‘Surely it is a great wonder’, Niccolò Machiavelli wrote to his friend Francesco Vettori in 1514, ‘to contemplate how blind human beings are in matters that involve their own sins.’ But it isn’t really very strange. Few of us have the strength to face our flaws. Machiavelli knew that he was the real wonder: a connoisseur of depravity; an atheist who passionately hated the clergy, who thought the institution of the Catholic Church should be dismantled and replaced with the bloodstained altars of pagan Rome. He had lots of sex – from the abject to the sublime and everything in between – with beautiful women and young men throughout his marriage. He hung around with people he called ‘lice’: gamblers and reprobates in the taverns of the Tuscan countryside. He pranked his friends, cheated people out of money, played elaborately cruel practical jokes on holy men. Unlike the ordinary, unselfconscious sinners he despised, he made a study of human nature in its worse aspects, casting a practised eye over the hellscape of 16th-century Italy, with its warrior popes and courtesans and condottieri. He turned that realism into the foundation for the most original political theory of his time – possibly of all time.
And yet Machiavelli never held any proper political power. He was born in a shabby palazzo in Florence on 3 May 1469. Years later, in the midst of a political crisis, he reflected on his childhood, finding consolation in the memory of early hardship:
As for turning my face towards Fortuna, I should like to get this pleasure from these troubles of mine, that I have borne them so straightforwardly that I am proud of myself for it and consider myself more of a man than I believed I was … I shall get on as I did when I came here: I was born in poverty and at an early age learned how to scrimp rather than to thrive.
The Machiavelli were a prominent family, but their famous name hid a history of adversity. A cousin had rebelled against the Medici and tarnished the family’s reputation; worse, Machiavelli’s father, Bernardo, had inherited a staggering amount of debt. Bernardo preferred a quiet, scholarly life immersed in Latin books, and refused to find a profession, instead living off the profits from the family farm in the Tuscan countryside. One of Machiavelli’s earliest poems lampoons his father’s miserliness. He took pleasure in his ability to transcend these inauspicious beginnings, turning his face to fortune.
Machiavelli doesn’t come into the view of posterity until his thirties – ‘like Christ’, the scholar Sergio Bertelli once wrote, but that’s where the likeness ends. In 1498, he was confirmed to his first public position as a chancellor, working as a secretary, diplomat and negotiator for the Florentine government. The Medici had been forced to flee Florence in 1494, when the fragile peace that had held across the Italian peninsula since 1454 began to crumble. For four strange and chaotic years, the city was under the sway of the theatrical reforming preacher Girolamo Savonarola: Machiavelli was brought into government a few weeks after Savonarola had been burned as a heretic in the main piazza. With the Medici and Savonarola gone, Piero Soderini was elected gonfaloniere for life in 1502, ushering in what Florentines hoped would be a period of republican liberty, stability and peace. Machiavelli worked closely with Soderini in the chancery of the Florentine republic for 14 years. His diplomatic career ran parallel with the Italian Wars, a series of battles (accompanied by ever changing political allegiances) that ravaged much of Italy between 1494 and 1559.
In 1501 Machiavelli married Marietta Corsini. She and their children flit in and out of his personal correspondence: in 1503, after the birth of their son, Marietta reported that ‘the baby is well, he looks like you: he is white as snow, but his head looks like black velvet, and he is hairy like you. Since he looks like you, he seems beautiful to me.’ But these glimpses of domesticity mingle with wilder stories of courtesans and adventures in male brothels. La Riccia, named for her curly hair, was a favourite of Machiavelli’s, and so were the boys of Donato del Corno’s shop. Many years later, his friend Vettori observed that ‘you never would have married if you had really known yourself; my father, if he had known my ways and character, would never have tied me down to a wife.’
But being married wasn’t really a practical impediment. Away on a diplomatic assignment in 1509, Machiavelli wrote a letter describing a strange sexual encounter. He had stepped into his laundrywoman’s barely lit house to inspect a shirt, but instead, he ‘fucked her one’ (it’s better in Italian: la fotte’ un colpo):
Although I found her thighs flabby and her cunt damp and her breath a bit rancid, I was still so desperately horny that I went at it. And once I had done it, feeling like taking a look at the merchandise, I took a burning piece of wood from the fire that was there, and lit a lamp that was hanging above it; but no sooner was the lamp lit than it almost fell from my hands. Ye gods! I nearly dropped dead on the spot, that woman was so ugly.
