Deadly Sins. Greed, Wrath, Lust, Gluttony, and Pride: all these vices he possessed in more than full measure. It was as if he modeled himself on the Borgia family crest, whose heraldic device featured a black bull. Rather than conceal his failings, as his equally corrupt but more timid predecessors had, Rodrigo reveled in them, boasting of his sexual prowess and gargantuan appetites. In July 1501, Machiavelli received a report from Rome chronicling the misdeeds of the Pontiff. “Benefices are sold here like melons,” Agostino Vespucci explained to his friend. “[E]very evening, from the Ave Maria to an hour after sunset, twenty-five or more women are brought into the palace . . . until the whole [Vatican] palace is turned into a brothel filled with every obscenity.” In a break from the custom of the time, Rodrigo openly acknowledged his many children rather than passing them off as his nieces and nephews. He may have been no worse than some of the other recent occupants of the papal throne, but he embraced his sinful nature with unusual gusto.

Machiavelli himself had a decidedly mixed opinion of this powerful figure “who, of all the pontiffs that have ever been, showed how much a pope—with both money and an army at his disposal—could accomplish.” But, as Machiavelli also noted, his abilities were employed in pursuit of selfish ends, “to ensure the greatness not of the Church, but instead of the Duke [Cesare, his son].” In The Prince, Machiavelli treats him with grudging respect: “Alexander VI . . . never thought of anything but deception, and always found subjects on whom to practice this art. There never was a man who made promises more effectively, or affirmed an oath with as much solemnity, while observing them less. Nonetheless, his tricks always paid off, for he was well acquainted with this side of the world.”

Alexander’s oldest and most capable son, Cesare—known as Valentino—had followed his father into the Church. Elevated in 1493 to the College of Cardinals at the age of eighteen, he was insulated to some extent from the squabbles that set one minor state against the other. Of course the Renaissance Church was a highly political institution and, as his father’s right-hand man, he was a force to be reckoned with in temporal as well as ecclesiastical matters, but since he was prohibited by the nature of his office from producing legitimate heirs and founding his own dynasty, he remained largely on the sidelines while others fought to rearrange the map of Italy to their liking. Within the Church his future was unlimited, and to one of a more placid temperament the prospect of ascending to the very pinnacle of power without risk to life and limb might have seemed an attractive alternative. But to Cesare, honors won by peaceful means seemed hardly worthy of a man.

Despite the fact that Cesare did not allow his office to interfere unduly with his lifestyle—even his generally tolerant colleagues in the Holy College complained that he preferred the doublet and hose of a courtier to the scarlet robes of a cardinal—he was restless and discontented. A handsome, athletic man, he was already exhibiting the telltale “flowers” of syphilis—the Gallic disease, it was often called by Italians, who believed it had arrived with Charles’s invading army in 1494—proof that, like his father, he was not inclined to take his vow of celibacy literally. Another rule he apparently found onerous was the one prohibiting men of the cloth from engaging in acts of violence. When his sister Lucrezia was discovered in flagrante with a valet in her husband’s employ, Cesare drew his sword and chased the man through the Vatican. The valet’s life was initially spared when he threw himself at the feet of the Pope, but his body was later discovered floating facedown in the Tiber—the kind of unfortunate accident that seemed to befall those who got in the way of the Cardinal.

The one man whose mere existence stood between Cesare Borgia and his fondest ambitions was his brother, Juan, who received the title the Duke of Gandía after marrying a cousin of the Spanish King. Described by a contemporary as “a very mean young man, full of ideas of grandeur . . . haughty, cruel and unreasonable,” Juan was nonetheless his father’s favorite and, it seemed to Cesare, the undeserving recipient of all those titles that rightfully should have gone to him. In 1496 Juan was appointed by Alexander second-in-command of the papal armies, a post for which Cesare thought himself far better suited. Events seemed to confirm Cesare’s judgment when Juan’s incompetence led to the army’s defeat at the hands of their own vassals, the insufferable Orsini counts, who were reluctant to submit to their papal overlord.

On the evening of June 14, 1497, the two brothers dined together at the home of their mother, the Pope’s former mistress Donna Vannozza. Riding home that night the two parted company somewhere near the Piazza degli Ebrei, in Rome’s Jewish quarter. When the Duke failed to return home, and when the following morning his bodyguard was found dead, his desperate father launched a massive search effort. After searchers spent a couple of days combing the slums and alleys of the Eternal City, a charcoal vendor came forward to report that on the night of the disappearance he had seen a body being tossed into the river near where the Duke had last been seen with his brother. (When asked why he had not told his story earlier, he explained that this was such a common occurrence he had not thought it worth reporting.) Dredging the Tiber, the Pope’s men discovered the Duke’s body, dressed in the clothes he had worn while dining with the Cardinal.

Suspicion immediately fell on Cesare, the man last seen in the Duke’s company and the one who had most to gain by his departure from the scene.ⁱ This, at least, was the rumor whispered in the rooms of the Vatican, though only out of the Pope’s hearing. Alexander was devastated by his favorite son’s death, “shutting himself away in a room in grief and anguish of heart, weeping most bitterly.” When he finally emerged from his isolation he appeared to be a changed man. “Life has lost all interest for us,” he declared. “It must be that God punishes us for our sins, for the Duke has done nothing to deserve so terrible a death.”

But after a period of mourning, and a well-publicized campaign to reform a Church that under his tenure had grown, if possible, even more corrupt than before, Alexander reverted to his old ways, this time lavishing on the likely murderer all the favors he had previously bestowed on his victim. “Even more than by anger or by any other emotion,” Guicciardini declared, discovering in this simple formula the lodestar of all his policies, “the Pope was motivated by his unbounded greed to exalt his children, whom he loved passionately.” Thrusting aside any suspicions he might have harbored, Alexander was now determined to set Cesare on the path to worldly triumph that had eluded his ill-fated brother.

The first step was for Cesare to exchange the robes of a prince of the Church for the sword and armor of a secular lord. Fortunately, a likely sponsor immediately stepped up in the person of King Louis of France, whose ambitions in Italy could best be realized by forging an alliance with the Pope. Soon Cesare was headed to France with the King’s guarantee of a dukedom in his pocket and, even more to his taste, the promise of a prominent role in the army of invasion.

