I

BORN IN POVERTY

“I was born poor and learned early on to deny myself rather than to enjoy.”

—NICCOLÒ MACHIAVELLI TO FRANCESCO VETTORI, MARCH 18, 1513

AS HE CONTEMPLATED THE WRECKAGE OF HIS ONCE promising career, Machiavelli consoled himself with the thought that he was, after all, no worse off than he had been when he had come into this world. Only his dreams of something better had been shattered. “I was born poor and learned early on to deny myself rather than to enjoy,” he recalled, finding comfort in the thought that he had nothing left to lose.

At first glance Machiavelli’s characterization of his circumstances seems willfully misleading. The Machiavelli were an old and respected family and by most measures the particular branch into which Niccolò was born in the spring of 1469 was solidly middle-class.i Niccolò’s father, Bernardo, was a man of property. He owned a house near the Ponte Vecchio, one of a cluster of buildings occupied by various cousins, grouped about a small courtyard with a loggia known as the chorte di Machiavelli. This alone was enough to lift the family above the great majority of the urban poor, who owned little more than the ragged clothes on their back. Nor was this Bernardo’s only piece of real estate. Furnishing the city house with wine, oil, eggs, meat, and fresh vegetables was his farm in Sant’ Andrea in Percussina, situated some ten miles south of Florence along the road to Rome. Even in lean times the family could fall back on its own resources to feed and clothe itself.

The status of the Machiavelli in Florence was measured by more than material possessions. Bernardo could claim descent from the minor nobility (through the Castellani family), a connection that, while it brought little in the way of tangible profit, conveyed real benefits in the form of prestige. In the countryside Bernardo’s superiority to his neighbors was marked by quaint ceremonial gestures that carried a distant echo of once vital feudal obligations: every Saint Peter’s Day, a member of the parish of San Piero a Nebbiavole offered in tribute a half pound of candle wax, and when the priest of the local church of San Michele a Mogliano died, Bernardo, in recognition of his role as fatherly protector of the community, was among those consulted in naming his successor.

In the city the family was equally well established. For centuries the Machiavelli had belonged to Florence’s ruling elite. Niccolò’s ancestors had been prosperous bankers and merchants, dealing mostly in the lucrative wool and silk industries. Bernardo himself, though he never held elective office, was a friend of some of the most powerful and prominent men in the city. One of them, the Chancellor of Florence, Bartolomeo Scala (an intimate of Lorenzo de’ Medici himself), called Bernardo his “friend and familiar” and estemed his erudition so highly that he made him a principal character in his De Legibus, a philosophical dialogue on the origins of the law. Nothing indicates his high standing in the community as surely as this: Bernardo Machiavelli was someone in whose mouth Scala could place learned paraphrases of Plato and Cicero without fear that contemporaries would find the image ludicrous.

In other words Bernardo Machiavelli was an intellectual. He had earned a reputation as an amateur scholar and expert on legal matters, something confirmed by the honorific messer used by his peers when greeting him on the Ponte Vecchio or Piazza della Signoria. He was the prototypical scholarly dilettante. Years after his death, when it was brought to Niccolò’s attention that strangers had been mistakenly buried alongside his father in the Machiavelli family crypt in Santa Croce, he quipped: “Well, let them be, for my father was a great lover of conversation, and the more there are to keep him company, the better pleased he will be.” Bernardo had both the inclination and the leisure to cultivate his mind, secure in the knowledge that his various properties would provide sufficient income to support his family.

But despite this solidly bourgeois standing, Niccolò was not mistaken in characterizing his origins as less than promising. True, he never suffered the dire want of many of his neighbors for whom even a slight economic downturn meant hunger; nor did he ever have to endure the humiliation of begging charity from his richer relatives. But in the world of late-fifteenth-century Florence, both Bernardo and his son Niccolò lived uneasily on the margins of respectability. In fact the earliest surviving documents in Niccolò’s hand—two letters from 1497 written when he was twenty-eight years old—reflect a painful recognition of social insecurity. They involve a property dispute between his family and the powerful Pazzi clan. Hoping to counter the uneven odds, Niccolò put his case before the influential Cardinal Giovanni Lopez. In the first letter Machiavelli refers to his own kin as “pygmies . . . attacking giants.” In a follow-up letter to this same cardinal, he seems anxious to remind his correspondent that, despite appearances, the Machiavelli are at least as respectable as their more powerful rivals: “And whoever would wish justly to weigh the merits of our house against that of the Pazzi, all other things being equal, would declare ours the greater in liberality and manliness of spirit.” Of course, as Niccolò knew, the scales were never fairly weighted, and any contest between unequal combatants would favor the strong over the weak. As he remarks bitterly in his play La Mandragola, “a man who doesn’t have pull with the government of this city . . . can’t find a dog to bark at him, and we’re good for nothing but to go to funerals and to meetings about some marriage, or to sit all day dawdling on the Proconsul’s bench.” Surprisingly, at least for those who regard him as the preeminent exponent of ruthless power politics, Machiavelli’s natural point of view was that of the vulnerable. This marginality, the sense that he was on the outside looking in, was vital to Niccolò’s self-conception. This self-conception in turn was vital to the formation of his thought.

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Niccolò Machiavelli was born on May 3, 1469, in the family house just south of the Ponte Vecchio. The modest residence stood on the Via Romana, which led from the city’s oldest and busiest bridge to the southern gates. From his bedroom window young Niccolò could watch not only the steady stream of farmers on their way to market, but also more exotic figures who were a reminder of the vast international reach of Florentine commerce: walking shoulder to shoulder with the humble peasants were long-distance merchants with their mules piled high with goods from Turkey, Arabia, and far-off India, as well as tourists—including numerous dukes, duchesses, cardinals, and even an occasional emperor or king—who had come to worship at the city’s many sacred shrines and delight in Florence’s unparalleled works of art and architecture.

