Biographies & Memoirs



“Since [Machiavelli] is unable to remedy the faults of mankind, he will do nothing but laugh at them.”


BURYING HIMSELF IN MUSTY ANNALS OF THE PAST, Machiavelli was able to take his mind off the troubles of the present. With ink-stained fingers and stacks of yellowing documents by his side, he delved into the parade of folly that constituted the long and troubled history of his native city. The tramp of armies and roar of cannon were little more than distant rumors, drowned out by the sounds of chickens clucking and scrabbling in the yard below. Now in his mid-fifties, Machiavelli remained physically vigorous (as his gymnastics with the beautiful Barbera suggest) and mentally acute, but he no longer felt the same need to plunge headlong into the maelstrom. Perhaps it was simply that he had learned to live with disappointment. He would accept whatever came his way, willing, as always, to labor on behalf of his native land. But he did not expect to play the same vital role in affairs of state as he had in the reign of Piero Soderini, when the decisions he made could change the course of history.

Machiavelli may have preferred to turn his back on what was happening beyond the fields and orchards of Sant’ Andrea, but he could not ignore for long the great events transpiring just beyond the horizon. The tragic farce of the failed plot against Cardinal Giulio had played out against a backdrop of growing menace. In 1516 the kings of Spain and France had signed the Treaty of Noyon, in which the Spaniards recognized the French claim to Milan in return for recognition of their rights in Naples. The treaty brought a rare interlude of calm, but each side was merely biding its time, regrouping and rearming for a more decisive battle.

Now the rivalry threatened to erupt with renewed violence. The two great monarchs of Europe—Francis I, who had succeeded Louis XII in 1515 as King of France, and Charles, who had taken the Spanish throne the following year—had no intention of laying down their weapons until a final decision had been reached. In June 1518 the Flemish-born Charles added to his Spanish throne the title of Holy Roman Emperor. With territories stretching from the North Sea to the Rock of Gibraltar, from the ancient city of Naples to the virgin forests of the New World, Charles V’s empire was a vast, unruly patchwork of languages, peoples, and religions.i But despite the difficulties involved in managing such an unwieldy patrimony, Charles had more than enough energy left over to settle old scores with the Most Christian King of France.

One might have hoped, along with Machiavelli, Guicciardini, and countless other Italian patriots, that faced with yet another cataclysmic war on native soil, the states of the peninsula would put aside their own differences long enough to present a unified front against the common enemy. But once again the Italians proved complicit in their own destruction. As they had in 1494, each city-state looked to its own short-term advantage, forging alliances with one or the other of the great powers and switching sides whenever they could cut a better deal.

Machiavelli might well have resigned himself to a placid retirement had Fortuna, a creature of infinite jest, not taken it upon herself to stir the pot once more. In the fall of 1523 history took one of those sudden turns of the kind that made it so difficult to predict the trajectory of a man’s life. On September 14, Pope Adrian VI breathed his last, leaving the stage with as little fanfare as he entered it. Like Pius III, who had filled in between the reigns of Alexander VI and Julius II, he had been a stopgap pope, a compromise candidate when the top contenders had battled to a draw. The conclave to which Cardinal Giulio now hurried proved to be one of the most contentious in recent memory. The French King and the Holy Roman Emperor both realized that the new Pope could swing the balance of power in Italy and so they engaged in a bitter proxy war, deploying phalanxes of cardinals inside the Sistine Chapel like well-disciplined soldiers. After more than fifty days, Cardinal Giulio—who had the backing of the Emperor—prevailed over the French cardinals. On November 19, 1523, he was crowned with much pomp in St. Peter’s, taking the name Clement VII.

After an interlude of less than two years a Medici was again seated on the papal throne, but there was no reason to suppose that, as far as the people of Florence were concerned, the arrangement—so breathlessly anticipated before the fact—would prove any happier than it had the first time. Having one of their own in the Vatican had merely given the Medici delusions of grandeur; they used their enhanced prestige not to promote the prosperity of their native city but to glorify their own family. Their ambition was embodied in the new tombs Michelangelo was currently working on in the family church of San Lorenzo. Compared to the austere Old Sacristy, which contained the remains of Cosimo and his two sons, the New Sacristy, commissioned by Cardinal Giulio before his departure for Rome, was a grandiose monument to the younger generation of the family. The two tombs of Giuliano and Lorenzo are the work of a genius at the height of his powers, but their marmoreal splendor is out of all proportion to the nonentities who occupy them. The New Sacristy, with its seamless integration of sculpture and architecture, is one of the masterpieces of Renaissance art, but also a testament to the decay of the communal spirit that had animated Florentine life for centuries.

For Machiavelli, Giulio’s elevation offered one last chance to make his mark on the public stage. Pope Leo had always regarded the former Second Chancellor with suspicion, but Machiavelli’s relations with the new Pontiff were cordial. Over the years he had shown himself a loyal servant, swallowing his pride to take on even the least prestigious assignments, and both his dedication and the quality of his mind continued to impress Clement. Even his association with the conspirators of the Orti proved to be little more than a temporary embarrassment.

With his friend now seated on the papal throne Machiavelli felt reinvigorated. After years spent in dull retirement it was time to dust himself off and see if he might yet make a contribution. By the beginning of 1525 he was close to finishing his Florentine Histories. As he had before when he sat with the completed manuscript of The Prince on his desk, he asked Vettori whether he should make the trip to Rome and present the work to his patron. “My dear friend,” Vettori replied with his usual equivocations:

I don’t know whether to tell you to come with the book or not, since the times are not conducive to reading and to gift giving. But on the other hand, the night I arrived . . . the pope himself asked after you and whether you had completed the Historia as he anticipated. And when I told him that I had seen part of it and that you had reached the death of Lorenzo, and that it was something that would give satisfaction, and that you wanted to come and bring it to him but, due to the gloomy times, I had dissuaded you, he said to me: “He should have come. I am certain that his books will give much pleasure and be read eagerly.” These are the exact words he said to me, but I would not place too much faith in them, since you might come and still find yourself emptyhanded. Given the pope’s current state of mind, this could well happen.