For the Republic of Florence the return of the ambitious Cesare Borgia to Italian soil at the head of an army was about as welcome as the plague. Papal relatives always proved troublesome since the territories in which they could fulfill their ambitions abutted those of the Florentine empire and often lay within what Florentines considered their sphere of influence. During the reign of Sixtus IV, the Pope’s desire to provide his nephew Girolamo Riario with his own fiefdom embroiled Florence in a two-year war that almost extinguished the independent republic. Geography alone made the Pope and his spawn a threat to Florentine independence. To the south lay the Papal States, the region near Rome that constituted the most ancient possession of the Holy See; to the east and north the Romagna: both regions owed theoretical allegiance to the heir of Saint Peter, however much each vassal might act as if he commanded an independent state. Should Alexander and Cesare succeed in forcing these unruly dependents into submission, they would virtually encircle the republic. It is not surprising, then, that in the Palazzo della Signoria news of Cesare’s arrival in northern Italy was greeted with near panic.

Everything indicated that Cesare was unlikely to settle for less than his predecessors. As a newly minted lord with a high-sounding title but little real power, he now contemplated the patchwork of Italian states like a ravenous man surveying a mouthwatering buffet. The only decision was which delicacies he should pop into his mouth first.

Once Milan fell to the French—with Cesare, Duke Valentino, riding into the city triumphantly at the King’s side—he was free to set off in pursuit of his own territorial ambitions. First to attract his covetous eye was Forli, the same small state Sixtus had bequeathed to his nephew and that was still in the hands of his widow, the formidable Caterina Sforza. The unhappy outcome of Machiavelli’s earlier mission to Forli had resulted from Caterina’s conviction that Milan, under her uncle Ludovico Sforza, was in a better position to rescue her from the clutches of the Borgia than the weak, vacillating Florentine Republic. With her uncle now driven from Milan by the French, it seemed she had placed her bet on the wrong horse. Nor was this her only misstep. “[I]t would have been safer for her,” Machiavelli observed dryly, “had she not been hated by the people.” Caterina had run out of champions. After a brief siege, Valentino’s army stormed her last remaining citadel, captured the Countess, and threw her into prison.ⁱⁱ Thus the son of Pope Alexander destroyed the last vestiges of the fiefdom his predecessor had hoped to establish for his nephew, Girolamo Riario, once again demonstrating how difficult it was to build a secular dynasty on a foundation of papal power.ⁱⁱⁱ

This sobering lesson was lost on Valentino, who was determined to grab as much as he could while his father still sat on the Throne of Saint Peter. After snapping up Forli, Valentino seized Pesaro and Rimini on the Adriatic coast. “This lord knows very well,” Machiavelli wrote in a report to the Ten setting out the Duke’s overall strategy, “that the Pope can die any day, and that he needs to think before his death of laying for himself some other foundation, if he intends to preserve the states he now has.” In the space of a few short months Cesare Borgia had shown himself to be a far more energetic and capable leader than his late brother, but far from satisfying him, each new success—enthusiastically recounted by Alexander, who sorely tried the patience of his visitors with tales of his son’s exploits—merely whetted his appetite for tastier morsels.

Florence looked on with apprehension as the Duke picked off one small territory after another on the borders of Tuscany, but there was little it could do to slow his triumphant progress across central Italy. The one card Florence had to play was diplomatic. Both the Republic of Florence and Duke Valentino were clients of the same patron—the Most Christian King Louis of France. Though Louis had thus far turned an indulgent eye toward his new vassal—in fact most of Valentino’s conquests were made with an army that included French troops—he also realized that his long-term success in Italy would be jeopardized if he lost the goodwill (and hard cash) of the Florentine Republic. To deal with this growing crisis, as well as the continuing stalemate before Pisa, the government of Florence appointed Francesco della Casa special envoy to the French King. Accompanying him on this critical diplomatic mission was the Second Secretary of the Chancery, Niccolò Machiavelli.^iv

Della Casa and Machiavelli set out for France on July 18, 1500, arriving on August 7 in Nevers, where the King’s peripatetic court had temporarily alighted. With its throngs of ambassadors and clerics, lords and ladies—both great and small—ministers and secretaries, as well as countless hangers-on and supplicants attracted by the prospect of advancement or the hope of redress, the court of the Most Christian King was a far more splendid stage than any on which Machiavelli had previously performed. By comparison, Countess Sforza’s castle in Forli had been little more than a rustic stronghold.

But if the stage was far grander, the part the two envoys from the Florentine Republic could expect to play was proportionally diminished. Their insignificance was made abundantly clear when della Casa and Machiavelli attempted to navigate the bureaucratic maze, competing for attention with men who represented far greater powers and whose governments provided them with far more substantial resources. “The French are blinded by their own power, and only think those who are armed or ready to give money worthy of their esteem,” Machiavelli reported to the Signoria. “They see that these two qualities are wanting in you, so they look upon you as Sir Nihil [Nothing] . . . . Our degree and quality, on an unwelcome errand, do not suffice to bring sinking things to the surface . . . . [The republic] should try to obtain by bribery some friends in France who would be stirred by more than natural affection, since that is what has to be done by all who have affairs at this Court. And he who refuses to do it is like one who would win a suit without feeing his attorney.”

Though signed by both ambassadors, the dispatch—written in Machiavelli’s own hand—reflects the pithy analysis of the junior partner. No one was quicker than the Second Chancellor to size up a situation and discover where real power lay. Whatever they were told by the Cardinal de Rouen or any of the King’s other ministers, they would receive little satisfaction without something tangible to offer their hosts. As usual, however, the Signoria was trying to do diplomacy on the cheap, sending men of little standing who cut rather shabby figures at the glittering French court.

But in Machiavelli the Florentines always got better than they deserved. Despite complaining about the meager level of support, Machiavelli was zealous in carrying out his mission, promoting his government’s policies and sending to Florence a series of dispatches filled with penetrating analyses. As if to compensate for their miserliness, his superiors at the Chancery were generous in their praise. “I don’t want to forget to tell you,” reported Biagio Buonaccorsi, “how much satisfaction your letters give everyone; and believe me, Niccolò, when I tell you, since you know that I have no talent for flattery, that when I found myself reading those earlier letters of yours to certain citizens, many of the highest rank, you were highly commended, and it pleased me greatly, and in a few words I artfully confirmed their verdict, showing how easily you did it.”

Machiavelli’s worth was proven even more emphatically when della Casa took ill, leaving his assistant to carry on without him. Most of his time at court, which by September had relocated to Melun, near Paris, was spent trying to patch up the quarrel that had arisen between the two states over the conduct of the war with Pisa. While Machiavelli suggested delicately that the disaster was attributable to the incompetence and treachery of the Swiss troops, the King pointed the finger at the Florentines, who failed to deliver the promised fee. Unless Louis were paid the 38,000 francs he claimed he was owed, Machiavelli reported, “he threatens to erect Pisa and the neighboring territory into an independent state.”

