“O Italy! O Princes! O prelates of the Church! the wrath of God is upon ye, neither is there any hope for ye, unless ye be converted to the Lord. O Florence! O Italy! these adversities have befallen ye for your sins. Repent ye before the sword be unsheathed, while it be yet unstained with blood; otherwise neither wisdom, power, nor force will avail.”


ON THE MORNING OF MARCH 3, 1498, MACHIAVELLI left his home near the Ponte Vecchio and set out for the monastery of San Marco on the northern outskirts of town. Here, far from his accustomed haunts—and in a departure from his usual routine—he attended a sermon delivered by Girolamo Savonarola, the charismatic monk whose messianic visions had alternately inspired and convulsed the city for six tumultuous years.i

Savonarola was not a prophet of peace but a preacher of fire and brimstone, and his apocalyptic sermons unhinged a populace already agitated by years of war and civil unrest. So intemperate were his jeremiads that the Pope himself had issued a decree forbidding the friar to speak in public, a policy meant in part to silence denunciations launched against the Holy Father and the Church he led. Throughout this Lenten season, and despite calls from cooler heads for the people of Florence to follow the example of Jesus, the city was torn apart by factions whose approach to settling political disagreements was to hurl abuse at their opponents or even to resort to the dagger and the club. Most numerous were the piagnoni (weepers or snivelers), pious followers of Savonarola who dominated the councils of government and policed the streets for signs of immorality. Arrayed against them were a variety of parties, like the arrabbiati (angry ones), or the aristocratic compagnacci (the rude companions), and the sinister bigi (grays), a secret society plotting to restore the disgraced Medici to power. The always bitter rivalries had recently turned even uglier, as angry words gave way to acts of vandalism and intimidation. Now all eyes turned toward the modest church where the friar was expected to issue his challenge to Pope Alexander VI, an act of defiance that could well plunge the city into civil war.

On this late-winter morning the paths of two of the truly remarkable figures of the Renaissance crossed, one ascending, the other headed even more precipitously in the opposite direction. For the obscure young man, an anonymous face in the crowd, it was a first tentative step on a rising ladder, while for the famous preacher—who from his current perch atop the pulpit stood a few steps closer to heaven—this was a final opportunity to pull back before his plunge toward a fiery death. Years later Machiavelli might well have had this moment in mind when he wrote of the “countless men who, that they might fall to earth with a heavier crash, with this goddess [Fortune] have climbed to excessive heights.”

There is no other place on earth where such an encounter could have occurred. Not only are Savonarola and Machiavelli both monumental figures in the history of Western thought, but one would be hard pressed to find two men who embodied such divergent and mutually uncomprehending philosophies: one a religious extremist, spiritual father of fundamentalism, the other an ardent secularist who dared to contemplate a world without God or morality. Nowhere but in this creative, contentious city could two such remarkable, and remarkably different, men have been thrown together by the hand of fate. It is not an exaggeration to say that on this chilly morning at the beginning of March, in the modest church a few blocks south of the Porta San Gallo, two worlds collided.

Unlike most of the crowd packed into San Marco that day, Machiavelli had not fallen under the spell of the charismatic Dominican friar. As Savonarola thundered from the pulpit, those in the audience wept and sighed, shouted their agreement or turned inward, gnawed by some secret guilt exhumed by the speaker. “O Italy!” he cried. “O Princes! O prelates of the Church! the wrath of God is upon ye, neither is there any hope for ye, unless ye be converted to the Lord. O Florence! O Italy! these adversities have befallen ye for your sins. Repent ye before the sword be unsheathed, while it be yet unstained with blood; otherwise neither wisdom, power, nor force will avail.” These were dark times, he proclaimed, but it was the deepest gloom that preceded the first faint glimmer of a new dawn. If only the citizens would turn away from sin they might step confidently into the light of a blessed day.

Machiavelli was unmoved. He passed a clinical eye over the scene of near hysteria, scoffing at the notion that the speaker was divinely inspired and instead dissecting the speech as if it were a performance in order to discover the tricks Savonarola deployed to keep his audience in thrall. “The people of Florence do not think that they are ignorant or rude,” he wrote in The Prince, “yet Girolamo Savonarola convinced them he conversed with God . . . . [M]ultitudes believed him without ever having seen anything extraordinary to compel their believing it.”

Though Machiavelli was outwardly conventional in his religious life, the kind of mysticism that was his stock in trade left him cold. In fact, while Machiavelli did not belong to any of the factions that were battling for control of the republic, his sympathies clearly lay with the preacher’s opponents. He was an educated and sophisticated young man, steeped in the classical literature Savonarola deplored as a distraction from the Gospels and an avid consumer of those low pleasures for which Florence had once been famous. He had little use for the self-appointed guardians of public virtue who did their best to stamp out vice and corruption. From his point of view the friar and his “boys”—processions of youths dressed in white who patrolled the streets on the lookout for sins and sinners—were more than a minor nuisance since he was one of those whose morals were most in need of reform. Whenever one of these pious gangs came into view a cry went up, “Here come the boys of the friar!”—the signal for gamblers to pocket their dice, whores to scatter, and ladies of the better sort to hide their jewelry.

No doubt Machiavelli was one of the first to duck inside the nearest doorway. He had a certain grudging respect for the discipline and ardor of the friar’s pious legions, but he objected to those grand spectacles of communal self-abnegation that were a feature of life in Savonarolan Florence. Chronically short of cash, he cringed at the sight of his wealthier compatriots casting their silks, jewels, and indecent objets d’art into the great “bonfires of the vanities” kindled in the Piazza della Signoria—extravagant gestures of repentance that only the rich could afford.

Machiavelli’s skepticism toward charismatic religious figures like Savonarola is apparent in a letter he wrote some years later recounting the sudden success of another preacher, “a friar of Saint Francis who is half hermit and who, to gain more repute as a preacher, claims to be a prophet.” Like his more famous predecessor, this cut-rate Jeremiah predicted that they would “suffer fire and sack,” that “there would be a great dying and great famine.” And just as they had a decade and a half earlier, Florentines flocked to hear this prophet of doom, demonstrating once again that nothing was more certain to fill the pews than forecasts of imminent apocalypse. While his friends shed tears of repentance and promised to mend their ways, Machiavelli saw no reason to change his habits.“I didn’t actually hear the preacher,” he admitted, “for I don’t usually get involved in such matters.” Still, he remarked sarcastically, the friar’s gloomy prophesies did manage to demoralize him sufficiently that for one night at least he canceled a planned rendezvous with his favorite courtesan.

This morning, pressed by the crush of fervent disciples who credited Savonarola with the gift of prophecy—“I believe Christ speaks through my mouth,” he proclaimed—Machiavelli listened with an attentive but skeptical ear. In fact it was his presumed immunity to the blandishments of the preacher that explained his presence in San Marco. He had gone at the request of Ricciardo Becchi, the Florentine ambassador to the Holy See, “to give you, as you wished,” Machiavelli reminded him, “a full account of what is going on here regarding the friar.” As far as we know it was his first political assignment, the moment when, after twenty-eight uneventful and unproductive years, Machiavelli walked onto the stage and took his place as an actor in the great political drama of the day. Admittedly, it is a small part—that of a witness standing in the wings and offering occasional asides while the star commands most of our attention. But it is a role that suited him well. Throughout his career as a diplomat, for which this assignment was something of an audition, Machiavelli proved himself a perceptive analyst of character. Attending this morning’s sermon offered him an opportunity to exercise his critical faculties on the most compelling and controversial figure of the age.

