Six Drops
The rope bit into his wrists. His arms, wrenched behind his back and lashed together, bore the full weight of his body as the pulley hoisted him toward the ceiling of a Florentine jail cell in February 1513—then released. The fall was sudden, the stop brutal, the shoulders dislocating with a sound that the men who administered the strappado had learned not to hear. They dropped him six times. Six jolts designed to shatter not merely the joints but the will, to extract a confession from a man whose name had appeared on a list of conspirators plotting to murder the city's newly restored Medici rulers. Niccolò Machiavelli had nothing to confess. He had played no part in the conspiracy—this much is established by the historical record, though the distinction between innocence and mere lack of evidence would not have troubled his torturers. What is remarkable, what exceeds the merely biographical and enters the realm of the mythic, is what happened next: with shoulders likely dislocated and muscles torn, he asked for pen and paper.
He wrote sonnets. Two of them, addressed to "the Magnificent Giuliano" de' Medici, mixing pathos with an audacity that borders on the unhinged. "I have on my legs, Giuliano, a pair of shackles," he began, then reported that the lice on his cell walls were as big as butterflies, that the boom of keys and padlocks around him sounded like Jove's thunderbolts. Worried the poems wouldn't impress, he complained that the muse he had summoned had slapped him in the face rather than serve a man chained up like a lunatic. To the heir of a dynasty that prided itself on artistic patronage, the forty-three-year-old former diplomat, former Secretary, former architect of a citizen militia that had actually conquered Pisa—this man now languishing in filth and agony—submitted the outraged complaint: "This is the way poets are treated!"
It was an absurd gambit. It was also, in miniature, everything Machiavelli would become: the marriage of ruthless calculation and incandescent wit, the willingness to use whatever instrument was at hand—even a sonnet, even a joke—in the service of survival. The question that has haunted five centuries of readers is whether this man, who understood power with a precision that terrified his contemporaries and continues to unsettle ours, was its apostle or its victim. The answer, characteristically, is both.
By the Numbers
The Florentine Secretary
1469–1527Lifespan (58 years)
14 yearsIn active diplomatic service for the Florentine Republic
40+Diplomatic missions across Italy, France, and the Holy Roman Empire
6Drops of the strappado endured in prison
~50,000Population of Florence during Machiavelli's tenure
3,000+Members of Florence's Great Council, its chief democratic body
350 yearsBetween The Prince and Italian unification—the end Machiavelli envisioned
The Republic of a Poor Man's Son
Bernardo Machiavelli was a doctor of laws who could not practice law—or rather, could not practice it openly. Barred from public office in Florence as an insolvent debtor, he lived frugally on a small landed property near the city, supplementing his meager income from the "restricted and almost clandestine exercise of his profession," as Britannica delicately puts it. He was poor. He was also a man who spent a considerable portion of what little he had on books. His library, modest but curated, was the first political education of his son Niccolò, born on May 3, 1469, in the Santo Spirito district of Florence.
The Machiavelli family had been wealthy once—prominent since the thirteenth century, holders of Florence's most important offices. Two of Bernardo's cousins had been beheaded for opposing Cosimo de' Medici, who had effectively ended the historic republic in 1434 to protect the family bank's enormous fortune. This is the inheritance Niccolò received: not money, not power, but a name associated with republican defiance and a father who taught him that ideas, at least, were cheap. Florence in the 1470s and 1480s was a thriving center of philosophy and a brilliant showcase of the arts, governed by the widely beloved Lorenzo de' Medici—Lorenzo the Magnificent—who managed to rule for decades "without the Florentines' feeling the brunt or shame of being ruled." It was the great trick of the Medici: tyranny that didn't feel like tyranny, patronage so lavish it anesthetized dissent.
Bernardo seems to have gained his son entrée to the scholarly circles orbiting Lorenzo. Niccolò learned Latin well, probably some Greek, attended lectures by Marcello Virgilio Adriani at the Studio Fiorentino, and acquired the humanist education expected of officials in the Florentine Chancery. But Lorenzo died in 1492. Two years later, the Medici were expelled from the city. Into the vacuum rushed Girolamo Savonarola, a Dominican friar who had been attracting popular supporters with his thinly veiled accusations against the government, the clergy, and the pope. Savonarola effectively ruled Florence for four years, imposing a theocratic regime of moral purification. Machiavelli disdained the preacher's pious "lies" even while admiring his republican reforms—an early display of his capacity to hold contradictory judgments in productive suspension. In The Prince, composed years later, he would immortalize Savonarola as an "unarmed prophet" who must fail.
