Machiavelli: Political, Historical, and Literary Writings

Introduction

Machiavelli in the Florentine Renaissance

MARK JURDJEVIC

I love my native city more than my soul.

—Machiavelli to Francesco Vettori, 16 April 1527

Machiavelli stands out in the Western political and philosophical canon for the degree to which he rooted his arguments, hopes, and quarrels in the vocabulary of place. Like all great thinkers, of course, he also explored universal dimensions of the human condition. The major questions and themes of his thought transcend the particulars of his context and explain his enduring relevance for us today and for his readers in the centuries between our time and his. But over the course of his life the medium for his reflections was increasingly his native city of Florence. The writers who preceded him, whether luminaries of antiquity such as Plato and Aristotle, or medieval thinkers such as Thomas Aquinas or William of Ockham, tended to discuss politics in terms of its ideal ends and in ways meant to transcend local particularities. For Machiavelli, however, Florence’s traditions, history, and culture—its perversities and failures most of all—were the idiom in which he wrote, spoke, and thought. Machiavelli’s search for the universal truths of political life was inextricable from his search for particular answers to the interrelated crises afflicting his life, Florence, and Italy.

Put slightly differently, Machiavelli’s imagination—his outlook, priorities, and desires—were distinctly urban. He is the Western canon’s most thorough analyst of urban life and politics: its rewards and satisfactions as well as its frustrations, instabilities, and dangers. We see this at a personal level in his frank frustration every time he was compelled to spend time in the countryside. For example, when confined for an extended period to his farmhouse in the village of Sant’Andrea in Percussina, roughly ten miles south of Florence, he bitterly and precisely quantified his absence from Florence: since my latest disasters, I have not spent a total of twenty days in Florence.¹ In that same letter, he contrasts his intellectually emancipating reading of classical texts with the confining trivialities of his rural existence—slumming around with the local innkeeper, miller, and other workers, cooped up among these lice. On other occasions, he lamented the isolation of rural life with dry humor, such as his concluding farewell in a letter to his brother-in-law: I shall give your regards to the chickens.² But whatever the voice—despairing, detached, comic—the message never changed: time spent away from Florence was time wasted.

We see this aspect of Machiavelli’s psyche most bluntly and importantly in his formal writings. It is perhaps least evident in The Prince, though even there we see a preponderance of examples culled from the experience of city-states during Machiavelli’s day. Discourses on Livy derived universal conclusions about the potential benefits of conflict in political life through meditation on the historic urban battles for supremacy between the city’s plebeians and senators. The Mandrake reflected on the social benefits of deception through a sharp-eyed and satirical assessment of urban marriage culture. His constitutional proposals for the Medici family in the early 1520s adapted his republicanism to address the competing ambitions of Florence’s complex social divisions. And his last and most substantial work, the Florentine Histories, reconstructed more than two centuries of factional street battles in pursuit of larger questions about urban state building and the struggle between public and private expressions of power in a city of great families who cherished their tradition of republican freedom and yet all aspired to be bosses themselves.³

In one sense, Machiavelli’s urban outlook and priorities make him a relatively typical example of an Italian Renaissance intellectual. Most historians, humanists, chroniclers, notaries, chancellors, and secretaries—whether Dino Compagni and Giovanni Villani in the fourteenth century or Leonardo Bruni and Matteo Palmieri in the fifteenth—celebrated urban values. The Renaissance resurrected the mental world of the ancient city-states, celebrating their culture of citizenship and high estimation of the active life, wealth, public oratory, and political engagement.⁴ It was a fundamentally urban phenomenon that could have happened only in the uniquely urbanized Italian context. Owing to its strategic central Mediterranean location, Italy had long been the hub of many land and sea trade routes and prospered from major shipping ports on both sides of the peninsula, Pisa and Genoa on the west coast and the maritime giant of Venice on the east. As a result of the dominance of mercantile wealth, Italy was the most urbanized area in Europe in the Middle Ages and Renaissance. By the mid-fifteenth century, one in four Italians was an urban dweller, as opposed to one in twelve elsewhere on the continent.⁵ By the end of the century, seven of the ten largest European cities were Italian while smaller towns—Bologna, Perugia, Parma, Ferrara, Mantua, Padua, among many others—dotted the peninsula from Naples to Milan. Everywhere else in Europe, the martial values of rural feudal aristocracies provided the dominant tropes of political culture, but in Italy, where urban merchant elites held sway, political culture privileged civic values conducive to commerce.⁶ Little wonder, then, that Machiavelli’s political thought expressed itself in distinctly urban terms.

Yet Machiavelli was never an uncomplicated or straightforward product of his context. A major strain of his writing implicated the mercantile urban dimension of the Italian peninsula and Florence in particular in the tragic powerlessness of Italian states in his own day. He certainly recognized that Florence’s urban dynamism and proud status as one of Europe’s greatest banking powers was the product of its merchant culture. He also understood that to create the circumstances enabling Florence to become the economic powerhouse that it was in his day, the city’s merchants had been compelled in the thirteenth and fourteenth centuries to fight a long and bloody civil war for control of the city against its nobles, whose culture of lawlessness and violence conflicted with a commercial way of life. His Florentine Histories narrated in detail the long and vicious conflict that culminated in the destruction of the Florentine nobility. And yet at the same time he recognized that the triumph of merchants over nobles in Florence—and Italy by extension—was also the cause of Italy’s slavery in the present.⁷ Florence and almost every other Italian state, lacking a fighting class of their own, depended on hired mercenaries to fight their wars. When the great dynastic rivalry between Valois and Habsburg led to their invasion of Italy and protracted wars for peninsular dominance, Florence and the other Italian states found themselves militarily outmatched by monarchs who could still rely on the martial power of their fighting nobility. Thus, we see that Machiavelli’s constant contrast in his most famous texts, The Prince and the Discourses on Livy, between the worthlessness of mercenaries and the necessity of one’s own arms was an abstract expression of his conflicted ambivalence about Florentine commercial culture and Italy’s urban precocity in general.