The report Machiavelli sent to Ricciardo Becchi reveals both the strength and weakness of his methods. His indifference to spiritual matters certainly caused him to underestimate the appeal of Savonarola’s message, but if he was blind to many of the friar’s virtues—without which his hold on the people of Florence would be inexplicable—this handicap allowed him to see all more clearly the rhetorical devices the friar employed to win the impressionable to his cause. “[H]e began with great terrors, with explanations that to those not examining them too closely were quite effective,” Machiavelli recorded. But while Machiavelli was inclined to view the great preacher as something of a fraud (“he follows the mood of the times and shades his lies to suit them,” he declared), he appreciated the friar’s courage in standing up to the most powerful lord of Europe: “[H]ad you heard with what audacity he began to preach,” he told Becchi, “and how he proceeded, it would have stirred no small amount of admiration.”

As always, Savonarola’s exegesis of Scripture carried a pointed political message. Taking as his subject the book of Exodus, Savonarola told the story of God’s chosen people persecuted by a cruel and corrupt potentate. “But the more they oppressed them, the more they multiplied and increased,” he read, gesturing toward the crowd to make explicit the link between the ancient Hebrews and his own followers. In a characteristic act of hubris, he then proceeded to cast himself in the role of Moses leading them out of bondage. But if Savonarola was Moses, who was to play the vengeful Pharaoh bent on defying God’s will? It was here that the Dominican preacher stepped onto dangerous ground, for he assigned the villain’s role to Rodrigo Borgia, the corrupt and sensual man who now occupied the Throne of Saint Peter as Pope Alexander VI. “[H]e seeks to set all of [the people] at odds with the Supreme Pontiff,” Machiavelli reported to Becchi, “and, turning toward him and his attacks, says of the pope what could be said of the wickedest person you might imagine.”

As Becchi read Machiavelli’s report he realized that Savonarola had no intention of backing down. The Florentine government was already in hot water with the Pontiff, and its continued inability or unwillingness to rein in the disobedient friar had strained the relationship past the breaking point. The mere fact that Savonarola had delivered the sermon was a brazen act of disobedience, since he was currently forbidden by the Pope to speak in public.ii “So,” the Pope had recently grumbled to the Florentine envoy, “you are allowing Friar Girolamo to preach again. I would never have believed that you would treat me this way.” Unless they dealt with the rebellious monk, he told them, he would place the entire city under interdict. Such a ban would jeopardize not only the souls of Florentines but, perhaps of more immediate concern, their worldly goods, since any merchant in a foreign land placed outside the protection of the Church risked having his possessions confiscated. Torn between their loyalty to the Friar and their own well-being, Florentines that morning vacillated between hope and fear, resignation and anger.

Savonarola’s address to the believers in San Marco was the climactic moment in a bitter contest of wills between the Dominican monk and the Pontiff. It also marked a critical juncture in the history of the republic after four years of upheaval during which the entire peninsula of Italy—from Naples in the south to Milan in the north, with Florence caught uncomfortably in between—descended into chaos. In 1504 Machiavelli wrote a poem looking back on this gloomy period when the land lay “filled with blood and dead men . . . when discordant Italy opened into herself a passage for the Gauls and suffered barbarian peoples to trample her down.” He treats the Dominican preacher with typical ambivalence:

But that which to many was far more distressing and brought

on disunion, was that sect under whose command your city lay.

I speak of that great Savonarola who, inspired with heavenly vigor,

kept you closely bound with his words.

But many feared to see their country ruined, little by little,

under his prophetic teaching.

That ambivalence was already present in his letter to Becchi of 1498, written with the words of Savonarola still ringing in his ears. This was, in effect, his first diplomatic dispatch, the first time he set pen to paper to offer his sober analysis of a highly fraught political situation. Future missions would take him to exotic courts and involve elaborate ceremony and official credentials, but few would rival the raw emotional intensity of this initial assignment. It would be another three months before Machiavelli took up his position in the government of Florence, but it was in San Marco, where he had gone as an emissary to an alien territory of the soul, that Machiavelli’s remarkable career really began.

•  •  •

The age that made Savonarola’s remarkable rise possible and precipitous fall inevitable, a chaotic time where frightened people turned to those who promised that present troubles were merely a prelude to certain redemption, had arrived four years earlier with the invasion of Italy by Charles VIII, Most Catholic King of France, at the helm of a massive army. The French invasion of Italy opened a psychic chasm, dividing time into a golden-hued “before” and an ash-gray “after.” “With them,” wrote Francesco Guicciardini of the marauding hordes, “a flame and a plague had entered Italy which not only overthrew states, but changed their forms of government and the methods of warfare.

“Before,” he continued, providing a brief sketch of the world as he knew it in his youth, “Italy had been principally divided into five states: the Papacy, Naples, Venice, Milan and Florence, each seeking to preserve its own possessions, watchful lest any should usurp what belonged to another and grow so strong that the rest should fear him . . . . Now owing to this invasion of the French everything was turned upside down as if by a sudden storm; the unity of Italy was broken and shattered.”iii It was in this “broken and shattered” world that Machiavelli had his first professional success as a civil servant in the pay of the Florentine Republic and it was in contemplating the wreckage of his native land that his dismal view of the human condition was forged. It was a world of flame and ash, of chaos, ruin, and disease.iv It was a world that made possible not only the meteoric career of the Dominican preacher whose apocalyptic visions tapped into the troubled mood of the times, but also of the cruel tyrant Cesare Borgia, who dazzled all of Europe with his daring exploits before he too came to grief—a world presided over by capricious Fortuna, equally generous in her bestowal of sudden favor and sudden death. And it was a world that, ultimately, gave rise to Machiavelli’s most imaginative creation, the ruthless antihero who strides across the pages of The Prince.

In The Art of War, Machiavelli provides a vivid description of Italy on the eve of the French invasion. Corrupt and complacent, greedy for profit and incapable of finding common ground for the common good, its leaders were singularly ill-prepared for what was to come:

Our Italian princes, before experiencing the shocks of foreign wars, were accustomed to believe that it was sufficient for a prince to be able to devise a sharp answer in his writing office, to pen a fine epistle, show wit and readiness in his words and sayings, be able to lay schemes, deck himself with gold and gems, sleep and eat with greater luxury than other men, surround himself with many sensual delights, rule his subjects with avarice and haughtiness, become rotten with sloth, confer military promotion as a favor . . . nor did the poor wretches foresee that they were thus preparing themselves to fall a prey to the first enemy that should assail them. Hence, in the year 1494, came terrible alarms, sudden flights, and miraculous defeats, and thus three of the most powerful States of Italy have been repeatedly pillaged and laid waste.

It was late summer 1494 when Charles VIII, the twenty-eight-year-old king of France, crossed the Alps with an army of forty thousand well-trained and well-equipped men. This single impetuous and ill-conceived act put an end of the golden age of the Italian Renaissance, a time when the greatest artists, writers, and philosophers flourished under the indulgent regimes of the prosperous republics and minor principalities that divided the peninsula. These miniature polities, anachronistic survivors of the Middle Ages, were pathetically overmatched by the rising nation-states and their massive armies, as the King of France was in the process of demonstrating. Following the route of Hannibal’s legions, Charles’s battalions spilled row after row from the mountain passes and onto the fertile plains of Lombardy, heavy infantry—including the famed Swiss pike men, the most feared warriors of Europe—and armored cavalry carrying aloft banners bearing the fleur-de-lis of the royal house of France. Most terrifying of all were the bronze cannon hauled by teams of thickset horses, a gleaming array of firepower on a scale never before deployed on the battlefields of Italy.

One glimpse of this mighty host was sufficient to send shivers down the spines of the most battle-hardened condottiere.v The ragtag bands of hired mercenaries with which the petty states of “discordant Italy” had for centuries been accustomed to wage war upon each other would scatter like dry leaves in the wind before the coming onslaught. That is if they could even be persuaded to act together, a doubtful proposition given the age-old enmities that existed between the myriad states of the peninsula and the selfishness with which each prince pursued his own private advantage. Italians of the Renaissance occasionally acknowledged a common kinship, particularly when threatened by “barbarian” forces, but if they were a family it was of the most dysfunctional sort in which fraternal rivalries were more potent than brotherly love.