On May 24, 1498, the prophecy fulfilled itself. Savonarola was hanged as a heretic—having himself endured fourteen drops of the strappado—and his body burned in the public square. Several days later, emerging from obscurity at the age of twenty-nine, Machiavelli became head of the Second Chancery.
How so young a man, with no prior apprenticeship in the chancery, could be entrusted with so high an office remains, as Britannica notes, "a mystery." But the mystery dissolves if you consider what Florence needed in that moment: not a nobleman, not a Medici loyalist, not a Savonarola partisan, but someone unaffiliated with any faction, smart enough to be useful, poor enough to be hungry. Machiavelli was all of these things.
The Saddlebags Full of Books
For fourteen years—from 1498 to 1512—Machiavelli served the Florentine Republic with an energy that reads, even across five centuries, as almost manic. As Second Chancellor, he handled the city's correspondence and domestic reports. Within a month, he was additionally appointed Secretary of the Ten of War, the committee responsible for the republic's diplomatic and foreign relations. These were not ceremonial posts. War was never far off. France, Spain, and the Holy Roman Empire were sending formidable armies marching across the weak and perpetually sparring Italian states—Milan, Genoa, Florence, Venice, Naples, and any number of smaller duchies, marquisates, and republics found it nearly impossible to defend themselves for lack of a united front.
Machiavelli thrived on the urgency. He filled his saddlebags with books and galloped off to argue the Florentine case, then report back on what he had found. He was technically too poor for the rank of ambassador—officially a mere envoy—but he styled himself, "rather grandly," the Florentine Secretary. In one report, he described his duties as weighing what the ruler's "intentions are, what he really wants, which way his mind is turning, and what might make him move ahead or draw back." He wrote of the need "to conjecture the future through negotiations and incidents." All in all, as the New Yorker's profile of him observed, "it seems that he was expected to bring the gifts of a psychologist to the task of a prophet."
He embarked on more than forty diplomatic missions. He was sent to the court of Louis XII of France, to Pope Julius II, to the Holy Roman Emperor Maximilian I, and—most consequentially—to Cesare Borgia.
I step inside the venerable courts of the ancients, where, received by them with affection, I feed on that food which only is mine and which I was born for.
Borgia was the son of the Spanish Pope Alexander VI, at the height of his power when he received Machiavelli in the ducal palace of Urbino in 1502—by candlelight, as legend has it, dressed all in black, already a figure of self-consciously theatrical menace. He had recently conquered Urbino, along with a large swath of central Italy, by means of daring, speed, and treachery. Machiavelli especially admired a maneuver in which Borgia had asked the Duke of Urbino to lend him his artillery to help take a nearby town, then turned on the undefended duchy and took it instead. The envoy could not help but contrast Borgia's stunning effectiveness with the "frustratingly slow and prudent" Florentine republic, which displayed the deficiencies as well as the virtues of popular consensus. He wrote excitedly to his bosses in the Palazzo della Signoria of the lessons offered by this majestic enemy. In the ruthless young warrior he saw not a monster but a potential hero: a leader strong enough to expel the foreign armies and transform Italy from a poetic entity into a real one.
He also witnessed, at close range, the bloody vengeance Borgia took on his mutinous captains at Sinigaglia on December 31, 1502—a famous episode of calculated brutality that Machiavelli wrote up with the detachment of a surgeon describing an operation. In much of his early writing, a single lesson recurs: "One should not offend a prince and later put faith in him."
The Farmers in Red-and-White Trousers
The most practical lesson Machiavelli took from Borgia was the deployment of a citizen army. At one point in his campaigns, after his hired mercenaries had conspired against him, Borgia had been forced to draft peasants from his conquered territories. Machiavelli recognized the advantages immediately. Florence's own mercenary troops—the standard military instrument of the Italian states—were unreliable to the point of comedy. During the war against Pisa, the city's hired soldiers had ignominiously turned and fled once the fighting got too rough. Who, after all, was willing to die for a handful of florins? On the other hand, who was not willing to die for one's country?