The house in the heart of the Oltrarno—the section of Florence on the south bank of the Arno River that is still among the most charming in the city—no longer stands, but the surrounding urban fabric is largely intact. The neighborhood in which the young Machiavelli grew up, identified by the ancient heraldic symbol of the shell (Nicchio),ii is one of narrow streets and tiny, shaded squares, of small shops and unpretentious eateries. On summer days when the Arno became sluggish, a foul stench rose from the mud along the riverbank, a miasma made even worse by the dyers and tanners who used the waters to scrub away noxious liquids. It was then that plague-carrying rats multiplied, bringing contagion that ravaged the neighborhoods of rich and poor alike. Then, as now, it was not the most fashionable address in the city, but a few imposing palaces tucked in among more modest apartments were a reminder that powerful families lived among them. A few minutes’ walk from the main civic and religious centers, the Oltrarno was close enough to participate fully in the hustle and bustle of the thriving metropolis.

Within this busy urban neighborhood there was little to distinguish the Machiavelli home from dozens of others in the vicinity. By the late fifteenth century the most powerful families of Florence—like the Medici, whose palace on the widest street of the city, the Via Larga, set the standard for those that followed—advertised their wealth and status by constructing splendid homes that dwarfed their neighbors,’ but the Machiavelli residence would not have made much of an impression on the passersby. No architect had imposed his newfangled ideas of classical order on the rather haphazard collection of medieval buildings; the conglomeration was decidedly unostentatious, suggesting shabby respectability rather than vaunting ambition.

Like most Florentine families, the Machiavelli were unable to trace their origins back more than a couple of centuries, though, unlike some more pretentious or deluded lineages, they felt no need to invent fictitious pedigrees out of dragon slayers or Trojan heroes. In the centuries before Niccolò’s birth they had prospered as the city prospered, making a solid if not spectacular contribution to a metropolis that was becoming a center of trade, manufacturing, and finance.

The location of the city house, as well as the various properties scattered about the countryside in the hills just south of the city, indicates that the Machiavelli originated in the Val di Pesa, in the wine-making region of Chianti. As the population of Florence swelled in the twelfth, thirteenth, and fourteenth centuries, largely through immigration from the contado, the rural area just outside the city limits, families tended to settle in districts closest to the gates through which they had first entered. The less densely populated Oltrarno was a popular destination for new immigrants, particularly those from the region south of the city. It is almost certain, then, though there are no documents prior to the thirteenth century to prove this, that Niccolò’s distant ancestors were among those nameless tillers of the soil who, since before the days of the Roman Empire, cultivated grape and olive on the sloping, rocky hillsides that lie between Florence and Siena.

The insecure respectability that marked Niccolò’s life and that fueled much of his creative fire was the result of fortunate decisions made by long-dead ancestors and unwise choices made more recently. If Niccolò burned with ambition, it was due at least in part to the gap he perceived between the prestige of the Machiavelli name and the precariousness of current circumstances. In his dedication to The Prince he refers to himself as “a man of low and poor station,” a perspective that encouraged him to break with convention and propose startlingly new solutions to old problems. Had he been richer or more careful of his dignity, it is unlikely he would have made his career in the civil service, a form of employment too close to real work to be suitable for a gentleman and one that provided vital insight into the cruel economy of power. Equally important, the nagging sense that his family was in decline left him with a fierce ambition to make his mark.

The Machiavelli first enter history during the thirteenth century as adherents of the Guelph party, the group allied with the papacy in their often bitter quarrel with the Ghibellines, followers of the Holy Roman Emperor. Though these factions, which existed in most of the cities of northern and central Italy, ostensibly owed their allegiance to one or the other of the great universal lords of Europe, abstract geopolitical considerations often were less significant than the fact that party solidarity provided an opportunity to settle purely local scores. In the streets of Florence, as in Milan, Pistoia, and Siena, Guelphs and Ghibellines organized themselves into armed factions and slew each other with abandon as first one and then the other gained momentary advantage, burning down the houses of their enemies and driving the survivors through the city gates. Time and again the same bloody drama played itself out. While the victors celebrated, the exiles made their way to the nearest friendly city, where they plotted revenge on their insufferable compatriots. The most famous iteration of this familiar story involves the great Florentine Ghibelline Farinata degli Uberti who, after the triumph of the Guelphs in 1250, headed to Siena, where the Emperor’s men still clung to power. Demonstrating that loyalty to party and family meant more than loyalty to country, Farinata led the armies of Siena against his hometown, defeating them at the battle of Montaperti and briefly reasserting Ghibelline ascendance in Florence.iii

One of the earliest mentions of the Machiavelli family comes in the context of this Ghibelline triumph, when a contemporary chronicler listed them among the prominent Guelphs whose houses were plundered by their enemies. Fortunately for the Machiavelli and their allies, the quarrelsome and faction-ridden Ghibellines failed to consolidate their victory and by 1267 the Guelphs, the Machiavelli among them, had regained control. But the Guelphs proved equally belligerent, repeating the worst excesses of their ousted foes. This particular round of destruction was not entirely unproductive since the torching of the houses of the Ghibelline Uberti clan created much needed open space in the crowded heart of the city. The smoldering ruins of the Uberti towers were paved over and transformed into Florence’s main civic square, the Piazza della Signoria—a peculiar but effective bit of urban renewal.

The triumph of the Guelphs brought no peace to the city. The crumbs of the victory feast had barely been cleared when they themselves split into rival factions—the Blacks and the Whites—who now went about slaughtering each other with equal gusto.iv The Machiavelli, once again fortunate in their loyalties, joined the victorious Blacks, the faction that, under the lead of the Donati family, banished Florence’s most famous citizen, the poet Dante Alighieri, who had the bad luck to belong to the Whites. As a bitter, rootless exile, Dante took his revenge on the city that had betrayed him by providing eyewitness testimony that “through Hell [Florence’s] name is spread abroad!”

Niccolò’s ancestors joined in the street battles that were a feature of daily life in medieval Florence, ransacking the houses of their neighbors when they were on top and suffering the same fate themselves when Fortune reversed herself. If Niccolò would one day become the world’s most famous cynic, given his own family history and that of his native city, it is a view he came by honestly. While the Machiavelli were not among the leaders of the victorious Black Guelphs, by the mid-fourteenth century they were named as one of the “notable” citizen families of the Oltrarno neighborhood. Equally significant, contemporary accounts list the Machiavelli as popolani—that is among those prosperous merchants who were slowly pushing aside the old feudal aristocracy as the ruling class of the city.