The second matter Machiavelli raised with the King and his ministers was the increasingly threatening posture of Cesare Borgia. Sooner or later, he explained, Valentino’s ambitions in Italy would clash with theirs. Sparring with the powerful minister of the King, Machiavelli more than held his own. “[W]hen the Cardinal of Rouen told me that the Italians knew nothing of war,” Machiavelli recalled in The Prince, “I responded that the French knew nothing of statecraft, for if they had they would never have allowed the Church to grow so great.”

Satisfying as it was to knock the arrogant French Cardinal down a peg or two, Machiavelli also advanced the republic’s agenda by reminding Rouen of the dangers of unchecked papal power. Were Alexander and his son allowed to ride roughshod over the independent powers of Italy, how long would they tolerate Louis’s ambitions on the peninsula? The uncomfortable fact, at least as far as the French were concerned, was that in striking a deal with the Pope they were emboldening a man who already had turned on them once before and whose interests were ultimately at odds with theirs. As Machiavelli wrote in October, “if the King had conceded everything for [Cesare’s] expedition in Romagna, it was rather because he knew not how to withstand the unbridled desires of the Pope, than from any real desire for his success.”

Machiavelli’s strategy was to remind the French at every turn how dangerous Valentino was, a task made easier by the Duke’s natural aggressiveness. While Machiavelli was pleading his case before the French court, Valentino was threatening to pounce on Bologna; he had even entered into negotiations with Pisa to have himself declared its Duke, demonstrating that his ambitions could no longer be contained within the borders of Romagna but extended to Tuscany as well. “The Pope,” Machiavelli told his bosses, “tries by all means to compass the destruction of the King’s friends, to wrest Italy from his hands with greater ease.” Unfortunately, Machiavelli did not have the stage to himself. He had to wage a daily struggle with ambassadors from Pope Alexander who suggested that if only Piero de’ Medici were restored to Florence, the French would find the republic far easier to deal with. Machiavelli urged the Ten that the best way to counter this insidious campaign was to swallow their pride and pay the French the money they claimed was owed to them—a request his government quickly complied with. The arrival of Florentine ducats had an immediate impact; upon their receipt, the King conveyed a stern letter to Valentino ordering him to stop his meddling in Tuscany.

Machiavelli remained with the French court until late November, by which time the government had appointed Pier Francesco Losinghi to replace him. The five months he had been away from Florence had been difficult for Machiavelli. His penny-pinching bosses in the Signoria begrudged him every soldo so that he was forced to content himself with dingy, lice-infested lodgings and often showed up at court in robes worn at the cuff and too often mended. This was not only personally humiliating but also self-defeating since it was but one more indication in the eyes of his hosts that the state he represented was truly Sir Nihil.

The mission to France had come at a difficult moment in Machiavelli’s life. His father Bernardo had died in May, which meant that just as Niccolò was setting out on this crucial assignment he was burdened with new responsibilities.^v He was now officially the head of the Machiavelli household, with siblings and other relatives looking to him for advice as well as material support. During his months away in France his older sister, Primavera, died of fever and her thirteen-year-old son, Giovanni, seemed likely to follow her to the grave. Though, happily, the boy survived, this meant that Machiavelli’s list of responsibilities was that much longer.^vi When his brother, Totto, begged the government to cover the additional expenses of Machiavelli’s foreign posting, this was in part an acknowledgment that Niccolò’s salary, even when combined with the rents derived from their properties, was still insufficient to meet the family’s basic needs.^vii

But in some ways it was an enormously exciting time for Machiavelli. After more than thirty directionless years, he had found his calling. This was the work he felt he was made for. Politics, which to the average Florentine citizen was a normal part of civic life, was his consuming passion, and nowhere was the game played more ferociously and for higher stakes than in the great courts of Europe. These were not places for the faint of heart or the easily deceived. Latin orations modeled on Cicero delivered by ambassadors dressed in cloth of gold and sparkling with pearls, the culture of flattery and obfuscation—Machiavelli saw through it all. Beneath the glittering surface something far more savage was taking place. Observing at close hand the palace intrigue and backstairs deal-making at the royal court, he discovered a window into the soul of men and a true picture of society built on unequal relationships. Here, brazen self-interest and naked aggression were ingeniously concealed, sweetened with lies and sauced with piety, until even the most unpalatable cruelties seemed refined enough for a king’s table.

The mission to France was his first opportunity to view at close range the inner workings of one of the great power centers of Europe. The lessons he learned pleading before the King and his closest advisers were ones that would remain with him throughout his life and would shape his political philosophy. Perhaps the most important lesson was that, for all the high-sounding oratory, the only thing that mattered in those places where the fate of nations was decided was raw power. He who possessed it commanded the world, while he who lacked it could expect nothing but pity, a gift of the great to the less fortunate that was less than worthless. Machiavelli learned in France that he who could not bargain from a position of strength had better not bargain at all, for in any such exchange—as between a lion and a lamb—the stronger party was bound to devour the weaker. “There can be no proper relation between one who is armed and one who is not,” he wrote in The Prince, “nor is it reasonable to expect that one who is armed will voluntarily obey one who is not.” Any appeal to conscience or fairness was bound to fail when one party had his hands around the throat of another.

It was his profound understanding of this basic fact that transformed his difficult mission in France into a success. It was pointless, Machiavelli realized, to plead the justice of his case: he needed to demonstrate that the weak city-state of Florence and the powerful nation-state of France shared a common goal. To the skeptical Cardinal Rouen he pointed out that Florentines acted “not upon their good faith, but upon its being their interest to side with France,” while, by the same measure, the Pope’s ambitions for his son in Italy were incompatible with the extension of their power on the peninsula. In The Prince he elaborates on the arguments he used on the Cardinal to fashion one of his more memorable aphorisms: “[H]e who causes another to become powerful is himself ruined.” In other words, by backing Cesare and Alexander in their campaign to dominate Italy, the French were sowing the seeds of their own destruction. By contrast, Florentine weakness actually made her a more valuable ally, for the mighty kingdom need not fear her as a rival for supremacy. In the end Machiavelli was able to persuade his own government to yield upon a matter of pride and remind the French of the value of continued Florentine goodwill. The arrangement ultimately hammered out was that the republic would continue to bankroll Louis’s adventures in Italy in return for protection against her enemies, of whom the most dangerous continued to be Cesare Borgia and his indulgent father.

