THE LIFE OF CASTRUCCIO CASTRACANI OF LUCCA

COMPOSED BY NICCOLÒ MACHIAVELLI AND SENT TO HIS DEAREST FRIENDS, ZANOBI BUONDELMONTI AND LUIGI ALAMANNI

In The Life of Castruccio Castracani of Lucca Machiavelli blends biography, historical chronicle, and literary fiction to create a portrait of the ideal warrior prince. Since its first publication in 1533, it has traditionally been printed together with The Prince to provide an extension of Machiavelli’s vision of the ideal ruler.

Machiavelli relied on chronicles and accounts of Castracani’s life for historical facts, but invented characters and situations and reshuffled and conflated historical events in order to enliven his narrative. Machiavelli wrote this piece at an important moment in his life: After eight years of exclusion from Florentine politics, he was sent to the city of Lucca as an official emissary in the bankruptcy case of Michele Guinigi, whose family name Machiavelli was to use in the story as that of Castracani’s fictitious guardian.

Though Castruccio Castracani had been a dire enemy of Florence, causing untold damage to the city, Machiavelli did not allow this to affect his admiration for the self-made prince, who for a few years had turned the small town of Lucca into a foremost Italian power.

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Those who have given the matter some thought, dearest Zanobi and Luigi, will marvel that most, if not all, men who have accomplished great deeds and excelled above all others of their era were of low birth and obscure origins, or were tormented beyond compare. They were exposed to wild beasts, or had such lowly fathers that in shame they declared themselves to be sons of Jove or some other god. It would be an onerous task and objectionable to the reader to list all these men, as they are well known, so I shall pass over them. I believe that the lowly origins of great men is Fortune’s way of demonstrating that it is she and not Wisdom who makes men great. So that Fortune be acknowledged as supreme, she shows her powers very early in a man’s life, well before Wisdom could hope to play a role.

Castruccio Castracani of Lucca was one of the men who, despite the times in which he lived and the city in which he was born, did great things. Like others who rose to great heights, he did not have a fortunate or distinguished birth, as will become clear in my description of the course of his life. I considered it useful to bring his life to wider attention, as I feel it demonstrates many instances of skill and Fortune that will provide a powerful example to others. I have decided to present this work to you, my friends, since you, more than anyone else I know, delight in valiant deeds.

The Castracani were among the noble families of Lucca, though since the wheel of Fortune turns, the Castracani of that era had fallen on hard times. A boy named Antonio had been born into the family and raised to become a man of the church, and soon became Lucca’s canon of the order of San Michele. As a sign of honor, the people of Lucca addressed him as Messer Antonio. He had only one sister, who had been married to a Buonaccorso Cennami, but after she was widowed, not intending to remarry, she returned to live with him.

Behind Messer Antonio’s house was a vineyard that was surrounded by gardens, and thus could be easily entered from many sides. One morning soon after sunrise, Madonna Dianora (that was the name of Messer Antonio’s sister) was walking through the vineyard collecting herbs for the pantry, as women do. Suddenly there was a rustling beneath the branches of a vine. Madonna Dianora looked in that direction and heard what sounded like weeping. She walked toward the vine and saw the hands and face of a baby boy wrapped in leaves, who seemed to be calling out to her for help. Amazed and bewildered, but also filled with compassion and wonder, Madonna Dianora picked up the baby and carried him inside, where she washed him, wrapped him in white swaddling cloth, as was the custom, and presented him to Messer Antonio as soon as he came home. When he heard what had happened and saw the child, he was no less filled with amazement and compassion than she had been, and the two discussed what they should do. They decided to raise the child—Messer Antonio being a priest and she childless—so they hired a nurse, and brought up the child with as much love as if it were their own. They baptized the boy Castruccio, after their father.¹

With every year Castruccio grew in charm and character, proving himself in all things an intelligent and clever boy. He studied under Messer Antonio, who hoped that he would become a priest, and who intended, when the time came, to leave him his canonry and his other worldly possessions. Messer Antonio tutored him with this in mind, but soon realized that Castruccio was unsuited for the priestly calling. By the time the boy was fourteen he began to stand up to Messer Antonio and no longer feared Madonna Dianora, and he set aside his ecclesiastical books to follow his interest in weapons. In fact, nothing pleased Castruccio more than handling weapons, running, jumping, and wrestling with other boys his age. Here he showed physical skill and courage far beyond that of his peers, and if he did pick up a book, then only one that told of wars and the feats of great men. Messer Antonio was deeply grieved.