In the case of The Prince, Machiavelli had been dissuaded by his friend’s less than enthusiastic reception, but this time he ignored Vettori’s warning and set out for Rome with the manuscript in his saddlebag. He arrived in the Holy City late in May. Despite Vettori’s gloomy prediction, Clement received him warmly and gratefully accepted the work from his hands.ii

But, as Vettori correctly noted, the times were not conducive to the leisurely perusal of scholarly tomes. As Machiavelli and the Pope talked in the opulently furnished chambers in the Vatican, the conversation soon turned to the troubles facing the Italian people and the papacy in particular. Though Clement would not admit it, his difficulties were largely due to his own misjudgments. Like his cousin before him, the new Pope proved incapable of sticking to a single farsighted policy, shifting allegiances as easily as other men change their clothes. He had been lifted to the throne on the Emperor’s strong arm, but once in power he began to look for ways to wriggle free from Charles’s suffocating embrace. Shortly after he took office he secretly allied himself with the French, a policy that looked as if it might pay dividends when in October 1524 Francis arrived in Italy at the head of an apparently invincible army of forty thousand. But, as had happened so often in the past, French dreams were soon dashed on the plains of Lombardy. On February 23, 1525, Francis was routed by imperial forces near the northern Italian city of Pavia, leaving ten thousand of his best soldiers dead and maimed on the field of battle. Worse still for the French cause—and for the Pope who had staked his future on their success—Francis himself was captured and dragged off in chains to a Spanish prison.

With the French army decimated and their King held captive, all Italy lay open to the victorious imperial army. Florence quickly came to terms with the new master of Italy, paying 100,000 ducats for the privilege of not being invaded. But for Pope Clement the consequences were nothing short of calamitous. Even the usually resourceful Guicciardini was at his wits’ end: “I well understand that just now every good brain is puzzled,” he wrote, “but he who sees that by standing still he will be overwhelmed by destruction, ought to prefer the worst dangers to certain death.”

Small wonder, then, that the Pope was preoccupied. But while Clement was despondent, the crisis seemed to have rekindled some of Machiavelli’s old fire. Once again he found himself—almost by accident—at the very heart of the action. Believing that Clement’s despair provided an opportunity to translate his ideas into concrete action, he filled the Pope’s ears with plans, schemes, and theories that he had long ago set down on paper. It was clear, Machiavelli explained, that so long as the Pope had no reliable army of his own he would remain—to borrow a phrase he had used in another context—“an unarmed prophet,” a slave to those who could impose their will through powder, shot, and cold steel. The only solution was the creation of a national citizen militia, which to Machiavelli remained the cure for every ill. Humbly reminding the Pope how nobly his small force had acquitted itself before the walls of Pisa (while ignoring their abject failure at Prato), Machiavelli tried to convince Clement that he could mold the villagers and peasants of the Papal States into a fighting force capable of standing up to the Emperor and his Swiss pike men.

As Clement listened he caught some of his guest’s enthusiasm. Perhaps it was the delirium of despair, but standing still, as Guicciardini had observed, was not an option. With a sense of renewed purpose the Pope sent Machiavelli off to the Romagna with instructions to make an inventory of available resources. “[T]he matter is of great importance,” read the papal brief Machiavelli carried in his saddlebag, “and on it depends the safety of the Papal States as well as that of the whole of Italy, and practically the whole of Christendom.”

Machiavelli set out in high spirits, pleased to be on the road again in the fine summer weather and excited to be taking part in a mission of such vital importance to the future of Italy. He had every reason to be optimistic. Not only did the Pope appear to be fully behind the project, but the recently appointed President of the Romagna, whose cooperation was crucial to the success of the venture, was none other than his old friend Francesco Guicciardini. Unfortunately for Machiavelli, when he arrived in Faenza, capital of the Romagna, he found the phlegmatic Guicciardini less than enthusiastic. In the past Guicciardini had often chided his friend on his too vivid imagination, and this latest proposal struck him as one of those pie-in-the-sky schemes Machiavelli occasionally pursued without regard to practical details. While he did not oppose Machiavelli’s goals, he thought current conditions inauspicious for such a bold undertaking. “[I]f it could be brought to the desired fruition,” Guicciardini wrote to the papal secretary, “there is no doubt that it would be one of the most useful and praiseworthy things which his Holiness could do.” But, he concluded, “if he intends it as a remedy for present dangers, it is a provision which cannot come in time.”

In fact Clement had already begun to waver. While Machiavelli enjoyed Guicciardini’s hospitality in Faenza, the Pope blew alternately hot and cold. “When I asked him again if His Beatitude had made up his mind,” wrote the Pope’s adviser, “he replied that he wants to think about it some more.”

By the end of the month Machiavelli’s initial enthusiasm was gone, undone by the Pope’s vacillation. He packed up his bags and headed home for Florence, convinced that the Pope would never make up his mind. It had been a frustrating mission, and Machiavelli returned to his farm disgusted once more with affairs of state that seemed to bring him nothing but aggravation. His brief return to public life merely confirmed his conclusion made years earlier that those who toil on the people’s behalf “sow in sand and in water.”

