Biographies & Memoirs



“[Y]our adversaries are numerous and will stop at nothing.”


THE OUTPOURING OF JOY THAT FOLLOWED THE CONQUEST of Pisa was as understandable as it was shortsighted. Florence and Pisa had been bitter rivals for at least three hundred years, since the upstart inland power first began to challenge the great seaport as the preeminent city of Tuscany. Florence’s original conquest of her ancient foe in 1406 had been the crowning achievement of her centuries-long climb to imperial status, and Pisa’s successful rebellion in 1494 had been a crippling psychological loss. But what had begun in the Middle Ages as a clash of titans was now a spat between minnows. Florence was a military nonentity and Pisa a shadow of her former self. This mutual diminution took place within the context of a wider demographic and economic shift: Italy was no longer the vital corridor of commerce from East to West; centers of banking and trade like Florence and Milan were being marginalized; and the fleets of Pisa, Genoa, and Venice were overtaken by the Atlantic-based armadas of Spain and Portugal, and the rising Mediterranean power of the Ottoman Turks. What Florence had gained from Pisa’s recapture was primarily a boost to her self-esteem.

While Florentines dreamed of past glories, France and Spain vied for supremacy on the peninsula, thrashing about like two great beasts, destroying everything in the vicinity. Cities were ruined almost as an afterthought; governments were overthrown; and along the length and breadth of Italy, the countryside was despoiled by armies that found it more profitable, and a good deal safer, to prey upon the civilian population than to meet their adversaries in battle. Given the potential that Florence herself might well be trampled, her obsession with recapturing her longtime enemy seems myopic.

Spain and France were undeniably the two greatest military powers on the Italian peninsula, but the dominant personality of the moment was Pope Julius II. Born to a poor family in Albiola, a small fishing village near Genoa, he had succeeded his uncle as Cardinal of San Pietro in Vincoli (Saint Peter in Chains) when the latter was elected Pope Sixtus IV(1471–84). Unlike Cesare Borgia, who shed his cardinal’s robes before making a career as a soldier, Giuliano della Rovere (as he was called then) strapped his breastplate over his priestly vestments to lead the papal armies against the enemies of the Church. Ascending the throne following a decade-long exile in France during the reign of the Borgia Pope, the sixty-year-old Pontiff demonstrated through his militant defense of papal prerogatives that the passage of years had done nothing to dull his warrior spirit.

In The Prince, Machiavelli uses Julius to illustrate a point about the necessity of matching the man to the moment: “Pope Julius II acted impetuously in everything he did. He found the times and the situation conformed so well to this approach that things always ended happily for him.” His pugnacious nature, the ferocity that earned him the nickname Il Papa Terribile (The Terrifying Pope), may have fit the mood of the times, but his campaign to impose his will on the motley assortment of territories that made up his vast domain seemed likely to unsettle further an already unsettled situation.

Julius was in many ways an admirable figure. He shared with his predecessors—in particular with Sixtus and Alexander—a lust for conquest and an apparent indifference to the spiritual dimensions of his office. But unlike those paragons of the nepotistic impulse, Julius did not look on the Church simply as a vehicle to enrich his own family but as a worthy end in itself. As Machiavelli put it: “Julius not only pursued the same goals [as Alexander] but he added to them. He hoped to win Bologna, defeat the Venetians, and chase the French out of Italy; and in all these endeavors he succeeded—gaining all the more praise since everything he achieved was for the Church, and not for his own private gain.” The contrast with Valentino is telling: while the Borgia prince renounced his priestly vows to pursue his own personal aggrandizement, Julius, though equally aggressive, always viewed himself as a soldier toiling on behalf of a revitalized papacy.

In the realm of the arts, where he had the power to command the service of the age’s most talented men, he presided over unparalleled creativity, but even here his ambitions were often undermined by a restless spirit that led him to launch grandiose projects only to lose interest to a new enthusiasm. In 1506 he laid the cornerstone for a monumental new edifice to replace the crumbling Basilica of St. Peter (dating from late antiquity), destined to become the largest and most splendid church in Christendom. This was only the first step in a project of urban renewal that was meant to restore Rome to her ancient imperial grandeur. In pursuit of this ambitious goal he summoned Michelangelo from Florence (where he was busy making drawings for The Battle of Cascina in the Hall of the Great Council) first to work on his tomb and then to paint the ceiling of the Sistine Chapel.i In art, as in life, Julius was used to getting his way and, surrounded by the greatest geniuses of the age, including the architect Donato Bramante, who created the initial designs for the great basilica, and Raphael, whom he brought to Rome to fresco the chambers and audience rooms of the Vatican, he was largely successful.