In 1505, Machiavelli argued the case for a Florentine citizen militia before a skeptical government. His patron, Piero Soderini—the gonfaloniere, or chief magistrate, elected for life in 1502—backed him. On a brisk February day in 1506, several hundred Tuscan farmers paraded through the Piazza della Signoria, snappily dressed in red-and-white trousers and white caps. The scene had a commedia dell'arte air about it. The professional soldiers of Europe would have laughed.
Three years later, Machiavelli led a thousand citizen troops in the latest of fifteen years of attacks on Pisa. To general astonishment, the Florentines won.
It was the high-water mark. On September 16, 1512, the militia collapsed. Defending the neighboring town of Prato from Spanish troops allied with Pope Julius II—part of a wider conflict between France and the Holy League—Machiavelli's citizen soldiers broke ranks and ran as shamelessly as the most craven mercenaries. The defeat left Florence on the losing side. A long-resentful pro-Medici faction seized its chance. The republican government was overthrown. The Great Council—that body of more than three thousand citizens that had given Florence the most broadly representative government of its time—was dismissed.
The Medici rode back into the city after eighteen years of exile. Within days, Machiavelli's militia was disbanded. Within weeks, he lost his position. Within months, his name appeared on an incriminating list.
Then the rope.
The Evening Costume Change
He was released after a month behind bars, thanks to an amnesty granted upon Cardinal Giovanni de' Medici's election to the papacy as Leo X. ("God has granted us the papacy," the new Pope reportedly told his brother Giuliano. "Let us enjoy it.") For four days, Florence was alight with fireworks, bonfires, pealing bells, and cannonades—all greeting the weary former Secretary as he made his way home with ruined shoulders and no job.
Even now, Machiavelli hoped that "these new masters of ours" would find his services of use. He was experienced, vigorous at forty-three, and during his years of civil service had shown himself trustworthy. "My poverty is evidence of my fidelity and virtue," he confided to a friend. But no offer came.
That spring, still unemployed, he retreated to the family farm near San Casciano, in taunting view of the tower of the Palazzo della Signoria. It was a sprawling and ramshackle place, and he was sadly out of his element. He caught birds. He played cards. His worldly friends sent mocking regards to the chickens.
But in the evening—and here the most famous letter of the Renaissance takes over—approaching his study, he stripped off his muddy clothes and put on his ambassadorial attire. "Fitted out appropriately, I step inside the venerable courts of the ancients," he wrote to his friend Francesco Vettori on December 10, 1513, "where I am unashamed to converse with them and to question them about the motives for their actions, and they, out of their human kindness, answer me." Livy, Cicero, Virgil, Tacitus: for four hours he communed with the dead, forgetting every trouble, not dreading poverty, not frightened by death. "I feed on that food which only is mine and which I was born for."
And because Dante says it does not produce knowledge when we hear but do not remember, he wrote down everything their conversation had profited him. He composed "a little work on princes—a whimsy," he told Vettori, introducing, with devastating understatement, arguably the most famous book on politics ever written.
The Scandal That Would Not Die
The Prince, completed toward the end of 1513, was a book of strictly practical matters—armies and fortresses, ways of holding on to power—that Machiavelli resolved would demonstrate his usefulness once and for all. It discussed people and their actions "as they are in real truth, rather than as they are imagined." Never before or since, as the
New Yorker observed, has a writer so clearly proved that the truth is a dangerous thing.
The book circulated in manuscript for years but was not published until 1532, five years after Machiavelli's death. Within the decade, an English cardinal pronounced its author "an enemy of the human race." Machiavelli stood accused of having inspired Henry VIII to defy papal authority. Some thirty years later, in France, The Prince was blamed for inciting Queen Catherine de' Medici to order the massacre of two thousand Protestant rebels. His notoriety grew less through actual knowledge of the book than through the many lurid attacks it prompted, with titles on the order of Stratagems of Satan. The Catholic Church banned his works in 1559, placing him in the company of Plato, Aristotle, and Homer—a sentence that would have pleased him enormously.
What caused the furor? Here, stripped of context and placed end to end—a method not unfamiliar to his attackers—are some of the most salient points: "A prince, particularly a new prince, cannot afford to cultivate attributes for which men are considered good." "A wise ruler cannot and should not keep his word when it would be to his disadvantage." "Men must be either flattered or eliminated." "A man is quicker to forget the death of his father than the loss of his patrimony." And the distilled spirit of the dark brew: "How one lives and how one ought to live are so far apart that he who spurns what is actually done for what ought to be done will achieve ruin rather than his own preservation."