This volume showcases Machiavelli’s specifically Florentine preoccupations, which are often overshadowed by his two great early works, The Prince and the Discourses on Livy. We intend in no way to dispute the importance or originality of those texts. Instead, we wish to portray them not as intellectual ends for Machiavelli in and of themselves, as they often appear in other editions, but rather as means to an end, as analytical and historical tools with which he addressed contemporary crises and through which he understood the significance of Florentine history and his own role in it. Accordingly, we have included relatively few selections from the first two works (in part also owing to their widespread availability online and in other editions) and prioritized instead his letters, literary works, and above all else, his Florentine Histories, texts that demonstrate—however despairing or satirical the tone—the truth of Machiavelli’s likely confession to his friend Francesco Vettori that I love my native city more than my soul.⁸

By privileging Machiavelli’s Florentine writings, we also intend to reveal Machiavelli as a man of action, someone whose writings were less the product of abstract thought experiments conducted in the isolation of a book-lined study, as he famously portrayed the circumstances of the composition of The Prince, and more the result of action—whether in vigorous back-and-forth debates with friends, pressing analyses of immediate political and diplomatic crises, or his ceaseless attempts to participate in Florentine politics directly rather than reflect on them from a distance. Via this interpretation of Machiavelli—as first and foremost a political actor and pragmatic analyst and student of Florentine politics and society—we wish to introduce anglophone readers to a reading of Machiavelli that has generally been more fully explored by Italian scholars such as Gennaro Sasso, Mario Martelli, and Andrea Guidi.⁹ We also intend this volume to illuminate the substance of the Florentine Renaissance as much as the particulars of Machiavelli’s life. A distinguished historian of Renaissance humanism once remarked that Machiavelli was the Renaissance’s most incisive critic of humanism, even while his corpus was fundamentally inconceivable without it.¹⁰ The same contradiction applies to Machiavelli’s relationship with the Renaissance in Florence: he was a product of the humanist culture of the chancery yet rejected its most cherished convictions; he grew up in a city whose power derived from trade yet faulted mercantile culture for Florence’s weakness; he served Florence’s republican government and the Medici, its existential antagonists; he was an active participant in Florence’s most accomplished literary and intellectual communities yet linked the efflorescence of letters to political corruption. To confront Machiavelli’s ambivalence about Florence is to confront the larger tensions and contradictions in the culture of Renaissance Florence.

Niccolò Machiavelli was born in 1469 to a moderately affluent middle-class family. The Machiavelli did not belong to the great aristocratic clans that dominated Florentine politics, but they were nevertheless formal, if lesser, members of the ruling group with a modest tradition of political office holding dating back to the late thirteenth century.¹¹ In the centuries preceding Niccolò, the family’s most illustrious ancestor was a contemporary of Dante, Buoninsegna di Agnolo, who served twelve times as a member of the Signoria, the republic’s highest executive council. Although no member of the family subsequently played as significant a role on the city’s most powerful council, they did play a consistent secondary role in the city’s politics for the rest of the fourteenth century.¹² The family’s tradition of political office holding, however, did not extend to Machiavelli’s father and the household in which Niccolò was raised.

In the years immediately preceding Machiavelli’s birth, the family suffered intense political trauma. From the late fourteenth century until 1434 the government of Florence was an aristocratic oligarchy, but from 1434 until the end of the century the Medici family controlled the political life of the city. The Medici, first Cosimo and then his son Piero and grandson Lorenzo, maintained the façade of the city’s traditional republican constitution but divested it of any de facto significance by manipulating the city’s electoral process and by marshalling a powerful patronage network whose lifeblood was the immense wealth of the family bank. Like many families, the Machiavelli initially adjusted to the new reality of a Medici-dominated Florence without incident (and likely without much difficulty, because the Machiavelli, like all middle-class Florentines, had already been excluded from exercising real power by the aristocratic regime that preceded the Medici). In 1458, however, Girolamo Machiavelli, Machiavelli’s father’s cousin, joined the ranks of a growing opposition movement intent on dismantling the Medici regime. For this, he and his brothers were severely persecuted. Girolamo was arrested, tortured, and exiled in 1459, one brother exiled a year earlier, and another brother imprisoned and executed in the same year. Girolamo was eventually recaptured and died in prison in 1460. The family’s sudden pariah status in Medici Florence led Machiavelli’s father, Bernardo, to avoid politics and public life altogether. He largely abandoned his legal career and instead lived off the rents from various family properties. He never sought to reverse the formal disqualification from holding office imposed on him in 1458.¹³