In the vastly more complicated realm of Italian politics, where the egos were equally massive but the players more numerous and less tractable, Julius would have a much more difficult time arranging things to his liking. The application of an iron will to issues calling for pliability, nuance, and the capacity to compromise would lead to more tribulation for the already battered nation. But in truth, the problem lay less in the character of the man currently sitting on the papal throne than in the nature of the institution itself. The pope was an anomaly within Italy and unique among the great lords of Europe. He was both the ruler of one of the five major states of the peninsula—jockeying for position with his peers from Milan, Venice, Florence, and Naples—but also the head of Europe’s most powerful bureaucracy and spiritual guide for all of Western Christendom.ii Wearing these multiple and mismatched hats, he could not fulfill his role as father to his spiritual flock while protecting his interests as a secular prince; nor could he rule effectively in his own territory when so many of his resources and so much of his attention were directed to far-flung lands. No one saw these contradictions more clearly than Machiavelli, who wrote eloquently about the destructive role of the papacy in Italian history. “It is the Church,” he wrote in The Discourses,

that has kept, and keeps, Italy divided . . . . For, though the Church has its headquarters in Italy and has temporal power, neither its power nor its virtue has been sufficiently great for it to be able to usurp power in Italy and become its leader; nor yet, on the other hand, has it been so weak that it could not, when afraid of losing its dominion over things temporal, call upon one of the powers to defend it against an Italian state that had become too powerful . . . . The Church, then, has neither been able to occupy the whole of Italy, nor has allowed anyone else to occupy it. Consequently, it has been the cause why Italy has never come under one head, but has been under many princes and signori, by whom such disunion and such weakness has been brought about, that it has now become prey, not only of barbarian potentates, but of anyone who attack it. For which our Italians have to thank the Church, and nobody else.

Machiavelli was not alone in his resentment of the Church; in fact his views were fairly typical of Florentines, who too often had suffered at the hands of their erratic neighbor. But he was bolder than most in venting his anger in public, an audacity that won him the eternal hostility of an institution whose many powers included that of branding its critics not as only wrongheaded but positively evil.

Julius’s reign added to Machiavelli’s argument. The Pope’s determination to reinvigorate the Church, though it was a welcome change from the purely selfish policies pursued by Alexander, plunged Italy into new turmoil. The first salvo in his campaign was aimed squarely at Valentino, a task in which the Pope’s personal inclinations happily aligned with his official duties. With Valentino out of the way, however, others leapt into the vacuum. Quickest to profit from the collapse of Valentino’s empire in the Romagna were the Venetians, who swooped in and snapped up the papal dependencies of Faenza and Rimini. This cheeky bit of opportunism inevitably put the Most Serene Republic on a collision course with the new Pope, who had not maneuvered his entire life to obtain the papal tiara only to see his possessions filched by a nation of arrogant merchants.

Florence also had reason to fear the Venetians since a major commercial competitor now stood firmly astride their most important trade routes. One of Machiavelli’s tasks during his embassy to Rome in 1503 had been to encourage the new Pope to take a hard line with Venice. In truth, Machiavelli didn’t have to work hard to stoke the anger of the Pope, who told him through clenched teeth “that he would in no way tolerate such an injury to the Church.” Not content with presenting a dry recitation of his conversation with the Pope, Machiavelli offered the Ten a more expansive vision of what was at stake: “And I make, in short, the following prediction, that what the Venetians have done in seizing Faenza will either open for them a door on to all of Italy, or it will be their ruin.”

Perhaps he should have sent this warning instead to Venice, since he seemed to have a better grasp of what they had stirred up than the Venetians did. On December 10, 1508, Julius announced his latest version of a Holy League, this one aimed squarely at the Most Serene Republic of Venice. The new alliance was holy only in the sense that it had been arranged by the Pope; in every other respect it was a cynical arrangement that appealed to the signatories’ greed rather than serving any higher purpose. Julius’s alliance united long-standing enemies—including the Holy Roman Emperor and the Kings of Spain and France—by promising to each a portion of the rich lands that Venice now held across the length of Italy. To the Pope would go the cities illegally seized in the Romagna; to Emperor Maximillian the mountainous region of the Friuli; Louis coveted the northern cities of Brescia, Bergamo, and Cremona, while Ferdinand of Aragon would acquire the southern Italian ports that Venice had seized as part of her campaign to dominate the Adriatic coastline. The League of Cambrai, as it came to be called, was the most formidable alliance ever forged in Europe, at least on paper, though like any team made up of large egos it suffered from too many would-be leaders and too few willing to be led. Even with this handicap the coalition was strong enough to dominate the forces Venice could bring against them. On May 14, 1509, at Agnadello—near Cremona—league forces under Gian Giacomo Trivulzio routed the Venetians, largely because one Venetian captain, Niccolò Orsini, refused at the critical moment to come to the aid of his colleague Bartolommeo D’Alviano. Though the capital remained safe within its lagoon, “Venice lost in a single day the fruit of eight hundred years of painful toil,” as Machiavelli put it in The Prince. The Venetian diarist Marino Sanudo recorded the reaction when the news was announced in the Doge’s Palace:

At twenty-two hours Piero Mazaruol, a secretary, came running in with letters in his hand from the battlefield, with many gallows drawn on them. Thereupon the doge and the savi read the letters and learned that our forces had been routed. And there began a great weeping and lamentation and, to put it better, a sense of panic. Indeed, they were as dead men.

But while the battle appeared decisive, nothing was ever that simple in the tangled web of Italian politics. In fact the victors were immediately disoriented by their sudden victory, while the magnitude of the disaster steeled the resolve of the defeated. The resilience of the Venetians was demonstrated when, in July, they reconquered Padua. Though Maximillian attempted a quick counterstroke, Machiavelli, remembering his own experience at the imperial court the year before, warned the Florentine ambassadors at the Emperor’s court not to make any commitments since Maximillian “very often undid in the evening that which he had done in the morning.”

Despite Machiavelli’s warnings, the government, deploying its favorite tactic, decided to buy off the Emperor. Adding insult to injury, in November Machiavelli himself was ordered to Verona bearing the second installment of the 40,000 ducats the Florentine ambassadors had promised.