There lived in Lucca a fine gentleman of the Guinigi family by the name of Messer Francesco, who was graced with skill and valor far surpassing that of any other gentleman of Lucca.² He was a condottiere who had fought for many years under the Visconti of Milan, and was one of the foremost partisans of the Ghibelline faction in Lucca.³ Whenever he was in town, he would meet mornings and evenings with the other citizens beneath the balcony of the podestà, the chief magistrate’s palace, which is at the head of the Piazza di San Michele, Lucca’s main square. There he often noticed Castruccio playing war games with the other boys, and saw that he surpassed them in skill and that he even had some sort of regal command over them for which the other boys seemed to love and respect him.

Messer Francesco desired to find out more about the boy and when he was told the story of his background he resolved to take him under his wing. One day he called Castruccio into his presence and asked him where he would prefer to be, in the house of a gentleman who would teach him to ride and use weapons, or in the house of a priest where he would be taught nothing but services and Masses. It did not escape Messer Francesco that Castruccio brightened at the mention of horses and arms. The boy stood before him in modest silence, but when Messer Francesco encouraged him to speak, Castruccio replied that if Messer Antonio did not mind, nothing would make him happier than abandoning his priestly studies and taking up those of the soldier. Messer Francesco was pleased, and within a few days managed to persuade Messer Antonio, though it was in fact Castruccio’s nature that had swayed the priest, since he knew he would not be able to keep him in check much longer.

Once young Castruccio moved from the house of Messer Antonio Castracani the priest to that of Messer Francesco Guinigi the condottiere, one can only marvel at the swiftness with which the boy mastered the skills and customs of a gentleman. He became an excellent horseman, able to handle the wildest horse with great dexterity. Though still a youth, he stood out above all others in jousts and tournaments, so that in every feat, whether of strength or skill, no man could surpass him. All the while, Castruccio’s comportment was unfailingly modest. He never said or did anything that might displease: He was respectful to men stationed above him, modest with his equals, and pleasant to his inferiors. He was loved not only by the Guinigi family but by all of Lucca.

Castruccio had turned eighteen when the Ghibellines were ousted from Pavia by the Guelphs, and Messer Francesco Guinigi was sent by the Visconti of Milan to aid the Ghibellines. Castruccio went with him as captain of his company, and throughout the campaign showed so much prudence and courage that no other soldier acquired so much prestige. He became renowned and honored not only in Pavia, but in all of Lombardy.⁴

When Castruccio returned to Lucca he found that his standing had grown even more since he had joined the campaign, and he made sure to gain as many allies and supporters as he could, using all the methods necessary to win men over. Then Messer Francesco Guinigi died, leaving behind a thirteen-year-old son, Pagolo, with Castruccio as his guardian and the administrator of his estate. Before Messer Francesco died, he sent for Castruccio and entreated him to raise his son with the same devotion with which Messer Francesco had raised Castruccio, asking Castruccio to repay to his son the gratitude he owed him.

With Messer Francesco’s death Castruccio became Pagolo’s guardian, which further increased his standing and power. But some of the esteem in Lucca that had been his now turned into jealousy Certain men of influence, suspecting that he had his mind set on tyranny, began slandering him. Foremost among them was Messer Giorgio degli Obizi,⁵ the leader of the Guelph faction, who had hoped to become something like a prince of Lucca upon Messer Francesco’s death. In Messer Giorgio’s view, Castruccio was becoming the most influential man in Lucca on account of the admiration and prestige that his qualities inspired among the people, and so he began spreading rumors calculated to weaken Castruccio’s standing. At first Castruccio looked on Messer Giorgio’s efforts with contempt, but soon he began to worry that Messer Giorgio would not rest until he had blackened him in the eyes of the governor of King Roberto of Naples, and had him driven from Lucca.⁶