It was one of their own, Ludovico Sforza, lord of Milan,vi who had done the most to engineer the calamity. Known to history as Il Moro (the Moor) “because of his dark complexion and because of the reputation for cunning he had already begun to acquire”—it was rumored that he was in fact the bastard son of Duke Francesco Sforza and a slave girl—Ludovico had a streak of deviousness that in later centuries would undoubtedly have been described as Machiavellian. As it was, his contemporaries had no shortage of epithets to hurl at the man they blamed for their country’s travails.

The disaster began with a dynastic quarrel between Ludovico and the King of Naples, one that Sforza thought might most elegantly be resolved by encouraging the French King to reassert his ancestral claim to the Neapolitan throne. It seemed at first glance a clever idea: have the French do the fighting while he, Ludovico, stood on the sidelines and enjoyed the spectacle of his rival’s destruction. But the ruler of Milan, overly confident in his ability to control the forces he had unleashed, apparently lacked the imagination to picture the difficulties that would arise once the immediate objective was won. With a massive foreign army set loose upon Italian soil and with the other great monarchs of Europe itching to profit in some way, it was a strategy unlikely to accrue to the benefit of any Italian state.

For Florence, the arrival of the French army on Italian soil proved particularly challenging. At the time the republic was led by Piero de’ Medici, the twenty-six-year-old son and heir of Lorenzo the Magnificent, a man who shared little with his illustrious father besides the family name. In his Florentine Histories, Machiavelli explains that the outcome might have been far different had Lorenzo, rather than his son, been at the helm: “for when Italy was left deprived of his advice, no mode was found for those who remained either to satisfy or to check the ambition of Ludovico Sforza . . . . Therefore, as soon as Lorenzo was dead, those bad seeds began to grow which, not long after, since the one who knew how to eliminate them was not alive, ruined and are still ruining Italy.” For every virtue Lorenzo possessed, Piero seems to have substituted a corresponding vice. “He was a haughty and cruel man,” wrote Guicciardini, “who preferred being feared rather than loved. Savage and bloodthirsty, he had on occasion attacked and wounded men by night and been present at the deaths of several. He lacked that gravity which was necessary to anyone in such a position, for amid these dangers to the city and to himself he was out every day in the streets publicly playing football.”

Piero’s first instinct was to resist the French invasion, but when it became clear that neither the other Italian states nor even his own people would follow him in such a rash undertaking, he beat a craven retreat. On the morning of October 26, 1494, with public opinion turning decisively against him, Piero, accompanied by a small retinue of loyal followers, secretly rode out of Florence and headed for Pisa, where Charles was encamped with the bulk of his army. Hoping to be welcomed as a friend and ally, he was instead treated as a defeated enemy. Charles and his ministers were determined to extract the maximum penalty for his initial disloyalty, and Piero, desperate for some way out of the predicament he now found himself in, was more than willing to sell out his city to save his skin. In return for handing over the Florentine fortresses of Sarzana and Pietrasanta to the French, without which the republic was left blind and defenseless on its northern border, Piero received a promise from Charles to support continued Medici rule in Florence. Even more disturbing to the citizens of Florence was the almost certain loss of Pisa, her ancient rival whom she had finally conquered in 1406. Behind the screen provided by the French army the Pisans were even now preparing to rise up against their overlords and proclaim themselves once again an independent republic. While Charles made vague promises to restore the rebellious city after he had settled matters down south, it was clear to most Florentines that Piero’s treachery had stripped them of their most prized possession. To add insult to these almost unbearable injuries, Charles also demanded that Florence contribute 200,000 florins to the cause of subduing Naples.

To Florentines the loss of Pisa was not only a military and economic issue: it was a symbol of their current impotence brought about by Piero’s perfidy. Though no longer a vital international seaport—the silting up of the mouth of the Arno was slowly choking its once bustling harbor—its acquisition after centuries of bitter strife had elevated Florence in the minds of her citizens to the status of a great power. No sharper blow could be struck against her pride, and for much of Machiavelli’s career the reconquest of the wayward city was an undertaking—amounting almost to an obsession—that preoccupied the minds of those who toiled in the Palazzo della Signoria and upon which the majority of her blood and treasure was expended.

Piero returned to Florence on the afternoon of November 8 to face a population seething with anger. “[H]e threw out confetti [sweets], and gave a lot of wine to the people, to make himself popular,” wrote one contemporary, a desperate ploy that did little to instill confidence. When he and a few armed supporters tried to force their way into the government palace, those inside called out “Popolo e liberta!” (The People and Liberty), the ancient clarion call of revolution. The cry was quickly picked up by others gathered in the piazza, who drove Piero from the palace while the priors ordered the ringing of the great bell that from time immemorial had called the people of Florence to assemble in moments of greatest peril.

Soon the Medici and their partisans were being hounded from government buildings and accosted on the streets. When Cardinal Giovanni de’ Medici, Piero’s younger brother, tried to enter the square, he, too, was assaulted. Riding toward the family palace he called to his brother, “We’re finished!” Later that day, the apothecary Luca Landucci caught a glimpse of the young cardinal through an open window of the family palace “kneeling with joined hands, praying Heaven to have mercy.” By nightfall, both brothers, along with their closest allies, had fled the city, taking only as much of the fabled Medici treasure as they could shove into their saddlebags.

Thus ended, ignominiously, Medici rule in Florence, almost exactly sixty years since Cosimo, Piero’s great-grandfather, had returned in triumph following his exile by the Albizzi family. It had been an almost bloodless revolution, carried out with a swiftness and ease that made those who led it ask themselves why they had not sooner thrown off a yoke that was so lightly fixed.

Eight days later Charles entered the city accompanied by seven thousand Swiss infantrymen. He rode in full armor, a baldaquin raised high above his head to signify his role as a conqueror. Met at the San Frediano gate by the Signoria in full ceremonial robes and escorted by a contingent of forty well-born youths, the King and his army paraded through the streets, passing within a block of Machiavelli’s house. Machiavelli himself was undoubtedly among the citizens who lined the streets to watch as their city was occupied by foreigners. A few dutiful shouts of “Viva Francia!” could not disguise the general mood of despondency. The climactic moment came when the King dismounted between a double row of torches and ascended the steps to the Cathedral, though, “when he was seen on foot,” wrote Landucci, “he seemed to the people somewhat less imposing, for he was in fact a very small man.” As Guicciardini observed laconically, the ceremony was “a sight in itself very beautiful but scarcely appreciated, as all men were full of terror and alarm.” The entrance of a foreign army was humiliating for a city that for centuries had jealously guarded its freedom, and though the citizens might console themselves with the thought that the occupation was accomplished without bloodshed or destruction of property, there was no getting around the fact that a once great power had been brought to its knees. Many of the top generals were housed in the palaces of the Florentine nobility that had been marked for the purpose beforehand by French officials, leading Machiavelli to observe sarcastically that “King Charles of France was allowed to conquer Italy with chalk.”

If Florence had suffered a humiliating blow, the situation was not so bleak for the prior of San Marco, who had long foretold such trials and tribulation. Fra Girolamo Savonarola, a native of Ferrara, had come to Florence eight years earlier and had risen to fame by unleashing jeremiads against the corruption of his adopted city. His genuine concern for the plight of the wretched workers and his rage against those who exploited their labor won him a passionate following among the poor, but many wealthier citizens were also attracted to his message of salvation through mortification. His hair-raising sermons, often delivered before thousands packed into the Cathedral, had foretold the coming of another Cyrus to scourge Italy for her sins, and when Charles arrived at the head of a conquering army it took no great stretch of the imagination to convince the traumatized Florentines that his prophesies had been fulfilled. “[Y]our coming has lightened our hearts,” Savonarola told the King after his arrival in the city, so “pass on securely and triumphantly, inasmuch as He sends you.”