His journey through the territories recently held by the Venetians provided him with one more lesson in the horrors of war. “The invading soldiers have set to robbing and plundering the country,” Machiavelli wrote to the Ten, “and I hear and see terrible things such as I have never known of before.” He recalled the gruesome scenes he witnessed in his poem “On Ambition”:

Let him turn his eyes here who wishes to behold the sorrows of

others, and let him consider if ever before now the sun has

looked upon such savagery.

A man is weeping for his father dead and a woman for her

husband; another man, beaten and naked, you see driven in

sadness from his own dwelling.

Oh how many times, when the father has held his son tight in

his arms, a single thrust has pierced the breasts of them both! . . .

Foul with blood are the ditches and streams, full of heads, of

legs, of arms, and other members gashed and severed.

Birds of prey, wild beasts, dogs are now their family tombs—

Oh tombs repulsive, horrible and unnatural!

As he traveled through the Veneto he observed unrest in both town and country as forces of the Holy League tried to maintain their hold on the territories won from Venice. The resistance of the local population to the foreigners convinced him that his initial assessment had been correct, that the forces of the Emperor and his allies were losing ground and those of Venice were resurgent. Writing to his superiors in the Palazzo della Signoria he offered a cogent analysis of the situation based not on the traditional measures of armies and economic resources, but in terms of a class struggle. Because the Venetians in their empire had protected the popolo from exploitation by the local nobility, the peasants and laborers would remain fiercely loyal to their former overlords: “And thus so great a desire of death or vengeance has entered into the souls of these country folk, that they are become more hardened and enraged against the enemies of the Venetians, than were the Jews against the Romans; and it daily happens that some one of them, being taken prisoner, submits to death rather than deny the name of Venice . . . . Therefore, all things considered, it is impossible for those monarchs to hold these lands so long as the peasants have breath.”

This conclusion must have surprised his bosses, who, like most well-informed observers, believed that the Battle of Agnadello spelled the end of Venice as a major power. But Machiavelli peered beneath the surface and discovered deeper currents. In addition to the elements of class warfare that worked against the forces of the league, Venice’s resurgence was abetted by the nature of the coalition arrayed against it, a forced partnership among incompatible partners held together only by a common greed.

Nowhere was this more apparent than in the actions of the Pope himself. Julius had been the driving force behind the coalition, but now that he had properly chastened the arrogant Venetians he began to regret the monster he had summoned to do the job. Like Machiavelli, Julius was an ardent nationalist at heart. His first loyalty was to the Church he commanded, but he also cared deeply about the larger Italian nation—an as yet amorphous concept that was based not so much on political as linguistic and cultural bonds. No matter how often they were at each other’s throats, Italians remained convinced of their own superiority to those uncultured louts who despoiled their lands and pillaged their cities. The obvious fact that they possessed more of the civilized virtues than their tormentors merely made the humiliation harder to bear. Guicciardini expressed the common view that, like the ancient Israelites punished by God for their transgressions, Italians were the authors of their own troubles, for “if these powers had not been blinded by private greed and had not destroyed the common weal with shame and harm also to themselves, there is no doubt that Italy, restored to its pristine glory by their counsels and resources, would have been safe for many years from the attacks of foreign nations.” Machiavelli shared with his friend and colleague the conviction that Italy’s travails were the outward manifestation of an inner rot, but he also believed in ultimate redemption, a hope to which he gives eloquent voice in the ringing exhortation that endsThe Prince:

Against barbarian rage,

Virtue will take the field; then short the fight;

True to their lineage,

Italian hearts will prove their Roman might.

Similar sentiments lodged somewhere in Julius’s breast, no matter how deviously he went about achieving his goal. Having just encouraged foreign powers to help themselves to broad swaths of native soil, he now made an about-face and launched a campaign in which his former enemies became his friends, his former allies his sworn enemies. “Fuori i barbari!” (Out with the barbarians) was the new rallying cry as he cut a deal with Venice to drive out the Emperor and the French, whom he had previously emboldened.

For Florence the sudden realignment proved particularly uncomfortable. While nominally allied with papal forces, the city had remained on the sidelines during the War of the League of Cambrai—which was just the way the Florentines preferred things. But a war between her traditional ally, France, and her southern neighbor, the Pope, was likely to stretch even Florence’s elastic foreign policy to the breaking point.

Trying to ease the strain placed on Florentine diplomacy would occupy Machiavelli for the foreseeable future, but before grappling with these difficult matters he would have to deal with a crisis closer to home. On December 20, 1509, a masked man, accompanied by two witnesses, went to the house of the notary of conservators in Florence to denounce the Second Chancellor and declare that he was, and had always been, ineligible for the office he now held. “[He] contended that having been born of a father, etc.,” Buonaccorsi reported to his friend, “you can in no way exercise the office that you hold, etc.” Though his friends had rallied around him and, so far, had been able to beat back the challenge, Buonaccorsi urged Machiavelli “not to make a joke of it” since “your adversaries are numerous and will stop at nothing.”

The nature of the charge is not spelled out by Buonaccorsi, though apparently the scandal was so well known that it was being talked about “even in the whorehouses.” Given the reference to Machiavelli’s father, it is likely that his enemies were challenging him on the grounds that Bernardo was a specchio, that is prohibited from holding office due to unpaid taxes. Since Niccolò had assumed his father’s debts as well as his assets upon Bernardo’s death, he, too, his accusers claimed, should be barred from the Palazzo della Signoria.

