Niccolò Machiavelli

HIP/Art Resource

Niccolò Machiavelli; engraving by Robert Cooper, after Raphael Morghen and Bronzino, nineteenth century

“Is Machiavelli good, then, or is he evil?” asks the French scholar Patrick Boucheron in his discussion of The Prince, a book whose “whole program is to uncouple political action from conventional morality.” Is he advising political leaders to be treacherous, violent, and dishonest (as Diderot believed), or revealing to ordinary people the mechanisms behind their leaders’ dishonesty, violence, and treachery (as Rousseau believed)? “We would like to have an answer,” Boucheron writes, but the matter is better “set aside.” Machiavelli was simply saying “the truth about things.” Still, the question hangs in the air, if only because Boucheron’s anxiety over the deteriorating morality of politics today has him turning to the Italian for guidance.

Machiavelli has a way of prompting his commentators to assert their moral concerns. They do not want to be tarred with the villain’s brush. The British historian Alexander Lee closes his biography on a resolutely pious note: on his deathbed Machiavelli

knew how greatly he had sinned. Over the past fifty-eight years, there had been no crime he had not committed, no vice he had not indulged…. At every turn, he had thought only of himself, his ambitions and desires….

One can hear him inwardly shrieking with terror at the pains of Hell.

It’s a harsh conclusion after the mostly sympathetic picture painted over the 570 preceding pages.

Niccolò di Bernardo dei Machiavelli was born in Florence in 1469, the year that Lorenzo de’ Medici, Il Magnifico, came to power in the city. “Let’s acknowledge that he often exaggerates,” writes Boucheron, reacting to Machiavelli’s claim that he was “born poor and learned to work before having fun.” Boucheron’s short book is based on a series of radio talks and retains a spoken voice that constantly seeks complicity and dramatic effect. Lee explores Machiavelli’s background soberly, at length. The family, once well respected, had fallen on hard times, partly because relatives on both the father’s and mother’s side had conspired against the Medici, partly because Bernardo, Niccolò’s bookish father, had inherited debts, was unable to pay his taxes, and hence was excluded from holding public office or practicing law, the profession for which he had studied. Rumors that he was an illegitimate child compounded the problem, since that would also have excluded him from public office.

The family had a house in Florence and a farm some seven miles to the south. On occasion Bernardo was obliged to sell his clothes to make ends meet. Such transactions were recorded in his memory book, a typical instrument of domestic economy in a Florentine household. “Coldly, methodically, Bernardo recorded the minute facts of family life,” Boucheron elaborates, something that “reminds us that all power starts at home.” Lee details Bernardo’s twenty-year debt-repayment plan and his despair when he was not properly compensated for a consignment of brushwood. He shows him compiling a topographical index to Livy’s Ab urbe condita in return for a copy of the book. Power is conspicuous for its absence.

The family ambition was that Niccolò should overcome the stigma that had obstructed Bernardo and participate in public life. He was sent to school, then educated by private tutors, one of them a priest who sexually abused him. This was not unusual, nor was Niccolò’s eventual bisexuality. Boucheron does not believe that he went to university; Lee gives evidence that he did. He was eight when the Pazzi conspiracy against the Medici failed—the conspirators’ corpses were hung from the windows of Palazzo Vecchio, the seat of government—after which the constitution was rewritten to give more power to Il Magnifico. Niccolò was twenty-three when Piero de’ Medici, Lorenzo’s son, was chased out of Florence because of his inept handling of a French invasion and the priest Girolamo Savonarola became the main force in the city. Again the constitution was rewritten, this time along republican lines. But the economically vital subject city of Pisa seized the chance to break away from the Florentine republic. Niccolò was twenty-seven, still unemployed, still on the margins, when in 1497 Savonarola ordered the first Bonfire of the Vanities in Piazza della Signoria, a sixty-foot pile of fashionable clothes, books, paintings, dice, card games, and musical instruments. A year later, after fierce factional tensions, Savonarola himself was burned in the same place.