The one person Machiavelli apparently did not blame for the failure of his scheme was Guicciardini. His recent sojourn at the presidential palace in Faenza had strengthened a bond that was growing closer with each passing year. It was a relationship built on mutual admiration; however much the two disagreed on specific policies, neither doubted the other’s sincerity and genuine passion for the well-being of Italy. It didn’t hurt that the wealthy Guicciardini treated his guest royally. Crossing swords with his aristocratic friend was always made more enjoyable by the good food and wine that accompanied their lively debates.

Their friendship was marked by a warmth that went beyond intellectual respect and high-minded ideals. The reserved, aristocratic president of the Romagna and the irrepressible former Second Chancellor, like many who come from varied backgrounds and possessed contrasting temperaments, discovered in their differences a source of both wonder and amusement. When Machiavelli insisted on addressing Guicciardini by his honorific, Guicciardini shot back: “I must warn you that if you address letters to me with ‘Illustrious,’ I shall address yours ‘Magnificent,’ and thus, with these reciprocal titles we shall each of us please the other. But soon enough it will turn to mourning when we find ourselves, I say all of us, with our hands full of flies at the end. So decide how much weight you wish to give to titles, measuring mine against those you would delight in having given to you.”

Not all their correspondence is marked by similar compliments. In fact they felt sure enough of their mutual affection to goad each other mercilessly. Shortly after Machiavelli returned to Florence, Guicciardini asked his friend to survey a piece of property he had purchased. “[F]or about three miles about, you can see nothing pleasing,” Machiavelli began his report. “The house cannot be called bad, but neither would I call it good.” It was an assessment made by a poor man who believed that wealth made for careless judgments. But if Guicciardini had no eye for real estate, Machiavelli, according to Guicciardini, had his own blind spot. Pretending to be hurt by his harsh verdict, Guicciardini sent a sharply worded retort. Adopting the persona of the offended estate herself,Milady Property of Finocchieto, he wrote:

You are accustomed to your Barbera who, like all of her kind, seeks to please all and to seem rather than to be. However in this case your eyes, accustomed as they are to meretricious company, are not satisfied with what is but rather by what seems to be. As long as they detect some vague hint of beauty, they fail to delve beneath appearances. But you who have read and written so much history and seen so much of the world should be able to discern that another mode of adornment, another beauty, a different manner of making oneself up and of presenting oneself is sought in a woman who lives with everyone and loves no one.

Bringing up the less than chaste habits of his mistress might seem like hitting below the belt, but if Machiavelli felt the need to leap to the defense of his lady love that letter has not come down to us. Instead, when he next writes to Guicciardini it is to offer him a recipe to relieve his constipation, repaying him for all the delicacies he had consumed at his table with a concoction of bitter aloe, saffron, and Armenian bole.

Though Machiavelli returned to Florence having achieved little, his efforts did not go unrecognized. In September 1525 his name was finally added to the electoral rolls, making him a full-fledged citizen of the republic he had served for so long. Though his friends teased him that the honor had been won through the charms of his mistress Barbera, it is more likely that it came at the urging of the Pope, who perhaps felt bad that he had put Machiavelli through so much trouble for nothing. In any case the honor was largely empty since real power was jealously held by Cardinal Passerini da Cortona, sent by Clement to supervise the two Medici bastards, Ippolito and Alessandro, who governed much as their fathers had—with a combination of arrogance and incompetence that marked all the descendants of Il Magnifico.

Machiavelli seemed to regard being imborsato (having his name placed in the electoral bags) as little more than a consolation prize and was determined not to let politics rule his life. In October his oldest son, Bernardo, came down with “double tertian fever,” and as long as he was in danger Machiavelli could think of nothing else. Once his recovery was assured, Machiavelli’s attention turned to other matters, most notably a production of La Mandragola that Guicciardini was organizing in Faenza for the Carnival season of 1526. With the international situation going from bad to worse, one might have thought that the two greatest political minds of the day might have had better things to do than worry about the staging of a frivolous comedy, but as Guicciardini noted it was in times such as these that diversions were most welcome. “Honored Niccolò,” he wrote, “I shall begin to answer you with the comedy, because it does not seem among the less important things that we have on our hands, and at least it is something over which we have some control, so that it is not a waste of time to think about it, and now more than ever recreation is needed amidst all this tumult.” Machiavelli agreed with his friend about the benefits of distraction, but he also knew that laughter is often the most direct path to deeper truths. Trying to explain a particularly obscure passage in La Mandragola, Machiavelli told his friend that he should interpret its meaning as: “time is endlessly repeating but we are always the same”—a notion that also lay at the heart of his political philosophy.

As it turned out the performance in Faenza had to be postponed indefinitely.iii Laughter might be an antidote to the poison of political strife, but it could not keep reality at bay. Foreign armies, restless and ill-disciplined, roamed the land, feeding themselves by starving the native population, while powerful men hatched schemes for deploying their lethal power. Friends contemplated mutual betrayal, while sworn enemies slipped discreetly into bed together. Rumor and conjecture filled the information vacuum as civilians tried to make sense of a shifting tapestry that followed no discernible pattern. Before he could put the finishing touches on the performance, Guicciardini was swept up in the maelstrom, summoned to Rome on urgent business with the Pope. Machiavelli did not have much time to grumble about the change in plans; soon he, too, would be plucked out of his present idleness to play his own small part in the unfolding drama.

•  •  •

With Francis’s calamitous rout at the Battle of Pavia, Charles had become the master of the Italian peninsula. But in the tangled web of European politics no victory was final and no defeat irretrievable. Success, in fact, brought to the victor its own set of problems. The Emperor’s triumphant troops were a motley assortment drawn from the four corners of his empire, underpaid and underfed; to maintain them in the field indefinitely and preserve their discipline was almost impossible. And even though Charles ruled more territory than any monarch since the Roman Empire was divided between east and west, along with the immense expanse of his realm came an equally long list of troubles, from the fragile colonies of the New World to the religious quarrels of the Old. Charles, in short, was vastly overextended.