The timing of the incident is significant. Bernardo Machiavelli’s troubles were old news. The fact that they were dredged up at this particular moment suggests a politically motivated attack on the part of the growing, if still largely underground, movement directed at the Gonfaloniere and the man who was now often referred to as Soderini’s “hatchet man.” The anonymity of the denunciation was disconcerting since Machiavelli had no opportunity to confront his accuser, but it was also reassuring since it implied that the mysterious figure lacked the support to move openly against him. In the end the scandal blew over and Machiavelli remained in his job, but it was an ominous sign.

In June 1510, Piero Soderini sent Machiavelli back to the French court. In the upcoming battle between King Louis and the Pope, Soderini would adopt the usual Florentine policy of delay and distraction, an evasive tactic that, Machiavelli had long ago discovered, always seem to irritate those toward whom it was directed. Though his natural inclination was to back the French, Florence’s traditional ally, in his secret instructions Soderini reminded his assistant that “although the Pope as a friend is not worth much, as an enemy he can do much harm.” Arriving at Lyons on July 7, Machiavelli dispatched a letter with the usual disclaimer that he expected to achieve nothing “save that of keeping your Excellencies well informed of all that happens from day to day.”

Machiavelli’s pessimism was well founded. Not surprisingly, Louis had little patience for Florentine equivocations. “[T]here is no way out,” Machiavelli informed the Ten after a tense encounter with the king. “[The French] seek to entangle you in this war.” On August 9 he wrote again: “Your Excellencies may believe, as they believe the Gospel, that should there be war between the Pope and this sovereign, you will not be able to avoid declaring for one side or the other.”

It was not enough, however, to urge his compatriots to take decisive action. An even more critical task was to encourage a little less decisiveness on the part of the French, which he did by reminding the King’s advisers how securing an Italian empire always appeared simpler on paper than it proved to be in fact. The problem, as he saw it, was that “if they make war alone, they know what they bring upon themselves; but that if they engage in it with allies, they will have to share Italy with them, and therefore be involved in a greater and more dangerous war among themselves.” This is typical of Machiavelli’s analysis, which dispenses with all piety and pageantry in favor of a dry account of exactly where each party’s interest lay.

It is doubtful whether anyone at the French court appreciated being lectured by this underpaid emissary of a second-rate power, but some at least recognized the wisdom of his words, shifting to a strategy that avoided an all-out military clash. This more cautious approach involved striking the Pope where he appeared strongest—at the aura of sanctity that gave him a standing among the lords of Europe out of all proportion to his tangible assets. Calling for a church council to sit in judgment of the reigning Pontiff, the French intended to raise questions of simony in regard to his election (a charge to which Julius, like all his predecessors, was vulnerable) as well as enumerating other crimes against his holy office. Thus Julius would be forced into a war on two fronts, defending his legitimacy as a spiritual leader while sparring with the French on the field of battle.

Machiavelli returned to Florence in October, much relieved to be done with the onerous and unprofitable mission, though the ill humor of the city was such that he might soon have wished he were back on the road. In the months he had been away discontent with the regime continued to build. The mood had grown so ugly, in fact, that according to one diarist the Eight (in charge of state security) could no longer walk in the streets for fear they would be attacked. The civil discord reflected both a general anxiety about the future and a hardening of differences that had always existed between oligarchic and democratic factions. Soderini was accused of favoring “new men” at the expense of the wealthy clans who traditionally dominated the halls of power, and of being a demagogue who harbored dictatorial ambitions. Nor did the recent success of the Pisan war work entirely to the government’s benefit since it increased suspicion that Machiavelli’s militia might become an instrument of tyranny.

Opposition to Soderini’s regime now began to coalesce around that most magical—and most reviled—name in Florentine history: Medici. While there had always been a minority among the elite who favored the return of the city’s former ruling family, these men—sometimes referred to as the bigi, sometimes as the palleschi (named for the red balls, palle, that formed the Medici crest)—knew the torment of a love that dared not speak its name. Since the majority still despised the Medici, their secret admirers, though an important constituency within the oligarchic faction, remained little more than a hidden cabal, fearful and conspiratorial. Young pro-Medici hooligans had been among the most militant agitators against Savonarola and his regime, but while they succeeded in destroying the hated preacher, the government that replaced him turned out to be equally hostile to their aims.

In the early days of their campaign the palleschi were not helped by the man whose cause they championed. Whenever they seemed to be making progress, Piero de’ Medici would engage in some clumsy attempt to overthrow the republican government by force, discrediting his supporters within the city and leading at least a few of them to the gallows. Piero’s death was a godsend to Medici sympathizers. Once the family was in the more capable hands of his younger brother, Cardinal Giovanni, the palleschi could state their preferences with more candor.

Though the climate now appeared more favorable, the palleschi did not entirely abandon their conspiratorial ways. On December 22, 1510, the state police uncovered a plot to assassinate the Gonfaloniere, led by known Medici sympathizer Prinzivalle della Stufa. Though the plot was unraveled before it could get off the ground, it offered further evidence of growing restlessness within the upper reaches of the ruling class.

Machiavelli spent much of the winter of 1511–12 building up the militia, spurred to new exertions by the increasingly dangerous international situation. The war between the Pope and France continued to simmer in the Romagna, next door to Tuscany, with possession of the strategic city of Bologna passing back and forth more than once. In October 1511, Julius declared another Holy League—this time directed at the Most Christian King of France—from the pulpit of the church of Santa Maria del Popolo in Rome, with the ambassadors of Spain and Venice on hand to demonstrate their solidarity.

