One method of torture used in Florentine jails during the glorious days of the Renaissance was the strappado: a prisoner was hoisted into the air by a rope attached to his wrists, which had been tied behind his back, and then suddenly dropped toward the floor as many times as it took to get him to confess. Since the procedure usually dislocated the shoulders, tore the muscles, and rendered one or both arms useless, it is remarkable that Niccolò Machiavelli, after reportedly undergoing six such “drops,” asked for pen and paper and began to write. Machiavelli had nothing to confess. Although his name had been found on an incriminating list, he had played no part in a failed conspiracy to murder the city’s newly restored Medici rulers. (Some said that it was Giuliano de’ Medici who had been targeted, others that it was his brother Cardinal Giovanni.) He had been imprisoned for almost two weeks when, in February, 1513, in a desperate bid for pardon, he wrote a pair of sonnets addressed to the “Magnificent Giuliano,” mixing pathos with audacity and apparently inextinguishable wit. “I have on my legs, Giuliano, a pair of shackles,” he began, and went on to report that the lice on the walls of his cell were as big as butterflies, and that the noise of keys and padlocks boomed around him like Jove’s thunderbolts. Perhaps worried that the poems would not impress, he announced that the muse he had summoned had hit him in the face rather than render her services to a man who was chained up like a lunatic. To the heir of a family that prided itself on its artistic patronage, he submitted the outraged complaint “This is the way poets are treated!”

Machiavelli believed that to succeed in life a man must be adaptable. Illustration by Lorenzo Mattotti

Machiavelli was not especially known for his poetry, and few would have called him a man with a claim to Medici support. His family was distinguished but far from rich, and had definite republican associations. Two of his father’s cousins had been beheaded for their opposition to the dynasty’s founder, Cosimo de’ Medici, who had effectively brought the historic republic to an end, in 1434, the better to protect the family bank’s enormous fortune. During Machiavelli’s youth, his father seems to have gained him entrée to the scholarly circles around the widely beloved Lorenzo de’ Medici, who had managed to rule Florence for decades without the Florentines’ feeling the brunt or shame of being ruled. But Lorenzo had died in 1492, and, two years later, the Medici were thrown out of the city. Machiavelli was twenty-five; Giuliano de’ Medici, Lorenzo’s youngest son, was fifteen. While Machiavelli had nothing to do with the religious regime of the Dominican preacher Savonarola, who replaced the Medici—he disdained the preacher’s pious “lies” even while admiring his republican reforms—he came into his own once the city turned against its savior and Savonarola (after suffering fourteen drops of the strappado) was hanged. In 1498, when both God and Savonarola’s supporters lost their government posts, Machiavelli found himself with a job. For the next fourteen years, he proudly served an independent city-state that had returned to its republican form, but was now carefully buttressed to withstand Medici forces lurking at its borders, or the threat that other wealthy families might pose. The chief safeguard of the city’s liberty was the Great Council: an administrative body with a membership of more than three thousand citizens, which gave Florence, with a population of some fifty thousand, the most broadly representative government of its time.

At the age of twenty-nine, Machiavelli was appointed Second Chancellor, with responsibilities for the city’s correspondence and domestic reports. His immense physical and intellectual energy (he casually boasted of making “Greek, Latin, Hebraic, and Chaldean” references) seems to account for his additional appointment, within a month, as Secretary of the so-called Ten of War, which sent him on remote diplomatic missions, usually in the face of impending crisis. War was never far off. These were years when France, Spain, and the Holy Roman Empire, battling over rival claims, sent their formidable armies marching across the weak and continually sparring Italian states; Milan, Genoa, Florence, Venice, Naples, and any number of smaller duchies, marquisates, and republics found it hard to defend themselves, for lack of a united front.

To make matters worse, the varied Italian powers relied on mercenary troops that traded sides more easily than today’s big-league ballplayers, signing a new contract as soon as a better offer came along. Machiavelli thrived on the urgency and the uproar, filling his saddlebags with books and galloping off to argue the Florentine case, then report back on what he had found. 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, it seems that he was expected to bring the gifts of a psychologist to the task of a prophet.