Machiavelli itemised her ugliness: her nose ‘slit open and full of snot’; her mouth ‘twisted to one side’, pooling with drool because she had no teeth; her ‘long, pointed chin that twisted upwards a bit, from which hung a flap of skin that dangled.’ He was so ‘assaulted’ by the stench of her breath that he vomited all over her. In the retelling, he arranges his own abjection on the page, coolly observing the consequences of physical want.
Back in Florence in 1512, a series of missteps undid gonfaloniere Soderini, and the ground was prepared for the return of the Medici. Giuliano de’ Medici entered the city, storming the Palazzo della Signoria. Soderini fled, and Machiavelli – tainted by association – was well and truly battered by the forces of fortune. Dismissed from government, he was soon implicated in an anti-Medici conspiracy. He was imprisoned and tortured with the strappado: his hands were tied behind his back with a rope and he was dropped six times from a height, probably dislocating his shoulders. Finally released, he retired broken and depressed to the family farm, an outcast from politics.
Though his visits to La Riccia and Donato’s shop were welcome distractions, Machiavelli was unable to turn his mind from politics. ‘I could not help but fill your head with castles in the air,’ he wrote to Vettori in 1513, ‘because since Fortune has seen to it that I do not know how to talk about either the silk or wool trade, profits or losses, I have to talk about politics.’ He spent the days chewing the fat with woodcutters on the farm and playing cricca in the tavern. But in the evening, he told Vettori,
I return home and enter my study; on the threshold I take off my workday clothes, covered with mud and dirt, and put on the garments of court and palace. Fitted out appropriately, I step inside the venerable court of the ancients, where, solicitously received by them, I nourish myself on that food that alone is mine and for which I was born; where I am unashamed to converse with them … and they, out of their human kindness, answer me. And for four hours at a time I feel no boredom, I forget all my troubles, I do not dread poverty, and I am not terrified by death. I absorb myself into them completely. And because Dante says that no one understands anything unless he retains [it], I have jotted down what I have profited from in their conversation and composed a short study, De principatibus.
Even now, at the distance of five centuries, Machiavelli’s words in The Prince still register physically: you brace for impact. Human nature is fundamentally rotten. Hope and virtue are for the weak, for life’s losers. Raw power must be dressed up in the trappings of piety, but never constrained by it. The ultimate aim of political life is glory and not, as philosophers had argued for centuries, the public good. Machiavelli dismantled traditional morality, but refused to offer a new ethic in its place. Instead he made simple, practical recommendations. Shed illusion. See people as they really are. Adapt nimbly to what you discover. He paid close attention to those princes and popes whose characters became his raw material. He fixated, for example, on Cesare Borgia, the illegitimate son of Pope Alexander VI, who had carved out a state of his own in northern Italy through considerable military intelligence and diplomatic cunning – and, of course, with the help of his father. ‘This lord is very splendid and magnificent,’ Machiavelli observed when he met Cesare for the first time in Urbino in 1502:
In arms, his courage is such that he can accomplish the greatest undertakings with ease. [When he means to acquire] glory and enlarge his domains, he neither rests, nor knows either fatigue or danger. No sooner is his arrival in a place known than he is gone … and these things, together with his perpetual good luck, make him a fearful and victorious [adversary].
Machiavelli admired Cesare’s audacity, and his instinct for cruelty. ‘There was such fierceness and virtù in the duke, and [he knew] so well … how men must be either won over to one’s side or else eliminated.’ Cesare exemplified Machiavelli’s concept of virtù: not the bloodless kind familiar from conventional philosophy, but a daring manliness exercised on the transnational stage of politics and diplomacy. This was virtù with an emphasis on the vir. But women could attain virtù, too. Machiavelli’s imagination was also captured by Caterina Sforza, the fierce ruler of Imola and Forlì, whom he met in 1499. (She was also a famous beauty, and Machiavelli’s friend Biagio Buonaccorsi begged him to send a sketch of her back to Florence.) Machiavelli described how Caterina had faced down a group of violent conspirators who had taken her children hostage and threatened to assassinate them, peppering the men with wild threats, and then lifting her skirts: she ‘uncovered to them her genital members, saying that she still had means for producing more children.’