While Florence hoped to repeat its performance in the League of Cambrai, standing aside to let others do the fighting, France was determined not to let the city off the hook. Louis increased the pressure on the republic by insisting that the church council he was organizing meet in Florentine-controlled Pisa. As far as Florence was concerned the only point to this otherwise futile exercise was to arouse the Pope’s fury at Florence for serving as host. Again Machiavelli was dispatched to the court of the French King in an effort to extricate Florence from its predicament. The one heartening sign was that there seemed little stomach among the cardinals for the schismatic council. Most remained either overtly hostile to the project or strangely reluctant to answer their mail. The only ones who showed any enthusiasm were three or four French cardinals, who were regarded as stooges of their King. In his pocket Machiavelli carried a note setting out the difficulties of Florence’s situation:

No one shows any wish to attend the Council, and therefore it only serves to irritate the Pope against us; and for this reason we make a request either that it shall not sit at Pisa, or shall at least be suspended for the present. No prelate seems to be coming from Germany; from France very few and very slowly. And it is a matter of universal astonishment to see a Council proclaimed by three Cardinals only, while the few others who were said to adhere to it, dissimulate their opinions and defer their arrival . . . . If, therefore, there should be no hope of agreement between the Pope and the King, and if the latter cannot be persuaded to desist altogether, he should at least be induced to delay for two or three months.

When Machiavelli met with the King in Blois, Louis showed little sympathy for his predicament, demanding that the government of Florence offer safe passage to those few cardinals willing to stick their necks out. Predictably, the Pope retaliated by placing Florence under interdict, a threat that on other occasions had almost brought the republic to its knees. But in the end the council proved to be something of a fiasco and the Pope was soon distracted by more pressing matters: so few cardinals attended that it was more of an embarrassment to the French King than a threat to Julius, who simply ignored the schismatic churchmen.

Frustrated in his attempts to depose the Pope by bureaucratic means, Louis, throwing aside Machiavelli’s more cautious counsel, now opted for a frontal assault. In the winter of 1512 a new army of invasion, led by the King’s brilliant twenty-three-year-old nephew, Gaston de Foix, marched across the Alps and onto the Lombard plains. Included among the vast host was a token force of three hundred Florentine lances.

On April 12, in fields near the Adriatic port of Ravenna, French forces under Foix met the army of the Holy League led by Ramón de Cardona, Viceroy of Naples. It was the kind of battle Machiavelli approved of—hard-fought and bloody. Of an earlier confrontation he noted with satisfaction that “it was fought with more virtue than any other that had been fought for fifty years in Italy, for in it, between one side and the other, more than a thousand men died.” Measured by this dismal standard—between ten and twenty thousand were left dead on the field—the Battle of Ravenna was a notable success. Indeed it bore little resemblance to the typical skirmishes of fifteenth-century warfare, anticipating instead the sanguinary orgies of later centuries.

Throughout the hotly contested battle the small Florentine contingent performed so poorly that the King complained to the ambassador that they failed to pull even their modest weight. His sour mood was provoked, perhaps, by the perplexing and thoroughly discouraging results of the confrontation. Though the French drove the papal army from the field, they lost their young commander, Foix, killed in a skirmish with retreating Spanish infantry. Loss of the dashing general was a blow from which they could not recover, particularly when in the coming months Julius reinforced his army with twenty thousand additional Swiss infantry. Despite their glorious victory, the French were soon, to quote a contemporary witness, “flying like mist before the wind.” It was a repetition of 1494, when early French victories were followed by defeat as a combination of local powers, backed by the might of Spain, harried the overextended and overtaxed forces of the King. Parma, Piacenza, and Bologna were lost in quick succession as the French army fled for home. Julius, the “Warrior Pope,” had proven himself once again a master tactician. “Out with the barbarians!” was his battle cry, and the sight of the French army turning tail must have filled his heart with joy. But the fact that this victory was accomplished only with the help of many thousands of Swiss and Spanish troops—foreigners who showed no signs of joining their fellow barbarians in departing Italian soil—demonstrates the limitations of the Pope’s wider strategic vision, which achieved short-term victories at the risk of long-term goals.

Among the greatest losers to emerge from the French debacle was Florence, whose contingent of three hundred lances had been too meager to please the King but too prominent to avoid becoming a target of papal wrath. News from Mantua, where the members of the league were meeting to divvy up the prizes, turned ominous when Florence’s ambassador, Giovan Vittorio Soderini, reported the arrival of Cardinal Giovanni de’ Medici and his younger brother, Giuliano. Reciting to all who cared to listen to the long list of missteps and misdeeds by the current government of Florence, the Medici brothers drummed up support for a proposed expedition against their native city. They were joined in this effort by Pope Julius, who publicly called for the resignation of Piero Soderini and his government, though even with the papal sanction the gathering army seemed less an official campaign than an expedition of freebooters. Offering 10,000 ducats as a down payment, Cardinal Giovanni finally managed to assemble about five thousand professional soldiers, hiring the victorious Ramón de Cardona to lead the ragtag band.

This was the direct thrust at Florence that Machiavelli and his colleagues had long feared and had strained every fiber to avoid. But having backed the wrong horse there was little they could do but gird for battle. The limitations of diplomacy had been reached, and now they would have to depend on their own soldiers, who, despite a few notable successes, had done little to show they could withstand a professional army bent on their destruction.