The annals of medieval Florence chronicle a tragic cycle of murder and arson that was one generation’s legacy to the next, but viewed from a distance a more constructive picture emerges. In his Florentine Histories, Machiavelli admits that “if in any other republic there were ever notable divisions, those of Florence are most notable . . . . From such divisions came as many dead, as many exiles, and as many families destroyed as ever occurred in any city in memory.” But he perceived that her greatest fault revealed her greatest virtue, for “in my judgment no other instance appears to me to show so well the power of our city as the one derived from these divisions, which would have had the force to annihilate any great and very powerful city. Nevertheless ours, it appeared, became ever greater from them.” However violently and spasmodically, Florence was wrenching itself free from ancient feudal bonds and asserting its autonomy in defiance of both Pope and Emperor. By the end of the thirteenth century, despite periodic orgies of bloodletting, Florence had transformed itself into a vital and independent state, dominated by merchants and bankers grown prosperous on the revived trade between East and West that was an unintended by-product of the Crusades.

In the Ordinances of Justice of 1293, Florence established a government that reflected the new order; the right to vote and to hold office would no longer be the privilege of the landed aristocracy but would be based on membership in one of the city’s merchant or professional guilds.v Flexing their newfound muscle, these merchants now sought to rein in the lawless magnates whose arrogance and violence had for so long disturbed the peace. Merchants and shopkeepers formed themselves into a citizen militia powerful enough to challenge the armored knights who were the source of the feudal aristocracy’s military power. First they tore down the towers in the city from which the great lords had waged war on each other, and then marched out into the countryside, smashing their castles and forcing them to swear allegiance to the commune. “[H]aving eliminated their nobility,” Machiavelli wrote in his Florentine Histories, “the republic was left in the hands of men nurtured in trade.”

The Machiavelli were among the families benefiting from the government established by the Ordinances of Justice, and from the end of the thirteenth century their name crops up regularly among the Three Majors, the chief elected offices of the land.vi The social transformation that brought families like the Machiavelli, the Medici, and the Pitti to the fore while marginalizing such feudal “magnates” as the Tornaquinci and the Pazzi, did not constitute a full-scale revolution in which one class seized power from another, but rather an evolution within a population in which such distinctions were already thoroughly confused. This confusion can be seen in microcosm among Niccolò’s own ancestors. In 1393, two Machiavelli brothers, Buoninsegna and Lorenzo di Filippo (Buoninsegna was Niccolò’s great-great-grandfather) inherited the run-down castle of Montespertoli in the Val di Pesa, formerly the possession of the noble Castellani. Thus, while their descendants continued to earn a living in the city as merchants, bankers, and lawyers, their titles and property in the countryside provided both income and social standing.

By the mid-fourteenth century the Machiavelli were firmly ensconced in the Oltrarno. The property on the Via Romana was purchased by the family from the powerful Pitti clan in the late 1300s. By that time, they were also in possession of various properties in the Val di Pesa south of Florence, including Sant’ Andrea in Percussina, where Niccolò would retire to write The Prince. But while the Machiavelli prospered along with the commune, they did not stand out from dozens of their colleagues. In the tax rolls of 1427, for instance, no Machiavelli is listed among the top bracket of households assessed at more than 10,000 florins.vii Nor did they stand out in the political arena. The great struggle for supremacy between the Albizzi faction and the rising Medici clan that dominated the early decades of the fifteenth century saw the Machiavelli discreetly on the sidelines, poised to retain their modest standing whichever side ultimately prevailed. When, in 1434, Cosimo de’ Medici, following a year of exile, drove his opponents from the city and established himself and his allies as the dominant power in the land, none of the Machiavelli suffered in the wholesale changing of the guard.

Like most Florentine families, the Machiavelli identified closely with their own neighborhood, investing not only their financial but their spiritual capital in the local community. Opposite the Machiavelli compound was the parish church of Santa Felicità, where the family claimed patronage rights over the small chapel of San Gregorio. Here young Niccolò spent many a Sunday morning gazing up at Domenico Ghirlandaio’s fresco of Christ’s deposition from the cross, commissioned by his cousin Alessandro, an experience that seems to have done little to instill in him either piety or an aesthetic sense.

If the overall picture of the Machiavelli as the fifteenth century unfolded was one of comfortable prosperity, in the decades before Niccolò’s birth there were signs of future difficulty. The source of these troubles was largely Bernardo himself. Though Niccolò never seems to have reproached his father, for whom he showed a deep affection, it is clear that Bernardo had none of the characteristic Florentine aptitude for business. One can comb through his diary, which he kept for thirteen years of his adult life, and still have no idea what Bernardo did to earn a living. The pages are filled with various mundane transactions—the sale of wool or firewood from the farm at Sant’ Andrea in Percussina, a dispute with a butcher over payment for a delivery of spring lambs for Easter, endless haggling over the dowry for his daughter’s wedding—but he never seems to have contemplated the possibility of adding to his modest patrimony through investment or hard work. The frugality of the family budget is suggested by numerous transactions recorded with one Matteo, a dealer in secondhand clothes, justifying Niccolò’s claim that growing up he “learned to deny myself rather than to enjoy.” The impression left by Bernardo’s diary was that he was singularly lacking in ambition, particularly when compared with his compatriots, who were known throughout Italy as shrewd businessmen, greedy for gain, and ambitious as the devil.

Bernardo had been trained in the law, but there is little indication that he ever earned money by pursuing this potentially lucrative career. On his tax return of 1480, he wrote: “messer Bernardo . . . practices no gainful employment”—a statement that seems as much a boast as a plea for understanding. Whatever his financial circumstances, he was too much a gentleman to consider bolstering the family fortune through work. His circumstances and attitude are remarkably similar to that of Michelangelo’s father, a member of the minor nobility, who proudly told the ruler of the city: “I have never practiced any profession; but I have always up to now lived on my slender income, attending to those few possessions left to me by my forebears, seeking not only to maintain them but to increase them as much as possible by my diligence.”

The most tangible result of Bernardo’s education seems to have been the acquisition of debt he had difficulty repaying and that served as a handy excuse whenever he fell behind on his taxes. Like his son, he was both garrulous and gregarious and preferred to spend his time discussing the news of the day rather than earning a florin. He was a man in no particular hurry, content to rely on an inheritance sufficient to allow him the leisure in which to pursue his intellectual interests.