The circumstances of his youth thus taught Machiavelli two fundamental ways of relating to hierarchy and power. On the one hand, his family had a proud tradition of involvement in Florentine politics as respectable members of the popolo, the city’s affluent middle class. In a culture that measured families by the achievements of their ancestors, the Machiavelli family had good reason to take pride in its name and to expect a share in the distribution of the city’s power. Girolamo no doubt thought in these terms when he decided to join the popolo challenge to the Medici and to attempt to reverse the steady centralization of the city’s government around an increasingly smaller number of elite families. On the other hand, the ease with which the Medici regime destroyed Girolamo and his brothers for their political presumption sharply and darkly underscored the preponderance of power enjoyed by the ruling circle and the potentially lethal dangers of contesting—or even appearing to contest—their hegemony. Machiavelli grew up in a household profoundly affected by that destruction. His father was clearly acutely aware of the family’s political vulnerability and the perils of tacking a political course independent of the Medici and their inner circle. Pride and defiance, vulnerability and fear—these were the dominant themes in the life of the Machiavelli family during Niccolò’s youth.

Those contrasting themes powerfully informed Machiavelli’s view of himself, his ambivalent relationship to Florentine society, and virtually all his writings, public and private. He certainly shared his father’s keen awareness of the social and political gulf that separated the Machiavelli and the city’s powerful ruling houses. Unlike his father, however, Machiavelli never passively or peacefully accepted subordinate status, and, as with his rebellious relative Girolamo, pride and resentment often led him to lash out at his presumed social betters and the culture of entitlement that he clearly felt characterized noble families.

We see this in the very first surviving document in Machiavelli’s hand, a letter from 1 December 1497 to a cardinal seeking assistance in a property dispute between the Machiavelli and the Pazzi family, a wealthy Florentine clan as venerable as they were powerful: for if we, mere pygmies, are attacking giants, a much greater victory is in store for us than for them. . . . It is honorable to have competed, especially having a competitor at whose nod everything is done immediately.¹⁴ That letter—our first glimpse of Machiavelli, however brief—already displays a keen proclivity for conflict, sharp words, and disdain for noble entitlement. The next day, Niccolò drafted another family letter that proudly proclaimed the Machiavelli family’s nobility of virtue rather than blood, a favorite trope of Renaissance humanism: Whoever might wish to weigh our house with the house of the Pazzi on an accurate scale, if he determined the two to be equal in everything else, will determine ours far superior in generosity and virtù of spirit.¹⁵

Years later, in a public rather than private context, we see him boldly proclaiming a similar combination of social resentment, barbed language, and threats. The prologue to The Mandrake, Machiavelli’s unsparing comic satire of Florentine society, opens with Machiavelli directly addressing the audience, warning them of the dangers of slandering the play’s author: "Yet if anyone supposes that by finding fault he can get the author by the hair and scare him or make him draw a back a bit, I give any such man warning and tell him that the author, too, knows how to find fault, and that it was his earliest art; and in no part of the world where sì is heard does he stand in awe of anybody, even though he plays the servant to such as can wear a better cloak than he can."¹⁶ Even though he needed and frequently sought the support of powerful patrons, he always refused to accept the legitimacy of his society’s social hierarchy or his status as servant to those in power, often with painful and costly consequences.

The Florence of Machiavelli’s youth was a prosperous republican city-state and a major power, along with Naples, Rome, Milan, and Venice, in a decentralized Italian peninsula dotted with small city-states. The city derived its power from the substantial wealth of its merchant families, particularly those involved in two major dimensions of the Florentine economy: banking and the woolen and silk textile industries. The city’s mercantile origins and character were evident in its lowland, river location. Whereas military priorities determined the geography of most Tuscan towns, such as Siena, Volterra, Montepulciano, and Montalcino, all of which were located on defensible hilltops, Florence’s valley location on the banks of the Arno River was the result of mercantile considerations. The Arno provided the abundant freshwater required by the production process of the city’s booming textile economy, freshwater and fuel for the mills that produced the bread necessary to sustain the many thousands of urban workers (twenty-three hundred bushels of grain per day in the years before the Black Plague), and a gateway to the sea for exporting finished products.¹⁷

In Machiavelli’s account of Florence’s origins, mercantile ambition gave birth to the first settlements that subsequently became the city. In the Florentine Histories, he wrote that it is a thing very true, as Dante and Giovanni Villani have shown, that since the city of Fiesole had been placed on the summit of a mountain, to make its markets more frequented and more convenient for those who might want to come to them with their merchandise it had ordered the place for them not on the hillside but in the plain between the foot of the mountain and the Arno River. These markets, I judge, were the cause of the first buildings that were put up in those places, as the merchants were moved by the wish to have convenient shelters to hold their merchandise, which in time became solid buildings.¹⁸ In spite of Florence’s fundamental commercial ethos, however, Machiavelli had remarkably scant interest in business and commercial affairs, one of many dimensions of his unconventionality. He himself described his obsession with politics as a byproduct of his inability to engage the traditional Florentine pursuits of textiles and banking: Fortune has seen to it that since I don’t know how to talk about either the silk or the wool trade, or about profits and losses, I must talk about politics.¹⁹