Passing on was something Charles was eager to do in any case since his real business was further south in Naples. Having secured his supply lines and replenished his bank account, Charles and his army left the city on November 28, heading for their confrontation with the overmatched armies of Alfonso, King of Naples.vii

With the departure of Charles and his army, Florentines could set about the vital task of rebuilding their political institutions corroded by sixty years of domination by the Medici family. But as soon as they slammed the gates shut behind the departing Swiss pike men, the normal divisions that beset the ruling class of Florence began to reassert themselves. As Machiavelli recalled: “After 1494 when those who had been princes in Florence were expelled from the city . . . there was no proper government, but rather a state in which anarchy and ambition were commingled and public business was going from bad to worse.” It was a quarrelsomeness that, time and again in Florentine history, was resolved only by the strong hand of the tyrant. If that were to be avoided under present circumstances, the leading citizens must show a greater devotion to country and less devotion to personal interest than was usually the case.

The first months following the departure of the French were dominated by a struggle for power between the ottimati (optimates), who wished to retain the oligarchic nature of the Medici regime in which real power was shared only by a handful of rich and powerful families, and the popolani (populists), who believed that the only way to preserve their hard-won liberties was to enfranchise a wider and more representative cross-section of the citizenry. On December 14, under pressure from both sides to provide guidance, Savonarola made the fateful decision to jump, body and soul, into the political arena. “[T]he will of God is that the city of Florence be ruled by the people and not by tyrants,” he proclaimed from the pulpit, throwing his immense prestige behind the popular party, which, with his backing, was able to drive their more conservative colleagues from the palace.

The most important feature of the new government was the Great Council, modeled loosely on that of their sister republic Venice, a representative body that would serve as a legislature and the pool from which the various executive officers were chosen. Unlike the Venetian model, however, in which membership was the privilege of a narrow aristocracy, the Florentine Great Council would be open to a wide spectrum of Florentine citizens, from wealthy bankers and merchants to small shopkeepers and artisans. In his “Treatise on the Constitution and Government of Florence,” Savonarola set down his rationale for a more democratic system: “Now the Florentine people, having established a civil form of government long ago, has made such a habit of this form that, besides suiting the nature and requirements of the people better than any other, it has become habitual and fixed in their minds. It would be difficult, if not impossible to separate them from this form of government.” This government was unrepresentative by modern standards, but it was a great advance over the tyrannies that dominated most of the Italian peninsula and over the Medici oligarchy that preceded it. Though the urban proletariat—the unskilled labor that provided the muscle for the city’s various industrial enterprises—was still excluded from representation, the council was perhaps the most democratic assembly in Europe.viii

The establishment of the Great Council placed real power once again in the hands of an unwieldy body that not only spoke for but actually included a wide swath of the citizenry. As it was finally constituted it included 3,500 citizens, though only one third, serving a six-month term, were seated at any given time. Historians have calculated that, in a population of roughly 40,000 to 50,000, this council represented a little under half the male population over thirty, a remarkably expansive franchise for the day. Florence had reconstituted itself as a true republic, responsive to the will of the people to a degree remarkable in an age of deep social and economic inequality. It was this government, where in raucous sessions in the Hall of the Great Council butchers rubbed shoulders and matched wits with wealthy bankers in ermine-lined robes, that Niccolò Machiavelli would serve throughout his career as a civil servant.

•  •  •

There is no record of what Machiavelli was doing during these transformative days. In November 1494, when angry citizens drove the Medici from power, Machiavelli was already twenty-five years old, an age, even by cautious Florentine standards, when a young man might play a responsible role in the public arena. And yet there is no indication that he participated in any significant way in the great political upheaval. This might seem peculiar for someone who obviously thought deeply and felt passionately about politics. But a closer examination of his career reveals a certain passiveness, a tendency to stand on the sidelines and observe rather than thrust himself into the fray, particularly when the outcome was as uncertain as it was in the tumultuous days following the French invasion. In the service of his country Machiavelli was willing to risk life and limb, but when it came to determining what sort of government was best suited to make it prosper, that was a matter for intellectual inquiry rather than violent action.

This did not mean he was indifferent. A quarter century later Machiavelli analyzed the faults of the government he would soon be serving.ix “After [the fall of the Medici], the city decided to resume the form of a republic,” he wrote, “but did not apply herself to adopting it in a form that would be lasting, because the ordinances then made did not satisfy all the parties among the citizens.” He believed that the government set up after the fall of Piero was deeply flawed, too weak to prevent the ruling class from splitting into rival factions, but he shared Savonarola’s belief that any constitution that did not take into account the Florentine’s natural love of liberty was doomed to failure. “Never will the generality of Florentine citizens be satisfied if the Hall [of the Great Council] is not reopened,” he later explained to Giovanni de’ Medici, emphasizing that a city accustomed to freedom would never embrace tyranny. As always with Machiavelli, the first consideration—to which all other things were subservient and, in fact, irrelevant—was: What works and what doesn’t? The most elegant solutions on paper were worthless if they did not account for real human passions and failings, while the most morally repugnant systems should be considered if they improved the average man’s lot in life. To this simple and irrefutable logic Machiavelli would cling all his days.

At the time, Machiavelli watched developments with keen interest, but he was not one of those hotheads who took to the streets agitating for radical change. This was simply not in keeping with his temperament. Wry bemusement was his normal response to those who fanatically pursued rigid ideologies. This detachment may be explained in part by his continued marginality: even with the change of government, his father’s fecklessness guaranteed that his particular branch of the family was unlikely to reap any political reward, no matter how broad the franchise.

As Machiavelli continued along the meandering path first set out by his father, the city in which he lived and that was the sole object of his affection—the provider of intellectual stimulation and low pleasures—continued to bubble and seethe. Above all the continued defiance of Pisa rankled, and the inability of the government to deal with it effectively undermined its credibility. No Florentine could countenance the citizens of their former possession enjoying a liberty they themselves took for granted, and while the new government strained every resource to reverse the humiliation—the Ten of War were soon renamed “the Ten Expenders”—Florentines found themselves impoverished by taxes that seemed to purchase only defeat and incompetence. Despite the popular base of support, the new government would be judged as the old had been, on whether it succeeded in preserving Florence’s Tuscan empire. As Machiavelli put it in his narrative poem, The First Decennale, addressing Florence herself:

So all Tuscany was in confusion; so you lost Pisa and those

states the Medici family gave to the French.

Thus you could not rejoice as you should have done at being

taken from under the yoke that for sixty years had been crushing you,

because you saw your state laid waste.

Lacking the means to reconquer the city, the new government pinned its hopes on Charles’s promise to return Pisa. Florentines, as one might imagine, followed the news of his progress to the south with more than academic interest. At first all seemed to go well. So intimidating was the French army that the southward journey was less a military campaign than a triumphal progress. Pope Alexander VI, who had initially taken up the Aragonese cause—the tilt of his policy confirmed when he married off his second son, Juan, to Maria Enriquez, a cousin of King Ferdinand of Aragon—reconsidered when Charles’s vast army arrived on his doorstep. Like Florence, Rome was forced to accept a French occupation, a humiliation the Pope would not soon forget or forgive. At the end of January 1495, Charles finally set out to challenge the army of King Alfonso of Naples. “So with his conquering army he moved upon the Kingdom like a falcon that swoops or a bird of swifter flight,” wrote Machiavelli, imparting epic grandeur to what was in fact a rather pathetic affair. As expected, the Neapolitan forces were no match for the French. By February, King Alfonso and his successor, his eldest son, Fernandino, had both abdicated in quick succession, neither one able to muster more than token resistance, and on the 22nd of the month Charles entered the southern capital having barely struck a blow in anger.

But having labored so long for the prize, at the very moment he achieved his goal King Charles saw all his dreams turn to dust. Again turning to Machiavelli’s evocative verse:

When the report of a victory so great and so easy came to the

Ears of that first mover of Italy’s distress [i.e., Ludovico Sforza],

well he learned his folly clear, and afraid of falling into the

trench that with so much sweat he had dug,

and aware that his own might did not suffice, that Duke,

striving to save the whole, along with the Pope, the Empire and

Saint Mark [i.e., Venice], formed a huge army.

As a more astute statesman might have foreseen, Charles’s success had achieved what no amount of diplomacy could have—near unity among the quarrelsome states of Italy, who were now determined to drive the invader from their soil. It also should have come as no surprise that leading this effort was the treacherous Duke of Milan, who having invited in the French King had now decided that Charles had overstayed his welcome. Each man had used the other for short-term advantage, unable to grasp that their long-term interests made them natural rivals.

In March 1495, Pope Alexander, still smarting from his recent humiliation at the hands of Charles, called for the creation of a grand alliance to drive the French from Italy. The selfish motives of the signatories were glossed over by the Pontiff, who titled the new arrangement “The Holy League.” Most worrisome for the French King, who knew he could sweep away any army the states of Italy could muster against him, was that his success had aroused the jealousy of the other great monarchs of Europe—King Ferdinand of Spain and Maximillian, Emperor of the Romans—who now saw an opportunity to join the game by casting themselves as the protectors of Italian liberty.x

The only major Italian power that refused to join this sacred cause was Florence, which, under the leadership of Savonarola, had its own ideas where righteousness lay. Guicciardini summed up his city’s policy: “We were then pressed to join the league, whose princes hoped to unite Italy to discourage Charles from ever returning. This was rejected because they would not return Pisa to us, and if we did not have Pisa back, the unity of Italy was of no use to Florence. Disunity was more to our purpose.” It was just this kind of selfish parochialism that had permitted the disastrous invasion in the first place, but Florentines—no different in this regard than the natives of Milan, Venice, Ferrara, Urbino, and countless other states—identified too strongly with their own locality to embrace the unity and common purpose that Machiavelli would urge so eloquently in The Prince.

With a hostile army now far in his rear, Charles was effectively trapped on the wrong side of the Alps. In the spring of 1495, he set out from Naples, reversing the triumphant march of the year before.xi On July 6, the armies of Charles and the Holy League met at Fornovo, just south of the northern Italian city of Parma. It was one of the bloodiest battles ever fought on Italian soil—“a great slaughter” Guicciardini called it—but despite the effusion of blood neither the French nor the Italians could claim a decisive victory. Tactically the results were inconclusive, but strategically the French emerged the big losers. Charles had staved off utter destruction but his only option now was to retreat across the Alps and abandon the land that not many months before had seemed so ripe for the picking.

For Florence, and for Savonarola in particular, the result was disastrous. His decision to opt out of the Holy League placed him in a precarious situation. Not only had it enraged Pope Alexander, but the people of Florence were growing increasingly bitter as the promised benefits of the French alliance failed to materialize. “[Charles] ignored the treaty made with us in Florence and sworn so solemnly on the altar,” Guicciardini complained. “[W]e kept faith with him so completely, giving him so much money and remaining his only allies in all Italy, and he perfidiously sold us and our possessions to our enemies.”

But Savonarola had more important things on his mind, chief among them the renewal of the Holy Church through “scourgings and terrible tribulations.” For the messianic friar, war and disease were to be welcomed rather than feared since the worse things got the sooner the day of rebirth would arrive. Likewise, the diplomatic isolation caused by his refusal to join the Holy League was to be embraced since it hastened the final reckoning with the institution he called a “false, proud whore.”

Pope Alexander VI had so far been more than tolerant of the rebellious prior of San Marco. He looked on indulgently as Savonarola hurled abuse at him from the Cathedral of Florence, perhaps even acknowledging in private that much of what he said was true. As Guicciardini summed it up: “[Alexander] was not disturbed by those things which offended his honor as long as his profit and pleasure was not interfered with.” It was only when Savonarola’s spiritual crusade spilled over into foreign policy that Pope Alexander began to take notice. In November 1496, Alexander demanded that Savonarola place himself and his monastery under the supervision of the Lombard Congregation of the Dominican order, where he would be under more stringent supervision. When Savonarola refused, Alexander was forced to act. At first he tried to buy off the friar with the promise of a cardinal’s hat, to which the Dominican monk replied with scorn: “It is not my habit to seek human glory. Away with that! . . . I want no hats, no miters large or small. I want nothing unless it be what you [my Lord] have given to your saints: death. A red hat of blood: this I desire.”

Savonarola’s confrontational attitude placed the government of Florence in an awkward position. No one had been more responsible for the successful transition from Medici to republican rule than he, and his followers (the frateschi or piagnoni) generally dominated in the Great Council he had done so much to establish. But while his popularity among the people remained undimmed—his sermons at San Marco and the Cathedral continued to draw thousands of tearful worshippers—his belligerent policies were threatening the profits of the international bankers and merchants who remained a powerful force in Florentine politics.

As the confrontation with the Holy Father shattered the consensus that prevailed in the early days of the renewed republic, the prior of San Marco was unable or unwilling to address the growing divisions. Instead he focused on the spiritual rebirth of a city that had, in his estimation, long ago succumbed to luxury and vice. While their leaders quarreled in the Palazzo della Signoria, he organized young boys into religious confraternities and sent them marching about town to the sound of pipes and drums, carrying crucifixes and holy images and crying “Long live Christ and the Virgin, our queen.” While some of their parents were moved to penitence, many others—like Machiavelli himself—maintained a resentful silence. The culmination of this program of spiritual reform came on February 27, 1496, when the followers of Savonarola erected a huge bonfire in the Piazza della Signoria into whose flames Florentines were expected to toss their vanities: mirrors, jewels, silks, revealing gowns and lascivious books, indecent paintings and unnecessary adornments—in short all those inessentials that distinguished Florentine life from that of a dreary provincial capital.

Savonarola, for all his personal virtue—his piety and incorruptibility—was a divisive figure. In curbing the worst excesses of life under the Medici, he also deprived the citizens of much that made life enjoyable. Savonarola himself, according to an early biographer, had found his true calling after a dream he had as a young man in which he was doused in icy water that “extinguished the carnal heat of desire, while its coldness froze in him every wordly appetite”—a remedy the preacher would no doubt have liked to apply to the Florentine population as a whole. As far as Savonarola was concerned, the greatest works of art and literature were little different from revealing gowns or ostentatious jewelry since both distracted impressionable minds from focusing on the important work of salvation. Some of his most violent opponents were young aristocrats who objected to his attempts to police their lifestyles, robbing them of the pleasures and privileges to which all wealthy young men feel entitled. Banding together under the title of thecompagnacci, these well-born youths began a campaign of harassment and intimidation. Their boldest stroke came on May 3, 1497, when they sneaked into the Cathedral, dragging behind them the carcass of a dead donkey and smearing the pulpit with excrement just before Savonarola was set to deliver his sermon.

But if these delinquents hardly inspire our sympathy, they represented the class that had fostered the great artistic achievements that made Florence celebrated throughout the world. Their fathers and grandfathers had been the patrons of Donatello and Leonardo. Under Savonarola’s more austere regime many men of genius fled or so transformed their art in response to the new mood as to become unrecognizable. The young Michelangelo was among those who hurriedly abandoned the city after the fall of the Medici, though this had as much to do with his close personal ties to the ruling family as to the uncongenial atmosphere created by Savonarola.xii Among those who remained and fell under the spell of the charismatic preacher was Sandro Botticelli, but the works he painted in this period, filled with religious fervor and dark foreboding, are a far cry from the sensual and joyous works for which he is famous.xiii To Florentines like Machiavelli—worldly, sophisticated, addicted to carnal pleasures, and fond of open intellectual debate—the moral astringents prescribed by Savonarola and his followers were unwelcome medicine for dubious maladies. “Thus,” wrote Francesco Guicciardini (whose own father was a supporter of Savonarola), “a great division and violent hatred had grown up in the hearts of the citizens, so that between brothers or between fathers and sons there was dissension over the question of the friar.”

