Few texts loom so large over concepts of leadership as Niccolò Machiavelli’s The Prince. Though characterised by its author as nothing more than an opusculo (a ‘little book’), it established a completely new way of thinking about power; and – as the adjective ‘Machiavellian’ testifies – continues to dominate our political imagination 500 years after its completion.

At its heart is a deceptively simple question: how can a prince who has gained a state with the help of fortune and another’s arms maintain his power? Machiavelli was not the first person to tackle this. Since the beginning of recorded history, learned men had been advising princes about the qualities they needed to cultivate; and these ad hoc works later evolved into a distinct literary genre, the so-called specula principum (‘mirrors of princes’). This had acquired particular significance during the Renaissance. From the fourteenth century onwards, a growing number of treatises began to be produced, the most striking examples of which were Bartolomeo Platina’s De vero principe (c. 1478) and Francesco Patrizi’s De regno et regis institutione (c. 1481–4). But where Machiavelli differed was in his approach. Whereas earlier Renaissance writers had generally argued that a prince could safeguard his rule by cultivating Christian virtue, Machiavelli rejected such an idea as dangerously – even wantonly – unrealistic. The problem, as he saw it, was Fortune. Just like a coquettish girl, she gives or withholds her favour without regard for human merit. If you stuck blindly to a particular moral code, or were too weak-willed to stand up to her, she would invariably treat you badly. Only a circumspect man, who could ‘beat and coerce’ her would receive her favour, Machiavelli argued. What a ruler needed, therefore, was not virtue but virtù – the quality of being a man. He needed to be daring and courageous; he needed to forsake the base pursuit of wealth; and – most importantly of all – he needed to govern in such a way that he would earn glory and honour. In practice, this meant relying on his own soldiers rather than treacherous mercenaries; being parsimonious rather than generous; cruel rather than kind; and dishonest rather than honest. Most of all, it meant avoiding hatred at all costs.

It is a bold and original argument, so much so that it still retains its ability to shock. Yet, nevertheless, The Prince presents something of a puzzle. Precisely because Machiavelli’s book is so surprising, so different from most previous political writings, it is sometimes difficult to know how it should be interpreted – even in the context of his own oeuvre. Many of his other works – such as the Discorsi sopra la prima deca di Tito Livio and the Istorie Fiorentine – appear oriented more towards republicanism than princely rule, making The Prince even more of an enigma. Since the text first appeared in 1513, it has evoked strong, but contrasting opinions. Some early readers saw it as a handbook for tyrants. In his Discours sur les moyens de bien gouverner (1576), for example, Innocent Gentillet (1532/3–88) claimed that The Prince proposed ‘a tyrannical, rather than political science’; while Cardinal Reginald Pole (1500–58) painted Machiavelli himself as ‘an amoral teacher of force, fraud, cunning, and deception’. It was also this view which later influenced Richard III’s famous monologue in Shakespeare’s play. Others thought that The Prince was merely a satire, and that Machiavelli was really a critic of tyranny. It was for this reason that the French historian Abraham-Nicolas Amelot de la Houssaye cast Machiavelli as a latter-day Tacitus, and that Maximilien de Robespierre later claimed him as the architect of the French Revolution. Others still believed that Machiavelli was merely describing the world of politics, rather than recommending a particular course of action. In The Advancement of Learning (1605), Sir Francis Bacon praised Machiavelli for writing ‘what men do and not what they ought to do’ – and The Prince as a work of empirical science avant la lettre. And a final group felt that Machiavelli was really just proposing a technique of politics, which could be used either badly or well.

Yet if we want to understand the ‘meaning’ of The Prince, we should start with Machiavelli himself. Regardless of what one thinks of Machiavelli’s hopes for posterity, it is impossible to deny that The Prince was written in a specific context, for a specific readership, with a specific aim in mind. As such, it is only by taking account of the political circumstances in which he wrote his treatise, his intellectual background, his private motivations and his hopes and fears that we hope to establish what – if anything – he was trying to ‘do’ with The Prince, how it related to his other works and how he wanted it to be read.