The ruler of neighboring Pisa in those days was Uguccione della Faggiuola of Arezzo. He had first been elected by the Pisans as their military commander, and afterward had made himself their prince.⁷ In his entourage were a few men of the Ghibelline faction who had been banished from Lucca, with whom Castruccio communicated with the aim of bringing the Ghibellines back to power in Lucca with Uguccione’s help. Castruccio revealed his designs to his allies in Lucca, who also resented the power of the Obizi family. They set up a plan, and Castruccio carefully began to fortify the tower of the Onesti family⁸ stocking it with munitions and provisions so that he could barricade himself in it for a few days if necessary.

On a night that Uguccione and Castruccio had agreed on, Uguccione rode out from Pisa with a large force and positioned his men on the plain between the mountains and Lucca. When Castruccio gave him a sign, Uguccione advanced on the Gate of San Piero and set fire to the portcullis, while inside, Castruccio called the populace to arms and forced open the gates so that Uguccione and his men could overrun the town and kill Messer Giorgio and all his family, friends, and partisans. The governor of Lucca was chased from the town, and Uguccione of Pisa rearranged the government to his liking, but at great cost to Lucca, for he banished more than a hundred families, some of whom fled to Florence, others to Pistoia, cities ruled by the Guelph faction, and so became enemies of Uguccione and the town of Lucca.

Florence and the other Guelph strongholds saw the Ghibelline faction as having gained too much power in Tuscany, and they forged an alliance to reinstate the banished Guelph families of Lucca. Gathering a large army, they marched on Val di Nievole, occupied Montecatini, and went on to Montecarlo to secure the mountain pass to Lucca.⁹ In the meantime, Uguccione had enlisted many men from Pisa and Lucca, as well as German cavalrymen he brought in from Lombardy and marched on the Florentine encampment. When the Florentines heard of the enemy’s approach they retreated from Montecarlo and posted themselves between Montecatini and Pescia. Uguccione took up position outside Montecarlo, some two miles from the enemy, but for a few days there were only light skirmishes between his cavalry and the Florentines, as Uguccione had fallen ill and did not want his soldiers to engage the enemy in all-out battle. Uguccione’s health deteriorated and he was taken to Montecarlo to be treated, leaving Castruccio in charge of the army¹⁰ This led to the ruin of the Guelph army, for they took courage at the news that the enemy forces were without their commander. Castruccio was aware of this, and decided to reinforce this conviction by remaining inactive for a few days, feigning fear, and not allowing his forces to leave camp. At this the Guelphs’ insolence grew, and they began parading every day in full battle formation before Castruccio’s forces. Once Castruccio felt that he had studied their formation and emboldened them enough, he decided to engage them in battle, firing up his soldiers with a speech assuring them that victory would be theirs if they followed his command.

Castruccio had seen that the enemy had gathered all their power at the center of their formation, leaving the weaker men on the flanks; consequently he did the opposite, putting his most valiant men on his flanks, and those of lesser mettle in the center.¹¹ Castruccio’s forces then marched out in this formation, and the moment he sighted the enemy, who with their usual insolence had come to find him, he ordered his weaker squadrons in the center to slow their step and the squadrons on the flanks to quicken theirs. In this way, when the two armies met, only their flanks would engage in battle, while the center battalions remained out of action. Castruccio’s center forces stayed so far back that the enemy’s powerful center could not reach them: thus Castruccio’s most skilled soldiers fought the enemy’s weakest, while the enemy’s most valiant men could neither attack those who were out of reach in front of them, nor come to the aid of their weaker flank squadrons. As a result, Castruccio sent the two enemy flanks in headlong retreat, and the enemy’s center forces, seeing their flanks exposed, turned and ran as well, robbed of the chance to demonstrate their prowess.

The rout and slaughter were great. More than ten thousand men were killed, among them many captains and prominent Guelph nobles from throughout Tuscany as well as princes who had rallied to aid them, such as King Roberto’s brother Piero, the king’s nephew Carlo, and Prince Filippo of Taranto.¹² Castruccio, on the other hand, lost only about three hundred men, among them Uguccione’s young and valiant son Francesco, who was killed at the very beginning of the attack.

This victory brought Castruccio such prominence that Uguccione became jealous and suspicious, and was possessed by the idea of destroying him. Uguccione was convinced that the triumphant victory had not increased his own power but in fact had decreased it. Consumed by these thoughts, he waited for the opportunity to strike at Castruccio, which presented itself when Pier Agnolo Micheli, a man of great accomplishment and repute, was murdered in Lucca. His murderer fled to Castruccio’s house, and when the officers came to arrest the murderer, Castruccio sent them away. The murderer managed to escape with his help. Uguccione, who was in Pisa, heard of the incident and saw the perfect chance to even the score with Castruccio.¹³ He sent for his son Nieri, to whom he had given the rule of Lucca, and ordered him to invite Castruccio to a banquet in order to apprehend him there and put him to death.

Castruccio gladly accepted the invitation to Nieri’s palace, not suspecting foul play and was seized at the dinner. But Nieri feared that the people of Lucca would be outraged if he put Castruccio to death without justification, so he locked him in a dungeon and waited for his father to send word on what he should do next. Uguccione was furious at his son’s wavering and cowardice, and set out from Pisa with four hundred horsemen to bring the matter to a conclusion. But he had not yet reached Bagni¹⁴ when the Pisans took up arms, killed his deputy and all the members of Uguccione’s family in Pisa, and made Count Gaddo della Gherardesca their new lord.¹⁵

Uguccione heard the news from Pisa before he arrived in Lucca, but he knew that it would be unwise to turn back and give Lucca the opportunity to imitate Pisa’s example and close its gates to him too. However, the people of Lucca had also heard the news, and despite Uguccione’s arrival seized the opportunity to try to free Castruccio. They flocked to the town squares to denounce Uguccione, took up arms, and began to stir up unrest, demanding that Castruccio be released. Uguccione, fearing the turn of events, freed him, upon which Castruccio immediately rejoined his allies. With the support of the populace, he attacked Uguccione, who was compelled to flee with his men, escaping to Lombardy to the domain of the Princes della Scala, where in due course he died in poverty¹⁶

From being a prisoner, Castruccio now practically became prince of Lucca. With the help of his partisans and the populace’s renewed favor, he was elected captain general of the army for a year. He was determined to increase his standing even further through war, and set out to win back for Lucca many of the towns that had revolted after Uguccione had been driven out. He marched on Sarzana with the backing of the Pisans, with whom Castruccio had formed an alliance, and during the siege built a fortress that was later walled in by the Florentines and is today known as Sarzanello.¹⁷ Within two months he had conquered Sarzana, and then went on to occupy Massa, Carrara, and Lavenza. Soon all of Lunigiana was his, and to secure the mountain pass that led from Lombardy to Lunigiana he stormed Pontremoli, driving out Messer Anastagio Palavisini, who was its prince. When Castruccio returned victorious to Lucca and was greeted by large crowds, he felt the time had come to make himself prince, and with the support of some of the foremost men of Lucca—Pazzino dal Poggio, Puccinello dal Portico, Francesco Boccansacchi, and Cecco Guinigi—all of whom he had bribed, he made himself lord of Lucca, and then in a solemn ceremony was elected prince by the people.¹⁸

When King Frederick of Bavaria, the Holy Roman Emperor, came to Italy to claim his imperial crown, Castruccio offered his allegiance. He rode out to meet him with a cavalry of five hundred, leaving Pagolo Guinigi, who was held in high esteem by the people in memory of his father, in charge of Lucca. Frederick received Castruccio with much ceremony, bestowing on him an array of privileges and making him his governor in Tuscany¹⁹ In the meantime, the Pisans had expelled Gaddo della Gherardesca,²⁰ and, fearing his retaliation, had turned to Frederick, who appointed Castruccio as prince of Pisa. The people of Pisa accepted Castruccio as their new ruler, as he was a Ghibelline who could keep them secure from the Guelph faction, and from the Florentines.