On June 18, Alexander’s bull of excommunication against Savonarola was read in solemn tones in the churches of Florence; candles were snuffed out to symbolize the friar’s exclusion from the community of Christian fellowship. Even devoted followers were shaken, torn between loyalty to their leader and their fear lest they, too, be cast out and denied the sacraments that were the only sure path to salvation. Luca Landucci, up until then a devoted follower, was disturbed when he witnessed the disobedient friar distributing the Eucharist: “[I]t seemed a mistake to me, although I had faith in him; but I never wished to endanger myself by going to hear him, since he was excommunicated.”

The government was itself now almost evenly divided between the frateschi (followers of the friar), led by Francesco Valori, and an ever increasing number of citizens who were convinced that Savonarola’s intransigence was leading them over a cliff. When Alexander tried to force their hand by demanding that they forbid Savonarola from preaching in public, ferocious arguments broke out in the Great Council. The case against Savonarola was perhaps most succinctly put by the merchant Giuliano Gondi, who advocated that the friar be locked away in San Marco:

This man preaches that the Pope is not the Pope, that we should have no belief in him, and other things of the sort that you would not even say to a cook . . . . Must we be against all Italy and the big powers of Italy and against the Supreme Pontiff as well? The Roman censures mean that we are in rebellion against the Holy Church, and many merchants have dispatched their goods to Naples and to other places so as not to be robbed or butchered.

Among his fellow merchants, the core of the Florentine ruling class, these arguments struck home: while they might have been willing to gamble with their immortal souls, when it came to their worldly possessions they were less inclined to risk it all.

The atmosphere of crisis was heightened by the continued machinations of Piero de’ Medici, who still deluded himself that the majority of Florentines would welcome his return. Backed by Venetian money and a papal blessing, he appeared on the morning of April 28 before the walls of Florence with about six hundred cavalry and four hundred on foot, expecting the grateful citizens to rise up against their oppressors, throw open the gates, and invite in their savior. When, after a few nerve-racking hours, the welcome failed to materialize, Piero turned tail and slunk away.

In the aftermath of the abortive attack it was discovered that Piero had been counting on more than spontaneous enthusiasm. An informant told the state police that a number of prominent Florentines had been in close contact with the city’s former ruler and were plotting to seize the city gates and open them just as Piero’s army arrived. Only a preemptive strike by the frateschi, who dispatched their own loyalists to man the walls, averted disaster. The conspirators included some of Florence’s most distinguished citizens—men like Niccolò Ridolfi, Lorenzo Tornabuoni, and Bernardo del Nero. They were arrested, tried, and convicted of treason. Sentenced to death, they appealed the verdict to the Great Council on the basis of a law that Savonarola himself had advocated, but Francesco Valori and the other leading frateschi refused their petition, fearing that a prolonged trial would serve to rally the opposition. Ignoring the very law they had earlier promoted as a vital tool in the fight against despotism, they led the convicted men in chains to the Bargello where, in unseemly haste and in the dead of night, they had them beheaded. Even loyal followers of Savonarola were shaken by the brutal crackdown. The death of the young and handsome Lorenzo Tornabuoni in particular was mourned by all Florentines. “I could not refrain from weeping,” wrote the Savonarola loyalist Luca Landucci, “when I saw that young Lorenzo carried past the Canto d’ Tornaquinci on a bier, shortly before dawn.”

In the short run at least, the pro-Savonarolan regime emerged from the incident intact, if not exactly covered in glory. But in elevating expedience above principle the government and its spiritual leader lost much of their moral authority. The incident is perhaps most intriguing for the light it sheds on Machiavelli’s own attitudes. The self-serving reversal is exactly the kind of maneuver that he often recommends, and in other contexts one might well expect him to favor such a course. But in a discussion in The Discourses, Machiavelli takes a different position:

When [the accused] wished to appeal they were not allowed to do so, and the law was not observed. This did more to lessen the reputation of the Friar than anything else that befell him. For, if the right to appeal was worth having, he ought to have seen that it was observed. If it was not worth having, he should not have forced it through. The event attracted more notice in that this Friar in not one of the many sermons which he preached after the law had been broken, ever condemned the breach or offered any excuse. For, since it suited his purpose, to condemn it he was unwilling, and to excuse it he was unable. Since this made it plain to all that at heart he was ambitious and a party-man, it ruined his reputation and brought on him much reproach.

This is from a chapter with the unwieldy title “It is a Bad Precedent to break a New Law, especially if the Legislator himself does it; and daily to inflict Fresh Injuries on a City is most Harmful to him that governs it”—a context that helps explain the unexpectedly principled stand Machiavelli takes. Rejecting the medieval scholastic tradition in which political theories were based on the notion that human institutions should conform to God’s plan, Machiavelli was determined to test them in the harsh laboratory of experience. Savonarola’s policy was flawed not because it is inherently evil to turn against a law when it no longer suits one’s purpose, but because it undermined the source of his authority—his ability to persuade others of the righteousness of his cause. The man whom, in another context, he famously declared an “unarmed prophet,” had forfeited through his moral cowardice the one real weapon he possessed.

In February 1498, Savonarola, defying the interdict placed on him by Pope Alexander, began to preach once again before expectant throngs in the Cathedral. “[T]his excommunication is a diabolical thing [and] was made by the devil in hell,” he thundered from the pulpit. The Signoria, hoping to assuage the Pope’s wrath while preserving its credibility among the still numerous frateschi, ordered him to retreat to the less public venue of San Marco. It is here that on March 2 and 3, Machiavelli attended two sermons, informing the Florentine ambassador to Rome that Savonarola was determined to force a confrontation. “[H]e seeks to turn all against the supreme pontiff and, using his own attacks against him, says of him as one would the wickedest person you could find”—a report that could hardly have encouraged Ricciardo Becchi, who, like the government he represented, was desperately trying to head off a violent clash.

•  •  •

As far as we know this is the only substantive contribution Machiavelli made to the dramatic events that led to the downfall of Savonarola. He did not play a prominent role in the opposition, but it is clear that he was sympathetic to their cause. Becchi, to start with, was an opponent of the frateschi whose appointment as Florentine ambassador to the Holy See was meant to demonstrate that the government had distanced itself from the rebellious friar. But despite their skeptical attitude toward Savonarola, neither Becchi nor Machiavelli belonged to the arrabbiati or the bigi whose hostility toward the popular party found expression in ever more brazen acts of defiance. Neither group would have appealed to Machiavelli since both were dedicated to reestablishing a more oligarchic form of government. Instead, Machiavelli should be counted among the growing number of citizens who cherished the popular democracy established after the expulsion of Piero de’ Medici but who now saw that the greatest threat to its continued existence was the increasingly erratic and fanatical behavior of Savonarola himself.

On March 25, 1498, the struggle for the soul of Florence took an unexpected twist when a Franciscan brother, Francesco da Puglia, issued a challenge from the pulpit of Santa Croce to Savonarola: to walk with him through a gauntlet of fire to test the friar’s claim that he was the appointed mouthpiece of God. For the past four years the Franciscans had watched helplessly as their rivals, the Dominicans, dominated the city’s spiritual life and pocketed the lion’s share of bequests from wealthy Florentines who believed that Savonarola and the order he led were in close communication with God. Once the bull of excommunication had been issued, and pronounced with ill-concealed joy in the Franciscan church of Santa Croce itself, those monks who had endured years of frustration and humiliation saw an opportunity to strike back.