What saved the Emperor, at least for the moment, was the fact that his many foes lacked the will or foresight to take advantage of his weakness. Ever since Ludovico Sforza had played his dangerous game with the French King in 1494, the statesmen of Italy had attempted to secure their realms through subterfuge rather than strength of arms, until all virtue was lost and the country reduced to abject servitude. Elaborate plots replaced sound military strategy, the art of conspiracy substituted for martial valor. Pope Clement was only the most nimble practitioner of this sly art, making solemn commitments one day only to break them the next, infuriating everyone with his pusillanimous and devious conduct.iv Machiavelli, for one, was thoroughly fed up, telling Guicciardini, “I have to conclude that this gang here will never ever accomplish anything honorable or heroic to justify either living or dying.”

One could argue that this is exactly the world he himself had promoted in The Prince: “Since a prince is required to play the beast, he must learn from both the fox and the lion, because a lion cannot defend himself against snares, nor the fox against wolves.” But what separated the current Pope from the idealized prince he had conceived was that there was too much of the fox and none of the lion in him. There was nothing Machiavelli despised more than weakness, and all the intricate plots and counterplots spun by the Pope and his allies were little more than the desperate ploys of men lacking courage or conviction. With his eyes set firmly on the ultimate objective—the liberation of Italy from the barbarians—Machiavelli was willing to forgive a great deal if it helped achieve his goal. He was, however, unsparing toward those who sacrificed the ultimate objective for short-term advantage or who were simply too inept to get from point A to point B without tumbling into a ditch. Had the Pope’s erratic course brought freedom to Italy, Machiavelli, like most of his countrymen, would have ignored his faults. As it was, those faults contributed to the looming disaster.

It was a disaster that both Machiavelli and Guicciardini foretold but could not forestall. “I vent my feelings against these princes, who have done everything possible to bring us to this pass,” Machiavelli wrote in despair. Guicciardini was hardly more sanguine.“As to public affairs, I do not know what to say because I have lost my bearings . . . . If I am not deceiving myself, we will all be better acquainted with the evils of peace when the opportunity for making war has passed. One never sees anyone who, when bad times approach, did not seek in some way to try and cover himself, except for us, who want to meet them unprotected in the middle of the road.”

During these troubled days the two men remained in constant touch, hoping to discover some way out of the morass. In January 1526, to the surprise of many (including Machiavelli), Charles agreed to release the French King in return for territorial concessions and a formal revocation of any claims he had in Italy. Compliance was to be assured by sending two of the French King’s sons to Spain and arranging a marriage between Francis and Charles’s sister, Leonora. Machiavelli thought the plan was madness on the Emperor’s part. “It would be, as I have said, a foolish move for the emperor to release the king,” Machiavelli wrote to Guicciardini, though, he added, “it would be smart for the king to promise anything to obtain his freedom.” Machiavelli, who had literally written the book on how to behave in such situations, proved prophetic once again. As soon as he safely crossed the Pyrenees, Francis backed out of the agreement, a breach of promise for which the Pope—no stickler in such matters—quickly absolved him on the grounds that it was made under duress.

“[T]here will be war in Italy, and soon,” Machiavelli glumly concluded. Since a victory by Charles would reduce them all to servitude, the only option for Italians was to arm themselves and side with France, a course of action with which Guicciardini heartily agreed. In fact the President of the Romagna was already beginning to put such a plan into motion, urging the Pope to make a stand, like Julius before him, for Italian liberty. “Those dreading war should be shown the perils of peace. Over-prudence is now imprudence, and it is no longer possible to undertake measured enterprises. It is indispensable to resort to arms to avoid a peace that makes us slaves.” Prodded by Guicciardini and other Italian patriots, the Pope finally signed an anti-imperial pact. The League of Cognac, as this new alliance was called, included France, Venice, Florence, Milan, and the papacy, a coalition that, at least on paper, should have been more than sufficient to stand up to Charles.v

Having made the decision to confront the Emperor, one of the first orders of business was to shore up the crumbling defenses of the Pope’s native Florence, which stood directly in the path of any army descending on Rome. Clement, who had received one of the first copies of Machiavelli’s Art of War, immediately sent for the former Second Chancellor to discuss the state of the city’s fortifications. After making a brief inspection, Machiavelli headed to Rome in late April 1526, where he delivered a report titled “Provision for the creation of the office of the five superintendents for the walls of the city of Florence.” He remained in the Holy City only a few days, but when he returned to Florence, he carried with him a document from Clement naming him secretary of the new commission in charge of the reconstruction project. “Machiavelli has left with the orders for the supplies and officers to be carried out,” Guicciardini wrote to his brother Luigi in Florence: “people are to start the fortifications in the way that you will learn from him . . . . Machiavelli was the man who fostered this plan, hence please be obliged to treat him well during his stay and in the other matters that may be required because he has earned his share full well.”

For the first time since he had been thrown out of office fourteen years earlier, Machiavelli held an official position with the Florentine government. And though his new title, Secretary to the Overseers of the Walls (with son Bernardo appointed his assistant), was a far cry from the distinguished Second Chancellor and Secretary to the Ten, securing the defenses of the city he loved was a task worthy of his efforts. Machiavelli took to the work with his usual zeal, walking the miles of the city’s fortifications, supervising the digging of trenches, and overseeing the repair of crumbling towers. “[M]y head is so full of ramparts that nothing else can enter it,” Machiavelli told Guicciardini, overjoyed to find himself useful once more.