•  •  •

Burdened by the demands of his job and by continuing personal and financial worries, Machiavelli nonetheless kept up that good-natured and often ribald correspondence that no amount of anxiety could suppress.^viii Biagio Buonaccorsi, Agostino Vespucci, and his other friends continued to fill him in on the latest gossip. Office politics was often more compelling, and had more immediate impact on their day-to-day lives, than great affairs of state. In August, a colleague in the Chancery passed along an assessment of the grumpy Antonio della Valle in which he claimed to have discovered the source of their boss’s perpetual nitpicking: “Every day Ser Antonio’s stomach bothers him, but we’re learning how to deal with it; I believe it’s because he doesn’t have his lady Agostanza here to warm him up and give him a workout on the seesaw.”

If a discussion of Madonna Agostanza’s bedroom habits was justified by the irritability it provoked in their boss, no excuses were needed to pass along an obscene anecdote or scurrilous rumor. Gambling, whoring, and other unsavory escapades seem to have occupied a great deal of their free time, though often it is hard to tease out a thread of truth in the exaggerated yarns they spun. Machiavelli’s own proclivities are hinted at by Andrea di Romolo, who tried to entice him back to the city with memories of one courtesan who lived near the Arno. More potentially damaging allusions are contained in a letter by Agostino Vespucci: “When in jest and to relax our minds we were speaking about you, how you so abounded in charm and drolleries, that we were so often forced to be delighted, to smile, even sometimes to laugh when you were present, Ripa added that there was no way you could stay in France without grave danger, since sodomites and homosexuals are stringently prosecuted there.”

Though obviously offered tongue-in-cheek (Vespucci follows up his little joke with another more far-fetched tale involving sexual relations with a horse), the reference to sodomy—which in Florence was a crime punishable, in theory at least, by burning at the stake—can’t be dismissed out of hand. The term, which encompassed not only sex between men but also “unnatural” sex with a woman, was one that attached itself from time to time to Machiavelli’s name. His taste for whores, which he made no effort to conceal, and the various sexual affairs he conducted with more passion than discretion throughout his life, opened him up to slander by his political enemies who trafficked in sordid tales about his private life when they ran out of substantive arguments. Whatever the mechanics of Machiavelli’s sexual performances, and whether or not, as has also been suggested, he occasionally engaged in such acts with boys, his behavior was unremarkable. Florence, both before and after Savonarola, was a city of sexual license where illegitimate children were commonplace, whores innumerable, and the lines between hetero- and homosexuality less precisely drawn than in our day.^ix As Machiavelli’s own correspondence makes abundantly clear, his own range of experience was no wider than that of his friends and colleagues. He was the first to admit he was no saint, but unlike some of his more pious compatriots, he at least had the honesty to admit his failings.

•  •  •

Upon his return from France in December 1500, Machiavelli found his desk piled high with urgent matters needing his attention. In the months he had been away his stock had risen, and with increased confidence in his abilities came increased demands on his time. In February 1501 he was sent to the Tuscan city of Pistoia to mediate between two rival factions, the Pantiachi and Cancellari, who, like the Guelphs and Ghibellines of medieval Florence (or like the Montagues and Capulets of Romeo and Juliet), seemed bent on painting the town red with each other’s blood. Exposure to the hatred and violence of this provincial city—whose ferocity was disproportionate to the prize being contested—offered Machiavelli further evidence of the brutal nature of power politics. His attempts to broker a truce were ultimately futile. Here in one small city on the Arno was the world in microcosm, where hatred stoked over generations proved more compelling than reason, a bitter lesson that Machiavelli would remember when composing The Prince.

It was Valentino, however, testing the limits of his French confinement like a caged tiger, who continued to draw the attention of the Ten and the Signoria. If his master had shortened the leash a bit, forbidding him to gobble up Bologna and Florence, there was still other prey to stalk. Among the more tempting prizes was Piombino, a midsized city on the western coast of Tuscany. Valentino was not discouraged by the fact that to reach this seaport he would have to lead his army through Florentine territory. In fact, he seemed less interested in acquiring the city than in seeing how far he could go before his French overseers reined him in.

In early spring 1501, the lead divisions of Valentino’s army began to stream through the Apennine passes and onto the Tuscan foothills, pillaging the towns of the Mugello foothills as they advanced. Thoroughly alarmed, the Florentine government sped a promised 38,000 francs to Louis along with a reminder of the commitments he’d already made to them. Fortunately, Florence was not solely dependent on French troops. While awaiting the French response the Florentines began to muster their own troops for the defense of the capital. Most of the organizational details fell to Machiavelli, Secretary to the Ten of War, who did not allow skepticism about the strategy his government was employing to interfere with his duties.

As always he worked zealously on behalf of the state, while using the daily frustrations of his office—the incessant quarrels with various captains over pay and dispositions—as grist for the analytical mill that was turning slowly in his head. He had received a traditional humanist education, built around the great classical authors and texts, so it was only natural for him to compare his own experience to the ancient models set forth in Livy, Plutarch, and Thucydides—almost always discovering that the present fell far short of the past. “I have heard,” he wrote, “that history is the teacher of our actions, and especially of our rulers; the world has always been inhabited by men with the same passions as our own, and there have always been rulers and ruled, and good subjects and bad subjects, and those who rebel and are punished.”

Comparing the professional soldiers of his own day with the citizen militias of the Roman Republic, Machiavelli extolled the virtues of the latter: “[A]s long as the Roman republic continued incorrupt,” he would later write in The Art of War,

no citizen, however powerful, ever presumed to avail himself of that profession [of arms] in peacetime so as to trample upon the laws, to plunder the provinces, or to turn tyrant and enslave his country . . . . The commanders, on the contrary, contenting themselves with the honor of a triumph, returned with eagerness to their former manner of living, and the common soldiers laid down their arms with much more pleasure than they had taken them up. Each resumed the calling by which he had gotten his bread before, and none had any hopes of advancing himself by plunder and rapine.

Compare this happy picture to the professional soldiers for hire Machiavelli was forced to deal with on a daily basis:

Mercenary captains are either skilled at arms, or they are not [he wrote in The Prince]. If they are, you cannot trust them, because they will always aspire to achieve greatness for themselves, either by suppressing you who are their master, or by suppressing others whom you wish to protect. If, instead, they are not courageous and skillful soldiers, they will ruin you just the same.

The habit of viewing current events through the prism of the classical past was not unique to Machiavelli, but few could speak with the authority of the Second Chancellor of Florence, who combined theoretical knowledge with a wealth of practical experience.

Even at this early stage Valentino had made a powerful impression on Machiavelli. His boldness stood in stark contrast to Florence’s indecision. While Valentino led his own troops into battle, seizing the initiative through quick movements and judicious application of force, Florence depended on the favor of distant lords and mercenaries whose loyalty was to themselves rather than to their employers. The city’s impotence was amply demonstrated in the spring of 1501 when Valentino was allowed to cross Florence’s borders unchallenged.