This trial by fire—which quickly caught the imagination of the Florentine people, who were themselves perplexed as to how to judge Savonarola’s claims—was a throwback to the more superstitious Middle Ages when supernatural intervention into the lives of the faithful was believed to be a normal occurrence. If God had recently cut back on such overt signs of his favor, the pious still believed in the possibility of miracles, and the climate of near religious hysteria fostered by Savonarola’s sermons made the test proposed by Brother Francesco all the more plausible. The monastery of San Marco was itself the center of disquieting visitations. In the winter of 1495, one monk wrote, “diverse figures and monstrous animals would appear to disturb the sweetness of their prayers, and they often spoke ugly, dishonest, and filthy words to the friars, along with certain expressions exhorting them to seize the sensual pleasures of this life.” This was to be expected in a city on its way to becoming a new Jerusalem as the demonic spirits, finding themselves under attack, made one final attempt to steal back the souls they had lost.

Given Savonarola’s long-standing claim of prophetic powers, the challenge was difficult to dismiss. While Savonarola knew it was a cheap stunt meant to discredit him in the eyes of his followers, many of those closest to him enthusiastically embraced the opportunity to prove their faith. Among the most eager was his chief lieutenant, Fra Domenico da Pescia, who offered himself in place of his revered leader.

Now events proceeded with their own momentum. The trial had captured the public imagination not only, as some cynics claimed, because of excitement over what promised to be an entertaining spectacle, but because it was likely to relieve the almost unbearable tensions that had been building over the past months. For those Florentines, perhaps the majority, who were genuinely perplexed as to where righteousness lay, the trial offered a way to resolve their dilemma. Even the government, initially skeptical, ultimately agreed to give the test its sanction, setting up the pyre in the great square before the Palazzo della Signoria.

On April 7, 1498, the Saturday before Palm Sunday, the citizens of Florence flocked to the Piazza della Signoria to witness the great event. Snaking across the square was a large structure of pitch-soaked timber forming a tunnel more than seventy feet long. Once set ablaze, two men—Fra Domenico on behalf of Savonarola, and Fra Giuliano Rondinelli for the Franciscans (Brother Francesco having found a willing substitute)—would enter and proceed along the length of the two-foot-wide passage. Should Fra Domenico survive the ordeal unscathed it would be declared a miracle; Savonarola would be vindicated and the Pope, who had denied him the protection of the Church, would be exposed as an impostor and a fool.xiv

The Franciscans arrived first, two hundred of them gathering beneath the portico on the south side of the square. Then came the Dominicans, 250 monks from San Marco, trailed by Fra Domenico holding aloft a large crucifix. Finally came Savonarola himself, flanked by two monks who offered some protection from the restless mob that lined the street. With the arrival of the principals, all now seemed ready for the ordeal to begin. But as minutes lengthened to hours with no sign of action, the crowd grew increasingly hostile. A soaking spring rain did little to improve the collective mood. When, after hours of delay, heralds announced that the trial had been called off, the citizens who had gathered hoping for a cathartic release turned ugly. They felt cheated and sought out someone to blame.

Though they focused their rage on Fra Domenico and Savonarola, the truth was that it had been the Franciscans rather than the friars of San Marco who were responsible for the fiasco. While the citizens of Florence waited in the rain, both Fra Francesco da Puglia and Giuliano Rondinelli were inside the palace quibbling over every detail—objecting, for instance, that the consecrated Host Fra Domenico intended to carry with him into the fiery tunnel might offer spurious protection—intending to drag negotiations out so long that the trial would have to be called off.

The Franciscans were certainly playing a cynical game, but who could blame the public for turning on Savonarola? It was he, after all, who had promised that the coming of the New Age would be marked by divine portents. For eight years he had preached his doctrine of trial and redemption to a people eager to accept his verdict that they were indeed God’s new chosen people. If he could not even pull off the minor miracle planned this afternoon for their edification, what good was he? Even Luca Landucci, who was aware of the duplicitous role the Franciscans had played, was disillusioned: “[W]hen the dispute ended in the Franciscans leaving, the Dominicans soon followed them, causing great perturbance amongst the people, who almost lost faith in the prophet.”

As Savonarola and the brethren of San Marco withdrew toward the monastery, they were forced to run a gauntlet not of fire, as had been intended, but of enraged humanity at least as dangerous to life and limb. Over the course of a single afternoon Florence had been transformed. Before the events of Saturday, Savonarola, for all the doubts that were beginning to bubble up, remained the most popular and influential man in Florence. Some in power had grown disillusioned with the Dominican friar but they were still afraid to move against him lest this provoke an uprising among his legions of devotees. Following the fiasco in the Piazza della Signoria he was almost universally reviled, and his opponents in the government were emboldened. In fact events had already raced past them. On Sunday morning, Savonarola’s colleague Mariano Ughi, substituting for his master on the pulpit of the Cathedral, was pelted with stones and driven from the altar. Other known adherents of the monk were attacked in the streets, and soon the cry “To San Marco!” could be heard ringing across the city. By midday the monastery of San Marco was besieged by an angry crowd. Some had come spontaneously, responding to the sudden change in mood, but many belonged to organized squads of vigilantes organized by groups like the compagnacci, almost certainly with the connivance of the government itself. Shouting “Kill the traitor!” and “Dead or alive!” they began to launch stones at the buildings behind the monastery’s high walls. The monks, not entirely unprepared, now rushed to gather arms—including battle axes, crossbows, and small artillery—that had been stockpiled in recent days.

Meanwhile, summary justice was being dispensed in the streets as the friar’s most prominent supporters were set upon by angry mobs. Among those murdered was Francesco Valori, who had slipped out of the monastery through a secret tunnel only to have his skull split open by a man who struck him from behind. As for Savonarola himself, the moment he had heard the angry crowd assembling in the square below he retreated to the high altar of the church and prostrated himself in prayer. It was not physical cowardice that caused him to flee the battle, but mental anguish as he saw all that he had built over the years come tumbling down. The people he had hoped to lead into the Promised Land had turned against him; the New Jerusalem he hoped to found proved no more than a mirage.

His followers had demonstrated that they were prepared to fight to the death, but Savonarola knew the cause was lost. Wishing to avoid a bloodbath, he sent an emissary to the Signoria requesting a delegation tasked with negotiating his surrender. At 3 A.M., with the crowd having imparted a sense of urgency to the proceedings by setting fire to cloister doors, Savonarola, along with his trusted lieutenants, Fra Domenico and Fra Silvestro, was led from San Marco in irons. The man who only a few days earlier had been regarded as a prophet was now almost universally despised. He was kicked and spat upon as he stumbled along the streets leading from the monastery to the cell awaiting him in the tower of the Palazzo della Signoria; only the escort of heavily armed guards saved him from being torn apart by the enraged mob.

Over the course of the next month and a half Savonarola and his fellow prisoners were subjected to repeated rounds of torture meant to extract confessions that would justify retrospectively the harsh treatment they were receiving at the hands of the government. The procedure was complicated by interference from Pope Alexander, who claimed jurisdiction over members of the cloth and who hoped to have the miscreants shipped off to Rome, where he could render justice himself. But despite the tempting prospect of having the whole mess taken off their hands, the Signoria were reluctant to submit to a precedent that might in future lead to greater papal interference in their affairs. In the end, emissaries from the Pope—led by a Spanish expert in church law, Francisco Remolins—were allowed to conduct a separate interrogation where the unfortunate prisoners were once again subjected to the strappado in an attempt to add to the already voluminous confessions.