To meet the threat, the Eight issued a decree meant to expand the number of soldiers in the militia and turn them into a fighting force that could compete on equal terms with the professionals they would soon be facing: “Seeing the great utility of the Infantry Ordinance [it read], desiring to ensure the safety of the present government and liberty amid the dangers to which they are now exposed, the Nine are hereby empowered to enlist under our banners for the entire year 1512, no less than 500 light horse, armed either with crossbows or matchlocks at the pleasure of the men; ten percent of the number may be armed with lances.” After years of cautious support, the government was now finally committed to a citizen militia as the best means of defending their lives and liberty. The task of preparing their defenses fell once again to Machiavelli, who spent much of the spring of 1512 in the saddle, traveling about the countryside, recruiting soldiers in Pisa, Arezzo, and Poggio Imperiale, and inspecting the frontier forts at Valiano and Monte San Savino.

As Spanish forces accompanied by the Medici brothers approached the borders of Tuscany in August 1512, Florence had reason to hope it might yet avert disaster. The army led by Viceroy de Cordona was small—numbering about five thousand infantry and another two hundred heavily equipped men-at-arms—far outnumbered by Machiavelli’s beefed-up militia. In addition, the invaders were a motley crew, ill fed and ill supplied. So uncertain was Cordona that victory could be achieved that instead of launching a direct assault on Prato—the city some thirteen miles north of Florence, where the bulk of the militia was gathered to meet the invaders—he sent emissaries to the Signoria to see if they might arrive at a negotiated settlement. Their demands, while not unreasonable for an army on the verge of certain victory, seemed harsh when the outcome was uncertain. Cordona insisted not only that the Medici be allowed to return to the city as private citizens, but that Soderini and his pro-French regime be deposed; and, to compensate him for the inconvenience he had already been put through, he demanded a fee of 100,000 ducats—a repetition of the extortion to which Florence was regularly subjected.

Meanwhile, in the increasingly restive capital, Soderini moved against the internal opposition whose disloyalty increased as the distance between the Spanish forces and the city walls shrank. Twenty-five of the most prominent pro-Medici stalwarts, many of whom were in direct contact with the Cardinal and his brother, were rounded up and thrown into prison. Upon learning of the terms demanding his resignation, Soderini called a special session of the Great Council where he offered to sacrifice himself for the sake of peace. “To test the mood of the people,” Machiavelli reported in a letter he wrote a month after the events,iii “[Soderini] assembled the entire council and explained to them what had been proposed, offering to abide by their will. And should they decide that his departure would hasten the restoration of peace, he would return to his home.” Soderini almost certainly knew his offer would be rejected. It was one of those grand gestures that politicians often engage in to rally support and garner sympathy, a ploy that apparently proved successful since, as Machiavelli continued, “[e]veryone rejected this and even expressed their willingness to offer up their lives in his defense.”

For the moment Florence was buoyed by an uncommon sense of unity and purpose, but beneath the confident surface were gnawing doubts about the city’s capacity to withstand the assault. Machiavelli himself admitted: “It was decided initially not to deploy these men in the countryside, because they were not deemed strong enough to resist the enemy.” Despite their improved armaments and greater numbers, the militias suffered from a lack of leadership and experience in the heat of battle. Guicciardini, writing with the wisdom of hindsight, was harsher in his judgment, asserting that the forces Florence was relying on for her salvation “were of such a sort, that never in the memory of man had there existed any less worthy of their pay.”

With the negotiations at an impasse, Cordona decided to test the mettle of these green troops and assaulted the walls of Prato. But with little in the way of artillery, the attack was repulsed with ease, much to the jubilation of the Florentines. So discouraged was the Viceroy that he almost abandoned the entire campaign. Hoping, however, to salvage one last scrap of honor from what appeared to be a major fiasco, he sent a second delegation to Florence with a proposal to withdraw his forces in exchange for the paltry sum of 3,000 ducats—a far cry from the 100,000 he demanded only a few days earlier—in addition to bread to feed his half-starved troops and a lifting of the banishment of the Medici. Unfortunately, the circumstances that forced Cordona to sweeten the terms made Soderini and his colleagues less inclined to accept them. Years later Machiavelli harshly criticized his old boss’s rejection of this proposal, though there is no indication that he spoke up at the time. He discusses Soderini’s brave but foolish refusal in The Discoursesin a chapter titled “Prudent Princes and Republics should be content with Victory, for, when they are not content with it, they usually lose.” If what Cordona was offering Soderini was something less than victory, it was, as Machiavelli pointed out, something close to it. Accusing his compatriots of excessive pride, Machiavelli wrote that “[r]ulers of states, when attacked . . . cannot make a greater mistake than to refuse to come to terms when the forces attacking them are a good deal stronger than their own, especially if overtures are made by the enemy.”

Of course the problem was that the superiority of the Spanish forces was far from obvious at the time the decision had to be made. Cordona had dropped his most onerous conditions precisely because he himself doubted he could achieve victory. But Machiavelli is correct when he points out that Soderini’s rejection was foolhardy. There were in fact plenty of signs that a renewed assault on Prato would yield different results. Florentine stinginess over the years when it came to equipping and training its troops left serious deficiencies in the ranks. The city had agreed to supply squads with matchlocks, for example, but had provided so little ammunition that they were forced to strip lead from the roofs of the houses of Prato to make bullets.