The best fortress for the prince is to be loved by his people.
To underscore how shocking such notions were, they should be compared with others from the genre in which Machiavelli was consciously working: the "Mirrors of Princes," professional primers offered to young monarchs. Erasmus, whose Education of a Christian Prince was written just two years later, spun his pious counsel around the thesis "What must be implanted deeply and before all else in the mind of the prince is the best possible understanding of Christ." Machiavelli proposed the best possible understanding of the methods of Cesare Borgia.
But here is the complication that has kept five centuries of scholars arguing: the book is not what its most inflammatory quotations suggest. It is both worse and better. Machiavelli writes that Borgia's ruthlessness had brought peace and order to territories where weak petty rulers had allowed robbery and murder to go unchecked—that "with a few exemplary executions" Borgia had proved "more genuinely merciful" than the Florentines, who, guarding their reputation, had allowed the town of Pistoia to be destroyed by factional fighting rather than intervene. Cruel measures were to be used only out of necessity, ended quickly, and converted into benefits for the prince's subjects. Rulers who perpetrated needless cruelties are rebuked, regardless of their achievements. "These means can lead to power," Machiavelli confirms, then adds: "but not glory."
And threaded through the book, easily missed amid the glittering malice of the famous aphorisms, is a drumbeat of a different kind: "A prince must have the people on his side, otherwise he will not have support in adverse times." "A prince need not worry unduly about conspiracies when the people are well disposed toward him. But if they are his enemies and hate him, he must fear everything and everybody." And the forthright climax: "The best fortress for the prince is to be loved by his people." Whether the prince turns out to be a lion or a fox, The Prince sets a trap to render him, in relation to his people, a lamb.
The Two Machiavellis
The puzzle that has driven scholars to distraction for half a millennium is the relationship between
The Prince and Machiavelli's other major political work, the
Discourses on Livy—a sprawling commentary on the Roman historian that he began writing around 1514 or 1515 and completed sometime in 1518 or 1519. Where
The Prince is short, ruthless, and addressed to monarchs, the
Discourses is long, passionate, and explicitly republican. "It is not the particular good but the common good that makes cities great," he writes there. "And without doubt this common good is observed nowhere but in a republic."
The conventional explanation is that one book is insincere—that Machiavelli, the true republican, wrote The Prince merely to win Medici favor, or, conversely, that the Discourses represents a scholarly exercise while the grimly pragmatic Prince reveals the real man. But Machiavelli never repudiated either work. He refers to The Prince in the Discourses in a way that suggests he viewed them as companions, not contradictions. The more honest answer, proposed by the scholar Mark Hulliung, is that "both" Machiavellis need to be given equal weight—that the man who wrote a handbook for princes and the man who wrote an ode to republican liberty were the same person, thinking about the same problem from different angles: how do you create and maintain a political order in a world where fortune is malevolent, men are unreliable, and the stakes are annihilation?
The Discourses makes an argument that is, in its way, even more radical than The Prince. It claims that ordinary people are more prudent, more stable, and of better judgment than princes. "A people is more prudent, more stable, and of better judgment than a prince," Machiavelli writes flatly. Where princes confuse their liberty with their ability to dominate, the masses are more concerned with protecting themselves against oppression. A republic can adapt to changing circumstances in ways that a principality cannot, because its diversity of citizens means it can always find the right leader for the moment. Rome could call on the cautious Fabius Maximus when patience was needed and on the aggressive Scipio when the time came to strike. "If Fabius had been king of Rome," Machiavelli observes, "he might easily have lost this war, since he was incapable of altering his methods according as circumstance changed."
The argument is grounded in a devastating insight about human psychology. People are constitutionally incapable of changing their fundamental nature. A cautious man cannot become bold; an impetuous one cannot learn patience. The prince who succeeds is the one whose character happens to match his times—and since times change, every prince will eventually be undone by the very qualities that made him great. Only a republic, with its "diversity found among its citizens," can escape this trap. It is the earliest and most rigorous case for institutional adaptability over individual genius.