Borgia’s policy was to put as much pressure as he could on the republic without actually provoking a French backlash. In May, with his army on Florentine soil, he demanded they reward his insolence by offering him a condotta (contract) as a captain in their army. Reports of atrocities committed by his troops added to the urgency to strike a deal. “The whole morning,” wrote Luca Landucci in his diary, “we heard nothing but the iniquities of Valentino’s troops; among other things they sacked Carmigiano, and carried off all the girls they found there, who were gathered in a church from all the country round.” Too weak to confront their tormentor on the field of battle, Florence was forced to buy him off by offering him a contract to supply three hundred men-at-arms in return for the exorbitant fee of 36,000 ducats.

This was less a traditional contract than a form of extortion, though in truth in the hiring of mercenary troops there was often little to distinguish the two. Valentino was proving that, in addition to his other talents, he was adept at running a Mafia-style protection racket. Fortunately the republic was saved from further bullying by Louis, who summoned his vassal to help with the reduction of the Kingdom of Naples, which, by the terms of the Treaty of Granada—signed secretly in November 1500—had been divided between France and Spain.^x Valentino himself was ordered to capture the strategic city of Capua, which he treated with his characteristic brutality. “They killed without pity priests, monks and nuns, in churches and convents, and all the women they found: the young girls were seized and cruelly abused; the number of people killed amounted to around 6000.” On August 19, the French army occupied Naples and, for a few weeks at least, Florence could relax while Valentino, with all the arrogance and cruelty of a conquering hero, enjoyed himself with a harem he created by seizing forty of the most beautiful women in the city.

•  •  •

At the same time Valentino was wading in gore and indulging in sensual excess in Naples, Machiavelli’s life in Florence was taking a more domestic turn. Sometime in August 1501, Machiavelli—now thirty-two years old—married Marietta Corsini, a young woman from a distinguished family in the adjacent neighborhood in the Oltrarno, the Gonfalone Ferza (the Banner of the Whip). The Corsini, like the Machiavelli, were an old and respected Florentine family, well represented among the office holders who ran the city, though not among the great clans who dominated the halls of power. The union was professionally advantageous for Niccolò since Marietta’s sister was married to Piero del Nero, a member of the Ten of War and thus, effectively, Machiavelli’s boss. It was one more sign that Machiavelli was well regarded in the upper echelons of the government; in marrying Marietta Corsini, Niccolò was marrying up.

As head of the household Machiavelli conducted the negotiations for the marriage contract himself. Marietta remained in the background and had little say in the matter. Instead, Machiavelli haggled over the dowry over a period of months with Marietta’s father, Luigi, and possibly her brother, Lanciolino. There is no question of a romantic motive.^xi Marriage in Renaissance Florence was largely an economic arrangement between two families. At most, the groom would have examined his intended—either himself or through third parties—to determine whether she was physically suitable and of good character, while the prospective bride had little input, relying on the male members of her family to protect her interests.

We have no records of the various contracts or ceremonies involved, though we know enough about the process to paint a detailed, if somewhat generic, picture. After an initial marriage contract (sponsalia)—arrived at only after many offers and counteroffers—the bride would have been escorted to the house of her husband where the wedding feast was laid. Months or even years could pass between the initial sponsalia and the moment when the bride left her father’s house to live under the roof of her husband. The wedding feast was the public face of a union that was as much civic as private, the moment when the community gave its blessing to the joining of two families. Given Machiavelli’s modest means, this was unlikely to have been an elaborate affair, but it would have included not only members of both families, but also friends and neighbors who were politically and financially invested in the successful merging of two respected clans. Only after the plates were cleared and the guests had departed was a more intimate union forged as the couple retired to the bedroom to consummate marriage.

No doubt Niccolò and Marietta followed these time-honored customs, though neither the bride nor groom was an important enough personage to have the event recorded for posterity. Nor did Machiavelli himself feel compelled to memorialize the occasion. True, his marriage to Marietta Corsini marked a profound change in his life, the moment when he began to build his own household, looking forward to fatherhood and assuming the added burdens of supporting a family of his own. But it was also something prosaic, the next step in a logical progression from youth to maturity. It is telling that having taken this momentous step he saw no reason to alter his habits or his outlook on life. His passion continued to be his job; his time was taken up with work and with friends, who no doubt spent many a hilarious hour at the tavern making obscene jokes at the expense of their newly married friend. He found little time, and spared little thought, for the young bride who waited for him while he pursued his various pleasures.

Like Niccolò’s mother, Bartolomea Nelli, Marietta remains a shadowy figure. But few Renaissance women—and almost all of these, like Caterina Sforza or Lucrezia Borgia, are members of ruling dynasties—are anything but two-dimensional. Custom relegated women to the domestic realm, to housekeeping and childrearing, and even in these limited roles they almost never received the credit they deserved. Writers on domestic issues tended to treat women with patronizing indulgence or, worse, with outright contempt. The Venetian aristocrat Francesco Barbaro in his influential essay “On Wifely Duties” speaks of the wife’s “obedience [to her husband], which is her master and companion.” In his Books on the Family, Leon Battista Alberti lists the characteristics of an ideal wife—“to wish to appear a woman of honor, to command the household and to make herself respected, to care for the welfare of the family and to preserve the things that are in the house.” Even in this limited and distinctly female role, she can only hope to fulfill her potential by listening attentively to her husband, who should instruct her with the patience and forbearance one might use with a child.

A relationship in which the husband claimed absolute authority over his submissive wife was encouraged in Florence by the large age difference between the two. Marrying at thirty-two, Machiavelli fell within the normal range for men. Marietta’s age at the time of her wedding is not known for certain, but she was almost certainly in her late teens. Though her family was at least as distinguished as her husband’s, she was a young girl of far less education and worldly experience. For all his imagination when it came to matters of state, there is no indication that Machiavelli was more enlightened than his peers when it came to relations between the sexes. In fact one can glean from various remarks scattered throughout his writings that he possessed the usual prejudices of males of his class. “I hope I shall never be a husband if I can’t get my wife to do what I want,” remarks Callimaco, the hero of his play La Mandragola, an attitude of superiority reflected in somewhat softer terms by Callimaco’s servant, who says, “with gentle words you can usually get a woman where you want her to go.” There is no question of Machiavelli treating his wife, or any of the other women in his life, as an equal. Men who doted on their wives were considered fools and, in all likelihood, cuckolds who deserved what they got for having turned the natural order of their households upside down.