The major issue of Florentine politics during Machiavelli’s early years was the growing tension between the city’s venerable republican tradition and the disproportionate power of the Medici family, led in Machiavelli’s early years by the charismatic Lorenzo the Magnificent. In theory at least, the government retained a republican constitution stipulating short terms of office and frequent rotation of officeholders, consistent with other Italian communal regimes such as Venice and Genoa. The Signoria, a committee of nine priors, exercised executive authority, rotating in and out of office every two months. The priors were advised by two councils, the Twelve Good Men and the Sixteen Standard Bearers, whose ranks were drawn from the city’s four neighborhoods. Legislative power was distributed more widely in the Councils of the People and the Commune, with roughly five hundred members who served for six-month terms.²⁰ Although the short terms of office suggested a wide distribution of office holding within the ruling group (roughly five to six thousand adult men), in practice, eligibility for office was circumscribed to roughly a third of that number through a system known as the scrutiny. Irrespective of the relatively small number of people who actually served on the major committees, Florentines embraced a republican political culture that celebrated the principle of shared self-governance.

Florentine republicanism became an increasingly empty shell over the course of the fifteenth century, however. What began as a limited quarrel between the ruling aristocratic oligarchy led by Rinaldo degli Albizzi and a growing faction led by Cosimo de’ Medici culminated in Cosimo’s overwhelming triumph in 1434. Once in power, Cosimo’s regime manipulated the government’s electoral system to ensure that only Medici partisans held office, declared frequent states of emergency that enabled the Medici to circumvent the constitutional mechanisms intended to prevent the concentration of power in a single family’s hands, and strategically dispensed the wealth of the family bank to maintain the loyalty of their sizeable patronage network. Following Cosimo’s death in 1464, Medici control of the city and its government faltered in the face of challenges to the rule of Cosimo’s son, Piero. But upon Piero’s death in 1469, the year of Machiavelli’s birth, his son Lorenzo assumed the mantle of power and swiftly restored the family’s domination of the city. Like Cosimo and Piero, Lorenzo also faced moments of intense internal opposition, such as the failed Pazzi conspiracy against Lorenzo’s life in 1478. Machiavelli, aged nine, must have witnessed Lorenzo’s sustained, public, and bloody execution of the conspirators (if he did, he must have thought of the similar fate of his ancestor Girolamo, who had also dared to oppose the Medici). But in spite of the conspiracy and a war against Lorenzo waged by the pope and the king of Naples, Lorenzo nevertheless increased the family’s power and further centralized their control of key government councils and magistracies.

In the years immediately preceding Machiavelli’s formal entry into Florentine political life, Medici power collapsed, and the city reasserted the substance of its republican institutions and fell increasingly under the influence of Girolamo Savonarola, a charismatic Dominican friar widely believed to possess prophetic powers. Upon Lorenzo’s death in 1492, leadership of the regime passed to his son Piero, who in short order proved unequal to the task. Piero’s troubles were compounded two years later after the French king Charles VIII renewed his claim to the Kingdom of Naples, marching on Italy at the head of a twenty-five-thousand-strong army. As Charles approached Florence in November 1494, Piero attempted to divert the looming threat by delivering to the French king the keys to several major Tuscan fortresses. The discontent he thereby caused in Florence and his absence from the city provided an opportune moment for a group of anti-Medici conspirators to evict the family from the city and dismantle their system of electoral controls. The leaders of the coup had intended to replace Medicean government with a narrow aristocratic regime similar to the one that had ruled Florence from the late fourteenth century to the rise of the Medici in 1434.²¹ Their plans suffered a serious and unexpected setback when Savonarola, whose apparent prediction of the arrival of Charles VIII had confirmed for many Florentines his status a prophet, intervened in the city’s constitutional debates and ultimately succeeded in persuading the Florentines to adopt a broader, more populist, and inclusive republican government.

Savonarola’s rise to power was a major catalyst on Machiavelli’s political thought. Savonarola was first and foremost a religious reformer who urged Florentines to adopt an austere and ascetic Christian lifestyle.²² In this respect, and this respect only, Savonarola was part of ancient and pan-European tradition of eschatological preachers who used the specter of the imminent end of times to urge their audiences to abandon worldly desires and embrace the early primitive Christianity of the church fathers. His reform program was entirely consistent with that tradition: he waged a campaign against a broadly conceived understanding of vice that included gambling, homosexuality, prostitution, poetry, and luxury in general. In addition, he fought the essential foundations of Renaissance humanism’s intellectual agenda—the recovery, dissemination, and celebration of the pagan wisdom of Greek and Roman antiquity.

In other respects, however, Savonarola radically departed from tradition. He swiftly attained a position of public authority in Florence that far surpassed the power of most itinerant preachers of repentance, owing to a combination of his perceived status as a prophet and his appealing vision that Florence would soon be a new Jerusalem, the center of world Christianity, and that God’s favor would manifest itself in an era of unimaginable prosperity and power. Further, Savonarola intervened in Florentine political life on an unprecedented level for a preacher and an outsider (from Ferrara) lacking powerful Florentine family connections, influentially weighing in on the pressing diplomatic, constitutional, and legal issues of the day.²³ He particularly incurred the wrath of pope Alexander VI by urging the Florentines not to join the papal league through which Alexander hoped to expel the French from Italy. Most significantly, in terms of Machiavelli’s writings, Savonarola played a critical role in persuading the group who had expelled the Medici and were at the helm of the republic in 1494 to abandon their vision of an aristocratic oligarchy in Florence and instead to embrace a more inclusive and populist republicanism. Like Machiavelli, Savonarola condemned the traditional Florentine reliance on mercenaries and, again like Machiavelli, favored a citizen militia, though the proposal outlined by Savonarola’s follower Domenico Cecchi was considerably less populist than the approach Machiavelli would ultimately take.²⁴ Always a polarizing figure, the friar led attacks on papal corruption that led to his excommunication, which in turn lent ballast to the escalating efforts of his enemies in Florence to bring him down. Waning confidence in his prophetic powers led to his arrest, torture, and execution, along with two of his chief lieutenants, in 1498.