Machiavelli at last profited from upheaval. After Savonarola was executed and his supporters purged, he was elected both second chancellor and secretary of the Ten of War, important government posts that had fallen vacant. “He was the ideal candidate,” Lee writes: “relatively obscure; able, but not outstandingly brilliant; and, crucially, untainted by success in any quarter.” He was also completely unprepared. He had attended the lectures of Marcello Adriani, who suggested that one should, in Lee’s words, “harness the wisdom of the ancients to rise above factional conflicts.” He had read Lucretius and made notes on his understanding of the balance between determinism and free will and the chances of controlling fate by understanding “the cause of things.” But he had no experience of administration or diplomacy. After striving to find a place for himself in Florence, he was suddenly faced with the problem of finding a place for Florence in the chaotic world of Italian and European politics.


Lee’s fine book describes in dogged detail Machiavelli’s involvement in a long series of wars and diplomatic negotiations: first Florence’s hapless campaigns to recapture Pisa, then its struggle not to fall victim to the expansionary ambitions of Cesare Borgia in Romagna, the pope, the Venetian Republic, the Duchy of Milan, the Spanish House of Aragon that came to possess Naples and Sicily, the French king, and the Holy Roman Emperor. Other threats came from Switzerland, which had a powerful army, the Duchies of Modena and Ferrara, then Bologna, Imola, Lucca, Genoa, and Siena. The feudal system whereby the pope and the Holy Roman Emperor had afforded their protection to smaller city-states in return for tax income was now nearing its end. The concept of the nation-state, gaining ground in Spain, France, and England, was still far from producing the notion of a people’s right to self-determination.

Everything was up for grabs. The French king wished to possess Milan, but so did the emperor. Both the Spanish and the French believed they had a right to Naples. The Venetians, the pope, and the emperor all believed they had a right to the towns of the Veneto and Emilia-Romagna. Each sought alliances in a rapidly shifting pattern of opportunism and treachery. Meanwhile, the exiled Medici family offered support to any of Florence’s enemies that might return them to power. Again and again towns were besieged, their outlying territories laid to waste, their merchandise seized, men slaughtered, women raped.

To complicate matters further, most states did not keep a standing army for fear that its commanders would seize power. Instead they employed condottieri, mercenary military commanders with private armies who waged war on their behalf. With no commitment to a campaign beyond their own wealth and prestige, the condottieri were perfectly capable of halting it at a crucial moment to ask for better terms or of sacking a defeated town and keeping the booty. Asked to collaborate, they invariably plotted against one another.

Machiavelli found himself negotiating with friends and enemies as a Florentine envoy. In the summer of 1499 he was in Forlì, trying and failing to hammer out an agreement with Caterina Sforza. In 1500 he spent five frustrating months following Louis XII around France, begging his protection for Florence at a price that could never be agreed on. In 1502 he was seeking to mollify Cesare Borgia, who moved from town to town settling old scores, on one occasion inviting two condottieri to negotiations and having them strangled, then waking Machiavelli in the early hours to dictate terms to Florence.

These were not easy journeys, traveling on horseback, in all weather, across mountains and swamps. Accommodation and couriers were expensive and often had to be paid from his salary. Louis XII made him wait days for an audience. Courtiers and envoys from other states gave conflicting news and advice or spread false information about his intentions. When proposals were made, messages had to be sent to Florence for a response. Couriers could not always get through. Their dispatch bags were sometimes stolen or confiscated. A letter hidden in a shoe might prove unreadable on arrival. Since republican Florence was run by a series of committees, decision-making was slow and confused, especially when responding to demands for money. The Florentines wanted security but were averse to taxes. The military situation could change rapidly. The words “alarmed,” “temporize,” and, above all, “too late” turn up again and again in Lee’s account.

In 1503 Machiavelli was in Rome for a papal conclave that coincided with a recurrence of the plague. “Everywhere he looked, there were dead bodies.” In January 1504 he was back in France, in 1505 in Perugia, then Mantua, then Siena. “All these intrigues were making his head spin,” writes Lee. In 1506 he was trying to deal with Pope Julius II, who was marching north to reconquer towns in Romagna and Emilia. In the winter of 1507 he set off on a six-month journey to negotiate with the Holy Roman Emperor Maximilian, following his army as it tried and failed to invade northern Italy from the Tyrol. In 1510 and 1511 there were increasingly desperate missions to France.