This fecklessness determined the trajectory of Niccolò’s life. The fact that Bernardo was in arrears with his taxes meant that he was officially listed as a specchio (literally on the board), that is, barred from holding office. This was both a political and a social impediment since election to political office was the medium through which Renaissance Florentines measured their status.viii Even during the height of the Medici regime, when real power was concentrated in a few hands, politics still played a central role in the Florentine citizen’s life. The traditional legislative bodies continued to meet and debate in the Palazzo della Signoria and, to a large extent, social standing was determined—and useful connections made—by success in elections that were hotly contested even when the offices to which they led had been reduced to futility.

Thus Bernardo fell short on the most significant measure of a Florentine citizen’s social standing. His friendship with Chancellor Bartolomeo Scala reveals that the debt preventing him from holding elective office did not exclude him from polite society, but it did mean that he was always a marginal, even eccentric figure. This was the way Bernardo preferred things. His daily itinerary shows him puttering about his estates, tending in desultory fashion to the meager economy of his household, reading his books in quiet and generally enjoying his life as a cultured gentleman of modest means. This impression is only reinforced by the most ambitious undertaking recorded in the pages of his diary: the compilation of an index for a new edition of Livy’s monumental history of Rome.ixThe project, which required him to provide a list of “all the cities and mountains and rivers that are mentioned” in the text, involved a good deal of scholarly detective work, a task in which he was aided by the loan of a rare volume of Ptolemy’s world atlas. This was his true calling: to sift through ancient books in search of obscure facts—a pedant’s dream of paradise. It speaks to Bernardo’s priorities that the only payment he received for all his hard work was a copy of the precious volumes for his own library, a transaction that suggests the Florentine’s love of classical learning but an atypical disdain for hard cash.

While Bernardo’s diaries provide only the most grudging glimpses into his life, Niccolò’s own writing may shed some additional light. Niccolò’s satirical play Clizia includes a description of an elderly Florentine gentleman, one Nicomaco, who sounds a lot like his own father, a modest man of affairs and an amateur scholar: “He spent his time as a good man should,” recalls his wife, Sofronia.

He got up early in the morning, heard mass, bought the provisions for the day. Then, if he had business in the public square, in the market, with the magistrates, he attended to it; if he didn’t, he either joined with some citizen in serious conversation, or he went into his office at home, where he wrote up his ledger and straightened out his accounts. Then he dined pleasantly with his family, and after he had dined, he talked with his son, advised him, taught him to understand men, and by means of various examples, ancient and modern, showed him how to live. Then he went out. He spent the whole day either in business or in dignified and honorable pastimes. When it was evening, the Ave Maria always found him at home; he sat a little while with us by the fire, if it was winter, then went into his office to go over his affairs. At nine o’clock he had a cheerful supper. This ordering of his life was an example to all the others in the house, and everybody was ashamed not to imitate him.

The pleasant domesticity Sofronia describes offers a window onto the household in which young Niccolò grew to manhood. Particularly revealing is the passage in which Nicomaco guides his son’s moral development, drawing lessons from both ancient and modern examples just as Bernardo must often have done with young Niccolò.

Niccolò often complained about his own poverty, but he never blamed his father. In fact, father and son were cut from the same cloth. His admission that he knew nothing of “either the silk or the wool trade, or profits or losses,” could as easily have come from Bernardo’s mouth.

Father and son resembled each other in other ways, too. Both were sensitive about the family honor, which they guarded as a precious commodity even as they allowed more tangible assets to slip through their fingers. One incident stands out from the rather dry recitation of daily transactions that forms the bulk of Bernardo’s diary. It concerns the pregnancy of the serving girl Lorenza, who had been seduced, perhaps even raped, by one Niccolò d’Alessandro Machiavelli, a second cousin and neighbor in the Oltrarno, while she was living under Bernardo’s roof. Throughout the investigation of the incident and the bitter recriminations that followed, Bernardo seems motivated primarily by a desire to uphold his reputation. Typically for a man of his class, he is less concerned for the unfortunate girl than for his good name, which had been besmirched by the recklessness of a young relative.

The importance of the incident to Bernardo is reflected in the number of pages he devotes to it, but a more serious blow to the family’s reputation is passed over in silence. This concerned another relative, also a second cousin, by the name of Girolamo Machiavelli. Though a far more distinguished citizen—he was a professor of law at the University of Florence—Girolamo more seriously damaged the family name than the lecherous Niccolò d’Alessandro. In the summer of 1458, during one of the periodic struggles between the ruling clique and a faction seeking more democratic representation, Girolamo spoke out forcefully against the electoral controls imposed by Cosimo de’ Medici and his henchmen. This courageous act resulted in Girolamo’s arrest and, when he persisted in agitating against the regime, eventual imprisonment. This was a rare instance in the annals of the Machiavelli family when one of its members had stood apart from the anonymous crowd of respectable popolani, but the results of this bold act would not have encouraged his kinsmen to follow in his footsteps. Girolamo’s rashness only served to reinforce Bernardo’s aversion to politics.

A clue to Bernardo’s attitude toward his wayward cousin comes in Bartolomeo Scala’s De Legibus, where the author attributes to his friend the following bit of political wisdom, won presumably from hard personal experience: “For it often happens that men who are just and principled risk losing their good names and reputation because they are the innocent heirs or relatives of someone in disgrace.” But if Bernardo had actually vented these bitter feelings to his friend, he seems not to have heeded his own advice. In 1458, the same year that Girolamo spoke out against the government, Bernardo, then a mature man of thirty-three,x compounded his kinsman’s indiscretion by marrying Bartolomea, widow of the apothecary Niccolò Benizi. Other members of the Benizi family, though not Niccolò himself, had been implicated in Girolamo’s machinations against the government and had been among those exiled for sedition. It is unlikely that Bernardo intended by his choice of bride to make a political statement but the questionable association certainly did nothing to deter him. If this speaks well of Bernardo’s independence, it also confirms his impracticality.