When Frederick returned to Germany, leaving a governor in Rome, all the Tuscan and Lombardian Ghibellines who were his followers turned to Castruccio for help, each promising to support him with their cities’ forces if Castruccio would help them regain power. Among these were Matteo Guidi, Nardo Scolari, Lapo Uberti, Gerozzo Nardi, and Piero Buonaccorsi, all Ghibellines, and Florentine exiles. Castruccio’s design was, by combining his forces with theirs, to become prince of all Tuscany. In order to strengthen his position even further, he allied himself with Matteo Visconti, the prince of Milan,²¹ and began arming Lucca and its territories. As Lucca had five city gates, he divided its territories into five sections, which he armed and put under captains and banners so that he could swiftly and with ease bring together twenty thousand men, not counting those he could call on from Pisa.

It was at this time that Matteo Visconti was attacked by the Guelphs of Piacenza, who had ousted the Ghibellines with the help of forces sent by Florence and King Roberto of Naples. Visconti asked Castruccio to attack Florence so that the Florentines, forced to defend their homes, would withdraw their army from Lombardy Castruccio obliged, and marched on Valdarno with a large army, occupying Fucecchio and San Miniato,²² causing great damage to the land and forcing the Florentines to withdraw their men from the battle with Visconti.

But as the Florentine army marched back toward Florence, an emergency forced Castruccio to return to Lucca. The Poggio family had been powerful enough to make Castruccio not only a great man, but prince. But now they felt that they had not been sufficiently rewarded, and joined with other families of Lucca to trigger a revolt to topple Castruccio. One morning they seized the opportunity, killed Castruccio’s chief magistrate, and incited the populace to rise up. But Stefano di Poggio, an old and peaceable man who had not taken part in the conspiracy, stepped forward, and with his authority compelled the conspirators to lay down their arms, offering to act as mediator with Castruccio and to ensure that he would grant them what they demanded. The conspirators, however, laid down their arms with no greater prudence than they had taken them up in the first place, for when news of the conspiracy reached Castruccio, he immediately headed back to Lucca with some of his soldiers, leaving Pagolo Guinigi in charge of the rest. In Lucca, Castruccio was taken aback to find that the uprising had subsided, but still took the precaution of posting armed men throughout the city. Stefano di Poggio, who was certain that Castruccio would be obliged to him for his intercession, stepped before him, pleading clemency not for himself, as he felt he had nothing to fear, but for the other members of his family. He entreated Castruccio to pardon the recklessness of youth, and reminded him of the favors and friendship that the di Poggio family had accorded him. Castruccio replied with grace, reassuring the old man and declaring that he was happier at finding the uprising abated than he had been angry at hearing of its outbreak. He asked Stefano to have everyone come to him, affirming that he thanked God for the opportunity to demonstrate his clemency and charity. Assured by Stefano, they all came, and Castruccio had every one of them, including Stefano, seized and killed.²³

The Florentines had in the meantime retaken San Miniato. But Castruccio felt he should put an end to the war, as he knew he could not venture far from Lucca until he had secured peace. He appealed to the Florentines for a truce and found them quite willing to accept, as they were exhausted and wanted to put an end to the expense. They agreed to a two-year peace and that each side could keep the territories it was then holding.

Freed from the burden of war, Castruccio set about ensuring that he would never again have to face the kind of dangers he had faced at home, and under various pretenses eliminated all those whose ambition might make them aspire to become prince. He spared no one, depriving his potential rivals of their citizenship and possessions, and those he managed to capture of their life. Experience, he avowed, had shown that he could not place any trust in their loyalty. So that he would be more secure he built a castle in Lucca, using the stones of the towers of those he had exiled and killed.²⁴

During the period of peace with Florence, while Castruccio was building up his fortifications in Lucca, he did everything he could to increase his power short of going to war. He had his mind set on occupying Pistoia, knowing that once it was his he would almost have one foot in Florence. To this end he gathered supporters throughout the mountains.²⁵ As for the factions in Pistoia, Castruccio made certain that each placed its trust in him. The city was divided, as it has always been, between White and Black factions: The leader of the Whites was Bastiano di Possente, and the leader of the Blacks, Iacopo da Gia.²⁶ They both conducted secret talks with Castruccio, as each wanted to drive the other party out. The tensions between the White and Black partisans grew until finally they took up arms, Iacopo positioning his forces at Pistoia’s Florentine Gate, Bastiano at the Lucca Gate. Both leaders trusted Castruccio more than they did the Florentines, considering him more resolute and ready to fight than the Florentines were, and so both covertly sent to him for help. Castruccio promised Iacopo that he would come in person, and Bastiano that he would send Pagolo Giunigi, and told them when to expect them. He sent Pagolo over the Pescia road, while he headed directly to Pistoia. At midnight both Castruccio and Pagolo arrived at Pistoia, and as allies they were allowed through the gates. Once inside, Castruccio gave Pagolo a sign, at which point Castruccio killed Iacopo da Gia, and Pagolo killed Bastiano di Possente, and then they slaughtered or took prisoner all their supporters. Castruccio and Pagolo occupied Pistoia without further opposition, expelling the magistrates from the Signoria, and Castruccio compelled the populace to show him obedience, annulling many old debts and making many promises. He did the same for all the territory around Pistoia, a good part of the people having come into the city to see the new prince. Everyone was impressed by Castruccio’s qualities and filled with hope, so the people of Pistoia soon calmed down.²⁷

In the meantime, the populace of Rome had become unruly because of rising costs triggered by the loss of the pope, who had moved to Avignon.²⁸ The Romans blamed the German governors for the disorder and daily murders. Enrico, the Holy Roman Emperor’s governor,²⁹ found he was helpless, and feared that the Romans might turn to King Roberto of Naples and have him expelled from Rome and the pope reinstated. Having no closer ally than Castruccio to turn to, he sent him word beseeching him not only to send forces but to come to Rome in person. Castruccio realized that he had to act immediately, both to pay his debt to the emperor and also because if the emperor was expelled from Rome, his own position would be severely weakened.³⁰ He left Pagolo Guinigi in charge of Lucca and rode with six hundred horsemen to Rome, where he was received by Enrico with much pomp and ceremony. With Castruccio present, the emperor’s cause quickly gained so much ground that peace was restored without bloodshed or violence: Castruccio had arranged for a large quantity of grain to be shipped from Pisa, thus removing the reason for much of the turmoil. Thus, partly reprimanding, partly punishing the leaders of Rome, Castruccio forced them to submit to Enrico’s government. Castruccio was made senator of Rome and accorded many other honors by the Romans. He took office with much fanfare, wore a brocaded toga with the words “This is what God wants” embroidered on the front, and the words “And what God wants shall be” embroidered on the back.³¹

The Florentines were angry that Castruccio had taken over Pistoia after agreeing to a period of truce, and deliberated on how best to make the city rebel. They felt that this might be easy enough, seeing that Castruccio was away in Rome. Among the exiled Pistoians in Florence were Baldo Cecchi and Iacopo Baldini, both fearless men of authority. The two sent word to their friends in Pistoia, and with the help of the Florentines entered the city one night and chased out or killed all of Castruccio’s supporters and officials, restoring liberty to Pistoia. This news greatly angered Castruccio. He took leave of Enrico and returned to Lucca in a relentless march. When the Florentines heard that Castruccio was back, they knew that he was bound to strike at them without delay, and decided to forestall him by entering the Val di Nievole with their army before he could get there with his. They were aware that if they held the valley, they could hinder him from reaching and regaining Pistoia. Gathering a large army of Guelph supporters, they positioned themselves on the Pistoian plain, while Castruccio marched his army to Montecarlo. But he decided not to confront the Florentines on the plains of Pistoia, nor to wait for them on the plains of Pescia, but, if he could, to encounter them in the Pass of Serravalle, judging that victory would be his if his design succeeded. Castruccio knew that the Florentines had thirty thousand men to his twelve thousand, and though he had confidence in his skill and his men’s valor, he did not want to risk being engulfed by the superior numbers of the enemy forces should he engage them in the open.

Serravalle is a castle town between Pescia and Pistoia, on a hill that blocks the Val di Nievole. It is not inside the pass itself, but about two bowshots above it. The pass is not steep, because it slopes up gently on both sides; but it is narrow, especially on the hill where the waters divide, so that twenty men standing side by side can hold it. This is where Castruccio wanted to meet the enemy: in part because his fewer men would have the advantage, but also because he did not want his troops to see the enemy forces before the battle, as he was worried that his men might be alarmed if they saw their great numbers. A German, Messer Manfredi, was the lord of Serravalle. Before Castruccio had become ruler of Pistoia, Messer Manfredi had been allowed to keep possession of the castle, even though it lay within the spheres of both Lucca and Pistoia. But as he promised to remain neutral, neither city moved to attack him. Furthermore, he was in a strong and secure location, and so was left alone. But now Castruccio wanted to occupy the castle of Serravalle. He had a good friend in Serravalle and made arrangements that on the night before he was to engage the Florentines in battle, his friend would allow four hundred of Castruccio’s men through the castle gates and murder the castellan.

In order to encourage the Florentines to enter the pass, Castruccio did not move his army from Montecarlo, and the Florentines for their part wanted to move the battle from Pistoia to the Val di Nievole. So they set up camp beneath Serravalle with the intention of crossing the hill the following day. But Castruccio, having secretly seized the castle under cover of darkness, marched his troops out of Montecarlo in the middle of the night and furtively arrived at the foot of Serravalle at dawn. Thus Castruccio and the Florentines, each on their side of the pass, began climbing the slope at the same time. Castruccio had sent his infantry along the main road and four hundred cavalrymen along a path on the left toward the castle. The Florentines, on the other side of the hill, had sent some four hundred horsemen ahead, followed by their infantry and then their men at arms. They did not expect to find Castruccio up on the hill because they did not know that he had taken the castle. Hence the Florentine horsemen were utterly taken aback when they climbed the slope and came upon Castruccio’s infantry. They found themselves so close to them that they barely had time to slip on their helmets. Unprepared soldiers were attacked by troops who were prepared and well ordered. Castruccio’s spirited men pushed back the Florentines, who could barely stand up to them, though some did try. But as word spread through the rest of the Florentine army, confusion ensued: The cavalry was hemmed in by the infantry, and the infantry by the cavalry and the baggage train. The men in front, hindered by the narrowness of the pass, could go neither forward nor back, so that in all the confusion nobody knew what could or should be done. The Florentine cavalry, meanwhile, was fighting hand to hand with Castruccio’s infantry and was being cut down and slaughtered, unable to defend itself because of the adverse terrain. The horsemen tried to stand their ground, more out of desperation than valor, because having the mountains on both sides, with their comrades behind them and the enemy in front, they found no road open for escape.

Castruccio saw that he did not have enough men to make the enemy retreat, and so sent a thousand infantry by way of the castle to join the four hundred horsemen he had positioned there. They struck the enemy’s flank with such fury that the Florentine troops, unable to stand up to the onslaught, began to flee, defeated more by the terrain than by Castruccio’s forces. The soldiers in the rear ran toward Pistoia, scattering over the plain, each man for himself.

The defeat was total and bloody. Many commanders were captured, among them Bandini de Rossi, Francesco Brunelleschi, and Giovanni della Tosa, all Florentine noblemen, as well as a number of Tuscans and Neapolitans sent by King Roberto to fight for the Florentines and the Guelph cause. When word of the rout reached the Pistoians, they immediately drove out the Guelph factions and surrendered to Castruccio, who then went on to occupy Prato³² and all the castles of the plains on both sides of the Arno. He then set up camp with his men on the plains of Peretola, some two miles from Florence. He stayed there many days, distributing loot and celebrating the victory, mocking the Florentines by coining money and setting up races with horses, soldiers, and whores. He made efforts to bribe some influential Florentines to open the gates of Florence under cover of darkness, but the conspiracy was revealed, and Tommaso Lupacci and Lambertuccio Frescobaldi were arrested and beheaded.