In the meantime Guicciardini, now invested with the exalted title of Luogotenente (Lieutenant-General) of the papal army, hurried north to take charge of the forces of the league. Finding them in disarray, in early July Guicciardini asked Machiavelli to come join him in Piacenza to help instill some discipline in the ragtag army. Reluctantly, Machiavelli set aside the important work on the city’s fortifications and hurried to his friend’s side, but even he could make little headway. “He came to reorganize the militia,” Guicciardini told Roberto Acciaiuoli, Florentine ambassador to France, “but seeing how rotten it is, he has no hope of having any respect from it. Since he is unable to remedy the faults of mankind, he will do nothing but laugh at them.”

Here Guicciardini captures in a few deft strokes a perfect likeness of his friend: a man of contradictions, of light and shadow, laughter and tears, prone to outbursts of enthusiasm that were inevitably followed by bitter disappointment. When duty called he did not excuse himself on the grounds that, at fifty-seven, the rigors of travel or camp life were too onerous, or that in the past his service had been flung back in his face. He remained hopeful that this time would be different, and when he saw his best efforts come to nothing, he turned away with a rueful grin and a derisive shrug as if to say that he expected nothing more. Roberto Acciaiuoli, for his part, appreciated the effort though he despaired of the outcome: “I am glad that Machiavelli gave the orders to discipline the infantry,” he replied to Guicciardini. “Would to God he might put into action what he has in mind, but I doubt whether it is like Plato’s Republic.” In other words, Machiavelli was too much the dreamer to stand much chance of success. How ironic that he who famously declared he preferred to “stick to the practical truth of things,” should turn out to have been an idealist all along!

But it seemed to be his fate in these dark days to be caricatured as a man of ideas with little sense of the way the world really worked. Even a philosopher with both feet planted firmly on the ground was, after all, still only a philosopher, ill equipped to handle practical chores best left to professionals. While in Piacenza he spent some time in the camp of the famous mercenary Giovanni delle Bande Nere (Giovanni of the Black Bands), whose small army was the one truly capable fighting force in the anti-imperial league. According to the writer Matteo Bandello, who claims to have been there, the battle-tested general thought it might be amusing to teach the author of The Art of War a lesson. Opening Machiavelli’s book to the chapter on infantry drills, Giovanni asked him to attempt to put into practice what he’d written by marching his three thousand men about the parade ground. Machiavelli gamely took up the challenge but, not surprisingly, proved hopelessly out of his depth. The troops were soon milling about in confusion and could only be disentangled by the prompt intervention of their captain. “How great the difference is,” Bandello sneered, “between someone who knows and who has not set in operation what he knows and someone who, as well as knowing, has often rolled up his sleeves and . . . has derived his thoughts and mental view from outward deeds.”

Poor Machiavelli! The incident was embarrassing, but the test was hardly fair. More than any writer before him, he brought philosophy down off its pedestal to where it could make a real difference in the lives of real people. If his theories did not always stand up to their initial contact with hard fact, he was enough of an empiricist to revise them in light of new data. And for a man with no formal military training he had done surprisingly well by his country, leading Florence to victory against her ancient rival Pisa and helping in the current crisis to defend her against her

For the remainder of 1526 the forces of the League of Cognac sparred with those of the Emperor. The league scored a victory with the capture of Cremona, but this was followed by notable reverses, including a revolt in Rome led by the Colonna family that forced the Pope to flee to the fortress of Castel Sant’ Angelo. In the wake of this disaster, Clement was obliged to sign yet another humiliating truce with Charles—one he broke almost immediately by ordering the mercenary captain Paolo Vitelli to launch an attack on Spanish-held Naples.

The league suffered an even more grievous blow late in November when Giovanni delle Bande Nere was killed after being struck in the leg by a cannon ball. He had been Italy’s ablest commander, a man who Machiavelli believed was capable of leading the papal armies to victory and fulfilling, at least in part, the dream laid out in the final chapter of The Prince. Without their finest general, the cause of the Pope, and of Italy itself, seemed more desperate than ever.

Still the conflict dragged on in fits and starts, a kind of endless Purgatory with ultimate victory and final defeat equally inconceivable. Machiavelli was not spared in all this pointless to-ing and fro-ing, traveling to Milan, Cremona, and then in November to Modena, crossing the Apennine passes on horseback in the sleet and bitter cold. This ceaseless motion was beginning to take its toll. He delayed his departure from Modena for a few days to recuperate from the rigors of the trip; when he finally set out for Florence, he was determined to travel by “daily stages” to spare his aching body.

In fact Machiavelli was more fully engaged in government work than he had been for years, but the rewards were ever more meager in terms of both money and prestige. His duties were all the more onerous since they seemed to so little purpose. Despite Guicciardini’s capable management, the forces of the league, under the direct command of the dilatory Duke of Urbino, avoided bold action, principally because the Pope himself could not decide between peace and war. In the end he managed to choose the worst possible course, provoking the Emperor’s wrath while doing nothing to protect himself from the consequences. Fortunately, as Machiavelli pointed out, his enemies were hardly any better: “[T]he Spaniards could have beaten us several times, and they have not contrived to do so; we could have been victorious, and we have not known how; the Pope believed in a stroke of the pen more than in a thousand soldiers who could have kept him safe.”

