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 lod
gings 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 th
e 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.
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