Until a few months before writing The Prince, Machiavelli’s life had been framed by republican – rather than princely – government. When he was born, in 1469, Florence had been dominated by the Medici family, who exercised de facto authority through a network of clients and allies. In 1494, however, the French King Charles VIII marched into Italy, intent on conquering the Kingdom of Naples. In the ensuing chaos, the Medici were driven out, and a ‘popular’ republic was established. At first, this was overshadowed by the Dominican friar Girolamo Savonarola, whose attempts to turn the city into a ‘new Jerusalem’ nearly brought it to perdition; but after his execution in 1498, broad-based governments necessarily became the norm. The Great Council – with over 3,000 members – had the final say on legislation; the Council of Eighty appointed ambassadors and military commanders; and the Signoria – headed, in time, by the gonfaloniere a vita (‘standard-bearer for life’), Piero Soderini – acted as the executive.

From the outset, the Florentine Republic was perilously unstable. For all its ‘popular’ pretensions, civil society was bitterly divided. While the wealthiest families, known as the ottimati, wanted a greater share of public office, the rest of the political class, known as the popolo, were determined to restrict their influence as much as possible. Subject towns were in rebellion. Pisa – Florence’s main port – had been lost. On all sides, Florence was surrounded by enemies. Cesare Borgia was threatening from the Romagna; Venice was conspiring with the Pisans; and from abroad, the Medici were constantly looking for a way to return. Worst of all, Florence had few means of defending itself. Its only ally was France; and – in the absence of a standing army – it was reliant on mercenaries, who were not only exorbitantly costly but also as likely to flee as they were to fight.

Machiavelli was thrust into the heart of this danger while he was still a young man. On 19 June 1499, he was elected second chancellor of the Florentine Republic. This was a bureaucratic post, much like that of a civil servant today, and came with responsibility for handling Florence’s relations with its subject towns. The following month, he was also appointed secretary of the Dieci di balìa, a committee tasked with overseeing military operations during times of war; a few years later, he was given the task of re-establishing a citizen militia, as well. That wasn’t all. Throughout his public career, he was often sent on diplomatic missions abroad – and was widely admired for the perspicacity of his despatches.

During this period, Machiavelli penned several political works – generally in the form of reports, letters and poems. Unsurprisingly, most are devoted to exploring how the Florentine Republic could defend itself against its enemies, recover its territories and organise its military forces. Yet we can already see him experimenting with many of the ideas that he would later develop in The Prince. He was fascinated by Fortune. In the Ghiribizzi, written after watching Pope Julius II take Perugia ‘almost unarmed’ in 1506, he marvelled at her fickleness and argued that a good leader should know how to adapt himself to her wiles. He disparaged ‘foreign and hired arms’, while praising citizen soldiers for their loyalty. He was also convinced that cruelty could be a legitimate tool of government. The seeds of this were most likely sown in 1499, when the Florentine government voted to execute the mercenary commander Paolo Vitelli, on suspicion of treachery, but without any firm proof, simply pour encourager les autres. But it appears most vividly in Del modo di trattare i popoli della Valdichiana ribellati (‘On the manner of dealing with the rebellious people of the Valdichiana’). Written in the summer of 1503, this argues that, if Florence wanted to stop Arezzo from rebelling again, it needed to imitate Cesare Borgia, and be severe rather than kind. Even at this early stage, however, Machiavelli recognised that cruelty had its limits. In the Ghiribizzi, he noted that, if the rebel cities of the Valdichiana were treated too harshly, their hatred of the Florentines would soon outweigh their fear – with potentially disastrous results.

In 1512, however, everything fell apart. A papal-Spanish army advanced into Tuscany, sacked the nearby city of Prato and forced Piero Soderini from office – leaving the way clear for the Medici to return. At first, they had to tread carefully. Their position was far from secure. The popolo was hostile; their supporters were divided; and they were reliant on a foreign army, which aroused more hatred with every passing day. Aside from doing away with a few offices, they therefore avoided any wholesale reforms and showed themselves willing to work with former members of Soderini’s government. This gave Machiavelli cause for hope. He appears to have reasoned that, if he could show his worth to the Medici as a counsellor, they might allow him to keep his job. Indeed, given that he had known Giuliano de’ Medici in his youth, he may have been reasonably confident. He therefore penned a letter to the current head of the family, Cardinal Giovanni de’ Medici, outlining some of the ways they could avoid arousing further resentment. But, by then, the Medici’s policy had already begun to harden. Fearing that their caution would encourage rebellion, they began dismantling the old system of government. The Great Council was abolished, along with the militia; and the Council chamber itself was turned into a barracks. Machiavelli was alarmed. Realising that he was now in danger, he dashed off another letter in a desperate bid to prove his use. Known as the Ai Palleschi (‘To the Mediceans’), this clumsily written piece urged the Medici to purge the government of Soderini’s supporters, destroy what was left of the republic and govern Florence with an iron fist. It was an extraordinary position to argue, even if it did evoke some of his earlier ideas about severity. But it was all for nothing. He was too tainted by his association with the old republic to have a place in the Medici’s new order. On 7 November 1512, he was sacked from all his posts.