Having received word of the rejection, and with the situation of his army ever more desperate, Cordona decided to make one last attempt on the city. Late in the afternoon of Sunday, August 29, 1512, the Spaniards began bombarding the walls of Prato and managed to create a small gap in the defenses. Where professional troops would have quickly sealed the breach, Machiavelli’s green militiamen panicked at the first sight of the Spaniards surging forward, abandoning their posts and leaving the city to the mercy of these half-starved warriors. Like many a besieging army, the victors exacted a fearful revenge on the population whose stubbornness had contributed to their discomfort. Machiavelli recalled the mournful scene: “[A]fter minimal resistance, all fled, and the Spaniards, having occupied the city, then proceeded to sack it and massacre the men, a miserable spectacle of calamity . . . . More than four thousand died; the rest were taken and made, through various means, to pay ransom. Nor did they spare the virgins cloistered in holy sites, which were scenes of rape and pillage.”

Catastrophic as this was for the citizens of Prato, it might prove equally calamitous for the Florentines, who were now without means to defend themselves against a foreign army that had just showed its cruelty. Florence might have anticipated some mercy from Cardinal de’ Medici, who had no reason to reduce to rubble the city he had spent much of his adult life trying to reclaim, but had the citizens of Florence been able to read a letter he wrote to the Pope a week or so after the sack they would have found little comfort:“The taking of Prato, so speedily and cruelly,” he told Julius, “although it has given me pain, will at least have the good effect of serving as an example and a terror to the others.”

The “others” were the Florentines, who, much to the Cardinal’s satisfaction, seemed to be taking the lesson to heart. “[E]veryone began to fear a sack,” Machiavelli recalled, tacitly accepting some responsibility by admitting that the calamity was due largely to “the cowardice of our soldiers.” The mood in the city was approaching full-scale panic: respectable women checked themselves into convents; rich merchants fled the city with their valuables; and the guards at the Palazzo della Signoria charged with protecting the government abandoned their posts. Even more encouraging from the Cardinal’s point of view were the crowds of palleschi who now streamed into the streets and the piazzas proclaiming their devotion to the Medici cause. The old chant “Palle! Palle!” rang through the streets and squares of Florence once more. Political fortunes were turned topsy-turvy as Soderini’s supporters were shouted down and overwhelmed by the suddenly emboldened adherents of the former ruling family.

Also emboldened was Cordona. When Florentine envoys arrived in Prato, they found that the Viceroy’s demands had grown with his victory. Not only did he now insist they pay him 60,000 florins (soon raised to 120,000) for his troubles, but he told them that Soderini must resign and the Medici be immediately reinstated. The proposal was made slightly more palatable by maintaining the fiction that the Medici were to return to the city merely as private citizens, but once inside Florence, surrounded by their jubilant supporters and with Spanish troops within shouting distance outside the walls, no one doubted who the new bosses would be. Though Soderini himself was initially tempted to reject the demand, “relying,” as Machiavelli scoffed, “on idle dreams of his own,” the ground was swiftly crumbling beneath his feet. Only days earlier Soderini had stood before the Great Council and won overwhelming support for his defiance, but faced with an almost certain repetition of the horrors visited on Prato, public opinion swung decisively against him. A more direct form of pressure was applied when a group of young aristocrats with ties to the Medici broke into the Gonfaloniere’s apartments in the palace and threatened to run him through with their swords unless he released their twenty-five imprisoned colleagues. By the morning of Tuesday, August 31, only two days after the fall of Prato, Soderini conceded the game was lost. Rather than engage in what would almost certainly have been a bloody and ultimately unsuccessful resistance, he chose the only sensible course. Summoning Machiavelli, he asked him to approach their mutual friend Francesco Vettori. Though Vettori, who had served with Machiavelli on the mission to the Emperor four years earlier, had ties to the current government, he was also related to the Medici and was known to be sympathetic to their cause. Hurrying to the palace around midday, Vettori met with an evidently shaken Gonfaloniere in his private apartments. Soderini informed him that he had decided to step down but was concerned for his own safety and that of his family. Vettori agreed to allow him the use of his own house during the perilous hours while final arrangements were being made. It was only after the Gonfaloniere had slipped quietly out of the palace that Vettori went before the Signoria and recounted their conversation. At first they refused to depose Soderini, until Vettori explained to them that if he did not resign immediately he would surely be assassinated. No one, in the end, had the stomach for violent confrontation. The palleschiwere sober in their triumph, supporters of the republican government glum but resigned. A few hours later—accompanied by Vettori and an escort of forty cavalry—Soderini left the city by the Roman Gate and set out on the road that led to Siena and a life of exile.

Machiavelli was not unhappy to see him go. He remained ambivalent about his former boss, believing that he was a genuinely good man but that he lacked the backbone to be a real leader. His most reasoned postmortem on Soderini’s career comes in Book III ofThe Discourses: “Piero Soderini . . . conducted all his affairs in a good-natured and patient way. So long as circumstances suited the way in which he carried on, both he and his country prospered. But when afterwards there came a time which required him to drop his patience and his humility, he could not bring himself to do it; so that both he and his country were ruined.” He was, in fact, a prime example of a man unable to adapt “in conformity with the times.” Machiavelli had little patience for well-meaning incompetents since they often cause more suffering than those who are deliberately cruel. His final verdict was harsh. Upon hearing of Soderini’s death in 1522, Machiavelli composed a little verse that suggests a certain contempt for a man whose indecisiveness cost him and his city dearly:

The night that Piero Soderini ceased to breathe,

His soul journeyed to the mouth of Hell;

But Pluto cried: “Thou foolish soul,

No Hell for thee! Go seek the Limbo of the babes!