In his own writings Machiavelli enjoys skewering men who strayed from the “ideal” prescribed by moralists like Barbaro and Alberti. The foolish husband whose wife runs rings around him is a stock comic character, and Machiavelli squeezes maximum laughs from such situations in his two best-known plays, Clizia and La Mandragola. Here it is the men who are weak, easily deceived, and done in by their own vices—lust in the case of Nicomaco in Clizia, stupidity and greed in the case of Nicia in La Mandragola—while their wives are both more virtuous and more capable. In both cases Machiavelli gives the husband a name that is a variation of his own, demonstrating a generous capacity to laugh at himself.

This is not to say that these plays are necessarily an accurate depiction of his own marriage, but they do reflect a nuanced, if not entirely unprejudiced, attitude toward the potential of both sexes. He certainly had no trouble imagining strong, sensible women, women who, in the eyes of the pompous Barbaro, would have been condemned for not knowing their place. How much of Marietta is there in the character of Sofronia, the long-suffering wife in Clizia who must hold the family together while her husband recklessly pursues the object of his obsession? Perhaps a great deal, but it is also true that comedy often depends on reversing the normal order of things (which is why cross-dressing is such a staple of the genre). Despite his sympathy for his female characters, Machiavelli was capable of a misogyny distasteful to modern ears. Noting the vicissitudes of life, for instance, Machiavelli wrote “fortune is a woman and in order to be mastered she must be jogged and beaten,” words that elicit sympathy for the flesh-and-blood woman forced to share a house, and a bed, with the writer.

Marietta seems to have been devoted to Niccolò, but not so cowed by the master of the house that she didn’t feel free to lash out when she felt she had been wronged. Her main complaint was that he was so often out of town on business that she rarely got to see him. Only a year after their wedding, while Machiavelli was away on government business, she was berating him for abandoning her. “Lady Marietta,” wrote Biagio Buonaccorsi—whose job, it seems, was to look after her while he was away—“curses God, and says she has thrown away both her body and her goods.” Similar complaints are a regular feature of their correspondence, but a wife whose main complaint is that her husband is never around is a wife not entirely dissatisfied with her mate.

The following year, 1503, Marietta wrote the one letter we have from her hand. The short missive offers a precious glimpse into Machiavelli’s domestic world and is worth quoting in full:

My dearest Niccolò. You make fun of me, but without reason, for I would thrive if you were with me.^xii You know how happy I am when you are not down there [in Rome]; and now more than ever since I have been told how much disease is going around. How can I be content when I can rest neither day nor night. The happiness I find comes from the baby.^xiii So I beg you to send me letters a little more often than you do, since I have only had three so far. Don’t be surprised if I have not written, because I have not been able to since until now I have had a fever. I am not angry. For now the baby is well. He looks like you, white as snow, with his head a velvety black, and he is hairy like you. Since he looks like you he seems beautiful to me. And he’s so lively he acts as if he’s been in the world for a year. As soon as he was born he opened his eyes and filled the whole house with his cries. But our daughter [Primavera] is not feeling well. Remember to come back home. Nothing more. May God be with you and keep you safe.

I am sending you a doublet and two shirts and two kerchiefs and a towel, which I have here for you.

Your Marietta in Florence

There’s a tenderness to this simple note that belies the caricature of Machiavelli as a soulless hedonist, pursuing low pleasures while offering his sardonic take on the world around him. In assessing Machiavelli the man, one should recall these words along with seedier details revealed in his letters and his plays. Though it could not have been easy putting up with his infidelities and frequent neglect, there nonetheless seems to have been genuine affection between husband and wife, a bond cemented over the years by the shared love of their children.

Judged by the less sentimental measures favored by Renaissance Florentines, Machiavelli’s marriage was an unqualified success. By March 1506, when it was the turn of Agostino Vespucci to assume the pleasant chore of dropping in on Machiavelli’s family and filling him in on their progress, the household was already overrun by young children. “I’ll go to your house before heading off to the chancellery, and before I finish I’ll let you know what’s happening with your little troop,” Vespucci assured him. Later he reports: “I’ve just returned from your house, and took care of everything that you asked of me in your letter. All are well, excellent in fact, and Marietta was anxious for me to pass along her regards, as well as that of the children. As I said: all are well. Only Bernardo is a little bit fussy, but has no fever or other illness.”

•  •  •

Machiavelli, in any case, had little time to bask in domestic bliss. By the autumn of 1501 Valentino was back in Tuscany and renewing his assault on Piombino, which quickly fell to his forces. New and alarming reports concerning Valentino’s intentions landed on the Second Chancellor’s desk almost daily, including one in December that the Pisans had reopened talks to have Borgia declared their Duke, a move that would put an end to Florentine hopes of regaining the wayward city. Borgia’s promises to the French King precluded a direct assault on Florence but did not prevent him from toying with the republic like a cat with a wounded bird.

In June 1502, with Valentino making various provocative demonstrations in the vicinity, the citizens of Arezzo—a city some forty miles southeast of Florence that had been an important dependency since the fourteenth century—rebelled, offering to place themselves instead under the protection of one of Valentino’s chief lieutenants. The man to whom they turned was Vitellozzo Vitelli, the brother of Paolo Vitelli, whose execution at the hands of Florence had transformed the surviving sibling into an implacable enemy. The dimensions of the threat were exposed when Vitellozzo was joined by Piero de’ Medici, who hoped to use Arezzo as a launching pad for an attempt on Florence itself.^xiv

Though Valentino disavowed his subordinate’s action, he clearly enjoyed watching the squirming of a government he regarded as little more than a collection of pusillanimous shopkeepers.^xv His poor estimate of the republic’s fighting capacity was confirmed when a Florentine force detached from the Pisan campaign to rescue Arezzo turned back without striking a blow. All Florence could now do was go scurrying off once more to the King of France, whose friendship they had recently purchased at a high price.

Cesare Borgia clearly had the upper hand, but he still needed to tread carefully to avoid provoking Louis. It was a delicate three-way dance among partners who circled each other warily, daggers half drawn. Tensions only increased when Valentino added yet another state to his long list of conquests. His latest victim was the Duchy of Urbino, a mountain stronghold in the Marches about seventy miles east of Florence that he seized in a surprise attack on June 21.^xvi It was from a position of strength, then, that Valentino now requested from the government of Florence a delegation to discuss a new arrangement, one that acknowledged his supremacy in the region. Appointed to head the mission was Francesco Soderini, Bishop of Volterra; in the now familiar supporting role was Niccolò Machiavelli.