One of Machiavelli’s earliest letters and first commentary on Florentine politics was a letter to the Florentine ambassador in Rome, Ricciardo Becchi, that analyzed one of Savonarola’s sermons and the nature of his power. The Florentine government had charged Becchi to persuade Alexander VI to lift the ban on preaching that he had imposed on Savonarola. In spite of the ban, Savonarola nevertheless continued to preach in public, causing Becchi, in turn, to ask Machiavelli to provide him with a report on the content of Savonarola’s latest sermons and their relationship to the city’s politics. Machiavelli provided a summary of Savonarola’s sermons on Exodus from 2 and 3 March 1498, and an analysis of the role of spiritual charisma in Savonarola’s position as the leader of a faction densely embroiled in the city’s political conflicts. Machiavelli recounted with no small amount of admiration how Savonarola skillfully reaffirmed his special status as a vessel of God’s words, likened the political struggle between his faction and its opponents in Florence as a battle between those who soldiered under God and those who served the devil, and insinuated that political attacks against him would lead to the establishment of tyranny in Florence. In a famous phrase, he concluded that Savonarola was fundamentally a dissimulator: Thus, in my judgment, he acts in accordance with the times and colors his lies accordingly.²⁵ All the principal issues in his early reflection on Savonarola—the role of religion in politics, the formation and identity of factions, the power of speech, and the dangers of establishing new institutions—became major recurring themes of Machiavelli’s subsequent political thought.²⁶

Savonarola had a significant impact not only on Machiavelli’s writing but on his political career as well. In the spring of 1498, shortly after Machiavelli’s letter to Becchi, the Savonarolan experiment in religiously inspired popular republicanism entered its final chapter. From the outset, Savonarola had inspired as much hostility and fierce opposition in some as he inspired devotion and loyalty in others. His aristocratic opponents, known as the arrabbiati or the angry ones, resented many aspects of the friar’s program: the moral turn that public life had taken against traditional pastimes of drinking, gambling, and sexual adventure, the city’s rigid alliance with France, and, perhaps worst of all, Savonarola’s equally rigid support of the Great Council, the institutional linchpin of the popular republic. Growing antagonism between Savonarola and Alexander VI had led the pope to threaten the city with interdict and excommunication, which heightened the factional tensions in the city to the breaking point. After a Signoria took office for March and April of 1498 composed largely of anti-Savonarolans, events swiftly unraveled for Savonarola: a trial by fire intended miraculously to prove his elect status wound up confirming the opposite; an angry mob assaulted Savonarola’s stronghold, the Dominican convent of San Marco; and shortly thereafter the friar was arrested, interrogated, and burned at the stake as a heretic and false prophet.²⁷

The regime then purged the government of Savonarolan supporters. As part of the consequent reshuffling of many government offices, Machiavelli was appointed second chancellor, a position that he held until the collapse of the republic in 1512 and that brought him into close contact with the rulers of Europe. Machiavelli’s letter to Becchi, with its combination of lucid and pithy political analysis and sharply critical distance, no doubt played a role in signaling to those in power Machiavelli’s suitability for political appointment. Upon his appointment to the chancery, Machiavelli became an active participant in the military and diplomatic conflicts triggered by the French king Charles VIII’s march on Naples in 1494.

As second chancellor, Machiavelli was responsible for administering Florence’s relations with its subject territories in Tuscany, a largely bureaucratic position whose principal labors were the composition of diplomatic letters. A month after assuming the post of second chancellor, however, he was given an additional post as secretary to the Ten of War, a powerful committee responsible for military affairs. The Florentine government underwent a major constitutional innovation in 1502 with the transformation of the office of standard bearer of justice, the chief executive of the governing council, from a two-month rotational term, consistent with the other priors, to a permanent, lifetime tenure. Machiavelli’s standing and responsibilities in the Florentine government increased with the election of Piero Soderini, who had considerable confidence in Machiavelli’s judgment, as the new standard bearer for life. As a result of Soderini’s appointment, the government entrusted Machiavelli with greater diplomatic and military responsibilities, particularly regarding Florence’s campaign against rebellious Pisa, where ineffectual efforts by mercenaries in Florentine employ began to catalyze Machiavelli’s thinking about the merits of a citizen militia. After Machiavelli first began discussing a militia project in his correspondence from 1504, the project swiftly became reality: by 1505 Machiavelli had begun recruiting peasant conscripts from the countryside, and in 1507 Soderini made the fledgling initiative a formal part of Florentine government and policy by establishing a new committee, the Nine of the Militia, and appointing Machiavelli its secretary, entrusting it with essential elements of recruitment, organization, and supervision of the city’s new homegrown fighting force. Machiavelli remained closely involved in military matters until the surrender of Pisa in 1509.²⁸