Virtù was essential to defeating the capricious, tempestuous force of Fortuna. In The Prince, Machiavelli identifies Fortuna as a woman: ‘it is necessary,’ he writes, ‘in order to keep her under, to beat and maul her.’ His most important ideas – dependence and autonomy, Fortuna and virtù – were constructed on the foundation of sexual difference. If Caterina was an example of manly autonomy, Cesare Borgia’s ultimate downfall provided an example of the dangers of effeminate dependency. When his father died (many believed he had been poisoned), Cesare was left bereft of support. Machiavelli saw how the pope’s death unravelled the once fearsome duke, who was ‘carried away by that bold self-confidence of his’, ranting and raving with ‘words full of poison and anger’. His state was lost. Machiavelli reflected in The Prince that Cesare had ‘acquired his state with the Fortuna of his father and lost it with the same, though he had taken every measure and done all that ought to be done by a wise and able man to firmly fix his roots in the states which the arms and fortunes of others had bestowed on him’.
The Prince was dedicated to the dissolute Lorenzo de’ Medici and was intended to be Machiavelli’s ticket back to political life. But his timing was a little off. When he turned up at Lorenzo’s palazzo to present him with the book, someone else had just offered a pair of dogs. Lorenzo was so taken with his new pets that he didn’t pay any attention to the book. His ambitions crushed, Machiavelli retreated to the Rucellai gardens, where the humanists and philosophers, poets and playwrights of Florence gathered to converse and to stage their work. It was here in 1518 that Machiavelli dramatised the key themes of The Prince in his sexual comedy La Mandragola. The play follows the bold youth Callimaco, who dupes the beautiful – and married – Lucrezia into sleeping with him. Callimaco is a sensation in bed, and Lucrezia’s wafer-thin virtue crumbles. Callimaco impregnates her and so asserts his mastery over her aged husband, representative of an older generation made redundant by the audacity of the young. This was the triumph of manly virtù over virtue, the hyper-masculine over the weak; it was The Prince translated into the obscene language of Florence’s streets, a playbook showing how a ruler might found a new dynastic state through sheer moxie. La Mandragola played to sold-out audiences during carnival season and made Machiavelli famous. (It also allowed him to spend lots of time with his current obsession, the strawberry blonde Barbera Raffacani Salutati, who sang the madrigals between acts.)
In the following years, exiled from politics but immersed in the classical learning of the Rucellai crowd, Machiavelli wrote prolifically and with a sharpened sense of history. In the Discourses on Livy, he turned from considering the princedom to the republic and, through a close study of antiquity, investigated the role of civic discord in the preservation of liberty, arguing that social conflict was generative, not destructive; disorder should be cultivated, not resolved. The Art of War examined the value of a citizen militia and the role of the army as the foundation of a state’s liberty; and The Life of Castruccio Castracani of Lucca used biography to exemplify the importance of courage and ruthlessness. He began his Florentine Histories, a humanist history of his city modelled on Roman examples but woven through with political diagnoses first developed in his earlier writings (one contemporary reader thought his history was ‘more wise than true’). But he also honed his skills as a writer of poetry and drama: he wrote another comedy, Clizia, as well as satirical poetry and fine love sonnets, even a treatise in which he resurrected poor Dante’s ghost to spar with him over the Florentine vernacular.
When Lorenzo de’ Medici died of syphilis in 1519, aged 26, Cardinal Giulio de’ Medici took control of Florence’s government and Machiavelli had a chance to return to political life. In 1525, he brought a copy of the Florentine Histories to Giulio, now Pope Clement VII, in Rome. Its success finally brought him back into the Medici fold. But in 1527, in the chaos of the Italian Wars and the Sack of Rome, the Medici were driven out of Florence for a second time, and a second republic established. Machiavelli, who had the misfortune to be on the wrong side of every major Florentine political upheaval, died on 21 June 1527, entertained by the possibility of meeting Seneca and Plato, both pagans, in hell. ‘The worst that can happen to you is that you’ll die and go to hell,’ he wrote in La Mandragola. ‘But how many others have died! And in hell how many worthy men there are!’