Setting out on horseback, Bishop Soderini and Machiavelli arrived in Urbino on June 24, where they hurried to pay their respects to the new lord of the city. The palace to which the two Florentine envoys were now escorted remains one of the great monuments of the age. Begun some forty years earlier by Federico da Montefeltro, the successful condottiere and humanist patron, it projected an air of cultivation and refinement at odds with the violent profession of its master.^xvii With its classically proportioned courtyard, fine library—one of the most extensive in Europe—and its famous study paneled in inlaid woods conjuring with startling verisimilitude the trappings of a scholar’s life, the palace was a monument to Renaissance ideals if not realities.

Only a few days earlier the palace had been home to Federico’s cultivated but sickly son, Guidobaldo, and his accomplished wife, Elisabetta Gonzaga. The current occupant was a far more forceful figure, more along the lines of Montefeltro senior though without Federico’s interest in books and other scholarly pursuits. What Valentino did possess, however, was a flair for theatrical display, at least when such display could be employed to intimidate his rivals. This aspect of Valentino’s character was made immediately apparent to Soderini and Machiavelli, who were made to cool their heels in an antechamber, their anxiety and apprehension increasing with each passing minute while the new lord of the city spun his webs.

It was nearly midnight before the two envoys were admitted into the great man’s presence. In a setting made portentous by the flickering torchlight, Machiavelli came face-to-face with the man who, more than any other, exerted a strange fascination on him and who—seen through the mists of intervening years, and then in idealized and exaggerated form—would serve as a model for the ruthless tyrant of The Prince.^xviii

Unlike an earlier encounter with the equally charismatic Savonarola, this time Machiavelli did not prove immune to a great man’s charms. The dispassionate distance he was able to maintain when harangued by the preacher dissolved before the victorious general surrounded by the spoils of victory. The impact of this initial meeting can be judged by the amount of space in Machiavelli’s writings devoted to the career of Valentino, out of all proportion to his actual achievement. It is no exaggeration to say that Valentino was his muse, the mythical exemplar of the will to power that to Machiavelli was the engine driving all human history.

While the government Machiavelli served was weak, pointing this way or that as the wind shifted, or more often pointing no place in particular in the belief that it would thereby avoid offending anyone, Valentino was decisiveness itself. Machiavelli’s admiration comes through in the dispatches he sent from Urbino. “This Lord is of such splendid and magnificent bearing,” he reported, “and in war so decisive that there is no thing so daunting that it does not seem to him a small matter; and for the sake of glory and in order to secure his state he never rests, nor does he know weariness or fear. He arrives at one place before one hears he has left the other; he treats his soldiers well; he has acquired the best men in Italy: all of which, in addition to his eternal good fortune, makes him formidable and victorious.”

The admiration Machiavelli felt for Cesare Borgia was as much a product of emotion as reason. It resembles a schoolgirl crush, giddy and thoughtless. It was the adulation that literary types often feel for men of action. Though hardly uncritical of Valentino, particularly after his precipitous fall, Machiavelli was powerfully attracted to the Duke. Had Machiavelli ever summed up his feelings frankly, he might have declared: Here, finally, is a real man! Whatever his faults, Borgia made the most of his opportunities and through boldness and cunning put to shame a dozen states with more resources than he ever had at his command.

In the current circumstances, the awe with which the Second Chancellor regarded his host—an awe, incidentally, shared by the senior partner on the mission, Bishop Soderini—made him a less than ideal emissary. Valentino’s response to their overtures was to step up his intimidation. “We heard,” wrote Luca Landucci, “that Valentino had sent to say that he wished to make an alliance with us, or else he would come and attack us.” Machiavelli’s own report, though more nuanced, was essentially the same. “Well I know that your city is not well disposed towards me,” he quoted the Duke, “and would abandon me like an assassin; they seek to get me in hot water with the Pope and the King of France.” This scolding was followed by an explicit threat: “I have no love for this government, which I cannot trust; you must change it . . . . Know that if you refuse me as a friend, you will have me as an enemy.”

Up to this point Borgia had played his cards shrewdly, but in raising once again the specter of Piero de’ Medici’s return he went a step too far. At this impertinence Soderini and Machiavelli bristled, declaring they were happy with the government as it was currently constituted and that, in any case, it was no one’s business how they managed their own affairs. They also added that if he really wished to demonstrate his friendship the Duke would order his lieutenant to abandon Arezzo, something Borgia seemed unwilling to do.

The envoys were emboldened by the fact that for all his bluster, and despite the commanding military position he now occupied, Valentino was not free to act as he chose. Even as negotiations in Urbino dragged out inconclusively, another delegation was heading to the court of Louis to complain about the Duke’s high-handed behavior. Valentino remained dependent on the King who had taken the Republic of Florence under his wing. Soderini and Machiavelli played for time, knowing that once Louis got wind of what Valentino was up to, he would put a stop to his vassal’s bullying.

Machiavelli was unhappy at having to play this cowardly game, but before heading back to Florence he did manage a minor victory, extracting from Valentino a promise that he would do nothing until he had time to consult with his government. This was one of the few instances where the Florentine habit of avoiding hard decisions paid off. After a series of noncommittal responses to Valentino’s demands, Florence learned in late July that Louis, alarmed by the situation in Arezzo, was sending six thousand cavalry (at a cost to the republic of 40,000 ducats) to restore order. They arrived in Tuscany in August, and on the 28th, with French soldiers on his doorstep, Vitelozzo agreed to return the rebellious city to Florentine control. With Vitelli’s withdrawal the immediate crisis was over, though, as Landucci records in his diary, their French rescuers proved almost as destructive as their supposed enemies, looting the very people they were supposed to protect.

•  •  •

In September, Machiavelli was dispatched to the French camp before Arezzo as representative of the Ten of War. Busy as he was with details of provisioning and maintaining troops, his mind began to wander; he sought in the day-to-day frustrations of his job the outlines of a larger pattern. The fruit of this labor was his first concerted work of political philosophy. The brief essay, titled “On the Method of Dealing with the Rebellious Peoples of the Valdichiana,” demonstrates in miniature many of the salient characteristics of his more substantial books.^xix One of the most striking features of this brief work is his tendency to interpret events he actually participated in through the lens of the past. The essay opens with a reference to a famous incident from Roman history: “Lucius Furius Camillus entered the Senate after having conquered the rebellious peoples of Latium, and said—‘I have done all that war can do; now it is your turn . . . to assure your future safety as regards the rebels.’ ” From this historical parallel he swiftly extracts a universal lesson: “[T]he Romans knew that half measures were to be avoided, and that peoples must either be conquered by kindness or reduced to impotence.” Just as the Romans eschewed the middle course, so should his own government adopt a policy and pursue it to its logical extreme:

One can therefore approve your general course of conduct towards the inhabitants of the Val di Chiana; but not your particular conduct towards the Aretini, who have always been rebellious, and whom you have neither known how to win by kindness nor utterly subdue, after the manner of the Romans. In fact, you have not benefited the Aretini, but on the contrary have harassed them by summoning them to Florence, stripping them of honors, selling their possessions; neither are you in safety from them, for you have left their walls standing, and allowed five-sixths of the inhabitants to remain in the city, without sending others to keep them in subjection. And thus Arezzo will ever be ready to break into fresh rebellion, which is a thing of no slight importance, with Cesare Borgia at hand, seeking to form a strong state by getting Tuscany itself into his power. And the Borgia neither use half measures nor half way in their undertakings.