During these weeks of physical and emotional torment, Savonarola revealed something of his own conflicted soul. The official records of his confession were certainly manipulated to place him in the worst light, but they still manage to convey flashes of genuine human feeling. At first Savonarola told his interrogators exactly what they wished to hear: that he had been animated by a lust for worldly power and that his claims of prophecy had been a sham to persuade the gullible to follow him. “Regarding my own aim or ultimate purpose, I say, truly, that it lay in the glory of the world, in having credit and reputation; and to attain this end, I sought to keep myself in credit and good standing in the city of Florence, for the said city seemed to me a good instrument for increasing this glory, and also for giving me name and reputation abroad.”

Read to the public in the Hall of the Great Council, this admission of worldly ambition, written in the friar’s own hand, served its purpose, disillusioning those who still believed in Savonarola. “[H]e whom we had held to be a prophet,” wrote Landucci mournfully,

confessed that he was no prophet, and had not received from God the things which he preached; and he confessed many things which had occurred during the course of his preaching were contrary to what he had given us to understand. I was present when this protocol was read, and I marveled feeling utterly dumbfounded with surprise. My heart was grieved to see such an edifice fall to the ground on account of having been founded on a lie. Florence had been expecting a new Jerusalem, from which would issue just laws and splendor and an example of righteous life, and to see the renovation of the Church, the conversion of unbelievers, and the consolation of the righteous; and I felt that everything was exactly contrary, and had to resign myself with the thought.

But in subsequent appointments with the torturer Savonarola regained his true voice, recanting his previous confession: “Now listen to me. God, you have caught me. I confess that I have denied God. I have told lies. Florentine lords, be my witnesses. I have denied him from fear of torture. If I have to suffer, I want to suffer for the truth. I did get from God what I have said. God, you are giving me penance for having denied you from fear of torture. I deserve it.” Like Saint Peter before him, Savonarola now embraced his punishment, not for the crimes cited by his tormentors but for having, in a moment of weakness, denied his lord.

Now there was little to be gained by prolonging the agony. Both the civil government and the Pope’s ambassadors were determined to close out this sorry chapter as quickly as possible. On May 22, Savonarola and his two lieutenants were led to the scaffold erected in the Piazza della Signoria. First they were stripped of their sacred vestments (so they would not go to their deaths still bearing the symbols of the Church) and their guilt as heretics and schismatics proclaimed to the assembled crowd. Fra Silvestro was hanged first, followed by Fra Domenico. Savonarola came last, his eyes downcast, murmuring a silent prayer. According to Landucci, who witnessed the execution, a few of the remaining true believers lost their faith then and there, since they had expected at this final moment some sign from God that the dying men were blessed martyrs.

But even in death Savonarola had a subtle power over the minds of men. To prevent his body from becoming the focus of a clandestine cult, those who had hanged him now kindled a huge bonfire, turning the dangling bodies into crumbling ash, which they then hauled away in carts and dumped into the Arno.

As the crowd began to disperse, the citizens of Florence were gripped by anxiety about the future. Some were relieved that the man who had kept the city seething for years was now gone, anticipating, perhaps, a return to the days of Lorenzo de’ Medici when it seemed as if there was more joy to be had, when full purses and peace abroad had made the city sparkle and hum. Others mourned the dream that died along with the three monks on the scaffold, of a world spiritually reborn with Florence as its capital. Whatever their political convictions, few Florentines took any pride in the grim spectacle they had just witnessed. It had been a dirty business and most were ready to forget and move on.

On Saturday, June 15, 1498, three weeks after Savonarola’s death, Niccolò Machiavelli made his way to the Palazzo della Signoria, where he was nominated to serve as Second Chancellor of the Republic, an important post in the civil service of a governmentnow seeking to regain its balance after the recent convulsions.

i According to his own account, Machiavelli attended Savonarola’s sermons at San Marco on two consecutive days, March 2 and 3.

ii The government’s response to this demand was to prohibit Savonarola from speaking in the Cathedral, but they did not prevent him from delivering sermons at his own church of San Marco. This doomed attempt at a compromise solution revealed deep divides within the ruling elite.

iii For this period in history Guicciardini is a better guide than Machiavelli. Though at twenty-five Machiavelli was a grown man when Charles invaded while his friend Guicciardini was only eleven, Machiavelli’s Florentine Histories ends with Lorenzo’s death in 1492, while Guicciardini’s The History of Florence and The History of Italy both cover the entire Savonarolan period. Machiavelli probably ended his Florentine Histories in 1492 so he would not have to deal with the unfortunate Piero in a book commissioned by his cousin, Cardinal Giulio de’ Medici.

iv This is literally true since the French army carried not only the usual arsenal of war but also the as yet unknown disease of syphilis, a contagion probably brought back from the New World by the Spanish ships of exploration.

v These condottieri, literally “contractors,” named for the condotta, or contract, they signed with the state that employed them, were mercenary captains employed by the various governments of Italy to fight their battles. Leading small bands of professional soldiers, these captains were specialists in avoiding bloody combat since death and destruction, at least for their own men, was bad for business. They had no compunction, however, in meting out the same to civilians who happened to get in their way.

vi At the time, Ludovico was not officially the Duke of Milan, the title held by his young nephew for whom he was serving as regent. It was his desire to secure the title for himself that largely explains his machinations with the French.

vii In return for Florentine promises of financial and logistical support, Charles agreed that as soon as he conquered Naples he would restore the fortresses of Sarzana and Pietrasanta, as well as the rebellious city of Pisa. Ultimately, he would deliver on none of his promises.

viii To some extent the Great Council was not so much an innovation as a return to the pre-Medici forms when two large assemblies, the Popolo and the Commune, were said to embody the will of the people. But these two ancient councils had been marginalized by smaller and more tightly controlled steering committees.

ix Machiavelli’s “A Discourse on Remodeling the Government of Florence” was written in 1520 at the request of Pope Leo X (Giovanni de’ Medici). It is important to keep in mind the intended audience when analyzing Machiavelli’s prescriptions. The main thrust of his argument is that Florence, as well as the Medici family, would be best served if the government were placed once more on sound republican foundations. Despite the need to tailor his arguments to suit his audience, there is no reason to doubt the sincerity of his conclusions, which correspond with those expressed elsewhere in his writings.

x Emperor of the Romans was the title given to the man selected by the German Electors as Holy Roman Emperor but who had yet to receive his title from the Pope. This figure was the successor of Charlemagne, who was crowned Emperor by Pope Leo III on Christmas Day in the year 800, reestablishing, at least in theory, the Western Roman Empire that had collapsed after the barbarian invasions. Throughout the Middle Ages the Emperor was a powerful secular lord who at times claimed absolute rule over the Germanic regions of central Europe as well as large portions of Italy. By the Renaissance, his power was often more symbolic than real, though in the person of Maximillian’s successor, Charles V, the prestige of the title was combined with enormous political and military resources.

xi He left a portion of his army behind to protect his conquest, but they ultimately proved insufficient to prevent the kingdom’s recapture by Fernandino.

xii Michelangelo had been discovered by Lorenzo de’ Medici and for two years the first citizen of Florence had raised the young boy almost as a son in his palace on the Via Larga. Michelangelo’s relations with Piero were more difficult, but after Piero’s expulsion the artist feared he would be identified with the disgraced regime. The fact that he did not return to his native city for many years reflects in part the poor climate for art and artists there.

xiii It is hard to imagine that the artist who painted the terrifying Saint Mary Magdalene at the Foot of the Cross, with its backdrop showing a Florence aflame, is the same man who painted the pagan Birth of Venus some two decades earlier.

xiv Fra Giuliano, having made no claim of divine protection, did not expect miraculous intervention on his behalf. It was, in effect, a suicide mission—which is perhaps why Fra Francesco had found an excuse to back out. (He claimed he would enter the fiery tunnel only if Savonarola himself agreed to go with him.)

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