The “stroke of the pen” Machiavelli referred to was a truce signed between the Pope and the Emperor, the latest in an apparently endless series of treaties each rendered obsolete before the ink had dried. Given this record, no one, except perhaps the Pope himself, was surprised when the agreement failed to halt the advance of the imperial army. Part of the problem was that Clement had signed the pact with representatives of the distant Emperor, while command on the ground was in the hands of Charles, Duke of Bourbon. Whatever deals his master cut with the slippery Pope, Bourbon was more concerned with placating his twenty thousand ill-disciplined and rebellious troops, who were clamoring for blood and plunder. The treaty, Machiavelli noted, was “made in Rome, but not observed in Lombardy.” Worse still, in a desperate attempt to show his good faith, Clement had disbanded the forces needed for the defense of the Holy City, “living in Rome,” as Machiavelli scornfully put it, “in such a way as to let himself be captured like a child.”

Not surprisingly, the Emperor’s halfhearted attempts to rein in his rebellious commander were ignored. As Bourbon’s army marched southward, the Pope could not even count on the usual last best defense of the papacy—the conscience of troops who might hesitate before lifting a hand against the Holy Father. Though the Emperor was a devout Catholic, many of those who actually did the fighting were Germans—the famed Landsknechts led by Georg von Frundsberg—followers of Luther who regarded the Pontiff as the devil incarnate, and most of the rest simply thugs who would help themselves to the maidens and treasures of Rome as compensation for years of hardship. Even Machiavelli succumbed to despair. “[O]bserving the behavior of France and the Venetians, the poor order of our men, seeing how hopeless it is for the pope to sustain the war against the kingdom [of Naples] and the power and stubbornness of our enemies, we judge the war as good as lost.”

As the rogue army snaked south for a final reckoning with Clement, Florentines girded for a possible thrust in their direction. In February, the Eight again dispatched Machiavelli to Guicciardini, who was now in Parma, to urge the Luogotenente not to abandon his native city in her hour of need. For a man in his late fifties, the prospect of yet another journey on horseback in the dead of winter was daunting, but Machiavelli accepted the mission without complaint. He remained with the papal army as it moved south, from Bologna—knee deep in snow, as he reported—to Forli. It was a dispiriting march. The forces of the league could only tag along behind the imperial battalions, keeping a wary eye on them but doing nothing to halt their progress. Morale suffered and the troops under Guicciardini’s command began to melt away. “We began . . . to divide the army at Parma,” Machiavelli wrote to the Eight, “and we have been reducing it bit by bit right up to Forli.”

By early April the imperial army was only a few days’ march from Florence. The situation was sufficiently ominous that Machiavelli instructed Marietta and the children to leave Sant’ Andrea and take refuge inside the city walls. On April 17 Guido wrote to his father: “As for the lansquenets, we don’t worry about them any more because you have said you would try to be with us if anything happened. And so mona Marietta is no longer fretting. We pray that you write to us if the enemy should think of coming and damaging our property, because we still have many things in the country.”

Surveying the situation from Forli, Machiavelli, Guicciardini, along with what remained of the league’s forces, were faced with a painful decision: whether to move south to insert themselves between the imperial army and Rome, or to the west, where they could parry a thrust in the direction of Florence. “I do not believe there were ever more troubling matters than these,” Machiavelli wrote to Vettori, “where peace is necessary and war cannot be abandoned; and where we have a prince [Clement] on our hands who decides neither for peace nor for war.”

Guicciardini was equally disenchanted with his master. On April 16 he made his decision: “I have taken on my own initiative, as I have no assistance from Rome, to send towards Florence all the forces at my disposal.” Machiavelli was relieved. “I loveMesserFrancesco Guicciardini,” he gushed that same day, adding, as explanation for this sudden outburst, “I love my city more than my own soul.”

Returning to Florence a few days later Machiavelli found the city in an uproar. The Pope’s irresolution and the misgovernment of his relatives had turned even former allies against the Medici regime. Even the arrival of Guicciardini’s troops outside the walls failed to improve matters. Though they were there to defend the city, they behaved more as occupiers and laid waste to the countryside for miles about. Matters came to a head on Friday, April 26, when mobs of young citizens stormed the Palazzo della Signoria and tried to topple the government. Only the intervention of Guicciardini prevented a violent confrontation as he persuaded the young hotheads to turn in their weapons in exchange for a full pardon.

Fortunately for Florence, the Duke of Bourbon turned away at the last minute, the mere appearance of Guicciardini’s small army having been sufficient to discourage an assault. Instead, Bourbon and his men, hungry and ill equipped but spurred on by the promise of plunder, made for the undefended gates of Rome. The Duke of Urbino set out after them, but was, as usual, unwilling to risk open battle. Guicciardini, with Machiavelli riding by his side, followed, on hand to witness, but unable to do anything to avert, the disaster they had been warning of for so long.

The ragged imperial army arrived before the walls of Rome on the evening of May 4, 1527. After months, even years, in the field, the soldiers were cruel, desperate men, coarsened by the horrors of war and seething with resentment against civilians who had spent their days in idle comfort while they were exposed to the dangers of the battlefield and the miseries of camp life. Even those Spanish troops who remained within the Catholic faith now viewed Rome and its masters with contempt.

The mood of the besieging army grew more ominous when on the night of May 5 their leader, the Duke of Bourbon, was killed by a harquebus discharged from one of the towers. According to Benvenuto Cellini, the great sculptor and goldsmith, it was he who fired the fatal shot, aiming at one “whom I remarked to be higher than the rest.” It was an implausible, though not impossible, claim and, in any case, whoever was responsible for the Duke’s death hardly did the populace of Rome any favors since without their leader the last restraint was lifted from his troops. On May 6, 1527, German and Spanish soldiers poured through the sparsely manned walls and began their bloody rampage. In three days and nights, Christian soldiers managed to inflict more damage on the holy city than the Visigoths had more than a millennium earlier, burning and pillaging, sparing neither holy place nor holy person, scattering relics and putting to the torch countless shrines, bursting into convents and raping the nuns, murdering defenseless women and children, savaging clerics and civilians alike in an unmatched orgy of destruction.