When Machiavelli wrote in the preface to The Prince that his knowledge of the actions of great men was rooted in his lengthy experience of recent affairs, he was primarily referring to the tasks he carried out as secretary to the wartime Council of the Ten. As secretary to the Ten, Machiavelli was sent as a de facto ambassador to the key figures in the unfolding crisis of the early sixteenth century.²⁹ His first missions in 1499–1500 required him to negotiate the terms of service of Florence’s mercenary captains in the larger pursuit of the Florentine conquest of Pisa, a strategic seaport town at the mouth of the Arno and Florence’s gateway to the Tyrrhenian Sea, that had rebelled against Florentine rule in the wake of the French invasion. In 1500–1501, he was sent to the court of Louis XII, Charles’s successor, who had renewed French ambitions in Italy by laying claim to the Duchy of Milan. In 1502, he began a series of missions that revolved around the growing power of Pope Alexander VI’s son Cesare Borgia, a military adventurer intent on building a Borgia state in the Romagna. Borgia’s ambition, decisiveness, ruthlessness, and inscrutability, not least of all, made a powerful impression on Machiavelli, who dedicated chapter 7 of The Prince to a meditation on the merits of Borgia’s political tactics. In 1506 Machiavelli was sent to the papal court, where Pope Julius II was planning to seize Perugia and Bologna and had sought help from mercenary captains on the Florentine payroll. In 1507–8, Machiavelli, along with Francesco Vettori, with whom he became a lifelong friend, was sent to Germany to deal with the Holy Roman Emperor Maximilian I’s decision to embark on a campaign in Italy. His last two major missions were to the French court to navigate the growing crisis, particularly for the pro-French Florentines, caused by Pope Julius II’s alliance with Venice and Spain to expel the French from Italy.³⁰

Machiavelli, Soderini, and the Florentine republic all paid dearly for their loyalty to the French crown in 1512 when a Spanish army easily defeated Machiavelli’s militia, toppled the Florentine republic, and restored the Medici family to power. Machiavelli’s reversal of fortune was particularly swift. With Soderini in exile, Giuliano de’ Medici entered the city on 1 September, and the Medicean faction seized control of the government. Unlike events in 1498, when Savonarola’s downfall led to a major restaffing of government offices, the restored Medici left the chancery staff virtually intact, with one notable exception: in November, Machiavelli and his good friend Biagio Buonaccorsi, another close confidante of Soderini, were dismissed from office, with Machiavelli additionally barred from entering the government palace and confined to Florentine territory for one year. Shortly thereafter, the government began to investigate Machiavelli’s administration of payments to the militia, which required him periodically to report for questioning (each time he had first to seek permission to enter the government palace).³¹

The fact that Machiavelli had clearly been singled out revealed the extent of patrician hostility that had accumulated against him during his years of service under Soderini. From the outset of his appointment as chief magistrate of the republic, Soderini remained committed to the popular orientation of the republic that he had inherited from the Savonarolan years. He consequently faced concerted opposition from a group of powerful Florentine aristocrats who had expected—wrongly—that the creation of a lifetime standard bearer, explicitly modeled on the aristocratic Venetian republic’s office of a lifetime doge, would lead to greater aristocratic control over the government. This aristocratic group viewed Machiavelli with considerable suspicion and resentment. They viewed his prominence in Florentine politics as entirely inappropriate for his modest social standing; saw Soderini’s excessive reliance on him and Buonaccorsi, who they also viewed as an impoverished social upstart, as a way of circumventing their influence; and particularly feared that Machiavelli and Soderini’s militia project, which they had long opposed, was an attempt to build a private army on which to establish a tyrannical regime.³²

Machiavelli’s personality only exacerbated their hostility. He frequently refused to show the kind of deference that his social betters expected from the middle-class functionaries who formed the bureaucratic core of the government. His letters to the Ten of War, a committee made up of his social and political superiors, frequently chided them for their impatience, lack of vision, and poor political judgment.³³ Showing visible contempt for the intellects of his superiors was bad enough, but in the final text that he wrote from within the chancery, he crossed the line into outright political condemnation. In his Memorandum to the Mediceans, he warned the incoming Medici not to trust the very aristocrats who had conspired against the Soderini regime to assist the Medici restoration. He accused them of pandering between the people and the Medici in pursuit only of their own power and sharply concluded that if the Medici allowed them to continue to slander Piero Soderini, they would remove the muzzles from many mouths that will surely and most readily bite them.³⁴ Directing such harsh words at the aristocratic core of the Medici family’s ostensible allies and defending the figurehead of the former republic were risky moves, as Machiavelli’s dismissal and confinement to Florentine territory revealed.