All the time Machiavelli was away, he had to worry about his position at home. Was his mission perceived as a failure? Were his colleagues conspiring against him? Friends wrote advising him to hurry back. His bosses ordered him to stay. And he was married now. Children were born in 1502, 1503, and 1504. There were illnesses and anxieties. Not that this prevented him from pursuing affairs and visiting brothels, male and female. “Machiavelli is definitely an unsavory character,” Boucheron observes, commenting on a letter in which Niccolò describes “his ‘desperate rut’ with an old and atrociously ugly prostitute” while on mission in Verona. Lee gives the full story: tricked by low light and a bawd’s wiles, the Florentine envoy did not actually see the woman until, after sex, he lit a lamp and “nearly dropped dead on the spot.”


Overall, though, what emerges from Lee’s careful chronicling of these missions is Machiavelli’s diligence, his patience with his dithering superiors, his financial honesty, and his commitment to the Florentine cause. After every trip he wrote reports that went far beyond his brief. He was fascinated by the leaders he met and the way they dealt with the ups and downs of fortune: the ruthlessness of Borgia, the stubborn self-confidence of Julius, the hauteur of Louis XII, the ineffectual pleasantness of Maximilian. But he was equally fascinated by the domestic politics and traditions that largely determined their successes and failures: Borgia seeking to impose himself on lands that had sunk into anarchy; Louis benefiting from France’s unity, stability, and efficiency; Maximilian hampered by the loose affiliation of peoples that made up his empire.

Piece by piece, Lee shows Machiavelli collecting the material he would use in The Prince, the Discourses on Livy, and The Art of War. He also details his growing involvement in the war against Pisa. A siege in 1499 led to Florence’s condottiere Paolo Vitelli being beheaded for treason when he broke off engagement just when victory seemed assured. In 1504 an expensive project to divert the Arno to dry out Pisa’s port, thus depriving the city of supplies from the sea, turned into a fiasco. Eventually, Machiavelli became convinced that mercenary armies were part of the problem, not the solution. Having persuaded the Florentines to experiment with a citizens’ army, he raised it, trained it, and largely led it himself. Only a powerful sense of belonging to a community, he thought, would steel soldiers to face death. In 1509 Pisa was retaken.

Three years later, as a result of a shift in alliances, Florence succumbed to a Spanish army supported by the pope and the Venetians. With it came the Medici. Machiavelli tried to show his willingness to work with the family, writing letters of advice suggesting how best they might govern the city (“he would betray everything and say anything,” Lee comments). To no avail. He was dismissed, then implicated, erroneously, in a conspiracy against the Medici. He was imprisoned and tortured. From his prison cell, aware that the chief conspirators had been executed, he wrote a surprisingly ironic, delicate poem to Giuliano de’ Medici, son of Il Magnifico, whom he had known years before. Again to no avail. Then Pope Julius died and Giovanni de’ Medici, another son of Il Magnifico, was elected to succeed him. Medici power in Florence was suddenly assured. An amnesty was announced. Machiavelli retreated to his farm where after a period of depression he began to write.

Short summaries of Machiavelli’s works are almost always misleading. “Machiavelli tried to find princes to admire,” writes Boucheron, “but when he found none he was forced to invent a Prince on paper.” This is not the case. The Prince sets out to establish how power is wielded in a principality and what qualities are required in its leader. It concludes that different circumstances will require different qualities. Lee feels the book is marred by being too obviously an attempt to curry favor with the Medici by purporting to “reveal how princes could learn to master Fortune.” Again this is reductive. Analyzing the very different careers and qualities of Cesare Borgia and Pope Julius, Machiavelli observes:

If someone is behaving cautiously and patiently and the times and circumstances are such that the approach works, he’ll be successful. But if times and circumstances change, everything goes wrong for him, because he hasn’t changed his approach to match. You won’t find anyone shrewd enough to adapt his character like this, in part because you can’t alter your natural bias and in part because, if a person has always been successful with a particular approach, he won’t easily be persuaded to drop it. So when the time comes for the cautious man to act impulsively, he can’t, and he comes unstuck.