Thus Machiavelli subscribed to what one might call the “wasps’ nest” theory of politics: if you must disturb the hive, make sure you eliminate the residents’ capacity to do you harm. By harassing the rebellious Aretines with petty punishments that irritated them but didn’t lessen their ability to retaliate, the Florentines were increasing the odds of getting stung.

This remains one of Machiavelli’s favorite lessons. He returns to it time and again, most devastatingly in The Prince: “[M]en must either be coddled or destroyed, because while they avenge minor offenses they can do nothing against major ones. Thus if one must do harm to another, it must be such that it will not give rise to a vendetta.” Those advocating mild measures, as he noted in the context of the bloody strife in Pistoia, often inflict the worst damage, since, like a surgeon too squeamish to amputate a gangrened limb, they allow a local infection to spread to vital organs. If there is one thing Machiavelli abhorred, it was the middle way—the route, unfortunately, most often taken by his own government.

i Plausible candidates for the murder also include the various Orsini and their allies. It is unlikely the mystery will ever be resolved.

ii Ever resourceful, it was said that the still attractive Countess captured the eye of Cesare and that the two became lovers.

iii The first Medici Pope, Leo X, also tried to set up his relatives as feudal lords in the Romagna, with equally dismal results.

iv Francesco della Casa’s superior rank was indicated by the larger stipend he was initially granted by the government. When it was clear that Machiavelli was doing most of the work, his friends and relatives succeeded in granting him parity (Machiavelli et al., Machiavelli and His Friends, letters 13 and 14). But even with this increase of salary, Machiavelli was required to spend more than he received.

v His mother, always a shadowy figure in his life, seems to have died a few years earlier.

vi Machiavelli took a lively interest in the welfare of his nephew, Giovanni Vernacci, and remained close. A number of letters survive between the two, attesting to their abiding affection. In one from 1515, Machiavelli declared, “I shall always regard you as my son” (Machiavelli et al., Machiavelli and His Friends, letter 248, p. 314).

vii In fact while Totto managed to get the government to agree to an increased stipend, they apparently sent no additional money while Machiavelli was in France.

viii Unfortunately, for this period we have many more personal letters written to Machiavelli than from him. Much of what we have from Machiavelli’s own pen consists of official reports and analytical essays.

ix In fact the morality of the age was less apt to make a distinction between the sex of the two partners involved than in the orifices employed. Anal sex with a woman was no less reprehensible than with another man. Thus accusations against Machiavelli that he engaged in sodomy do not tell us whether the crimes alleged were of a hetero- or homosexual nature. In fact Florentines did not recognize homosexuality as a fundamental aspect of human nature. Only sexual intercourse between married partners was approved. All other varieties, including prostitution and sex with teenage boys, was included in that wider category of illicit sexuality. In theory, sodomy was punishable by death, but the severest penalties were rarely enforced. The government cracked down from time to time on this “abominable” vice, but without much success (see Rocke, Forbidden Friendships: Homosexuality and Male Culture in the Renaissance for an illuminating discussion of the issue).

x The terms of the treaty were left deliberately vague. Though the Aragonese dynasty in Naples was easily toppled, tensions over the division of spoils continued to simmer, shortly leading to all-out war between France and Spain.

xi It is telling that the most famous romance in Florentine history—Dante’s love for Beatrice Portinari—was an unconsummated passion between two people married to others. Love and marriage in Renaissance Florence belonged to separate realms. Lorenzo de’ Medici famously gave a tournament for his lady love, Lucrezia Donati, even as he was engaged to Clarice Orsini.

xii Marietta here uses the voi form of the word. This is more formal than the familiar tu, revealing, at least at this stage in their relationship, a certain stiffness.

xiii This is Bernardo, their oldest son. The daughter referred to later is Primarena, their oldest child, born in 1502.

xiv The one bright spot as far as Florence was concerned was the difficult relations between Piero de’ Medici and the papal family. Piero was married to Alfonsina Orsini and had close ties to that baronial family. Despite the fact that Paolo Orsini served for the moment as a captain under Valentino, the Borgia detested that powerful family and were often in open conflict with them. Restoring Piero to rule in Florence would greatly increase Orsini influence in Italy, something the Borgia hoped to avoid.

xv Machiavelli quoted the Duke as saying: “[I]t is true that Vitelozzo is my man, but I swear to you that I knew nothing of Arezzo” (Legazioni, Commissarie, Scritti di Governo, no. 103, p. 121).

xvi The element of surprise was achieved in large part because the Duke, Guidobaldo da Montefeltro, had no reason to expect an attack. He was an ally of Pope Alexander and was often employed as a condottiere in the papal employ.

xvii Federico da Montefeltro was one of the great characters of the Renaissance. Learned patron of Giovanni Santi, a mediocre painter best known as the father of Raphael, and Piero della Francesca, he was also deeply involved in the Pazzi Conspiracy to murder Lorenzo and Giuliano de’ Medici. Shortly after Machiavelli’s visit, the castle was the site for those rarefied conversations between lords and ladies that made Baldassare Castiglione’s Courtier the model of the refined gentleman for generations to come.

xviii As late as 1515, long after Valentino’s destruction and after Machiavelli had written The Prince, the Duke continued to serve as a model. In a letter written to his friend Francesco Vettori, Machiavelli referred to “Duke Valentino, whose deeds I should imitate on all occasions were I a new prince” (Machiavelli et al., Machiavelli and His Friends, 313).

xix The Valdichiana is the region south of Florence in which Arezzo is located. Scholars continue to debate when the essay was written and for what purpose. Originally it was thought to date from 1503, that is, almost contemporaneously with the events described, and that it was meant to be delivered as an official report in the Palazzo della Signoria. This, however, seems unlikely. Its style is aphoristic and literary, a far cry from the kind of report one might expect a secretary to deliver to his superiors. In it Machiavelli offers lessons to the government with an assurance inappropriate to one of his junior status. It is probable that it was meant to be incorporated into a larger work—perhaps his Florentine Histories—and the words placed in the mouth of a senior official.