Machiavelli’s standing with the Medici rulers went from bad to worse a few months later after the discovery of a notional conspiracy against the new regime. Inspired by humanist paeans to the glory of the Roman republic and the memory of Savonarola, who had always insisted on a republican constitution in Florence as a precondition for God’s favor, two Florentine patricians, Pietropaolo Boscoli and Agostino Capponi, began to plot an attempt on Giuliano de’ Medici’s life. As a first step, they compiled a list of people, Machiavelli included, who they hoped would be sympathetic to their plot. After the list fell into the hands of the regime, the Eight of the Guard (Otto di Guardia), the magistracy responsible for political crimes, arrested everyone identified in the list. Although the conspiracy amounted to little more than an act of defiant imagination, the Medici recognized that their return to Florence was widely unpopular and therefore reacted swiftly and harshly. Machiavelli’s name clearly stood out as a priority for them, because his arrest warrant stipulated that he, or anyone who knew his whereabouts, was to report to the government within the hour.³⁵ Another proclamation of the same day demanded that all Florentines surrender their weapons. The two proclamations, along with the financial investigation of militia payments a few months earlier, suggest that the Medici were particularly concerned that the conspiracy might be linked in some way to Machiavelli’s militia project and that he may have arranged for an armed fifth column within the city. Machiavelli turned himself in to face interrogation, torture, and imprisonment. Boscoli and Capponi were beheaded, two other people on the list, Niccolò Valori and Giovanni Folchi, were imprisoned in the fortress town of Volterra in western Tuscany, and Machiavelli languished in a prison cell in Florence.

Machiavelli’s release from prison twenty-two days later was largely the result of the sudden and unexpected intervention of good fortune. The repressive measures that the regime had adopted were a reflection of the uncertain context and the regime’s consequent insecurity. Unfolding at roughly the same time as the conspiracy, however, was a papal election triggered by the death of the warrior pope Julius II on 21 February. Giuliano de’ Medici’s brother, Cardinal Giovanni de’ Medici, emerged from the papal conclave in Rome on 11 March as Pope Leo X, prompting Leo’s less than purely spiritual reaction: Let us enjoy the papacy since God has given it to us.³⁶ The Florentines evidently overheard Leo because the city erupted in celebration, wine flowed from the fountains in the city’s public squares, and bonfires burned throughout the city for days. With the papacy now in Medici hands, the regime’s fears of dissent in Florence waned. The Medici opened the city’s prisons, issued a general amnesty for political prisoners, and lifted their fines.³⁷ I’ve gotten out of prison, Machiavelli wrote to Francesco Vettori, amid the universal rejoicing of this city.³⁸

Released from prison but still a disgraced and toxic political outsider, Machiavelli retreated to the family farmhouse in Sant’Andrea in Percussina, roughly ten miles south of Florence, and began, however reluctantly at first, to reinvent himself as a man of letters. In the years between his disgrace and fall in 1512 and his return to politics in 1520, he produced a body of writing of utterly astonishing originality and variety that included letters, plays, poems, The Art of War, and his first two major works of political thought, The Prince and the Discourses on Livy.

The first fruit of his enforced retirement from active political service was a lengthy exchange of letters with Francesco Vettori, whom Machiavelli had befriended on their ambassadorial mission to the court of Maximilian I in 1507 and to whom the Medici upon their return in 1512 had given the distinguished post of Florentine ambassador in Rome. Machiavelli had initially hoped that Vettori might be able to persuade the Medici to set aside their misgivings about Machiavelli and find him a political appointment.³⁹ He beseeched Vettori several times to intervene on his behalf, concluding with his famous declaration of willingness to carry out Sisyphean labor if only it might demonstrate the intensity of his wish to return to the vita activa: There is also my desire that these Medici princes might begin to employ me, even if they should begin by making me roll along a stone; because if then I couldn’t win them over, I should complain only of myself.⁴⁰

Vettori could do little for Machiavelli, however, given the degree to which the Medici mistrusted Machiavelli. A letter from Pope Leo’s secretary from February 1515 suggests that the family had already discussed Machiavelli’s merits and had formally decided against him: Cardinal de’ Medici asked me yesterday, in very strict confidence, if I knew whether your Excellency had taken Niccolò Machiavelli into your service, and when I replied to him that I had no news of it, nor did I believe it, his most reverend lordship spoke to me the following formal words: ‘I don’t believe it either; however, because there is news of this from Florence, I remind him that this suits neither him nor us. . . . Write to him on my behalf that I advise him to have nothing to do with Niccolò.’ ⁴¹

The contrasting fate of the two men upon the return of the Medici was a cause of evident tension and can only have impressed on Machiavelli yet again the degree to which in a political world dominated by princes and aristocrats, the Machiavelli were pygmies among giants. Machiavelli and Vettori had both served Piero Soderini and the popular republic in important positions, and both had helped Piero Soderini escape the city after the Medici placed a bounty on his head, yet Vettori was given an important ambassadorial post at the court of a Medici pope while Machiavelli was arrested, interrogated, and isolated.⁴² Francesco’s success in navigating the regime change had much to do with the fact that Francesco’s brother Paolo had played an instrumental role in undermining the Soderini regime and facilitating the Medici return. But the contrast in the two men’s fortunes also reflected the enduring importance of class prejudice and solidarity. Vettori was the scion of one of the city’s most ancient and powerful noble families, someone who, along with the other distinguished families of the Florentine ruling group, viewed the possession of high political office as a birthright. It was far easier for the Medici to forgive Francesco’s earlier republican inclinations, given his wealth, standing, and influential connections, than it was to forgive Machiavelli, whose modest social origins, already the cause of considerable contempt by the ottimati, were a source of political vulnerability.⁴³ Without any doubt, Machiavelli understood and deeply resented the power of these class distinctions, because all his subsequent writings caustically denigrated aristocratic culture as entitled, violent, and politically destabilizing.