The relation between character and circumstance is also crucial in the debate that made The Prince notorious. At the beginning of chapter 15, Machiavelli remarks:

If you always want to play the good man in a world where most people are not good, you’ll end up badly. Hence, if a ruler wants to survive, he’ll have to learn to stop being good, at least when the occasion demands.

“When the occasion demands…” Earlier, in a less celebrated passage, Machiavelli observes that in

hereditary monarchies where people have long been used to the ruler’s family…all a monarch need do is avoid upsetting the order established by his predecessors, trim policies to circumstances when there is trouble, and, assuming he is of average ability, he will keep his kingdom for life.

Here occasion doesn’t demand; no bad behavior is required. But in early-sixteenth-century Italy, power, as Lee’s biography remorselessly confirms, was a rollercoaster of internal factional intrigue and external predators. So a hierarchy of values had to be established: for Machiavelli the well-being of the polis was the supreme value, and the political survival of the prince was intimately tied up with it, since instability only breeds more instability. “When the occasion demands,” what is normally considered bad behavior can be the best course.

With the determination of a man who has had to struggle to join the elite and resents its complacencies, Machiavelli goes out of his way to emphasize this idea, pursuing his line of reasoning far beyond what was expedient to win the approval of the Medici. Borgia was ruthless, but in “forc[ing] people to respect authority” he fostered political unity and economic prosperity. Tackling this debate over whether ends justify the means as it emerged some years later in the Discourses, where Machiavelli insists that Romulus had to kill his brother Remus if he was to establish a lasting state in Rome, Boucheron is relieved to conclude that he allows us to “recognize the legitimacy of what [Romulus] has founded” while leaving us free to “condemn the founder’s violence.” This is caviling. Machiavelli doesn’t condemn the founder’s violence and would be dismissive of our niceties. He does not afford absolute value to individual moral goodness; it is always trumped by the long-term well-being of the community.

Lee prefers the Discourses to The Prince, in part because they focus on republics rather than principalities, and in part because they were written with a particular group in mind: the circle of intellectual, mostly republican friends around Cosimo Rucellai who were instrumental in helping Machiavelli come to terms with his fall from power. But though Machiavelli insists that a people flourishes best when it enjoys freedom, he is not an ideologue. One chapter of the Discourses is entitled “If some unexpected event should free a people used to living under a prince it is unlikely that they will be able to preserve this freedom.” Because they are not used to freedom; it is not part of their political tradition. Hence, they will soon end up “under a yoke that is often heavier than the one they had shaken off.”

Perhaps the text that best captures the complexity of both Machiavelli’s position and manner of exposition is his Life of Castruccio Castracani. Lee offers an engaging account of Machiavelli’s years in the political wilderness, his surprisingly sentimental love affairs, his friendships with the historian and statesman Francesco Guicciardini and the diplomat Francesco Vettori, his success as a writer of darkly comic plays in which foolish husbands and sighing lovers show the same passion for subterfuge that he had observed in international politics. Then in 1520, perhaps partly in response to the much-praised Art of War, the Medici at last began to bring Machiavelli back into favor. He was sent to Lucca to sort out a commercial dispute, and while the negotiations dragged on he wrote a brief life of Castruccio Castracani, the fourteenth-century condottiere and Duke of Lucca.

Lee is at a loss to understand why Machiavelli alters so many details of Castracani’s life, especially since his readers would have been aware of the facts:

Whereas Castruccio had, in reality, been born into one of Lucca’s most illustrious noble families, Niccolò concocted a cock-and-bull story about him being abandoned by his mother while still an infant and found under some vines in the garden of a priest called Antonio Castracani.

Lee supposes that Machiavelli is crafting “a version of Castruccio’s life which…could…inspire his readers to emulate the ideals of military and political leadership he had expounded in…the Arte della guerra and Il principe.”

It seems more likely that Machiavelli is exploiting his readers’ knowledge of the facts to give sense to the fable he is creating. All the changes he makes point in the same direction. His Castruccio is illegitimate, hence outside society, excluded. He is brought up by a priest but proves immune to the religious nurturing imposed on him. His qualities, that is, are innate, severed from any tradition. A local condottiere and aristocrat takes him under his wing. Castracani wins prestige, but also envy and enemies. In his situation the only way to survive is to defeat them, exploiting factional conflict to become Duke of Lucca. Then he has to see off his helpers, who are now jealous. From then on he simply reacts, brilliantly, efficiently, ruthlessly, to more and more extreme circumstances. He crushes enemies in the surrounding towns, but in doing so creates a highly unstable situation that only his personal brilliance can keep under control. Finally, after a magnificent victory over the Florentines, he succumbs to a chill and dies.

So much for governing Fortune. On his deathbed Castracani addresses the son of the condottiere who initially helped him. Having never married, never become part of society, he can offer no secure succession. The state he decides to leave to this young man is large, he says, but “weak and unstable. You own the city of Lucca, which will never be content to live under your reign.” The people of Pisa “will always scorn the rule of a lord from Lucca.” Likewise the people of Pistoia. The Florentines are hostile and offended. To suppose that “in Niccolò’s eyes, Castruccio was the perfect prince” is to miss the point. Lee acknowledges that Machiavelli is perhaps warning the Medici not to pursue “further territorial expansion.” More deeply, he is inviting them to consider their relation to the city they are governing and its republican traditions. It is pointless to have outstanding personal qualities if everything one builds is quickly destroyed because it is not part of an ongoing collective project.

Machiavelli followed up his life of Castracani with a detailed account of Lucca’s complex constitution, focusing on its failure, as he saw it, to balance the competing claims of common people and grandi (the rich and noble). Months later he was invited to draw up proposals for a new constitution in Florence. Someone had been paying attention.

This brings us to the essence of Machiavelli’s vision and vocation. In the Discourses he had argued that Rome achieved success not despite internal conflict but by harnessing such conflict, which is natural and inevitable, in institutions that allowed each area of society to control and complement the others. The idea was controversial. Nevertheless, Machiavelli set about devising a constitution for Florence that would appease all classes, balancing Medici power with republican aspirations. It was rejected.

This concern with inclusion, colored no doubt by Machiavelli’s having grown up in a family that felt excluded, is intimately connected to his insistence that the polis constitutes the supreme value. Religion should be at the service of the community, a valuable resource to be nurtured and respected regardless of whether it was true. And Machiavelli did respect it, to the point of writing an Exhortation to Penitence for the confraternity to which he belonged. He liked to be part of things. Equally, language, at least the vernacular, was the expression of a specific community, not something that an individual could manipulate, as Dante had claimed to have manipulated Florentine to make it the language of all Italy. Dante, Machiavelli felt, was speaking from the bitterness of exile and exclusion. Lee feels this attitude is “parochial.” But the implication was that a language of all Italy would come naturally if ever Italy were united, something, as Machiavelli explained in the Discourses, that the church made extremely unlikely, since the pope occupied the territories at its center and prevented any leader from conquering the entire peninsula while being unable to conquer it himself.

“I have always been most loyal,” he wrote to Vettori in 1513 in relation to his willingness to serve the Medici regime. “My poverty stands witness to my loyalty and goodness.” And he means loyalty to Florence. He was a civil servant, serving regardless of regime; the Medici were hardly worse than many others. They were part of Florence’s tradition. When Machiavelli traveled it was with Florence in mind; when he considered Rome’s past it was to apply it to the Florentine present. In 1521 he was offered a lucrative job as chancellor of the city of Dubrovnik. He refused. He wasn’t a mercenary. What mattered were family, friends, particularly circles of friends, lovers, the polis. Lee’s magnificently detailed biography shows throughout what a convivial fellow he was, how important to him were such qualities as solidarity, cheerfulness, willingness to advise, and practical joking, and how easily he could move from gambling in a village inn to debating in the government palace.

“When a storm is threatening” and our institutions are in crisis, Boucheron concludes his book, Machiavelli can “teach us to think in heavy weather.” He names Brexit and Trump as examples of our present crisis. Machiavelli no doubt would have been fascinated by Trump, but even more so by the circumstances and society that allowed him to be successful. And whatever he might have thought of Brexit or the American president, the slogan “Florence First” would have made sense to him.