Despite the association with a politically suspect family, Bernardo’s marriage was conventional in other respects. The Benizi were neighbors of the Machiavelli in the parish of Santa Felicità, and the young widow must have seemed like an eminently suitable match for the scholarly bachelor. “Above all else stick together with your neighbors and kinsmen,” wrote the Florentine patrician Gino Capponi, advice Bernardo apparently took to heart. In the fractious, violent world of Florence, such local alliances were often the best guarantee of family survival.

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Niccolò was the third child of the union between Bernardo and Bartolomea. He had two older sisters: Primavera, born around 1465, and Margherita, born 1468. Niccolò, born the following year, was the oldest son, and in this patriarchal society his arrival was a momentous occasion since it all but guaranteed that the family name would endure and prosper.xi The birth of a son after two daughters was particularly welcome since the cash-strapped Bernardo was already having difficulty salting away sufficient funds to provide the older girls with adequate dowries. To young Niccolò would fall the honor and the burden of carrying on the family name, a task made increasingly difficult by Bernardo’s carelessness.

As for Bartolomea, her individuality, like that of most of her sex in this male-dominated society, has largely been lost to history. Niccolò himself almost never mentioned his mother, and never provided any insight that would have put flesh on the bare bones of her biography. Bernardo makes frequent reference to “la mia donna” or “la Bartolomea” in his diary, but he leaves no room for the expression of feeling in the dry recitation of facts that make up his entries. What we can glean from these pages is that Bartolomea was a practical woman, a frugal housekeeper and helpmate to her husband in managing their modest properties. Only in the scandal over the pregnant serving girl does Bartolomea play a significant role; here, where sexual mores were involved and discretion required, a woman’s delicacy was used to elicit the truth where a man’s blunter approach might have proved ineffective. When it came to confronting the offending party and negotiating the financial settlement, however, Bernardo once again took matters into his own hands.

The only glimmer we have that Bartolomea was anything more than the typical middle-class housewife is the family tradition that when Niccolò was young she composed some religious verses for her son, a rare achievement in a world where many girls, even from good families, were barely literate. Employing her talents for pious ends reflects a conventional cast of mind, but the fact that she took the time and effort to write original poetry suggests a woman of more than ordinary ambition and ability.

It is difficult to determine Bartolomea’s contribution to Niccolò’s development. Like most Florentine mothers, she no doubt tended to his day-to-day needs while his father saw to his moral and intellectual development. Her apparent piety, in any case, made little impression on her son, whose career was marked by a disdain for priests and a contempt for religious hypocrisy. Niccolò may well have inherited from her his literary flair, but it is safe to assume that the conventional Bartolomea would have been horrified had she known the use to which he would put his talents.

It is easier to trace his father’s influence—not only the shared love of books and of history, but also the impracticality when it came to money, intertwined traits that give to both father and son the air of absentminded scholars whose heads are too filled with grandiose schemes to pay attention to the mundane details of daily living. But in the most important decision of his life—to enter government service and dedicate his life to the state—Niccolò ran in the opposite direction. It is above all Niccolò’s passion for public service that distinguishes him from his father. While Bernardo rarely set foot in the Palazzo della Signoria, center of Florence’s political life, Niccolò never felt more at home than within its crowded chambers, bent over his desk, where he handled much of the government’s correspondence. It is plausible to assume that his dedication to public service stemmed from a subconscious need to erase the political and financial failure of his father. Often the most patriotic men are those who feel politically and economically marginalized, who compensate for their social insecurity by more fiercely attaching themselves to the state that spurned them. Clearly, Niccolò set out upon a much different path than the one traversed by his father, but there is a strange sort of symmetry to their journeys. Niccolò’s passionate attachment to politics suggests a deep psychological need, perhaps born out of a sense that his father was a somewhat pathetic figure in the eyes of his peers.

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Given the copious documentation for his later life, much of it provided by Machiavelli himself, Niccolò’s early years remain frustratingly obscure. It is as if he walks onto the stage of history fully formed at the age of twenty-eight. What we know of his life before his memorable debut consists of a few dry facts indifferently recorded in Bernardo’s diary; one learns more from these pages about the two oxen he purchased to plow his fields than about his son. The copious correspondence, both personal and official, that opens an intimate window onto Machiavelli’s life begins only when he enters the public sphere. This is a pity, since Niccolò’s own voice—sardonic, insightful, and always fresh—would surely have vividly evoked the scenes of his childhood.

Even without the benefit of his unique perspective the view is fascinating enough. Machiavelli was a product of a remarkable city at the most remarkable period in its history. The small, independent Republic of Florence was something of an anachronism in an age of rising nation-states, a pygmy among giants, to paraphrase Machiavelli’s memorable description of his own family. Florence itself numbered no more than about fifty thousand souls—less than half its peak population reached in the mid-fourteenth century before the coming of the Black Death—while her Tuscan empire included merely a handful of small cities and rustic hamlets. The form of government that had evolved during the Middle Ages was republican; frequent elections and multiple, overlapping jurisdictions made for a lively, if inefficient, political system. The franchise was restricted to wealthy merchants and more modest artisans, but while the urban masses were excluded from any role in political life, Florence remained perhaps the most democratic state in Europe. At least in theory. In fact, the institutional weakness of the government invited its own subversion. Throughout the years of Machiavelli’s youth, real power was held by a single family—the fabulously rich Medici—and their cronies, a situation that elicited much grumbling and occasional violence from families who felt they had an equal claim to rule.

One way the Medici consoled their compatriots for the loss of any real say in their own government was by keeping the city prosperous and splendid. During his boyhood some of the greatest minds of the age were assembling in Lorenzo de’ Medici’s palace on the Via Larga, and many of history’s greatest works of art were taking shape in the studios about town: Sandro Botticelli, favored by the Medici family, was conjuring a mood of pagan sensuality in his Primavera (1478) and Birth of Venus (1482); Andrea del Verrocchio, churning out masterpieces of painting and sculpture assembly-line style, had just taken into his busy studio a talented young apprentice, Leonardo da Vinci, who startled the city with precocious works that surpassed those of his master; while his chief competitor, the equally industrious Domenico Ghirlandaio and his students—among whom was the young Michelangelo—frescoed the walls of the city’s churches with narratives in which holy miracles unfolded on the familiar streets of the city while its leading citizens looked on.

Nor was creativity confined to the artists’ studios. Impeding traffic and filling the streets with dust and noise were the massive building projects that proclaimed the taste, wealth, and vanity of the richest citizens, including the imposing palaces of the Pitti family, a few blocks to the south of the Machiavelli compound, and of the Strozzi, just beginning to rise near the Old Market. But if the bankers and merchants of Florence had abandoned medieval prohibitions against extravagant display, they still felt sufficiently uneasy to expiate their sins by spending lavishly on the city’s great ecclesiastical institutions. The interior of every sacred structure, from the Duomo to the local parish church, gleamed with gilded altarpieces and jewel-encrusted reliquaries paid for out of the profits of the city’s thriving wool and silk trade; bankers and lawyers vied with each other in the generosity of their bequests to charitable institutions, while others served the public good by opening the world’s first public libraries.

It was, in short, an exciting time to be alive. In many ways the city of Florence seemed to be the center of the universe, but there is little evidence that Machiavelli was deeply affected by the unparalleled visual culture of the city. Of greater interest to a young man whose gifts were literary and interests political were the remarkable poets and philosophers who congregated at the home of Florence’s leading citizen, Lorenzo de’ Medici. Not only was Il Magnifico a fine poet in his own right, but he attracted the greatest writers and thinkers of the day to the city, including the philosophers Marsilio Ficino and Pico della Mirandola, and the poet and scholar Angelo Poliziano. “This is an age of gold,” wrote Ficino in an understandable burst of pride, a verdict that history has largely confirmed.

Machiavelli grew to maturity in one of the most peaceful interludes in the turbulent history of Florence. Through the tireless diplomacy of Lorenzo de’ Medici the city became, in the words of Machiavelli’s friend and contemporary, Francesco Guicciardini, “the fulcrum of Italy”—the keystone in an elaborate system of alliances that prevented the rival states of Italy from destroying each other and that kept greedy foreigners from swooping in to pick up the pieces. In his History of Florence, Guicciardini summed up the mood of the city during the last decade of Lorenzo’s reign:

The city enjoyed perfect peace, the citizens were united and in harmony, and the government so powerful that no one dared oppose it. The people every day delighted in shows, revelries and other novelties; they were well fed, as the city was plentifully supplied with victuals, and all its activities flourished. Men of intellect and ability were contented, for all letters, all arts, all talents were welcomed and recognized. While the city within was universally enjoying the most perfect peace and quiet, without her glory and reputation were supreme because she had a government and a leader of the highest authority.

Fourteen years older than his friend, Machiavelli recalls that time with equal fondness, declaring that until Lorenzo’s death in 1492, “Florentines lived in very great prosperity . . . . For when the arms of Italy, which had been stayed by Lorenzo’s sense and authority, had been put down, he turned his mind to making himself and his city great.” Both men looked back on the years of their youth as an idyllic time that stood in stark contrast to the disorder that followed Lorenzo’s death when, in Machiavelli’s words,“discordant Italy opened into herself a passage for the Gauls and suffered barbarian peoples to trample her down.” Machiavelli’s pessimistic view of the human condition was forged when a peaceful childhood was violently shattered. The “ideal” ruler he conjures inThe Prince is not made for times of peace but is a grim figure at home in troubled times.

It would be a mistake to exaggerate the peacefulness of Florence during Machiavelli’s childhood. Even under Lorenzo de’ Medici’s firm guiding hand, there was plenty of political discord and even an occasional outburst of civic violence. It was only compared to the disastrous period that followed, that Lorenzo’s reign appeared to embody political and social harmony. Crucial to the development of Machiavelli’s political thought were the institutions that made Florence a laboratory of republican government and that fostered a vibrant, if often contentious, political climate. However firmly the Medici remained in control of the government, a daily round of commotions and recriminations formed the backdrop of daily life. Every citizen was a politician; debate did not end at the doors of the Palazzo della Signoria but spilled out onto the streets and piazzas, enlivening every conversation and coloring every relationship. Even during Lorenzo’s reign there was sufficient turmoil to stimulate the imagination of the budding political scientist. In fact it is hard to imagine the systematic study of politics originating anywhere else but here in Florence, where the average citizen expected to share in his own government and young boys were schooled in Cicero, Aristotle, and Livy to prepare them for the debates they would later hold in the Palazzo della Signoria.

Niccolò was nine years old when the bloodiest upheaval of Il Magnifico’s reign occurred—the Pazzi Conspiracy in which Lorenzo and his brother were set upon in the Cathedral of Florence. Lorenzo’s brother, Giuliano, was killed in the attack, while he himself was wounded. The assassination set off weeks of reprisals more sanguinary than anything seen for centuries in the streets of Florence. The sight of bodies being torn apart by angry crowds, as well as the anxiety provoked by rumors of foreign armies approaching the city gate, must have left a mark on the psyche of the young man, reminding him of the savagery that lay just beneath the surface of even this most cultivated city. This spasm of violence, as well as the lively factional quarrels that were more typical of Florentine political life, provided Niccolò with a unique opportunity to study the passions that drove men to compete in the civic arena, the thirst for power and the love of liberty, the tug of ambition and the belief in community, whose opposing imperatives kept the city at a constant boil.

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When it came to raising his children Bernardo shared the priorities of his compatriots. On May 6, 1476, Niccolò, who had just turned seven, began his formal education with “Maestro Matteo, master of grammar whose school is located at the foot of the Santa Trinità bridge, where he goes to learn to read his Donatello.”xii In 1480, the eleven-year-old Niccolò switched from studying Latin to studying “abacus,” that is, applied mathematics, an important subject in a town built on banking and trade. Niccolò’s education was typical of boys of his class, though it is clear that time spent delving into classical texts was more fruitful than time learning arithmetic. Like his father, Niccolò had no head for business, preferring to lose himself in a volume of poetry rather than pore through his own account books. Throughout his career and in his writings Machiavelli demonstrates a familiarity with the poetry, history, and philosophy of the ancient world, though there is little indication that, in addition to Latin, he mastered the newly fashionable but still esoteric Greek.xiii

For Florentine schoolboys of the Renaissance, being conversant with the major works of the classical past provided more than the basis of an elegant style or the dusty furnishings of the pedant’s mind. Dropping the names of Roman generals or quoting obscure Greek philosophers was essential to success as a public speaker, and success as a public speaker was essential to getting ahead in Florentine politics. The young read Scripture to prepare their souls for the world to come, but read Cicero, Aristotle, and Plato to learn how to tackle the responsibilities of civic life. The fact that Machiavelli largely rejected traditional religious doctrine did not mean that he rejected any ethical framework. “For when a child of tender years begins to understand,” he wrote in The Discourses, “it makes a great difference that he should hear some things spoken of with approval and some things with disapproval, since this must needs make an impression on him, by which later on his own conduct will be regulated in all the walks of life.”

Educated Florentines like Machiavelli found their moral bearings not by emulating the lives of the saints but by studying the deeds and adopting the attitudes of the ancient Greeks and Romans. “We call these studies liberal,” wrote the fifteenth-century pedagogue Pier Paolo Vergerio, “which are worthy of a free man: they are those through which virtue and wisdom are either practiced or sought, and by which the body or mind is disposed towards all the best things.” These studies were also called bonae litterae (good letters) or litterae humaniores (human letters) and the stories of great men and great achievements, as well as the salutary lessons to be learned from wicked men who received their comeuppance, provided a template against which to measure one’s own behavior. The constant back and forth between ancient history and current events that forms the structure of The Prince and the Discourses is not unique to Machiavelli, but is the product of an educational system that encouraged students to interpret the present in light of patterns set down long ago. Whenever he was in danger of succumbing to despair, Niccolò found solace in the great literature of the past. “Leaving the woods, I go to a spring,” he recalls in his famous letter to Francesco Vettori: “and then to one of the spots where I hang my bird nets. In my arm I carry a book: Dante, Petrarch, or one of those minor poets like Tibullus, Ovid. I read of their amorous passions and their loves and recall my own, and lose myself for a while in these happy thoughts.”

Machiavelli reached maturity without having done anything to distinguish himself from his peers. Florentines had a term for such young men: they were called giovani (youths), men who were no longer children but had yet to take on the adult responsibilities of marriage and child-rearing. Given the fact that Florentine men typically married in their late twenties or early thirties, they represented a large and potentially explosive element in the social fabric. Much of the violence that had plagued the city in earlier centuries can be attributed to these lawless young men who roamed the streets in search of adventure. One Florentine patrician summed up the general attitude toward these good-for-nothings who did little but “threaten bar keepers, dismember [statues of] saints, and break pots and plates.”

The young Niccolò Machiavelli was no worse, though not much better, than most of his peers. The best one can say is that while he can boast no record of achievement for these years, neither did he appear on the rolls of the Otto (the Eight), the police who patrolled the streets and attempted to curb the worst excesses of the giovani. Though he was certainly not living in monkish denial, much of his time was spent in study, either formally through the Studio, Florence’s university, or by delving into the numerous learned volumes in his father’s library.

In appearance the young Niccolò was unremarkable. He was of average height and possessed a wiry frame that would serve him well on many a harrowing voyage in service to his country and during his weeks of imprisonment, ordeals that would have overwhelmed a less robust constitution. His nose was aquiline, his lips thin, features that gave him a sharp and somewhat birdlike aspect. But the impression of hardness was relieved in conversation when his face lit up and his eyes sparkled with mirth. Unfortunately, there are no contemporaneous portraits of him, but those painted shortly after his death and based on the memories of people who knew him well emphasize the sardonic smile and curious expression that suggest both his keen intelligence and the impudent sense of humor that won him as many enemies as friends. In the best of them, there is a hint of kindness behind the wry smile, of sympathy as well as cynicism. Given the absence of a likeness taken from life, one must content oneself with the few descriptions available. The most precious comes from his wife, Marietta, who, upon the birth of their child, reported to her absent husband: “For now the baby is well. He looks like you, white as snow, with his head a velvety black . . . . Since he looks like you he seems beautiful to me”—a clue, if only an oblique one, as to his true appearance.

For a bright young man from a family with little money and little influence, literary talent was one of the few means of gaining entrée into elite circles. Early on, Machiavelli took the first tentative steps on the route to success already traveled by the poets Luigi Pulci and Angelo Poliziano. These talented but impecunious youths managed to parlay their gifts into a coveted seat at Lorenzo de’ Medici’s table, and Machiavelli saw no reason why he might not duplicate this feat of upward mobility. As part of this effort he dedicated one of his earliest works, a carnival poem titled “Pastorale,” to Giuliano de’ Medici, youngest son of Il Magnifico. This minor work offers a tantalizing clue that Machiavelli wished to join that glittering circle of poets and artists who congregated at the palace on the Via Larga. The unoriginal verses, in which local shepherds mingle familiarly with Apollo, Diana, and Jupiter, followed the erudite formula perfected by Angelo Poliziano, Lorenzo’s closest friend, and seem calculated to appeal to the refined tastes of his teenage heir. Given his father’s friendship with Bartolomeo Scala, another Medici client, it is clear that the Machiavelli were members, if only marginal ones, of the city’s dominant faction. Thus, despite later complications, Niccolò’s connection to the Medici began early. When in 1513 Machiavelli wrote to Giuliano de’ Medici from his prison cell, he was not an anonymous supplicant but an old acquaintance hoping to remind the young lord of happier times.

Perhaps Machiavelli’s failure to secure a place for himself at the Medici court owed something to his prickly personality. Though he never lacked for friends, those close to him knew he could be his own worst enemy. A few years later, when he was just beginning his career in the civil service, his friend Biagio Buonaccorsi had to intervene to prevent him from alienating his colleagues. “Write to Niccolò Capponi,” Buonaccorsi pleaded, “who grumbles and complains that you have never written him, and tell that asshole Ser Battaglione to ease up . . . . I spoke to Fantone about what I wrote you yesterday: he told me that four other lawsuits had been brought against you.” Everyone seemed to recognize his intelligence, but throughout his life he was hampered by his inability to flatter his superiors—a defect exposed most glaringly when his gift of The Prince was spurned by those who preferred servility to brilliance.

Even as he made a halfhearted stab at launching a literary career, Niccolò indulged the many pleasures the city had to offer. He was a frequent visitor to both the brothels and the taverns that lined the streets near the markets and that catered both to dissatisfied husbands and young men who were expected to spend the years between boyhood and married life sowing their wild oats. Even as a married man with young children, Niccolò made no effort to hide his taste for whores and the raucous conviviality of the tavern, habits he picked up early on.

His taste for low pleasures, however, did not distract him from his true passion. When he wasn’t at the whorehouse—or perhaps even when he was—his head was often buried in a book, most likely a volume of Greek or Roman history or one of the great triumvirate of modern Tuscans—Dante, Petrarch, and Boccaccio. Like Callimaco, the hero of his play La Mandragola, Machiavelli might have described spending his own youth “partly in studies, partly in amusement, partly in business.” His writing, rich in learned allusion but also earthy and filled with the crude vernacular of his native city, demonstrates an education that took place both in the classroom and on the streets.

At the age of twenty-eight there was little to distinguish Niccolò from countless equally directionless young men. He seemed content to live off his modest properties and spend his free time—of which he had plenty—in conversation with friends, and his money—of which he had less—on whores and gambling. “Because life is short,” he later wrote in the introduction to Mandragola,

and many are the pains

that every man bears who lives and stints himself,

let us go on spending and wasting the years as we will,

for he who deprives himself of pleasure

only to live with labor and toil

does not understand the world’s deceits.

He had by this time a fair amount of experience in “spending and wasting.” Half his life was over and he had little to show for it.

But despite the rather aimless course his life had taken so far, he burned with ambition. This, too, was encouraged by the get-ahead mentality of Florence. As one influential educational text claimed, men are motivated primarily “by eagerness for praise and inflamed by love of glory,” words Machiavelli will paraphrase in The Prince. He wanted to make his mark, to achieve something that would cause his name to be remembered by future generations. Not particularly well connected or well heeled, he lacked only the opportunity to demonstrate the singular talents of an obscure young man of modest means.


i It is difficult to classify Florentine families like the Machiavelli using familiar terms, either those that come out of the traditional divisions of feudalism or those that come out of modern sociology. They had ties to the feudal aristocracy, but were deemed popolani, i.e., men of the people, or members of the prosperous merchant class. They were aristocrats in the sense that they belonged to the governing class, but they were distinguished from “magnates,” who were barred from holding office. The Florentine ruling class combined elements of bourgeois merchant values and aristocratic privilege.

ii In the fifteenth century the city was divided into four main quarters: San Giovanni, Santa Croce, Santa Maria Novella, and, across the river, Santo Spirito. These quarters were each further subdivided into four gonfaloni, forming the sixteen traditional districts of the city. The gonfaloni, or banners, were the heraldic devices under which medieval Florentines marched into battle. Though by the time of Machiavelli’s birth the militia was a thing of the past, these ancient divisions still had political significance. The Sixteen gonfalonieri, or bannermen, were among the leading officials of the city. Florentines might also refer to their neighborhood by the name of the local church.

iii Farinata degli Uberti is one of the most memorable characters in Dante’s Inferno, where the poet places him among the heretics. When Dante, a prominent Guelph, describes his family, Uberti replies: “They were fierce enemies to me and to my forebears and to my party, so that twice over I scattered them” (Inferno, X). Apparently hatred between Guelph and Ghibelline was intense enough to be continued in the afterlife.

iv True to form, the Blacks also split into rival factions once they had driven their rivals from the city. The civil war led by the Cerchi and Donati families chronicled by Dino Compagni in the early fourteenth century was between two factions of the Black Guelphs.

v The original Ordinances included seven recognized major and nine minor guilds. The major guilds were comprised of mostly large-scale merchants and capitalists, while the nine minor guilds were mostly comprised of artisans, small tradesmen, and shopkeepers.

vi Between 1280 and 1530, the Machiavelli name turns up 130 times among the Three Majors. Compared to the record of powerful clans like the Medici, whose members served 196 times over the same period, this was a more than respectable showing (see Online Catasto of 1427).

vii The tax roll (Catasto) of 1427 is one of the best-studied documents of Renaissance Florence. Of the 9,780 households listed, including eleven bearing the Machiavelli name, only 137 (approximately one in 70) had an assessed worth exceeding 10,000 florins. Niccolò di Buoninsegna Machiavelli, Niccolò’s grandfather, had a declared net worth of 1,086 florins, all of it in the form of real estate. This placed him in the upper third in terms of total wealth, but far behind such plutocrats as Palla Strozzi (162,906) or Giovanni di Bicci de’ Medici (91,089), grandfather of Lorenzo the Magnificent (see Online Catasto of 1427).

viii Bernardo’s tax problems may also have been the source of a curious incident in Niccolò’s career when his enemies tried to claim he was ineligible for government service (see chapter 8). Ironically, his debt may also have interfered with his ability to make a living since those declared a specchio were also barred from practicing as notaries, a profession for which his legal training qualified him (see Atkinson, Debts, Dowries, Donkeys, 43).

ix This project of Bernardo’s was particularly significant for Niccolò, since his most sustained work of political writing is his commentary on this work of ancient history, his Discourses on the First Ten Books of Titus Livius.

x This was not an unusual age for a Florentine male to be married. While girls tended to marry in their late teens, boys were allowed a period of irresponsibility before settling down to raise a family.

xi It would be another six years before another child lived beyond infancy, Niccolò’s younger brother Totto. There was also a stepsister, Lionarda, born in 1457, Bartolomea’s only child with Niccolò Benizi. She did not grow up in the Machiavelli household and little is known of her.

xii This refers not to the famous Florentine sculptor but to Donatus, author of a Latin grammar that dates back to ancient times and was used as the initial primer for students of the Renaissance.

xiii Machiavelli often quotes Plato and Aristotle and was clearly familiar with their work and with the history of ancient Greece, but he always seems to have relied on Latin translations of their most important writings. Fluency in Latin would have been a normal acquisition for someone of his time and education, while knowledge of Greek continued to be reserved for true scholars. (See Villari, The Life and Times of Niccolò Machiavelli, I, 239ff for a fuller discussion.)

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