John Adams loved this book. John Pocock traced its diffusion throughout the Atlantic world and into the ideas that guided the framers of the American Constitution. The "neo-Roman" political theorists of our own time—Philip Pettit, Quentin Skinner, Maurizio Viroli—find in Machiavelli the source of their principle of "freedom as non-domination." The man whom an English cardinal called "an enemy of the human race" is, on this reading, one of the founding theorists of modern democracy.
The Playwright and the Pope
"After everything was lost" is the way Machiavelli referred to the years following his release from prison. But even while he lamented his fate and continued to angle for Medici favor, he wrote with a ferocity that suggests not despair but its opposite—a man who has discovered that having nothing left to lose is its own form of freedom.
He completed the Discourses. He devoted himself to poetry, working on classical themes in Dantesque terza rima. He wrote The Art of War, published in 1521. He composed his Florentine Histories, commissioned by Cardinal Giulio de' Medici and presented to the Cardinal—by then Pope Clement VII—in Rome in June 1525, receiving in return a gift of 120 ducats. He read aloud to friends in the increasingly anti-Medici circle that gathered in the gardens of the Rucellai palace. He discovered a gift for the theatre.
Most strikingly, in the midst of these dark years, he turned to comedy. The Mandrake (La Mandragola) is a satiric, bawdy, often scatological farce involving the timeless trio of aspiring lover, stupid husband, and venal priest, all conspiring to get a Renaissance Sophia Loren into bed. It was the greatest hit of Machiavelli's career. First performed in 1520, the production was so successful that Pope Leo X ordered a command performance at the papal court later that year. And so, seven years after everything was lost—thanks to the Pope's delight in a show that happily trafficked in adultery and the shifty morals of the clergy, this in the same year that Leo X excommunicated Martin Luther—Machiavelli at last came into Medici favor, and everything was more or less regained.
Virtù Against the Flood
Two concepts sit at the center of Machiavelli's intellectual universe, and neither translates cleanly into English. Virtù looks like "virtue" but means something closer to the full range of personal qualities—skill, courage, adaptability, ruthlessness when necessary, mercy when possible—that a leader must deploy to master circumstances. It is not moral goodness. It is not moral indifference. It is the capacity to do whatever the moment demands, to vary one's conduct "from good to evil and back again as fortune and circumstances dictate."
Fortuna looks like "fortune" but carries a violence absent from the English word. Where conventional representations treated Fortuna as a mostly benign, if fickle, goddess, Machiavelli's fortune is—in the Stanford Encyclopedia's precise formulation—"a malevolent and uncompromising fount of human misery, affliction, and disaster." In Chapter 25 of The Prince, his most famous discussion of the concept, he proposes an analogy:
"She resembles one of our destructive rivers which, when it is angry, turns the plains into lakes, throws down the trees and buildings, takes earth from one spot, puts it in another; everyone flees before the flood; everyone yields to its fury and nowhere can repel it."
Yet the furor of a raging river does not mean its depredations are beyond human control. Before the rains come, it is possible to take precautions—to build dykes and embankments. "She shows her power where virtù and wisdom do not prepare to resist her and directs her fury where she knows that no dykes or embankments are ready to hold her."
The relationship between these two concepts is the engine of Machiavelli's political thought. Virtù is what you build before the flood comes. Fortuna is the flood that comes regardless. The question is never whether disaster will arrive but whether you have built the infrastructure—psychological, institutional, military—to survive it. Machiavelli was deeply skeptical that any single individual could possess enough virtù to master fortune indefinitely. Pope Julius II succeeded because his impetuous nature matched his circumstances, but his consistency of conduct "would have brought about his downfall" had circumstances changed. Even the Emperor Severus, whose techniques Machiavelli lauds, succeeded only because he employed "the courses of action that are necessary for establishing himself in power"—he is not to be imitated universally.
This is why Machiavelli ultimately preferred republics: they contain multitudes. No single person can change their nature, but a republic, with its diversity of citizens, can rotate leaders whose qualities match the times. The adaptability that no individual can achieve, institutions can.