The contrasting fates and social standing of the two men, however, counted for less than their mutual intellectual respect, evident in the expansive political debate in their correspondence. Machiavelli continued to play the role of ambassador, in spirit if not in name, in the letters that he exchanged with Vettori that analyzed the rapidly shifting political landscape between 1513 and 1515. As the Florentine ambassador to Rome and a confidante of the Medici pope, Vettori was closely involved in the major developments of those years. Leo X was trying to secure power bases for his family: he arranged for his brother Giuliano to marry into the French royal family, who had long-term plans for Giuliano as ruler of Naples, a crown to which the French had claim; Leo appointed his nephew Lorenzo governor of Florence; and he secured the promotion of his cousin Giulio, the archbishop of Florence, to the cardinalate, paving the way for Giulio’s election as Clement VII, the second Medici pope, in 1523.⁴⁴ The primary larger diplomatic issue was the ambition of the French crown to conquer Milan. Although Louis XII had been evicted from Milan after his loss to the Swiss at the Battle of Novara in 1513, Francis I renewed the French claim to the city in northern Italy upon his assumption of the crown in 1515. Aided by Venice, which Louis XII had earlier persuaded to abandon the anti-French papal Holy League, Francis defeated the Swiss, the de facto rulers of Milan, at the Battle of Marignano in 1515. French and Venetian dominance of northern Italy led to a few years of relative peace, until the election of Charles V as Holy Roman Emperor in 1519 renewed major hostilities between the Habsburg and Valois dynasties.

In their discussion of these events, the two men took sharply opposing positions—Vettori skeptical, Machiavelli confident—on the predictability and rationality of politics, and hence its susceptibility to reliable analysis.⁴⁵ Vettori argued that politics was rarely a function of reason in which a prince’s course of action reflected a direct relationship with his statements. Instead, he stressed the degree to which unexamined habits, secret and hence unknowable priorities, and inscrutable irrationality determined events. He wrote to Machiavelli: it often seems to me that things do not proceed on the basis of reason, and on this account I think it superfluous to speak of them, discuss them, and argue about them. . . . We must believe that each of these princes of ours has some purpose, and because it is impossible for us to know their secrets, we have to guess at it from their words and actions, and some of it we just imagine.⁴⁶ Machiavelli more idealistically and ambitiously insisted on a direct correlation between words and actions, rejecting Vettori’s resigned acceptance of guesswork as a major component of political analysis. Vettori’s skepticism pushed Machiavelli to increasingly sustained arguments for the inherent intelligibility of politics. As he put it in his letter to Vettori of 20 June 1513: I believe it’s the duty of a prudent man to consider at all times what may harm him and to foresee problems that are distant, and to favor good and thwart what is bad in plenty of time.⁴⁷

Machiavelli’s correspondence with Vettori was closely tied to the composition of The Prince, one of Machiavelli’s earliest and certainly his most famous treatise on political thought. Much of our understanding of the context in which Machiavelli wrote the treatise and his hope that it might win favorable attention from the Medici arises from the Vettori correspondence. Vettori had written a letter detailing the three elements of his daily routine as ambassador in Rome: mornings spent discussing political minutiae of little import with the Medici circle, afternoons spent dining and socializing with various Florentines in Rome, and evenings spent in the company of ancient Roman historians such as Livy and Tacitus. Machiavelli’s reply of 10 December 1513, his most famous letter, mirrored the structure of Vettori’s letter but heightened the contrast between the mundanity of his daytime activities and the intellectual intensity and intimacy of his nocturnal reading of classical authors. After catching birds, chatting with travelers on the road outside his farmhouse that connected Florence and Rome, and gossiping and gaming with the village locals, Machiavelli returned home and through conversation with the ancients transformed himself back into an analyst of grand political questions:

When evening comes, I return home and enter my study; on the threshold I remove my workday clothes, covered in mud and dirt, and put on regal and courtly garments. And reclothed appropriately, I enter the ancient courts of ancient men, where, affectionately received by them, I nourish myself on that food that alone is mine and for which I was born, where I’m not ashamed to speak with them and to ask them the reason for their actions. And they, out of their humanity, answer me, and for four hours of time I feel no boredom at all, I forget every trouble, I don’t fear poverty, death doesn’t frighten me: I transfer myself entirely into them. And because Dante says there’s no knowledge without retaining what one has learned, I’ve made note of what I’ve profited from in their conversation and have composed a little work, De principatibus, where I delve as deeply as I can into reflections on this subject, debating what a principality is, of what kinds they are, how they are acquired, how they are kept, why they are lost.⁴⁸

Although Machiavelli portrayed The Prince as fundamentally a product of his intellectual encounter with ancient authors, the book was also in important ways a fusion of that reading with his former political activity, his debate with Vettori, and the major events of Florentine history during his lifetime. For example, in the chapters selected in this volume, we see that Machiavelli’s famous distinction in chapter 6 between the relative ability of armed and unarmed prophets to establish durable institutions stemmed not only from reflection on distant historical figures such as Moses and Romulus, who enforced their new laws by force, but also in large part on the unarmed prophet Savonarola’s sudden rise to power and equally sudden fall. The ninth chapter’s portrayal of nobles in general as arrogant and bullying political saboteurs of any regime in which they did not hold sway directly echoed his family’s troubles during his youth and the inability of the Soderini regime of which he formed a crucial part to protect itself from aristocratic opposition within. In chapters 12 and 20 he wrote about