Though Soderini’s regime outlived him by a few days, it was clear to everyone that one era had passed and a new one was beginning. On the first day of September, to the shouts of “Palle! Palle!” from the crowds lining the street, Giuliano de’ Medici returned to the city of his birth, his beard, which he had recently grown in the Spanish fashion, shaved to demonstrate his desire to abide by local customs. As he walked the streets of Florence, unaccompanied by those retinues so beloved by powerful men, his manner was respectful, his dress and comportment modest, winning him praise among citizens who remembered the high-handed manner of his brother Piero.

While Giuliano charmed everyone with his affable manner, his supporters, reinvigorated after their years in the shadows, began to flex their muscle. On the same day that Giuliano returned, and as the new Signoria prepared to take their seats, Luca Landucci watched as “all the citizens who considered themselves friends of the Medici, assembled at the door of the Palagio and in the Piazza, all fully armed, and barred every way into the Piazza.” With the palleschi mustered menacingly on the doorstep, free and open debate in the Great Council was impossible.

In fact the government remained rudderless until September 14, when Cardinal Giovanni de’ Medici, accompanied by four hundred lances and one thousand foot soldiers, made his triumphal entrance to the cheers of thousands of his supporters. Taking up residence at his boyhood home on the Via Larga—built by his great-grandfather Cosimo and, until the plundering that followed the Medici’s expulsion, filled to the rafters with priceless treasures of ancient and modern art—he played the role of the reluctant suitor dragged back into political life by the tearful supplications of his fellow countrymen. Two days after his return, the Medici and their supporters called a parlamento, a mass gathering of the citizens in the Piazza della Signoria where, as if by unanimous acclaim, the people of Florence called for a committee with special powers to reform the government. This was the oldest trick in the playbook of Florentine politics, one often exploited by earlier generations of Medici to consolidate their power. Though ostensibly an exercise in pure democracy, the seething mass, often surrounded by armed men who made the consequences of dissent immediately apparent, always ratified the wishes of those already in power. This gathering was no different from its predecessors. With one voice the citizens of Florence proclaimed their desire for radical reform.

The Balia, or special committee, tasked with implementing the reforms was comprised of forty-five leading citizens (soon expanded to sixty-six), all of them Medici loyalists. In short order they discarded all the changes that had occurred since 1494, reinstituting those small councils that had been the instruments of Medici control and stocking them with their trusted followers. Guicciardini’s verdict on the new government is terse. “In this way,” he declared in his History of Italy, “the liberty of Florence was crushed by force.” Even Francesco Vettori, who was sympathetic to the Medici and helped ease them back to power, was critical of the newly constituted government, complaining: “The city was reduced to the point of doing nothing save by the will of Cardinal dei Medici; and this method is the method of perfect tyranny.”

As for Machiavelli, the man most closely identified with the exiled Gonfaloniere, his reaction, at least for the moment, was muted. He navigated this latest and most tumultuous storm with the imperturbability with which he had navigated those minor tempests that too often agitated the government for which he worked. Though a political animal through and through, he never regarded himself as a party man. He contemplated the quarrels that consumed his superiors with a disdainful eye, seeing in their petty squabbles the telltale signs of ravenous human ambition, but also determined to rise above them as a devoted servant of the state, whichever party temporarily gained the upper hand. The letter he wrote to an unnamed noblewoman sometime that very month offers the best window into his mood, without the coloring provided by the traumatic events still to come. After describing in rather dry terms the momentous events that had just transpired, the Second Chancellor, apparently still secure in his job, concludes on an optimistic note:“The city remains most peaceful and hopes, with the help of [the Medici], to live no less honorably than in times past, when their father Lorenzo the Magnificent, of most happy memory, governed them.”

There may be an element of wishful thinking here. Machiavelli must have suspected that the big brooms currently deployed in the Palazzo might well sweep him out along with much else associated with the former regime. But his hopeful tone reveals something about how Machiavelli saw himself, as the consummate bureaucrat willing and able to serve any government. So great and simple was his patriotism that he could not conceive that anyone would regard him as other than what he was: a devoted servant of the city they all loved. The next few months would disabuse him of his naive assumption and shape his increasingly cynical worldview.

i The clash of wills and of egos that resulted is memorably evoked in Irving Stone’s The Agony and the Ecstasy.

ii The Pope’s title to large swaths of territory in central Italy was based largely on a document known as The Donation of Constantine. The document, purportedly dictated by the first Christian emperor of Rome, Constantine I, granted the Pope lordship over large tracts and transformed the Pope into a secular as well as spiritual prince. By Machiavelli’s day, many scholars—including most prominently Lorenzo Valla—suspected that the Donation was a medieval forgery, but the Pope would not countenance any challenges to its authenticity.

iii The letter in which Machiavelli recalls the events leading to the downfall of the Soderini government is addressed simply “To a Noblewoman.” Many scholars believe it was written to Isabella d’Este, the brilliant and cultured wife of Francesco Gonzaga, Marquis of Mantua (see Machiavelli et al., Machiavelli and His Friends, note 1, p. 495). Others believe it was meant for Alfonsina Orsini, widow of Piero de’ Medici.

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