Machiavelli was with Guicciardini in Orvieto, some fifty miles to the north, when he heard “the dreadful news from Rome.” He mourned, like all Italians, the destruction of the great capital, but he was hardly surprised. He had seen the horrors of war close up, and it was largely because of these experiences that he placed such a premium on strong leaders and stable states that protected their people from random violence. “Wherever you turn your eyes,” he had written after witnessing another battlefield, “you see the earth wet with tears and blood, and the air full of screams, of sobs, and sighs”—a scene now playing out on an even larger scale in Rome.

News of the horrific sack sent shock waves through the capitals of Europe, but nowhere were the reverberations felt more powerfully than in Florence, where the Pope’s humiliation shook the already fragile edifice of Medici power. With Clement now a prisoner of the imperial army, the citizens of Florence no longer saw any reason to defer to his representatives. On May 16 Cardinal Passerini was forced to step down; a few days later, he and the two young Medici heirs, Ippolito and Alessandro, were expelled and a new republic proclaimed, completing a thorough but bloodless change of regime.

Machiavelli was an emissary to an army that was now leaderless from a government that no longer existed. As he packed up his bags and prepared to return to his native city, he was torn by conflicting emotions. He rejoiced that the government would now be restored to its ancient republican form, but he was painfully aware that, once again, he had placed himself on the wrong side of history. For someone as politically astute as Machiavelli, it is remarkable how often he seemed to back the losing side, particularly since he was rarely moved by those ideological passions that are so often the undoing of political men. The explanation for this apparent obtuseness is simple. Machiavelli’s misfortune was to be a devoted servant of the state in an age when the state was dysfunctional. The same sense of crisis that motivated his greatest writing undermined his political career. In dedicating himself to the country he loved, he was pledging his loyalty to a faithless mistress, as fickle as Fortuna, whose whim ruled the fate of all mortals.

One of his companions on his homeward journey recalled that “he heard him sigh many times when he heard that the city was free. I think he was regretting his conduct, because in fact he greatly loved liberty; but he regretted having involved himself with Pope Clement.” Were those feelings of regret made more bitter by a sense of guilt? Five years earlier his friends who were willing to risk all in the cause of liberty had been banished or killed while Machiavelli survived and even prospered. Now the roles were reversed; the idealists had won the day, and those too timid to take a principled stand found themselves scorned by the victors.

Whatever his private regrets, Machiavelli believed he had acted in good faith. His unclouded conscience is suggested by the fact that as soon as he arrived in Florence he began to lobby for his old job back. While some regarded this as unmitigated gall on the part of someone who had only a few days earlier been serving the discredited Medici, he maintained that he had been working not on behalf of the regime but on behalf of all Florentines. The walls he had helped repair, the army he had persuaded to place itself between the city and their enemies, had saved Mediceans and republicans alike, and he saw no reason to apologize.

In fact he had some support among the new leaders of the city. Both Lodovico Alamanni and Zanobi Buondelmonti, who had returned following the expulsion of the Medici, spoke in favor of their old friend. They evidently held no grudges for what had happened five years earlier and tried to get the Signoria to reappoint Machiavelli to the vacant office of Second Chancellor. Unfortunately, Alamanni and Buondelmonti were in a distinct minority. Not only had his recent employment by Pope Clement sullied his reputation in the eyes of most Florentines, but by now his writings, though mostly unpublished and circulating only in manuscript form, had made Machiavelli notorious. One contemporary observed: “[The common people] hated him because of The Prince: the rich thought hisPrince was a document written to teach the duke how to take away all their property, from the poor all their liberty; the piagnoni regarded him as a heretic; the good thought him sinful; the wicked thought him more wicked or more capable than themselves—so they all hated him.”

This was a prelude of things to come. The man with such a wise and forgiving heart would not be forgiven by those he had mocked with his sharp tongue. He was not an evil man, as many of his contemporaries supposed and as history has assumed, but something worse: he was tactless. Pointing out uncomfortable truths turned out to be an unpardonable crime, while the countless acts of cruelty, treachery, and violence to which he bore painful witness—and that he tried to ameliorate through a philosophy rooted in a realistic assessment of human nature—were passed over with barely a yawn. Even before his death he had become notorious for his irreverence and the pleasure he took in exposing the bankruptcy of shopworn pieties. His compatriots split their sides laughing as his comic inventions Messer Nicia and Nicomaco strutted about the stage like pompous fools, but when he sought to fashion a theory of politics that might accommodate such flawed specimens, they balked, unwilling to follow his logic to the end. People could forgive almost anything but the shattering of their illusions. For a man who prided himself on his insights into the human heart, who could subtract the resentment derived from the murder of a relative from the resentment engendered by the loss of an estate and find the precise remainder, he was remarkably careless in assessing the effect his words had on others. Above all he was singularly incapable of playing the devious games he recommended to others as the way to get ahead.