He did it very well. Although his lack of wealth kept him from achieving the rank of ambassador—officially a mere envoy, he styled himself, rather grandly, the Florentine Secretary—his unblinking judgments made him the right-hand man of the republic’s chief official, Piero Soderini. He was set to work at the courts of King Louis XII of France, Pope Julius II, and the Holy Roman Emperor Maximilian, all the while studying the differing forms of government and temperament offered to his view. Like most psychologists, Machiavelli was insatiably curious about the human mind. And no one he met impressed him more than Cesare Borgia, the son of the Spanish Pope Alexander VI, who was at the height of his power when, in 1502, he received Machiavelli in the ducal palace of Urbino—by candlelight, as legend has it, dressed all in black, already a figure of self-consciously theatrical menace. Borgia 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.) Machiavelli 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 the need for popular consensus, and 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 a potential hero: a leader strong enough to expel the foreign armies and transform Italy from a poetic entity into a real one.

The most practical lesson that the dazzled envoy 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 of such a system, which were made particularly clear when Florence’s mercenary army, warring against Pisa, ignominiously turned and fled once the fighting got too rough. Who, after all, was willing to die for a handful of florins (particularly the meagre handful paid by the republic)? 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, and 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. Despite the commedia-dell’arte air, just three years later Machiavelli led a thousand citizen troops in the latest of fifteen years of attacks on Pisa, and—to general astonishment—the Florentines won.

Machiavelli’s military reputation remained sterling until 1512, when the militia, defending the neighboring town of Prato from Spanish troops, broke ranks and ran as shamelessly as the most craven mercenaries. Worse, the defeat left Florence on the losing side of a wider battle between France and the allied forces of Spain and Pope Julius II. With Florence vulnerable, a long-resentful pro-Medici faction seized its chance, and the republican government was overthrown. And so it happened that in September, 1512, after an absence of eighteen years, the Medici rode back into the city. Within days, Machiavelli’s militia and the Great Council were dismissed.

Although Machiavelli soon lost his position as Secretary, he seems to have believed that he maintained some authority, writing a formal plea on behalf of Piero Soderini, whom he had helped to escape on the eve of the Medici return. This exceptional document—published for the first time in English, as “A Caution to the Medici,” in “The Essential Writings of Machiavelli” (edited and translated by Peter Constantine; Modern Library; $17.95)—presents an argument against the Medici faction’s continued blackening of Soderini’s name. Machiavelli offers a political rationale (“The Medici government would only weaken itself by attacking a man who is in exile and cannot harm it”) for what seems an attempt to defend a friend and, in his name, the Florentine people. Of course, any illusions of influence were dispelled a few months later, in February, 1513, by jail and the strappado. Whether Giuliano de’ Medici ever read the sonnets that Machiavelli dedicated to him is a matter of dispute, but his intervention was not ultimately required. After a month behind bars, Machiavelli was released, thanks to an amnesty granted upon Cardinal Giovanni de’ Medici’s election to the papacy as Leo X, the first Medici pope. (“God has granted us the papacy,” he reportedly told Giuliano. “Let us enjoy it.”) For four days, Florence was alight with pride and the heady prospect of favors from the overflowing papal coffers: fireworks, bonfires, pealing bells, and cannonades all greeted the weary former Secretary as he made his way home.

Even now, Machiavelli hoped that “these new masters of ours” would find his services of use. He was experienced, he was (at forty-three) extremely vigorous, and during his many years of civil service he had shown himself a trustworthy man. “My poverty is evidence of my fidelity and virtue,” he confided to a friend. And he desperately needed a job. That spring, still unemployed, he retreated from the city to live with his wife and children on 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, catching birds and playing cards; his worldly friends sent mocking regards to the chickens. But in the evening, 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, in one of the most famous letters of the Renaissance, “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: he wrote their answers down and, adding observations from the history he had witnessed, toward the end of 1513 he completed a little book about statecraft—a book of strictly practical matters, dealing with armies and fortresses, with ways of holding on to power—that he resolved would demonstrate his usefulness once and for all to Giuliano, since it discussed people and their actions “as they are in real truth, rather than as they are imagined.” Never before or since has a writer so clearly proved that the truth is a dangerous thing.