Machiavelli’s contemporaries knew him as a scholar and historian, poet and dramatist. His reputation as the ‘murdrous Machiavel’ developed only after his death. The Prince was printed in 1532. A few years later, Reginald Pole would claim that the treatise was written ‘by Satan’s hand’. By 1559, Machiavelli’s name had been placed on the papal Index of Prohibited Books; in the same year, Jesuits in Ingolstadt burned him in effigy. But even his most ferocious critics ended up absorbing some of his ideas: Machiavel in Marlowe’s Jew of Malta sneers, ‘Admired I am of those that hate me most.’ Readers have always found what they wanted to in Machiavelli’s writing: the tyrant hungering for glory in The Prince, or the liberty-loving, ardent republican of the Discourses. During the Risorgimento, Machiavelli’s defence of republicanism in the Discourses foreshadowed the reunification of Italy; but his place on the Index of Prohibited Books was reconfirmed in 1897. Marx called the Florentine Histories a masterpiece; both he and Gramsci thought Machiavelli’s arguments for an armed citizen militia had inherently revolutionary potential. At the other end of the spectrum, two modern Italian prime ministers have written critical introductions to The Prince: Benito Mussolini, who admired Machiavelli’s articulation of the role of force in political life, and Silvio Berlusconi. I like Bertrand Russell’s assessment: ‘It is the custom to be shocked by him, and he certainly is sometimes shocking. But many other men would be equally so if they were equally free from humbug.’
Centuries of wildly differing interpretations of Machiavelli – tyrant or republican, revolutionary or fascist – fractured his thought from his life. His early biographers, Roberto Ridolfi most wonderfully, as well as feminist political theorists like Hanna Fenichel Pitkin, put the two back together again. (This revisionism hasn’t quite entered the popular imagination: trolls in the more nihilistic corners of the internet still debate whether Machiavelli was, in fact, an incel.) Today, Machiavelli’s ruthlessness and cynicism are mostly embraced by those at the contemptible end of the political spectrum: members of the Trump administration have adopted him as a patron saint; in the UK, we have Dominic Cummings, ‘the Machiavel in Downing Street’. But the Succession fans and trolls who revere Machiavellian shrewdness mistake his cynicism for insensitivity to the world, when in fact it reflected precisely the opposite. His cynicism developed from an almost unbearable clarity of insight (it is true that, more often than not, he was disgusted with what he saw). He obviously wasn’t a feminist – Fortuna, remember, was a woman to be mauled – but his ruthless self-inquiry is bracing to read at a time when the right has claimed a monopoly on political realism and popular feminism confuses the cheap pang of emotional recognition for thought.
It also ups the ante for his biographers: how to tell his life in a way that meets Machiavelli’s standards of stylish economy and ruthless realism? Alexander Lee attempts to surmount the challenge by piling up detail: his biography is nearly eight hundred pages long. I am not, on principle, opposed to long books, but Machiavelli provides the strange and particular in spades, and yet these elements are difficult to spot in Lee’s telling. Exhaustiveness is even deadlier when paired with cliché: in Lee’s book, servants often seem to be ‘chattering’ in the background in order to provide a bit of premodern colour; there is a great deal of weather and travel. To commune with the past, we require history writing that leaves space for the imagination. Otherwise, the dead remain indistinct. And the indistinct is what Machiavelli could not abide.
I like to imagine that Machiavelli had future biographers and critics in mind when he wrote to Vettori in 1515 that
Anyone who might see our letters … and see their variety, would be greatly astonished, because at first it would seem that we were serious men completely directed toward weighty matters and that no thought could cascade through our heads that did not have within it probity and magnitude. But later, upon turning the page, it would seem to the reader that we – still the very same selves – were petty, fickle, lascivious, and were directed towards chimerical matters.
He knew that the variety of his own writing – veering between the personal and the political, the sexual and the solemn – was astonishing, even disorienting. Rebuffing any future readers and commentators who might be foolish enough to try to pin him down, he assured Vettori: ‘if this behaviour seems contemptible, to me it seems laudable: because we are imitating nature, which is changeable; whoever imitates nature cannot be censured.’ Keep up, he urges us, as we peer over Vettori’s shoulder: ‘Turn the page, and spit.’
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