Machiavelli was understandably resentful. Over the Christmas period, he began criticising the Medici openly. Such dangerous talk unsettled his friends. Even those who hated the Medici began keeping their distance. Machiavelli couldn’t see anything wrong in speaking his mind, though. He was convinced that the Medici were still too weak to clamp down on dissent. In this, he was catastrophically wrong. In mid-February 1513, a plot to assassinate Giuliano de’ Medici was uncovered. It was an amateurish affair. As Giuliano noted, the plotters knew more about books than weapons. But the Medici could not afford to take any risks. The ringleaders were executed – and warrants were issued for the arrest of anyone who was even tangentially involved. Including Machiavelli. He was thrown in jail and tortured using a technique known as strappado. His hands were first tied behind his back. He was then lifted into the air by his wrists until his shoulders popped out of their sockets and he screamed in pain.

A few weeks later, Machiavelli was released in an amnesty granted to mark Giovanni de’ Medici’s election as Pope Leo X. After a brief period spent moping in Florence, he retreated, a broken man, to his farmhouse in Sant’ Andrea in Percussina, a few kilometres to the south. There, he became a gaglioffo – a good-for-nothing. As he told his friend Francesco Vettori, he spent most mornings in the woods, chatting with neighbours, or reading a book of poems by the stream. At lunchtime, he returned home to eat with his family, before heading to the tavern. The rest of his day was spent ‘slumming around’ with the locals, drinking and playing cards or backgammon. When in their cups, they’d often argue – generally over nothing more than a penny – and every so often, a fight would break out. It suited Machiavelli, though. It helped him to ‘get the mould out of [his] brain and let out the malice of [his] fate’.

But he had not entirely given up hope of one day returning to his former life. Every evening, he would go into his study, take off his rough, country clothes and ‘put on the garments of court and palace’. Then, seated at his desk, he began to write The Prince.

As he explained in the preface, he intended to offer the Medici ‘some token of my devotion’, in the hope that it might prove his value as a counsellor and win their favour. So as not to appear too obvious, it was couched in deliberately abstract terms. He began by discussing the different varieties of principalities, before gradually working his way around to that which most closely resembled the Medici’s own position.

Dedicated first to Giuliano, then, after his death, to Giuliano’s nephew Lorenzo, it systematically – if discreetly – addressed each of the challenges which threatened the stability of the Medici regime: social divisions, dependence on foreign or hired soldiers, lingering unrest and persistent financial problems. Since many of these had been familiar to previous Florentine governments, it was only natural for Machiavelli to draw not only on his reading of classical history but also his own experience – including many of the ideas which he had begun to develop while second chancellor. And, in the circumstances, his advice was perfectly reasonable. However shocking it seemed to some of his early readers, it was certainly intended to be taken seriously. Unless we assume that he emphasised his experience, only to mock everything he had ever learned, or dismiss the disappointment he reportedly felt when Lorenzo de’ Medici showed no interest in his book, there are no grounds for assuming that it was satirical. Nor, indeed, did he believe he was defending tyranny – least of all in the Aristotelian sense of a perverted form of monarchy. He never sought to defend arbitrary rule. He was careful to stress, as he had before, that cruelty must be tempered by circumstance; that social classes should be balanced; and that dishonesty should be used only according to necessity. It is just that his originality – his desire to show off the ‘novelty’ of his thought – sometimes occludes the practical, almost sympathetic, purpose of his work.

Books, however, are never quite what their authors intended them to be – any more than authors are just the sum of their books. Whatever Machiavelli may have wanted to do with The Prince, his readers are not constrained to respect his wishes – and never have been. There is no reason why The Prince cannot be read differently. Indeed, like all texts, it is ‘open’. Taken on its own terms – away from the context of Machiavelli’s own life – it can sustain any number of readings. Like Shakespeare’s Richard III, it can ‘add colours to the chameleon, / Change shapes with Proteus for advantages’. Such is the brilliance of Machiavelli’s writing, such the novelty of his argument, that we can find in its pages whatever model of leadership we want. And in the end, perhaps that is what makes it so compellingly, dangerously Machiavellian.

If you enjoyed this essay by Alexander, listen in through the link below to him in conversation with the EI team: