Biographies & Memoirs



“I believe that the following would be the true way to Paradise—learn the way to Hell in order to flee from it.”


MACHIAVELLI WAS A PESSIMIST BY CONVICTION, BUT his gloomy outlook did little to dampen his zest for life. Indeed, it was his honest appraisal of his own appetites that convinced him that any political theory worthy of the name must account for man’s bestial nature. Like many people with a jaundiced view of the world he did not see why this verdict should stop him, or anyone else, from enjoying himself while he could. Even at his lowest moments he never succumbed to despair, and when he was shut out of public life he continued to peer beyond the constricted horizons of his existence. While in the country he collared those who traveled the busy road that passed by his house and pressed them for news of the wider world; in the city he always plunged into the middle of heated discussions over the results of the last election or the latest diplomatic dustup. He was one of those gregarious men who combine a cynical disdain for human nature in the abstract with genuine warmth for people in the flesh. The more Fortune rebuffed him, the more he was inclined to see the comic side of life, discovering in laughter the best antidote to what ailed him. As he wrote to Francesco Vettori, quoting lines of Petrarch:

So if at times I laugh or sing,

It is because only thus

May I give voice to my anguished cries.

It was when his suffering was at its most acute, as in those desperate weeks spent in the dismal Le Stinche prison, that he tended to see the farcical side of life most clearly, consoling himself by composing humorous verses and meditating on the folly of existence. Work gave his life meaning, and he filled the empty hours by picking up his pen and doing battle with the Muses. It is no coincidence that it was in prison that he first referred to himself as a writer, complaining to Giuliano de’ Medici, “so the poets are treated!”

Plunging himself into his writing was not the only way he dulled his pain. While he was shackled in his dank cell he longed for the fresh air and simple comforts of Sant’ Andrea, but only a few weeks after his release the four walls of his house seemed only a little less confining. He sought distraction in the local tavern, just across the busy road that led to Rome, or, tiring of the boisterous atmosphere, he would tuck a book of poetry under his arm and seek a shady spot to read and spend some time alone with his thoughts. When rustic diversions grew stale he made the ten-mile journey on foot into the city, where he met old friends and caught up on the latest gossip.

Bored and frustrated, Machiavelli found consolation in the arms of women. “[E]very day we go to the house of some girl to restore our vigor,” Machiavelli tells Vettori, proof that poverty never pinched so tightly that he could not afford to indulge in those low pleasures to which he had become accustomed.

It is hard not to sympathize with Marietta, forced to stay home with the children during the many nights her husband was in town restoring his vigor in the brothels near the Old Market, while observing that, at least in this regard, Machiavelli was no worse than most of his peers. Florentine wives were expected to patiently tend to hearth and home while their husbands conducted their business and took their pleasures in the wider world. This inequity continued inside the home, where the husband possessed almost unlimited authority over his submissive bride. By the standards of the day, Machiavelli was not an inconsiderate master, his main fault consisting in neglect rather than cruelty. For over twenty-six years of married life, Marietta kept the household running smoothly and saw to the children’s basic needs, ensuring that her husband had the leisure and peace of mind to meditate on weightier matters.

Marietta’s personality, like that of most of women of the time, remains largely hidden from view. Even with limited information, however, it is clear that Machiavelli’s wife was no shrinking violet. She wasn’t shy about voicing her displeasure when her husband was away for extended periods, complaining vociferously to the friends he commissioned to drop by and see how she was doing. “Lady Marietta curses God, and says she has thrown away both her body and her goods,” wrote Biagio Buonaccorsi during one of Machiavelli’s many absences, grumbling that he was forced to bear the brunt of her temper since the real object of her wrath was nowhere to be found.

Machiavelli’s fictional portrayals of Florentine wives suggest an unromantic view of the marital state, but his unflattering depictions of the female sex—including his portrayal of Fortuna as a cruel and inconstant woman—reflect the ubiquitous misogyny of the age rather than any particular disillusionment with his own marriage. In his novella The Fable of Belfagor, Machiavelli’s title character is a demon sent by Pluto to investigate whether it is true, as he has heard, that wives are the source of all men’s ills. After testing this thesis by marrying a Florentine woman named Onesta, the demon Belfagor quickly returns to the Underworld, claiming he prefers Hell to the torments of the “marriage yoke.”

Fortunately, we have more to go on than this bitter assessment. More attractive than the nagging and unreasonable Onesta is Sofronia from his play Clizia, a long-suffering woman who is far more sensible and appealing than her lecherous husband, Nicomaco. In fact Machiavelli clearly identifies as much with the wife as with the husband, placing in her mouth cynical views that he might have espoused himself. Told of a monk who had helped a woman conceive, the sharp-tongued Sofronia replies: “A fine miracle, a monk making a woman pregnant! It would be a miracle if a nun should make her pregnant.” Even more intriguing in view of Machiavelli’s own family life is Sofronia’s monologue in which she recalls how Nicomaco’s infatuation with a young girl meant that “his affairs are neglected, his farms are going to ruin, his business ventures fail”—a poignant picture of a household turned upside down by a middle-aged man’s philandering. The fact that Machiavelli gives the foolish husband a name so similar to his own shows either admirable self-awareness or a deplorable lack of conscience about his own moral lapses.

Marietta’s greatest complaint about her husband was that he was so often absent, which suggests she derived a certain amount of pleasure from his company. If Niccolò and Marietta were never soul mates, they remained attentive to each other’s needs. Whenever they were apart, each inquired solicitously of the other’s health, and just as Marietta made sure to supply her absent husband with everything he needed to make his journeys more comfortable, Niccolò commissioned his friends to look after his family’s needs back at home. It is also apparent that despite prolonged absences and frequent infidelities on Niccolò’s part, they shared their bed for a considerable time. By 1514 they had six surviving children: four sons (Bernardo, Lodovico, Guido, and Piero), and two daughters (Primavera and Bartolomea).

Machiavelli was an affectionate father, though he was too restless and ambitious to find in family life an adequate substitute for his blighted career. In fact the crowded, laughter-filled house in Sant’ Andrea reminded him of responsibilities he could barely meet. One of the most extended glimpses into Machiavelli’s intimate feelings comes in a letter he wrote late in life to his son Guido:

My dearest Guido. I received a letter from you that has given me the greatest pleasure, especially since you write that you have quite recovered; I could not have had better news. If God grant you and me life, I believe that I may make you a man of good standing, if you are willing to do your share . . . . But you must study and, since you no longer have illness as an excuse, take pains to learn letters and music, for you are aware how much distinction is given me for what little ability I possess. Thus, my son, if you want to please me and bring profit and honor to yourself, study, do well, and learn, because everyone will help you if you help yourself.

Since the young mule has gone mad, it must be treated just the reverse of the way crazy people are, for they are tied up, and I want you to let it loose . . . take off its bridle and halter and let it go wherever it likes to regain its own way of life and work off its craziness. The village is big and the beast is small; it can do no one any harm . . . . Greet Madonna Marietta for me and tell her I have been expecting—and still do—to leave [Imola] anyday; I have never longed so much to return to Florence as I do now, but there is nothing else I can do. Simply tell her that whatever she hears, she should be of good cheer, since I shall be there before any danger comes. Kiss Baccina [Bartolomea], Piero, and Totto [Machiavelli’s brother], if he is there. I would dearly appreciate hearing whether his eyes are any better. Live in happiness and spend as little as you can. And remind Bernardo, whom I have written to twice in the last two weeks and received no reply, that he had better behave himself. Christ watch over you all.

The conventional sentiments—fatherly tenderness combined with sensible admonitions to study hard, as well as his surprising empathy for a poor, crazed animal—belie the sinister reputation of the writer of The Prince. In fact for all his radical notions, Machiavelli was a rather ordinary man, loving if sometimes selfish, pursuing his own pleasures even as he fretted over his wife’s health and his children’s prospects.

The other family member who played an important role in Machiavelli’s life was his nephew Giovanni Vernacci, son of his sister Primavera. Primavera had died when Giovanni was still a boy, and Machiavelli had taken him in. He looked after Giovanni’s interests in Florence while he was away on business, and regarded him as another son. Giovanni, for his part, returned his uncle’s affection, addressing him as “Honored and dearest foster father.” Machiavelli responded in kind, telling him, “aside from my own children, there is no man I cherish more than you.”

But family was never the focus of Niccolò’s attention or even the center of his emotional life. One of his favorite haunts was the shop of Donato del Corno, “at the sign of the horn,” a place with a reputation as a homosexual hangout. It is unclear whether Machiavelli himself indulged in an occasional illicit tryst with boys (a vice regarded by some as peculiarly Florentine), but he was certainly tolerant of such behavior in his friends.i Machiavelli’s easygoing attitude was widely shared by men of his class. More prudish Florentines may have condemned such behavior as unnatural—and on occasion those caught in the act were severely punished—but they did not regard those who engaged in same-sex encounters as men who differed in any fundamental way from their peers. Homosexuality was just another vice, like masturbation or visiting prostitutes, and not a deep-seated expression of one’s true nature.

In any case, it is clear that women remained the focus of Machiavelli’s sexual attention. He was always an unapologetic sensualist. Hypocrisy was far worse than promiscuity in his view. “It is certainly an amazing thing to contemplate how blind human beings are when it comes to their own sins, and how fiercely they persecute those they don’t possess,” Machiavelli wrote to Vettori. Commiserating with his friend after a mild scandal erupted over his sexual peccadilloes, Machiavelli continued:

And to put it more clearly, given your austere disposition, if it had been I—who enjoy as much as any man the caresses of a woman—who had stumbled into the room: as soon as I’d seen what was up, I would have said: “Ambassador, you will make yourself ill; I don’t think you’re allowing yourself sufficient diversion. Here there are neither boys nor girls. What kind of whorehouse is this anyway?

Professional disappointment drove Machiavelli to seek distractions outside his own home. After 1512, he plunged into a series of torrid love affairs. Some of the objects of his passion were courtesans—like the curly-haired beauty Lucretia, known as La Riccia, with whom, an anonymous accuser claimed, he had engaged in “an unnatural sex act,” or the singer Barbera Raffacani “who,” according to Guicciardini, “like all her kind, seeks to please all and to seem rather than to be.” Others, like the sister of his neighbor Niccolò Tafani, were women of respectable birth.ii

Machiavelli found in these women’s beds a sexual excitement he no longer found with Marietta, but there was more to these encounters than physical release. Lust sometimes led to love, an emotion that both elated and exhausted him, as he reveals in an unusually lyrical passage from a letter to Vettori:

[W]hile in the country I have met a creature so kind, so graceful, so noble, both in nature and in bearing, that neither my praise nor my love would be as much as she merits. I should tell you, as you told me, how this love began, how Love caught me in his nets, where he spread them, and what they were made of. You will see that they were nets of gold, woven by Venus and hung among the flowers. They were so soft and gentle that even though a hard heart could have severed them, I had no wish to do so . . . . Suffice it to say that, although I am nearly fifty [he was then only forty-five], I am no longer bothered by the heat of the day, nor am I exhausted by the rough roads or frightened by the dark hours of the night . . . . I have left behind all my troubles, and nothing in the world would induce me to seek again my freedom. I have banished, then, any thought of matters great and grave, and no longer take delight in reading of the ancients or of more recent doings. All has been transformed into sweet dreams.

It is hard to believe that even a few years earlier Machiavelli would have allowed himself to be so thoroughly unhinged by a woman’s charms. Love, in this case, was an obsession that took hold in a man who had little else to occupy his mind and engage his heart.

•  •  •

Vettori, who was used to his friend’s many moods, suspected that talk of abandoning his life’s work for the “tender thoughts” of love was a sign of despondency, and he tried to lift Machiavelli’s flagging spirits by engaging him in “the old game” of geopolitical chess. With the King of France vying with his old enemies the Spaniards for possession of Milan, what policy should the Pope adopt? “With your prudence and intelligence and experience, you will be better able to understand what I have tried to say,” the ambassador wrote, playing on his friend’s vanity. And Machiavelli, showing that love had not entirely addled him, rose to the bait, delivering in reply a lengthy and carefully reasoned dissertation on the current balance of power.iii

Machiavelli was amused when he saw how easily Vettori steered him from one obsession to another, but he also thought he detected in his fleeting passions a larger truth about human nature:

Anyone who read our letters, my honored friend, and saw their variety, would be greatly astounded, because it would appear at first that we were serious men, deeply engaged in serious matters, and that in our breasts resided nothing that did not bespeak sincerity and grandeur. But then, turning the page, he would discover that these same men are frivolous, inconstant, lascivious, and absorbed in trivial things. And if this manner seems to some undignified, to me it seems laudable: because we are imitating nature, which itself is changeable, and whoever imitates nature cannot be blamed. And though we have grown accustomed to dealing with such varied matters over the course of several letters, this time I wanted to do it in just a single one, as you will see if you read the next page.

This lighthearted letter reveals the cast of Machiavelli’s thought as clearly as any of his more substantial works. “[W]e are imitating nature, which itself is changeable, and whoever imitates nature cannot be blamed,” he tells Vettori, as succinct an exposition of his philosophy as one will find in all his writings.

Although Machiavelli enjoyed the pleasures of the flesh, he could never be satisfied without the stimulation of the mind. He called Love “that little thief,” and even in the heat of erotic passion he strained against invisible bonds. “I fear for my liberty,” he wrote Vettori about his latest lady love, “nor can I conceive of any way to unchain myself.” But even as he wrote these words he was seeking a key that would unlock Venus’s enervating trap. He craved mental exercise, something apparently more difficult to come by in Florence than carnal knowledge, and he prowled the streets in search of intellectual equals, men with whom he could share the ideas that were churning in his fertile brain.

By the winter of 1515, Machiavelli had reached rock bottom. It was a period when, as he confided to his nephew, “fortune has left me nothing but my family and my friends.” A few months earlier he had hoped that, through the strenuous efforts of Francesco Vettori’s brother Paolo, he might finally find a position with Giuliano de’ Medici. But this wish was shot down by the papal secretary, Piero Ardinghelli, who urged Guiliano to “write to [Paolo] on my behalf that I advise him not to have anything to do with Niccolò.”

Machiavelli took this latest setback philosophically, telling himself that since Fortune’s wheel never ceased its motion he had only to wait until it turned again. And, in fact, with the coming of spring a few green shoots began to appear in an otherwise bleak landscape. It was during that expectant season that he began attending informal gatherings at the garden belonging to the Rucellai family. Here, some of Florence’s most brilliant and learned men came to dine at their host’s well-appointed table and discuss erudite matters,iv and here among the cypresses and laurel Machiavelli rediscovered the camaraderie he missed from his days in the Chancery.

Machiavelli quickly shook off the cobwebs that clung to him after years of forced retirement and showed he had lost none of his acerbic wit. He was made much of by the mostly younger gentlemen he began to call his “noontime friends” (presumably to distinguish them from the more disreputable companions of the midnight hour), who regarded him as something of a mentor, while he was reinvigorated in their youthful company. With their encouragement he picked up The Discourses, begun a couple of years earlier and then set aside, dedicating it to his newfound friends of the garden Cosimo Rucellai and Zanobi Buondelmonti.

In exchanging the low company of Donato del Corno’s shop for the more rarefied atmosphere of the Rucellai gardens, Machiavelli was moving up in the world. Not only was he now warmly received by Florence’s cultural elite, but he found himself nearer the centers of power than he had been for years. Drawn to this luminous oasis of thought and culture as a moth to a flame, Machiavelli discovered the pleasures and the perils of hovering too close to the light.

The Orti Oricellari, as the Rucellai gardens were called, had for decades stood at the heart of the city’s intellectual life.v The piece of land, near the Porta al Prato just inside the city’s western walls, had originally been purchased by Bernardo Rucellai at the end of the previous century. At the time, the wealthy Bernardo had been among the most influential citizens of Florence, promoted to the highest ranks after marrying Lorenzo the Magnificent’s sister, Nanina. But his political fortunes waned with the expulsion of his wife’s family and with the rise of the popular government, to which he was vehemently opposed. Disillusioned with politics, Bernardo turned his energies toward less practical pursuits. Behind the high walls of his impeccably landscaped garden he created a green retreat in the bustling urban center, and established an informal academy where the best philosophers and writers could converse while wandering arm in arm among the exotic shrubs and drawing inspiration from the antique statues scattered among the foliage.

But while Bernardo withdrew from active participation in government, he had not entirely abandoned politics. In Florence the line between intellectual theorizing and political action was always porous, and those humanists who congregated in Bernardo’s gardens naturally tended to reflect their host’s oligarchic prejudices. During the final years of the Soderini government, the Orti Oricellari became a hotbed of pro-Medici agitation. Bernardo and his friends, in fact, were instrumental in facilitating the Medici’s return, secretly funneling funds to Giovanni, Giuliano, and their allies.

Given the fact that no one was more closely associated with the departing Gonfaloniere than Niccolò Machiavelli, it is not surprising that for years he was shunned by the luminaries who congregated in the Rucellai gardens. But by 1516 the mood in the city had changed and the nature of the conversations at the Orti changed along with it. Bernardo had died in 1514 and his role as cultural impresario was assumed by his grandson Cosimo, a more amiable and broad-minded As Machiavelli described him, the frail Cosimo appeared to have been a scholarly and courteous host. “I never met anyone,” he recalled some years after Cosimo’s death, “whose heart was more disposed to great and generous actions.”

Perhaps more importantly, the resentments that smoldered in the first days following the overthrow of the Soderini government had cooled with time. The Medici, with Giovanni now sitting on the papal throne, were so firmly ensconced that the ottimati, the Rucellai included, no longer felt threatened by a rising tide of populist feeling. In this more relaxed atmosphere, under the aegis of the urbane Cosimo, thoughts turned from contemporary politics to more arcane matters.

It is unclear exactly how Machiavelli first fell in with his “friends of the cool shade.” Many, like Anton-Francesco degli Albizzi and Zanobi Buondelmonti, belonged to the great magnate families of the city, and in their company the middle-aged former Second Chancellor must have cut a somewhat shabby figure. But by now his writings, which had been circulating for years among his friends—particularly the manuscript of the still unpublished Prince and perhaps a rough draft of The Discourses—were attracting a wider audience and exciting comment among a new generation of intellectuals. While wealth counted for something among the habitués of the Orti, a brilliant mind more than made up for a suspect pedigree. Machiavelli was welcomed into their lunchtime gatherings where, in his threadbare robes, he held forth surrounded by an admiring crowd of fashionable youths—no longer the disgraced civil servant but a modest legend, a brilliant conversationalist, wit, and provocateur.

Machiavelli’s attendance at these largely literary gatherings also reflects a subtle change in his own expectations. Though he continued to angle for a government job—and believed his well-connected friends might prove useful in this regard—the fact that he became such a regular at the Rucellai gardens shows he had come to terms with his role as a man of letters. It was as a writer and intellectual, rather than as the former Second Chancellor (a part of his résumé that might have hurt more than it helped), that Machiavelli was included in this sophisticated company.

•  •  •

Machiavelli has left us a description of these gatherings in The Art of War, which purports to be an account of a conversation between the commander of the papal army, Fabrizio Colonna, and Cosimo Rucellai that took place in the Orti Oricellari in the summer of 1516vii:

Fabrizio freely accepted the invitation and came to the gardens at the appointed time, where he was received by Cosimo, and some of his most intimate friends—among whom were Zanobi Buondelmonti, Battista della Palla and Luigi Alamanni. These young men—whose virtues and good qualities are so well known to everybody that it would be altogether unnecessary to say anything here in praise of them—were very dear to Cosimo, were of the same disposition, and were engaged in the same studies.

To be as brief as I can, then, Fabrizio was regaled there with every possible demonstration of honor and respect. But after the end of the entertainment and usual formalities, which generally are few and short among men of sense who are more desirous of gratifying the rational appetite, and since the days were long and the weather intensely hot, Cosimo under a pretext of avoiding the heat, took his guests into the most retired and shady part of the gardens. Then, when they had all sat down—some upon the grass, which is very green and pleasant there, and some upon seats placed under the loftiest trees—Fabrizio said it was a most delightful garden.

While the conversation that follows—in which Machiavelli uses Colonna as the mouthpiece for his own theories of modern warfare—is pure invention, it was based on those afternoons spent in the shade of Cosimo’s garden.

As a denizen of the Orti, Machiavelli reinvented himself. He greeted the change in career with a rueful smile and a shrug. The writer’s life was not his first choice, but after years of frustration at least it offered him an outlet for his talent and ambition. A most revealing insight into his state of mind comes at the beginning of The Discourses, dedicated “not to those who are princes, but [to] those who, on account of their innumerable good qualities, deserve to be; not those who might shower on me rank, honors and riches, but those who, though unable, would like to do so.”

How different this is from the dedication to The Prince! All hints of servility vanish as Machiavelli addresses his colleagues rather than his master. These were men with whom he had a relationship based on mutual respect rather than on need. In fact, in praising Rucellai and Buondelmonti, Machiavelli takes a swipe at the de facto lord of the city. We are living in a topsy-turvy world, he suggests, in which private citizens are fit to be kings, while those who actually rule deserve to molder in obscurity.

Machiavelli’s disillusionment with Lorenzo de’ Medici, following a similar disappointment with his cousin Giuliano, was not based merely on personal frustration. True, the arrogant princeling had spurned all his overtures. (There is even a story, probably apocryphal, that when Machiavelli finally worked up the nerve to present The Prince, the Medici lord ignored him in favor of a client who had come with a pair of hunting dogs.) More importantly, by 1517 the man whom Machiavelli had imagined as Italy’s savior had demonstrated he was as selfish, arrogant, and incompetent as his father, the hapless Piero. In 1514, shortly after completing The Prince, Machiavelli wrote that the Medici heir “has filled the entire city with high hopes,” but in the space of only a year or two Lorenzo had squandered all that goodwill. While his uncle the Pope urged him to act modestly, he paraded about the city surrounded by a large entourage of equally arrogant young men. He preferred to go hawking rather than attend to state business, and otherwise did his best to make himself obnoxious to his compatriots. Disgusted with the current state of his beloved republic, and disappointed in his own hopes, Machiavelli, like most of the men who enjoyed the hospitality of Cosimo Rucellai, turned inward, meditating on the vast cycles of history while leaving the here and now to take care of itself.

Inspired by the witty conversations of the garden Machiavelli composed a satirical poem (based loosely on a novella by the Roman writer Apuleius) titled The Ass, which he read aloud at their meetings as the verses flowed from his pen. Though a decidedly secondary work, The Ass captures Machiavelli’s mordant wit better than his more learned treatises. Placing himself in the character (and the body) of a beast, the author offers his insights on the human animal. “And our ass,” he writes in a barely disguised autobiographical allegory, “who has trodden so many of the stairs of this world to observe the mind of every mortal man . . . heaven itself could not prevent him from braying.”

A letter he wrote to one of his new friends, Luigi Alamanni, in December 1517, shows just how much he had begun to relish his new role as a literary wit: “These days I have been reading Ariosto’s Orlando Furioso. The poem on the whole is fine, with many marvelous passages. If you see him there [in Rome], give him my regards and tell him that my only complaint is that, having mentioned so many poets, he has left me out like a dog, and that he has treated me shabbily in his Orlando, something I would never do to him in my Ass.” Of course Machiavelli’s complaint is made in jest, but like his ironic barb in the first of his prison sonnets (“so the poets are treated!”) his self-deprecating humor carries a real sting. By now he was well acquainted with disappointment—as he said in his poem, “I do not mind bites or blows as much as I did, having come to resemble the [ass] I sing”—and if Ariosto chose to overlook his contribution to letters, he had come to expect nothing better.

Machiavelli’s literary gifts were comic rather than tragic, which might seem odd given his bleak view of the human condition. But comedy is the art of low expectations. While tragedy implies at least the potential for nobility in human nature, comedy traffics in the baser human instincts, territory with which Machiavelli was intimately acquainted. Machiavelli would not have been a comic genius had he thought well of people, but he would also have failed to elicit laughter had he condemned them too harshly. The comedian must be attuned to human frailty, but also possess the gift of empathy. The characters Machiavelli creates in his literary works are all flawed, to say the least. But so is he—and so are we. To say that his conception of the world is comic does nothing to minimize the seriousness of his message. Machiavelli’s pessimism is tempered by acceptance, his illumination of the dark corners of the human heart accompanied by an appreciation for the richness and unpredictability of our shared experience. Even his most scholarly essays have a satirical edge, and his most farcical satires a serious point. In all his writing cynicism is married to a generosity of spirit; the foibles of the human animal are exposed, but his response to this parade of deformities is not outrage but rather amused affection.

Machiavelli’s skepticism feeds his humanity. Even his harshest prescriptions are of limited scope since he has no faith in utopian schemes. Those who have used Machiavelli’s concept raison d’état to justify gulags and concentration camps misunderstand the nature of his theories. States, he insists, function best when they allow for dissent and accept the legitimacy of competing interests. In attempting to improve the human condition we can at best effect only marginal and temporary changes. Machiavelli is the natural enemy of anyone who, like Savonarola or Lenin, would seek to perfect the human condition.

Machiavelli’s genius shines through in his comedic masterpiece La Mandragola (“The Mandrake”), often called the greatest comedy in the Italian language. In this sex farce Machiavelli’s sharp wit is on full display, but also his humanity, his ability to probe the depths of the human soul and find both good and bad. We laugh at the ridiculous antics of the characters onstage, and the laughter is more heartfelt because we recognize ourselves and our neighbors in their weakness and self-deception. Better him than us, we think as we watch Messer Nicia, the foolish husband of the beautiful Lucretia, unwittingly facilitate his own cuckolding with Callimaco, her handsome young lover. The old man is crass as well as gullible, but his motive—to have his wife bear him a son who will carry on the family name—is one we can all sympathize with. Siro, the clever servant, and Frate Timoteo, the corrupt priest, are stock comic types, and the plot, hinging on the supposedly miraculous properties of a potent but deadly fertility potion (concocted from the mandrake root), is formulaic, but Machiavelli weaves the tale so deftly and molds his characters with such skill that the play pulses with life.

La Mandragola is both hugely entertaining and sharply revealing of the man who wrote it. Machiavelli begins by speaking directly to the audience, a strategy that makes the author a character in his own play:

The writer is not very famous, yet if you do not laugh, he will be ready to pay for your wine. A doleful lover, a judge by no means shrewd, a friar living wickedly, a parasite the darling of Malice will be sport for you today.

And if this material—since really it is slight—does not befit a man who likes to seem wise and dignified, make this excuse for him, that he is striving with these trifling thoughts to make his wretched life more pleasant, for otherwise he doesn’t know where to turn his face, since he has been cut off from showing other powers with other deeds, there being no pay for his labors.

Having exposed himself to the potentially jeering crowd, he then proceeds to caution his listeners that he can give as good as he gets:

Yet if anyone supposes that by finding fault he can get the author by the hair and scare him or make him draw 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 whereis heard [i.e., where Italian is spoken] does he stand in awe of anybody, even though he plays the servant to such as can wear a better cloak than he can.

Here is Machiavelli as he must have appeared in life, in Donato del Corno’s shop or in the garden of the Rucellai—both pugnacious and self-deprecating, telling tales at his own expense the better to disarm as he aims a few well-timed blows in your direction. His life is wretched, he admits, and his art little better. He has been reduced to hack work, forced to traffic in low comedy since he has found no market for his pearls of wisdom. But don’t think for a minute that because he’s down on his luck he’ll stand for any nonsense. Finding fault was his earliest art and, like writers in every age, he knows how to wound and even kill with the sharp point of his pen.

Machiavelli’s world is chiaroscuro, a shadowy landscape redeemed by sporadic incandescence. He begins the play with a song that captures his tragicomic view of life:

Because life is short

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,

and what ills and what strange events

crush almost all mortals.viii

He was no mindless hedonist, but Machiavelli was even more scornful of those ascetics who thought that the solution to all life’s problems was to mortify the flesh. Life is hard enough, he insists, without denying yourself the pleasures it offers. When the virtuous Lucretia finally yields to her lover, she offers a telling rationale. “Your cleverness,” she explains to Callimaco, “my husband’s stupidity, my mother’s folly, and my confessor’s rascality have brought me to do what I never would have done myself.” Like the clever prince, Lucretia applies a flexible morality to a corrupt world. For Lucretia to honor her marriage vows when her husband is both stupid and inconsiderate makes no more sense than a prince keeping his word with enemies who have no intention of keeping theirs.

Among the most memorable characters in the play is the greedy Frate Timoteo. Happy as he is to sell his services to the highest bidder, Timoteo is not simply a caricature. In a rare moment of self-awareness he confesses that “[I] put my finger in a sin, then . . . my arm and my whole body.” Machiavelli, with his usual psychological penetration, depicts the monk as a man who is aware of his errors but lacks the will to correct them. Wondering aloud how he got himself in this predicament he concludes, in words that echo certain passages in The Prince, “many times one comes to harm by being too accommodating and too good, as well as by being bad.”ix

Despite the vast difference between The Prince and La Mandragola—not the least of which is the fact that one is meant to instruct, the other to entertain—they reflect the same worldview. In each work deceit triumphs and old-fashioned virtues are portrayed as either naive or destructive. If the prince is justified in using every means, including cruelty and lies, to preserve his state, and the lover is rewarded rather than punished for his duplicitous scheme, this is because the author is concerned with the world as it is rather than as it should be. He is above all a realist, and what he sees when he wipes away the obscuring film of piety is a world in which each seeks his own advantage and uses any means necessary to achieve his ends. Neither work makes any sense unless the human animal is conceived of as self-serving. To put it another way: with subjects who behave like the characters in La Mandragola, any prince who is not equally clever will quickly lose control of his kingdom.

A few years after writing La Mandragola, Machiavelli returned to the stage with another comic offering. Written to please his latest mistress, the singer and actress Barbera Raffacani, Clizia is a broad sex farce adapted from a play by Plautus and set in contemporary Florence (rather than ancient Athens). In his prologue Machiavelli justifies the shift of time and locale by returning to a point he made repeatedly in The Discourses: “If into the world the same men should come back, just as the same events come back, never would a hundred years go by in which we should not find here a second time the very same things done as now.” Futile repetition, a predicament brought about by the inability to learn from our mistakes, is the essence of comedy.x It is also an essential ingredient in Machiavelli’s political philosophy. Try as we might, we cannot overcome our nature, and when faced with the same situation, we will fall into the same errors.

The plot of Clizia revolves around the rivalry between the elderly Nicomaco and his son Cleander for the love of the beautiful Clizia, Nicomaco’s ward. The hilarious picture of a middle-aged husband turning his life upside down as he lusts after a young beauty comes uncomfortably close to Machiavelli’s own situation. Like The Ass and La Mandragola, Clizia contains a large element of self-mockery. “It remains for me to tell you,” says Machiavelli,

that the author of this comedy is a man of great refinement, and he would take it badly if you should think, as you see it acted, that there is anything immodest in it. Comedies exist to benefit and to please the audience. It is certainly very helpful for anyone, and especially for young men, to observe an old man’s avarice, a lover’s madness, a servant’s tricks, a parasite’s gluttony, a poor man’s distress, a rich man’s ambition, a harlot’s flatteries, all men’s unreliability.

Despite the contrast in form and in tone, Machiavelli is revisiting themes set down in grander form in The Prince, showing men as they are in order to teach us how to live in the real world. In neither case does the author promise to lead his audience to the Promised Land, but by taking to heart what he has to say, we can achieve some small measure of control over Fortune’s wheel.

In his prologue to La Mandragola Machiavelli claims he was forced to turn to farce since he could not make a living by more honorable means, but it seems unlikely that he wrote any of his plays for money. Theater in Italy at this time was rudimentary, confined for the most part to a few aristocratic courts where amateur productions were occasionally staged to entertain the local nobility. The author profited, if at all, by pleasing his patron, who might then find more remunerative work for him to do. Machiavelli wroteLa Mandragola for the denizens of the Orti Oricellari. The Prologue where he steps onstage to address the audience has the feel of an inside joke meant for friends who knew him well and would appreciate the humor without taking offense at the more pugnacious barbs. The first production was staged for Carnival in 1520 in the Rucellai gardens, with the parts acted out by his “noontime friends” and the scenery painted by Andrea del Sarto and Bastiano (Aristotle) da Sangallo (who had worked with Michelangelo on the Sistine ceiling). Though it was an instant success, it netted him little in the way of material profit. Typical is the response of the artist and art historian Giorgio Vasari, who calls La Mandragola “a most amusing comedy” but can’t be bothered to provide the name of the man who wrote it.

The first performance of Clizia (in 1525) was an equally modest affair, staged in the country villa of Jacopo Falconetti, a wealthy friend of Machiavelli who attracted a diverse crowd to his sumptuous banquets. Known as Il Fornacciaio (the baker),xi Falconetti was a less sophisticated host than Cosimo Rucellai. Food and wine, both good and plentiful, were the inducements to make the journey to his retreat outside the San Frediano Gate, and Machiavelli, who appreciated both but could not afford to splurge himself, was grateful for his host’s generosity. It was here also that he met the voluptuous Barbera Raffacani, a woman whose charm and youth renewed his own animal spirits.

As a patron, Falconetti proved equally generous to his new friend, plowing under part of his garden to build a stage and calling on Bastiano da Sangallo once again to decorate the sets. The play was as great a success with the public as its predecessor, and the citizens of Florence flocked through the Porta San Frediano in large numbers to attend performances. Among those who made the journey to the countryside were the current leading men in the Florentine government, Ippolito and Alessandro de’ Medici. According to Vasari, however, it was the painter rather than the playwright who turned the success of the production into florins in his pocket. After painting the scenery for Clizia, Vasari recorded, Sangallo “acquired so great a name, that it was ever afterwards his principal profession.”

Still, if Machiavelli could not replace his lost civil service salary with income from his plays, other, less tangible benefits accrued. The popular success of La Mandragola and Clizia confirmed Machiavelli’s status as a man of letters. Forgotten was the bureaucrat whose misplaced faith in his citizen army had led to disaster, replaced by the image of the gadfly who held up a funhouse mirror to his fellow citizens, allowing them to laugh at themselves and each other—a cathartic release in which no one, least of all the author himself, was spared.

The fame of Machiavelli’s plays, if not the name of their author, quickly spread beyond the walls of Florence. The Venetian Marin Sanudo attended a performance of La Mandragola in his native city where “[t]he stage was so full of people that the fifth act was not performed; it was impossible to do so with so many people.” Machiavelli accepted his new-won fame with the cautious pleasure of one who has seen too many highs and lows to let the momentary adulation of the crowd go to his head. In any case, he never took his literary endeavors too seriously. When he signed a letter to Francesco Guicciardini with mock pretentiousness “Niccolò Machiavelli, Historian, Comic and Tragic Author,” he expected his friend to get the joke.

Ironically, his burgeoning fame as a comic writer opened doors that had long been closed to him. Shortly after La Mandragola’s initial run at the Orti Oricellari, Pope Leo heard a firsthand account of the brilliant new comedy, which piqued his interest. It was Machiavelli’s friend from the Rucellai gardens, Battista della Palla, who brought the work to Leo’s attention. Soon La Mandragola was staged for the Pope and his cardinals in the Vatican, a performance that, della Palla told the author, “everyone admires . . . much more than anything else I have brought to Rome with my own hands”—which perhaps says as much about the tastes of the Holy City as the merits of the play.

It is not actually surprising that a racy sex comedy should have won over the Pope when so many of Machiavelli’s more serious efforts had failed to make an impression. Leo, like most of his immediate predecessors, was a man of the world who appreciated a fine bottle of vernaccia far more than the finer points of theology. When he had first gone to Rome as a thirteen-year-old cardinal, his father had offered him some sensible advice: “Eat plain food and take much exercise, for those who wear your habit, if not careful, easily contract maladies”—advice that the pleasure-loving Giovanni ignored. Raphael’s famous portrait reveals a man who did not stint himself; his sharp, shrewd features have been softened by years of indulgent living, the sagging pockets beneath his narrowed eyes hinting at an unhealthy lifestyle. Seated next to his cousin, the brooding Cardinal Giulio, the Pope appears massive yet only half present in the room, his eyes glancing somewhere unseen, his brow furrowed as if he is too preoccupied by pressing matters to remain long. Raphael captures something unsettling about the man, a conspiratorial quality remarked on by his contemporaries who, after a few years of Leo’s surreptitious scheming, looked back with nostalgia on the straightforward violence of Julius.

According to popular legend, upon taking his seat upon Saint Peter’s Throne Leo remarked to his brother, “Giuliano, now that God has given us the papacy, let us enjoy it.” The sybaritic lifestyle of the Pope and his court, and the practice of selling indulgences to help fund it, contributed to the decision by a German Augustinian monk named Martin Luther to nail his Ninety-five Theses to the door of the church in Wittenberg, ushering in the Protestant Reformation. Like Savonarola, Luther was a man who felt an almost physical revulsion at the fallen state of mankind. Machiavelli, no less critical of humanity than the two monks, sought to accommodate man’s flaws rather than fight them, to devise practical schemes to deal with impulses that were natural to the human animal.xii

With the success of La Mandragola, the campaign Machiavelli had begun in prison with the humorous sonnets he composed for Giuliano de’ Medici finally began to pay dividends. During those agonizing weeks in his dank cell Machiavelli tried to portray himself as a harmless buffoon rather than a mortal threat to the new regime. Now the Pope himself seemed to be coming around. He appreciated clever men as long as they accepted the party line, and Machiavelli was now vouched for by men Leo trusted.

In fact a large part of the credit goes to his friends at the Orti Oricellari, many of whom had close ties to the Medici. Battista della Palla was but one of many distinguished Florentines who took up Machiavelli’s cause in Rome, promoting him in ways that Francesco Vettori, for all his affection, never would. Activity on his behalf in Rome was more than matched by efforts in Florence where many of the “friends of the cool shade” were in close contact with the influential Cardinal Giulio de’ Medici, the Pope’s cousin, who, after the death in May 1520 of Lorenzo de’ Medici, was Leo’s man in Florence. On March 20, 1520, Lorenzo Strozzi, one of Machiavelli’s friends from the Rucellai gardens, brought him to the palace on the Via Larga and introduced him to the Cardinal. After hearing of the meeting, Strozzi’s brother Filippo expressed his satisfaction: “I am very glad you took Machiavelli to see the Medici, for if he can get the masters’ confidence, he is a man who must rise.”

Giulio de’ Medici was the illegitimate son of Lorenzo the Magnificent’s brother, Giuliano, who had been murdered in the Cathedral during the Pazzi Conspiracy of 1478. Raised in the family palace on the Via Larga after his father’s death, the intelligent Giulio had, like his cousin Giovanni, been destined from early in life for holy orders. He had joined his cousins in exile following Piero’s expulsion in 1498, serving as Cardinal Giovanni’s aide and confidant throughout those difficult years. When Giovanni was elected Pope in 1513, the faithful Giulio reaped his reward, receiving the title Archbishop of Florence and gaining a place in the College of Cardinals. He can be seen in Raphael’s portrait standing at the side of the seated Pontiff, his dark, hooded eyes suggesting his introspective and melancholy cast of mind.

With the death of the Pope’s nephew Lorenzo in 1520, the capable Giulio was sent back to Florence to run the city on behalf of the Medici family. Unlike the last two candidates for the job, Giulio was a thoughtful and deliberative man, attuned to the sensibilities and prejudices of his people. The feckless Giuliano and the arrogant Lorenzo had soured the populace on Medici rule, and Cardinal Giulio was anxious to restore the family’s good name. His uncle, the beloved (at least in retrospect) Lorenzo the Magnificent, had pulled the strings while preserving republican forms, an arrangement that Florentines, attached to their ancient liberties but always fearful of the potential for civic violence, accepted as the price of peace. Lorenzo’s son Piero and grandson Lorenzo had failed to grasp this basic element of statecraft, offending their compatriots with their high-handed ways.

Part of Giulio’s strategy to improve morale in the city was to solicit proposals for the reformation of the government from the city’s leading intellectuals. A cultivated, scholarly man, the Cardinal served as head of the Studio, Florence’s university, earning the respect and friendship of many who might otherwise be expected to lead any opposition to Medici rule. Among those he turned to were the habitués of the Orti, Machiavelli included, who, like most of their fellow citizens, had grown disillusioned with a regime marked by extravagance, corruption, and incompetence. “[H]e willingly conversed in his leisure time with men learned in any profession,” noted one of Machiavelli’s friends approvingly. Whether Giulio’s calls for open debate about the republic’s future were sincere or part of some subtle scheme to smoke out potential opposition has long been debated. Filippo de Nerli, a frequent guest at the Rucellai gardens, was among the first to ascribe sinister motives to the Cardinal: “Zanobi Buondelmonti and even Niccolò Machiavelli showed their minds very plainly in this way; for I saw their writings, and all went into the hands of the Cardinal, who pretended to value them very highly . . . . He abused the good faith of certain, perhaps over-credulous, citizens, who were all the more easily tricked by seeing that he gave no ear to the complaints and remonstrances of trusty adherents, by who he was warned that he was playing a dangerous game.” Despite Nerli’s testimony, it is more likely that the Cardinal initially welcomed a free exchange of ideas, and that he reversed course only when he felt his authority was threatened.

Questions about the future of the Florentine government had arisen in part because, with the untimely deaths of Giuliano and Lorenzo, the two most prominent members of the reigning family were men of the cloth, who technically could not serve as rulers of a secular state.xiii Before Lorenzo’s death, Leo’s policy, like that of Pope Alexander before him, had been to use his office to carve out a powerful principality for his family in central and northern Italy. “The Pope and his Medici have no other thought than of increasing the fortunes of their house,” wrote the Venetian ambassador to the Holy See, “and his nephews, unsatisfied with dukedoms, pretend that one of them ought to be king.” Pursuing this nepotistic project, Leo had brokered his younger brother Giuliano’s marriage to a French noblewoman and tried to acquire on his behalf the cities of Modena, Piacenza, and Reggio. It was this venture that first inspired Machiavelli to conceive of a revitalized Italian state with Florence as its capital, a dream eloquently conjured in the last chapter of The Prince.xiv When Giuliano’s early death caused Leo to pin his hopes instead on his nephew Lorenzo, Machiavelli transferred his loyalty as well, though by now even he must have suspected it would come to nothing. The project reached a climax when Leo drove out the ruling Montefeltros of Urbino and brought the strategic duchy under Medici rule. But Lorenzo proved as flimsy a foundation upon which to build a dynasty as his uncle, disappointing both the Pope and Florentine nationalists like Machiavelli who could contemplate a revived Italian nation only as long as their beloved republic stood at its head.

Lorenzo’s death not only ended Pope Leo’s dreams of a powerful Medici state at the heart of Italy, but also threatened to undercut the family’s authority in its native city. It was in this context that Cardinal Giulio commissioned Machiavelli’s “Treatise on the Reform of the Florentine Government,” written in 1520 and dedicated to Pope Leo. Machiavelli was elated at finally being able to return to the problems that consumed him, and he took up the topic with his usual gusto, even if he knew his ideas were unlikely to be put into practice. Throughout the brief text Machiavelli walks a diplomatic tightrope, flattering his patrons while trying to nudge them in the direction of true republican rule. After praising the prudence of the Pope’s ancestors, particularly Cosimo and his grandson Lorenzo (Il Magnifico), Machiavelli gets in a subtle dig at the more recent representatives: “The Medici who were governing then, since they had been educated and brought up among the citizens, conducted themselves with such friendliness that they gained favor. Now, they have grown so great that, since they have gone beyond all the habits of citizens, there cannot be such intimacy and consequently such favor”—a tactful way of saying that Giuliano and the younger Lorenzo had been insufferable and squandered much of the goodwill their ancestors had built up. Machiavelli’s larger point, however, is that given Florentines’ love of liberty it would be next to impossible to impose princely rule on them. “[T]o form a princedom where a republic would go well is a difficult thing and, through being difficult, inhumane and unworthy of whoever hopes to be considered merciful and good.”

The bulk of the treatise is taken up by Machiavelli’s blueprint for a republican government to be established once the Pope and the Cardinal pass from the scene. It follows the familiar three-part structure he normally favored: “there are three sorts of men,” he declares, so “there [should] be also three ranks in a republic.” Here Machiavelli takes the theories he had developed at greater length in The Discourses and applies them to the specific needs of a small republic with a thriving middle class and a history of communal strife. His study of history, both Roman and modern Italian, had convinced him that the most successful governments were those that internalized and accommodated the inevitable clash of competing interests—the kind of controlled chaos that obtains in modern democracies. Again he displays the basic unity of his thought, from comic play to his serious political tract. If comedy is the art of low expectations, democracy is its political counterpart, a system that substitutes an achievable equilibrium for unobtainable perfection.

•  •  •

Nothing came of Machiavelli’s proposals or those of his colleagues who had heeded the Cardinal’s call to action. In a pattern that would repeat itself throughout the course of Giulio de’ Medici’s life, boldness was followed by timidity; the promise of a new beginning dissipated in a return to the status quo. It was a pattern that guaranteed disillusionment. Giulio was one of those well-meaning men who know what’s right in the abstract but who wilt in the face of harsh reality. When it became clear that he had no intention of restoring the citizens’ cherished freedoms, he stoked the very resentment he had hoped to quell.

Though Machiavelli was disappointed by the Cardinal’s cowardly retreat, he was not prepared to sever the ties it had taken him so long to establish. The Cardinal continued to hold him in high regard, and even employed him on a couple of minor missions that brought back faint memories of the glory days when Machiavelli had consulted with emperors and kings. In May 1520, he was sent to the ancient Tuscan capital of Lucca on government business. Though the issues at stake were trivial and involved financial matters that were of little interest to him—he was representing a group of rich Florentine creditors in a bankruptcy case—at least he was back in action again. In any case the work does not seem to have been too taxing since he had time in these months away from home to compose a brief “Summary of the affairs of the city of Lucca” and a more substantial Life of Castruccio Castracani, the medieval tyrant of that city. Though a minor work, dashed off in the course of a few months and based on secondary material, his friends of the Orti, to whom it was dedicated, “all decided it was a good thing, and well written.”

In fact the Life of Castruccio Castracani appears merely to have been a trial run for a more ambitious work that was now being promoted by Machiavelli’s friends. Looking for a way to help his impecunious friend, Zanobi Buondelmonti had approached the Cardinal with a proposal that he hire the former Second Chancellor to write an official history of Florence, a prestigious commission that would not only place him in the company of such men as former chancellors Leonardo Bruni and Poggio Bracciolini, but also provide him with much needed cash. It seems likely that the project was already under discussion when Machiavelli departed for Lucca and that he submitted the Life of Castruccio to the Cardinal as a sample of what he could achieve in the genre.

The work must have pleased the Cardinal because in November he offered Machiavelli the commission. Machiavelli himself wrote up a sample contract: “He is to be hired for ___ years at a salary of ___ per year with the condition that he must be, and is to be, held to write the annals or else the history of the things done by the state and city of Florence, from whatever time may seem to him most appropriate, and in whatever language—either Latin or Tuscan—may seem best to him.”

Before sitting down to write in earnest, Machiavelli was employed on another small errand on behalf of the republic. In May 1521 he was chosen to represent the Franciscan Brothers of Florence at the general meeting of the order being held in the provincial town of Carpi in the Romagna. As a diplomatic junket it was hardly more consequential than his mission to Lucca the previous year, but after years in the wilderness even these small signs that he was back in favor were welcome. When he arrived at Carpi, located some seventy-five miles north of Florence on the far side of the Apennines, Machiavelli was instructed to conduct the negotiations on behalf of the Franciscan monasteries of Florence that were seeking independence from the Tuscan chapter.xv It was a peculiar mission for a man who had so little religious feeling that many of his friends believed he was a secret atheist. Adding to the irony, he was also tasked by the Wool Guild (which was responsible for overseeing the Cathedral of Florence) with recruiting the popular preacher Fra Rovaio to deliver the Lenten sermons at the Duomo. When Machiavelli explained the nature of his mission, his friend Francesco Guicciardini joked: “It was certainly good judgment on the part of our reverend consuls of the Wool Guild to have entrusted you with the duty of selecting a preacher, not otherwise than if the task had been given to Pachierotto, while he was alive, or to Ser Sano [two well-known pederasts] to find a beautiful and graceful wife for a friend. I believe you will serve them according to the expectations they have of you.”

The main interest of this trip to what Machiavelli derisively called “the republic of clogs” (a reference to the Franciscans’ humble attire) is the correspondence it generated between the two greatest political thinkers of the age. Guicciardini, fourteen years younger than Machiavelli, was a haughty aristocrat whose disdain for human nature in general was combined with a snobbish contempt for the common people in particular. While both men favored republican government, Guicciardini believed Machiavelli placed far too much faith in the wisdom of the people. “To speak of the people is to speak of madmen, for the people is a monster full of confusion and error,” Guicciardini insisted.

In his writings Machiavelli combines cynicism with passion; Guicciardini has no better opinion of human nature but his habitual attitude is one of ironic detachment. Guicciardini’s cautious approach actually makes him the better historian. His History of Florenceand History of Italy are more accurate than Machiavelli’s treatment of the same subjects because he eschews grand pronouncements in favor of a straightforward narration of the facts. While Machiavelli likes to use one small fact as the foundation for vast theoretical structures, Guicciardini doubts that it is possible to draw any firm conclusions from the welter of conflicting data. It is an error, he says, “to wish to speak of the affairs of the world in general terms and according to fixed rules; since nearly all admit of exceptions.” After reading what he considered a particularly fanciful passage in The Discourses, Guicciardini remarked dryly that many things are “easier to describe in books and in the imagination of mankind, than to carry into practical effect.”

The two were drawn together by mutual respect and by their shared patriotism. Each watched with dismay as foreign armies marched across Italy, preparing to hurl themselves at each other in a final desperate bid for supremacy on the peninsula. “The Italians are not strong enough for resistance,” Guicciardini despaired, “and capitulation will bring about our enslavement.”

On the way to Carpi, Machiavelli stopped in nearby Modena, where his friend had been installed by Pope Leo as governor of Mantua and Reggio, and the two spent many hours discussing the dismal state of Italian affairs and drowning their sorrows in lively conversation lubricated by plenty of fine wine and hearty food. Reluctantly proceeding to the dusty village where the Franciscans had congregated, Machiavelli filled up the dull hours by writing to his recent host, and Guicciardini, his duties as governor apparently not overly taxing, responded in kind.

The exchange of letters from the weeks Machiavelli spent in Carpi have a feeling of whistling past the graveyard as the two men put aside for a moment their dismay at the current political situation to indulge in childish pranks and off-color humor. As Machiavelli admitted to Vettori, he used laughter to hide his tears, and the storm clouds gathering on the horizon gave a slightly frantic quality to their fun. To one of Guicciardini’s facetious letters Machiavelli replied:

Magnificent Lord Francesescus Guicciardinis . . . most exalted and most honorable. I was on the toilet when your messenger arrived, turning over in my mind the absurdities of this world, and trying to figure out just what kind of a preacher I would choose for Florence. He should be one after my own heart, because I am going to be as stubborn about this as I am about my other ideas. And because I have never let my republic down when I could help her out, if not by my actions then with my words, I don’t intend to disappoint her now. I know that I am at odds with the opinions of my compatriots, in this as in many other things. They would like a preacher to teach them the way to Paradise, and I’d like to find one who would teach them the way to go to the Devil’s lair . . . . [B]ecause I believe that the following would be the true way to Paradise—learn the way to Hell in order to flee from it. Seeing, in any case, how many are taken in by a fraud who hides under the cloak of religion, one can easily imagine how much faith there would be in a good man who walked in truth, and not in lies, treading in the muddy footsteps of Saint Francis.

Who but Machiavelli could conjure such a scene? Bodily functions and philosophy, heaven and hell, low comedy and high purpose, all are lumped together in a single hilarious image. He is being mischievous certainly, but as always he uses humor to make a serious point. We have no choice, he seems to be saying, but to chart a course through the infernal regions since this is the world we live in. What is The Prince if not a practical guide to navigating this blighted landscape? Machiavelli’s most helpful roadmap does not actually show us the way to heaven, but merely points out the deepest potholes along the road.

Not the least of the absurdities the two men had to contemplate was Machiavelli’s pathetically reduced circumstances, so out of keeping with his abilities and in such stark contrast to his former life. Guicciardini commiserated. “My dearest Machiavelli,” he wrote from the comfort of his own official lodgings: “When I read your title as ambassador to the Republic and of friars and recall all those kings, dukes, and princes, with whom you have negotiated in the past, I am reminded of Lysander who, after so many victories and trophies, was given the task of distributing meat to the same soldiers he had once so gloriously commanded.”

Most galling to the former Second Chancellor was that the provincial villagers of Carpi had concluded he was a man of no account and were treating him accordingly. Machiavelli was used to being treated as Sir Nihil by kings and emperors, but to be snubbed by men with straw in their hair and manure on their boots was more than he could bear. Writing to Guicciardini he cooked up a ruse to confound the bumpkins who had decided they could save a few ducats by scrimping on his food and lodging. At Machiavelli’s prompting Guicciardini sent off a series of important-looking dispatches under official seal, each carried by messenger accompanied by an entourage of armed guards. Machiavelli heightened the effect by hinting that he was at the moment involved in deep negotiations with the Emperor and the King of France. He described to Guicciardini the scene as these simple villagers found themselves caught up in great affairs of state:

I must tell you that when the crossbowman arrived with your letter and, bowing to the ground, declared that he had been sent expressly to me and in all haste, everyone snapped to attention and created such an uproar that everything was upset, and I was grilled for any news . . . . Soon, they were all standing around with their mouths open and their hats in their hands. I am surrounded as I write, and the more I write the more I am marveled at and seen as one inspired. And I, to make them gape some more, sometimes lift my pen and puff out my cheeks, which just starts them drooling.

Soon Machiavelli was receiving invitations to dine at the homes of the leading citizens, where his hosts would lay for him rustic feast on their finest silver and apologize for the simple fare. He took full advantage of the situation, “gobbl[ing] up,” he told Guicciardini, “enough for six dogs and three wolves,” and counting up the money he was saving by not having to provide his own meals.

Though the farce enlivened an otherwise thankless mission, Machiavelli was glad to put the walls of Carpi behind him. He was back in Florence by early June. Awaiting him on his arrival were the first proofs of The Art of War, just coming off the presses of the printer Filippo di Giunta. This was the one book of Machiavelli’s to be published in his lifetime and he was justifiably proud of the accomplishment. Dedicated to Lorenzo Strozzi, his friend from the Rucellai gardens who had introduced him to Cardinal Giulio,The Art of War rehashes many of the themes he had already laid out in The Prince and The Discourses, proclaiming the superiority of republics to principalities and, as always, the superiority of the citizen militia to mercenary armies. This remains Machiavelli’s great obsession: to discourage Italians from employing soldiers-for-hire, rediscover the martial valor of their ancestors, and, with patriotic fire in their eyes, drive the barbarians from their midst.

But for all his passion on the subject, The Art of War has held up less well than his other major works. Despite his years organizing and provisioning the citizen militias of Florence, Machiavelli was not a professional military man, and many of his prescriptions are impractical or counterproductive. His disdain for artillery and for military engineering, as well as his preference for infantry over cavalry, derive from his study of Roman history but have little to do with the realities of Renaissance warfare, where cannon and musket were changing the dynamics of battle.

Ultimately, The Art of War is significant less for its discussions of tactics or strategy than for Machiavelli’s insight that the way a society chooses to wage war profoundly shapes its internal structure. Mercenary armies are the scourge of well-ordered polities because “a good man could not make war his only profession, and . . . no wise prince or governor of a commonwealth would allow any of his citizens to do it.” By contrast, armies made up of citizen soldiers, mustered for a brief period at a moment of crisis, are the sinews of a vital organism, fueled by patriotic ardor and unified in a common purpose. When Rome conquered the world she accomplished this with “common soldiers [who] laid down their arms with much more pleasure than they had taken them up,” and by “commanders . . . contenting themselves with the honor of a triumph [who] returned with eagerness to their former manner of living.”

Machiavelli received from Cardinal Giulio the contract to write a history of his native city in November 1521. He was given a two-year stipend from the University of Florence to complete the work, at the rate of 100 fiorini di studio,xvi slightly more than half the salary he earned as the Second Chancellor and Secretary to the Ten. While the money certainly came in handy, just as important for Machiavelli was the opportunity to apply the ideas he had developed in his earlier works to the history of his native land. The commission would prove particularly delicate since his patron’s family had played such a crucial and controversial role in the history of the city he was chronicling. His strategy, as he explained to Guicciardini, was to avoid giving offense while still telling the truth as he saw it. It was the same high-wire act he had already practiced in his “Treatise on the Reform of the Government of Florence,” and one that, for the most part, he carried out nimbly.

While not a startlingly original work like The Prince or The Discourses, nor a literary masterpiece like La Mandragola, the Florentine Histories is solid analytical history, built around the dominant motif of the city’s endless factional violence. In The DiscoursesMachiavelli had praised the Romans for their ability to turn civil strife into constructive law, but he viewed the tumultuous history of Florence with a more critical eye. The Roman Republic had used the tension between the classes to forge a new consensus, but the history of Machiavelli’s own city was a dismal spectacle of carnage accompanied by no redeeming social evolution. “For the enmities between the people and the nobles at the beginning of Rome that were resolved by disputing were resolved by Florence by fighting,” he explains. “Those in Rome ended in law, those in Florence with the exile and death of many citizens; those in Rome always increased military virtue, those in Florence eliminated it altogether.”

After laying out this sorry history in gruesome detail, he proceeds to chronicle the rise of the Medici party in the first half of the fifteenth century. Though he admits that the Medici, beginning with Cosimo and continuing with his grandson Lorenzo, systematically dismantled the city’s democratic institutions, he portrays this process as a reasonable response to the chaos that preceded it. In effect, the citizens were willing to purchase peace at the price of losing some of their ancient liberties. Machiavelli originally intended to bring his history up to the current moment but he tactfully concluded in 1492 with the death of Lorenzo the Magnificent, happily relieving himself of the difficult task of finding something constructive to say about Giulio’s cousin, Piero, and the other younger and less impressive members of the family.

•  •  •

These were relatively happy years for Machiavelli. His sense of isolation lifted with his acceptance into the charmed circle of the Rucellai gardens, bringing him much needed camaraderie and also winning him friends in high places. He was not where he most wanted to be, in the very heart of the action, but at least he was treated with respect, even reverence, by men whose company he enjoyed and who stimulated his ideas. With the success of his comedies he had fame, if not fortune, and a series of passionate love affairs absorbed him when more scholarly pursuits temporarily lost their allure. Even the house at Sant’ Andrea seemed less a prison than a refuge where he could work on his history undisturbed but for the pleasant commotion stirred up by young children.

But there were signs the calm would not last. The optimism that had accompanied Giulio de’ Medici’s arrival in Florence had turned in certain circles into sullen resentment as promised reforms never materialized. Among the most disillusioned were members of the Orti Oricellari, long a bastion of pro-Medici sentiment, and among these the most vehement critics of the regime included Machiavelli’s close friends Zanobi Buondelmonti and Luigi Alamanni.

The extent to which Machiavelli himself participated in the whispered conversations is unclear. He was certainly aware that a new dark mood had overtaken the once idyllic—and largely apolitical—gatherings, but he lacked the ideological fire of his younger companions. In any case Machiavelli was never a man of action, particularly when it involved conspiracy against the duly elected authorities. While he certainly shared his friends’ aspirations, he remained skeptical of anything that involved potential violence.

Influence, in fact, flowed in the other direction. Buondelmonti, Alamanni, and the other denizens of the Orti had been inspired by the writings of the older man, particularly The Discourses, which laid out a convincing case for the superiority of republican government. Once reviled in that aristocratic milieu as the toady of a government with populist leanings, in retrospect the architect of the victory over Pisa seemed an almost heroic figure.

The transformation of the Orti Oricellari from a pro-Medici bastion to a nursery of anti-Medici sedition was typical of the twists and turns of Florentine politics. For the moment there was no danger that inchoate feelings of disenchantment would lead to open resistance. As long as a Medici sat on the papal throne, the alliance between Rome and the reggimento in Florence was simply too strong, and the profits accruing to Florentine merchants from increased business too attractive, for the ancient yearning for liberty to congeal into concrete action. All that changed on December 1, 1521, with the unexpected death of Pope Leo following a brief illness. Though only forty-five at the time of his death, the Medici Pope had worn out his welcome and his body through dissipated living. Worse still, he had never met the high expectations that accompanied his election, devoting his energies to aggrandizing his family rather than bolstering the moral reputation of the Church or the prosperity of his native city. Though an intelligent and cultivated man, he was negligent in tending to his spiritual duties and equally negligent when it came to rallying the Italian people to resist the foreign invaders. It was during his reign that Christianity was torn asunder by Luther and his followers—disgusted by the worldly excess they saw in the Vatican—and while the final enslavement of the peninsula did not take place in his lifetime, his corrupt and vacillating policy made such an outcome all but inevitable.

In the ensuing conclave a vigorous battle was waged between supporters of Cardinal de’ Medici and Machiavelli’s old friend Cardinal Francesco Soderini (brother of the former Gonfaloniere). In the end these two factions fought to a draw, ensuring the election of a colorless Dutchman, Cardinal Adriann Dedel, who ascended the throne on January 9, 1522, with the name Adrian VI.xvii In Rome the election of this nonentity drew jeers from the crowd outside the Vatican. In Florence the conflict between the two native-born cardinals merely helped widen the fissures that were opening within the ruling elite.

With his position threatened by the death of his cousin, Cardinal Giulio tried to still the voices of discontent by repeating his old trick of inviting proposals for reform. Among those who rose to the bait was Machiavelli (who resubmitted the plan he had drawn up a few years earlier) along with many others who believed the restoration of free institutions and open elections was just around the corner. But as he had three years earlier, Cardinal Giulio backed down at the last minute. Rumors began circulating that instead of restoring their liberties, the Cardinal was preparing to install two Medici bastards—Ippolito, illegitimate son of Giuliano, and Alessandro, love child of Lorenzo—at the head of the government, demonstrating that he viewed Florence as little more than family property.

Early in June 1522 a courier was intercepted by Florentine authorities as he was riding along the road toward Rome. In his saddlebag they found a letter addressed to Battista della Palla (the man who had been instrumental in convincing Pope Leo to stage the first Roman performance of La Mandragola) detailing a plot to assassinate Cardinal Giulio and proclaim a restored Florentine Republic. The Roman conspirators included not only della Palla but the two Soderini brothers; the leaders of the conspiracy in Florence were Zanobi Buondelmonti, Luigi Alamanni, and Jacopo da Diaceto, all of them close friends of Machiavelli from the Orti Oricellari. Buondelmonti and Alamanni managed to flee the city ahead of the constables, but other denizens of the Rucellai gardens, including Diaceto and Alamanni’s cousin (confusingly also named Luigi) were less fleet of foot. Led in chains to Le Stinche they were subjected to the usual harsh methods employed by the authorities to extract confessions. In an eerie reprise of the failed conspiracy of 1513, Machiavelli’s name once again came out during the interrogations. There was even testimony that Buondelmonti had planned to contact him but had been discouraged at the last minute because, as a poor man without connections, Machiavelli was in no position to help.

Cardinal Giulio’s retribution was swift, though not, under the circumstances, excessive. Displaying what for him was an unusual decisiveness, he had Diaceto and Luigi Alamanni beheaded in the courtyard of the Bargello, and prevailed upon the Pope to arrest Cardinal Soderini in Rome. (Piero Soderini was spared a similar fate since he died on June 13.) Though Machiavelli himself escaped unscathed, he was understandably distraught at the disaster that had befallen his friends. The “brotherhood of the cool shade” was disbanded once and for all, and with it a happy chapter in his life had closed.

Machiavelli himself never wrote of the disastrous events from the summer of 1522, though one can infer his troubled state of mind from the sparseness of his correspondence during these months. Most suggestive is the brief, bitter epitaph he composed upon learning of Piero Soderini’s death:

The night that Piero Soderini ceased to breathe

His soul journeyed to the mouth of Hell;

But Pluto cried: “Thou foolish soul

No Hell for thee! Go seek the Limbo of the babes!”

The sarcastic tone of these lines was almost certainly prompted by Soderini’s role in the fiasco. On a personal level Machiavelli had every reason to be loyal to his old boss. In fact Soderini had tried more than once to find employment for his former assistant, offering him a position as secretary to the Republic of Ragusa (modern-day Dubrovnik) and a lucrative sinecure as secretary to the condottiere Prospero Colonna. Machiavelli turned down both offers, in part because he was too devoted to his native city to contemplate leaving it for any length of time, and partly because he worried that having dealings with the disgraced Gonfaloniere would cause him trouble with the authorities at home. (At one point he explained to Vettori that he would not visit his old friend for fear that when he returned to the city he would be taken straight to Le Stinche.) For all Soderini’s kindness to him, and for all the happy memories of their past collaboration, Machiavelli could not forgive this final indiscretion. The disastrous consequences of Soderini’s scheming confirmed the verdict pronounced in The Discourses that he was a decent man but an ineffectual leader.

Machiavelli’s feelings were complicated by the fact that he himself had played a less than heroic role in the tragedy. He had little reason to regret not becoming entangled in his young friends’ harebrained schemes; he had always rejected such conspiracies both on practical grounds and on principle. Had Buondelmonti or Alamanni consulted him, he might have referred them to the chapter in The Discourses titled “On Conspiracies,” where he warns all who would set off down this most dangerous path that “there are very few, if any, who do not themselves get killed in the very act.” But he was sympathetic to their cause and it pained him to see them suffer.

In fact he remained on the Medici payroll, retiring to his house in Sant’ Andrea to complete work on the Florentine Histories commissioned by the very man who had just executed his friends. He felt conflicted, though whether his anger was directed more at the Cardinal or his rash friends is difficult to know. For the most part he seems merely to have escaped into his work and into idle distractions. It was at this time that he began frequenting the villa of Jacopo Falconetti, where he replaced the more cerebral pleasures of the Rucellai gardens with the brickmaker’s boisterous bacchanals. It was also at this time that he began his passionate affair with the singer Barbera Raffacani, turning as he often did to the delights of the flesh when the rest of his life seemed to be falling apart. The lighthearted romp Clizia was also a product of these listless days. His attitude toward the world and its troubles is summed up in a single line he wrote to his brother-in-law Francesco del Nero. “I’ll send your regards to the chickens,” he wrote from Sant’ Andrea, a wry commentary on his rustic retirement.

i He was less tolerant when it came to his own son, Lodovico, who, according to Vettori, “has a boy with him” who “plays with him, sports with him, walks about with him, whispers in his ear; they sleep in the same bed” (April 16, 1523, in Machiavelli, et al., Machiavelli and His Friends, no. 281, p. 349). While Vettori was inclined to laugh it off as youthful indiscretion, Machiavelli seems to have been upset by what he believed was taking place.

ii The identity of his lover at this time can only be guessed, but it seems likely that it was Tafani’s sister, since in a letter written a few months after revealing his affair, he urges Vettori to help her arrange a divorce from her husband, who was living with his mistress in Rome. (See letter no. 240 in Machiavelli et al., Machiavelli and His Friends, p. 295.)

iii Machiavelli ultimately concluded that the Pope should back the French since they would demand less in victory than the Spanish. The worst possible course would be “remaining neutral,” which was never “useful to anyone confronted with these conditions” (Machiavelli to Vettori December 10, 1514, no. 241 in Machiavelli et al.,Machiavelli and His Friends, pp. 295–302). Of course it was exactly this middle way that the Pope preferred.

iv Such gatherings had long been a hallmark of Florentine intellectual life. In the late fourteenth century, leading citizens like Palla Strozzi and Cosimo de’ Medici had attended talks at the Camaldolese monastery given by Ambrogio Traversari. The famous “Platonic Academy” sponsored by Lorenzo de’ Medici was, similarly, less a formal institution than a gathering of like-minded intellectuals who met to discuss the great philosopher’s work at Marsilio Ficino’s villa at Careggi. After Lorenzo’s death, Bernardo Rucellai played host to the Platonic meetings at his garden.

v The gardens took their name from a plant, the orecella, that had been imported by the Rucellai family and that was used to make a purple dye important for Florence’s thriving cloth industry.

vi Some have attributed Cosimo’s gentle nature to the fact that he was crippled from an early age. He attended gatherings at his garden by being carried about by servants in a specially made litter.

vii Such philosophical dialogues date back to the time of Plato. The form was revived in the Renaissance, when it was used by writers like Bartolomeo Scala, who turned Niccolò’s father into a character in one of his dialogues (see Chapter 2), and Cristoforo Landino, who set his Disputationes Camaldulenses in a rustic monastery near Florence.

viii Of course the sentiments did not originate with Machiavelli. They mirror closely Lorenzo de’ Medici’s famous carnival song: “How beautiful is youth that quickly flies away. He who would be happy, let him, for of tomorrow no one can say.”

ix See, for example Chapter XV of The Prince where he declares “for a man who strives after goodness in all his acts is sure to come to ruin,” or Chapter XIX where he says that “hatred may be engendered by good deeds as well as by bad ones.”

x Karl Marx makes this point when he says: “Hegel remarks somewhere that all great world-historical facts and personages appear, so to speak, twice. He forgot to add: the first time as tragedy, the second time as farce” (from The Eighteenth Brumaire of Louis Napoleon).

xi He was not a pastry chef, however, but a brickmaker. His country villa housed a large kiln, or “forno.”

xii In one respect, at least, Luther might be seen to have something in common with Machiavelli. His insistence that clergy should be allowed to marry was an accommodation to human nature that the Italian might well have applauded.

xiii There was even some talk of Giulio following the path of Cesare Borgia, forsaking a career in the Church for that of a secular lord, but Pope Leo rejected the idea.

xiv Paolo Vettori was chosen to serve as governor on Giuliano’s behalf, and it was in this context that the Vettori brothers sought Machiavelli’s counsel.

xv When Savonarola managed to wring a similar concession from Pope Alexander on behalf of the Dominicans, the independence he gained was a crucial component of his power.

xvi The fiorino di studio (florin of the studio) was worth barely half the standard gold florin, a sign that then, as now, academics were expected to spend their prestige when they ran short of hard cash.

xvii Adrian was also the compromise candidate between supporters of France and of the Emperor, so little known that he offended no one.

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