Liberty Was Unknown in Florence
The commission to write an official History of Florence placed Machiavelli in a delicate position. It was a plum assignment, carrying a salary of 57 gold florins a year (later increased to 100), offered by Cardinal Giulio de' Medici, the de facto ruler of Florence. Any sensible courtier would have produced a flattering narrative. Machiavelli agonized over how to present the Medici—and the result is anything but the work of a flatterer. Recounting how the family's desire to "wield exclusive power" had led it to crush all political opposition, leaving other parties with no alternative except plots and murderous conspiracies, he concluded bluntly that under the Medici regime "liberty was unknown in Florence."
The man who is still accused of teaching tyrants how to rule wrote, in a book commissioned by a tyrant's family, the most devastating indictment of their tyranny. It was not courage in the sense Thomas More would have recognized—More, who was beheaded for his refusal to condone royal power. It was something slipperier, more characteristically Machiavellian: the truth embedded in a structure of obedience, smuggled past the censor in the guise of scholarly dispassion. Machiavelli faced a dilemma, Britannica notes, "about how to tell the truth about the rise of the Medici in Florence without offending his Medici patron." His solution was to tell the truth anyway, trusting that the historical framing would provide deniability.
In 1522, a plot to murder Cardinal Giulio was found to have originated among the learned circle of the Rucellai gardens—Machiavelli's own circle. His closest friends were exiled or beheaded. He, however, was neither arrested nor implicated. Scholars have agreed that he knew nothing of the plot: he was too historically suspect a figure for his friends to risk including. But Ross King, in his biography Machiavelli: Philosopher of Power, points out how curiously often Machiavelli writes about political conspiracy, and the overt sympathy with which he handles conspirators. In the portion of the History he was composing that very year, he treats the fifteenth-century ringleader of a plot against the Sforza tyrant of Milan with the respect due to a Roman republican hero.
It may have been the incriminating scrap of 1513—the list that landed him in the strappado—that taught him the rules by which conspirators must proceed: confide in absolutely no one except when absolutely necessary, try to leave no one alive who might take revenge, and, above all, never put anything in writing.
The Walls That Held and the Man Who Didn't
Even military opportunities returned. In 1523, Giulio de' Medici succeeded to the papacy as Clement VII. Machiavelli was entrusted with maintaining Florence's fortifications. He did his job ecstatically and well. In April 1526, he was made chancellor of the Procuratori delle Mura to superintend the city's defenses. When, in the spring of 1527, the Emperor's armies thundered south through Italy, they bypassed Florence, judging the walls and forts too difficult to breach.
Instead, the army—angry, starving, part-Spanish, part-Lutheran, barely controllable—marched directly on to Rome, where soldiers poured through the walls and viciously sacked the city for days on end, robbing, raping, murdering, destroying. It was one of the great catastrophes of the Renaissance. Machiavelli himself helped Clement escape.
But he had done even more for Florence than he knew, and less for himself. In the ensuing chaos, the Medici regime in Florence was overthrown. The republic was restored. The Great Council was reinstated. This was everything Machiavelli had hoped for, even when he appeared to be working for the other side. He was not seen as brilliantly adaptable, however, but simply as being on the other side. As a Medici supporter, he found himself once again unemployed, subject to the same political suspicions as when the Medici had first returned fifteen years earlier.
At fifty-eight, he no longer had the resources to start over. He developed mysterious stomach ailments and took to his bed. Within weeks of the republic's restoration, attended by his loving children, his loyal friends, and a priest, Niccolò Machiavelli died.
I love my country more than my own soul.
Odd, that an expert at winning should have lost so much, and then lost it all again. A republican when the republic ruled, a servant of princes when princes returned, cast out by both when each suspected him of loyalty to the other. "To succeed in life a man must be adaptable"—this was his prime lesson, and he was determined to live by it. But a corollary, if contradictory, lesson was that "man cannot deviate from that to which nature inclines him." He could not stop telling the truth. He could not stop being funny about it. And he could not stop loving a city that never quite loved him back.
In however perverse a way, he was no less a martyr to his convictions than Thomas More, who was canonized for refusing to bend. More had the courage to stand in opposition to the moral direction of his times. Machiavelli was his times: he gave permanent form and force to its political habits and unspoken principles. Then, as now, it is a terrible choice.
The tower of the Palazzo della Signoria is still visible from San Casciano. Every evening, for fourteen years, a man in muddy clothes changed into ambassadorial dress and sat down to argue with the dead about how the living might be saved. The dead, out of their human kindness, answered him. Whether the living ever did remains the open question of his life.