•  •  •

Doctors no longer claim that one can die from a broken heart, but even the most scientific physician would admit that crushing disappointment can take a toll on a body already worn out from years of stress and overwork. On June 10, Machiavelli learned that the job of Second Chancellor went to Francesco Tarugi, an undistinguished functionary who had previously served as Secretary to the Eight. Though Machiavelli’s failure to get the appointment could hardly have come as a surprise, it was yet another bitter blow. In 1512 he had met disappointment with reserves of inner strength. These reserves were long since gone, depleted by age and years of frustration. Only two weeks earlier he had been riding about the countryside on the government’s business; less than two weeks later he was laid low with abdominal pain brought on, his son Piero believed, by an overdose of the same homemade remedy he had prescribed for his friend Guicciardini. The crisis was sudden and severe, striking down an elderly but still vigorous man in midstride.vii

Machiavelli’s death has spawned legends as persistent and contradictory as his life. From Piero we have a spare but almost certainly accurate account: “My very dear Francesco,” he wrote to his maternal uncle,

I can only weep in telling you that our father, Niccolò, died on the 22nd of this month, from pains in the stomach caused by a medication he took on the 20th. He confessed his sins to Brother Matteo, who kept him company until his death. Our father has left us in the deepest poverty, as you know.

Such a matter-of-fact account, from such an unimpeachable source, might seem uncontroversial, but those who revere Machiavelli as the great prophet of atheism dismiss Piero’s account of a priest administering last rites as a pious fiction intended to hide their hero’s true nature. But there is no reason to believe that Piero invented this deathbed scene. Machiavelli, as we have seen, was a harsh critic of Christianity, but he reserved most of his scorn for those corrupt priests who took advantage of the weak and the gullible. He was certainly never a devoted churchgoer, but he conformed outwardly to the conventions of the day, entering the sacrament of marriage and baptizing his children. There is no reason to believe that in his final moments he would have defied those traditions to which he had subscribed, if only casually, throughout his life.

In accepting last rites, Machiavelli may simply have been taking the path of least resistance, but it also possible that, like many nonbelievers, he had a change of heart as he felt his end approaching. It is likely that as he was faced with his own imminent death, he was apprehensive and unsure. He could not fall back on the comfort of simple faith, but neither was he certain that the soul was merely an illusion conjured by the material body. He was never doctrinaire, particularly when it came to such vast, inscrutable matters as life and death, and would not have presumed to know what awaited him in the world to come.

Easier to discern than the dying man’s innermost thoughts is the impact his passing had on those around him. This is most clearly revealed in a legend that quickly sprang up around his final vigil. The so-called “Dream of Machiavelli” is almost as old as Piero’s letter, but despite the ancient pedigree it seems too perfectly crafted to be anything but apocryphal. Lying close to death, the story goes, Machiavelli told his friends who had gathered at his bedside of a dream he had. In his vision he saw two columns of men. One consisted of miserable wretches dressed in rags. When he asked who they were, they replied: “We are the saintly and the blessed; we are on our way to heaven.” Then he spied another column, this one filled with men dressed in fine robes, deep in conversation. As he approached he recognized many of them: Plato, Plutarch, and Tacitus, all discussing grave matters of state. When asked what brought them here, they replied: “We are the damned of Hell.” Having told his story, Machiavelli turned to his guests and, smiling, declared that it was among these learned men, rather than pious fools, that he hoped to spend eternity.

It is an appealing story but one that, unfortunately, does not ring true. Certainly, the cynical wit was typical of Machiavelli, who rarely missed a chance for mischief; in fact the legend echoes some of his own words, including those famous lines in his letter to Guicciardini where he explains that the best way to get to heaven is to learn the path to hell.viii But Machiavelli was no philosopher-saint like Socrates, a creature of superhuman virtue unaffected by the torments of the flesh. He was the first to admit his own weaknesses, and a lofty indifference to adversity was hardly his style. Out of respect for this most down-to-earth of philosophers, who famously declared that he would rather stick to the truth of things than to fancies, one ought to treat this dream as a charming fiction.

The one form of immortality Machiavelli believed in wholeheartedly was the immortality conferred by a famous name. Perhaps this was the only way to better fickle Fortuna, whose writ had little sway beyond the grave. Though he could not be sure thathisname would endure in the world he was now departing, perhaps he took some comfort in the modest but real successes he had already achieved. The one thing he could not have anticipated as he closed his eyes for the last time, in the house of his ancestors near the Ponte Vecchio in the city he loved best in the world, was that his name would not only endure but that history would proclaim him one of the truly remarkable figures of a remarkable age.

i Not least of Charles’s headaches were the revolts inspired by Luther and his followers in the northern reaches of his dominions.

ii The Pope was evidently pleased with what he read since he awarded the author an additional 120 gold ducats.

iii The disappointment was more than made up for by a hugely successful run in Venice, where La Mandragola was performed before overflow crowds. In a development that must have pleased Machiavelli no end, his comedy was judged by most to be far superior to Plautus’s Menaechmi, being performed simultaneously to far smaller audiences.

iv After Charles’s victory at Pavia, Clement was forced to realign himself with the Emperor. But only a few months later he was discovered plotting with the chief minister of the Duke of Milan to betray the Spaniards. When this scheme unraveled he went crawling back once again into the Spanish fold.

v Henry VIII of England was to have been included in the new alliance but backed out at the last minute.

vi One of the main points of The Art of War is that amateur soldiers are preferable to professionals. For instance, “a good man could not make war his only profession” (Book I, p. 17). Giovanni’s demonstration may have been intended to show Machiavelli the error of his ways.

vii It is impossible to say with any certainty what killed Machiavelli. Some modern theories include a ruptured appendix or a gastric ulcer. It is also likely that the medicine Machiavelli used to treat his stomach problems accelerated his death.

viii It also recalls some lines in La Mandragola where the hero Callimaco says, “Don’t you know how little good a man finds in the things he has longed for, compared with what he expected to find? On the other hand, the worst you can get from it is that you’ll die and go to Hell. But how many others have died! And in Hell how many worthy men there are!” (La Mandragola, IV, i, in Chief Work, vol. 2, p. 805.)

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