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“The Prince,” Machiavelli’s how-to guide for sovereigns, turned out to be “a scandal that Western political thought and practice has been gazing at in horror and in fascination since its first publication,” to quote from Albert Russell Ascoli’s introduction to Peter Constantine’s new translation (Modern Library; $8; also included in “The Essential Writings of Machiavelli”). Circulated in manuscript for years, the book was not published until 1532—nearly five years after Machiavelli’s death—and received its first significant critique within the decade, from an English cardinal who pronounced the author “an enemy of the human race.” Machiavelli stood accused of having inspired Henry VIII to defy papal authority and seize ecclesiastical power for the crown. Some thirty years later, in France, the book was blamed for inciting Queen Catherine de’ Medici to order the massacre of two thousand rebel Protestants. (There seems to have been little besides her family connection to warrant the Machiavellian association.) His notoriety grew, less through knowledge of the offending book than through the many lurid and often skewed attacks it prompted, with titles on the order of “Stratagems of Satan.” Wherever a sovereign usurped power from the church or the nobility, whenever ostentatious deceit or murderous force was used, Machiavelli was spied in the shadows, scribbling at his desk amid the olive groves, his quill dipped in a poison so potent that it threatened the power structures of Europe.

What caused the furor? Here, out of context and placed end to end (a method not unfamiliar to his attackers), are some of Machiavelli’s most salient and satanic points: “A prince, particularly a new prince, cannot afford to cultivate attributes for which men are considered good. In order to maintain the state, a prince will often be compelled to work against what is merciful, loyal, humane, upright, and scrupulous”; “A wise ruler cannot and should not keep his word when it would be to his disadvantage”; “Men must be either flattered or eliminated, because a man will readily avenge a slight grievance, but not one that is truly severe”; “A man is quicker to forget the death of his father than the loss of his patrimony.” And, the distilled spirit of this 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.” To underscore how shocking such notions were, they should be compared with other examples from the genre in which Machiavelli was consciously working: the “Mirrors of Princes,” a type of professional primer offered by advisers to young or recently elevated monarchs, meant to shape their judgment and, with it, the future of the state. A philosopher could not hope for a more direct influence on the fate of mankind than by writing such a book; or, practically speaking, for a better advertisement for a royal job. Erasmus, whose “Education of a Christian Prince” was written two years after Machiavelli’s work—he presented his treatise first to Charles of Aragon and, after it failed to elicit the desired financial result, to Henry VIII—spun his pious counsel around the central thesis “What must be implanted deeply and before all else in the mind of the prince is the best possible understanding of Christ.” Machiavelli, on the other hand, proposed the best possible understanding of the methods of Cesare Borgia.

There is a context, however, that, if not ameliorating, is richly complicating and easily overlooked in the light of Machiavelli’s aphoristic skill. One doesn’t wish to fall back on the excuse that this is the way that rulers (or other people) often behave, although it is true that Machiavelli no more invented political evil by describing it than Kinsey invented sex. Like all the celebrated artists of his time and place—and statecraft was one of the Renaissance arts—Machiavelli was in thrall to ancient pagan models. But there is a crucial difference: a painter could situate a Madonna within a classical portico without disturbing the figure’s Christian meaning. Works that delve beneath the surface of classical forms to get at classical thinking—works of literature, philosophy, politics—require a recognition, at least, of the conflict between pagan and Christian ideals: strength versus humility, earthly life versus the hereafter, the hero versus the saint. For Machiavelli, the choice was not difficult. The Roman republic was for him the undisputed golden age; even before writing “The Prince,” he had begun a commentary on Livy’s “History of Rome,” closely analyzing the Roman system of liberty and leaving no doubt that he was a republican at heart. (“It is not the particular good but the common good that makes cities great. And without doubt this common good is observed nowhere but in a republic.”) But Christian piety had sapped the strength needed to bring this heroic form of government back to life. The great republic of his own era had failed because the men entrusted with its liberties did not know how to fight for them. He had seen his friend Soderini forfeit Florence by refusing to limit the freedoms ultimately employed against him by his enemies; that is, by trusting that goodness and decency could triumph over the implacable vices and envious designs of men.