The Florentines, alarmed by the defeat, were worried that they might have to forfeit their liberty to Castruccio, and to secure help they sent emissaries to King Roberto of Naples, offering him Florence and its dominions for his protection. The king accepted, not so much because of the honor the Florentines were according him but because he knew how vital it was for his own position that the Guelph faction keep the upper hand in Tuscany. He agreed that the Florentines would pay him a tribute of two hundred thousands florins a year, and sent his son Carlo to Florence with a cavalry of four thousand men.³³

In the meantime, the Florentines were given a respite from Castruccio and his soldiers as he was forced to leave for Pisa to crush a conspiracy set up by Benedetto Lanfranchi, one of the foremost men of Pisa. Lanfranchi could not bear his city being enslaved by a man from Lucca, and plotted to occupy the citadel, drive out the guards, and kill Castruccio’s supporters.³⁴ But in conspiracies, though it is good for secrecy to keep the number of conspirators to a few, these few will then not be enough to carry out the conspiracy. In his attempt to bring more men into it, Benedetto Lanfranchi involved one who revealed the plot to Castruccio. Nor did the plot’s exposure occur without the help of Bonifacio Cerchi and Giovanni Guidi, two Florentines exiled in Pisa.³⁵ Castruccio captured Benedetto, killed him, and sent the rest of his family into exile, and had many other Pisans of the noble classes beheaded. Castruccio now felt that Pistoia and Pisa could not be trusted and set about to secure them with diligence and force. This gave the Florentines time to gather their strength and await the arrival of Prince Carlo. When he arrived they immediately assembled a huge force that mustered most of the Guelphs of Italy, creating a massive army of more than thirty thousand infantry and ten thousand cavalry. The Florentines conferred as to whether they ought to attack Pistoia first or Pisa and decided that Pisa was the better choice, since the recent conspiracy against Castruccio made success more certain. Pisa also seemed the better option, since the Florentines felt that once they had Pisa, Pistoia would surrender of its own accord.

The Florentines marched their army out in early May of 1328, immediately occupying Lastra, Signa, Montelupo, and Empoli, and marching all the way to San Miniato.³⁶ Castruccio was not alarmed at the news of the extensive forces mobilized against him, as he believed that Fortune would now grant him power over all of Tuscany. He felt that there was no reason for the enemy to cut a better figure in Pisa than they had in the Battle of Serravalle, and that this time they would not have any hope of regrouping. Having gathered twenty thousand foot soldiers and four thousand cavalrymen, Castruccio stationed himself at Fucecchio and sent Pagolo Guinigi with an infantry of five thousand to Pisa.

Fucecchio, standing quite high above the plain, halfway between the Gusciana stream and the Arno River, is in a more secure location than any other castle in the Pisan territories.³⁷ If the Florentines besieged Castruccio there, they could not block provisions coming in from Lucca or Pisa unless they split their forces in two; nor could they approach Fucecchio or Pisa without being at a disadvantage, because if they marched up to Fucecchio they would be caught between Castruccio’s army and that of Pagolo Guinigi stationed in Pisa, and in order to march on Pisa they would have to cross the Arno, which, with the enemy at their back, they could do only at great risk. By not positioning himself with his army on the bank of the Arno but having his men line up along the castle walls, Castruccio encouraged the Florentines to choose the alternative of crossing the Arno, leaving considerable terrain between himself and the river.

Once the Florentines had occupied San Miniato, they knew that they had to either march on Pisa or face Castruccio at Fucecchio, and measuring one alternative against the other, decided to attack Castruccio. The Arno was shallow enough to be easily forded, though not without the infantry being submerged up to their shoulders and the horsemen to their saddles. On the morning of June 10, the Florentines assembled in battle formation and sent part of their cavalry and an infantry battalion of ten thousand into the river. Castruccio, ready and determined, attacked them with an infantry battalion of five thousand, and three thousand horsemen, and before the Florentines managed to emerge from the waters, Castruccio’s forces set upon them. Then he sent a thousand infantrymen upstream along the riverbank and a thousand downstream. The Florentine infantry was weighed down by the waters and their weapons, and were struggling to climb the rocky banks. The horses that had managed to cross first had churned up the riverbed with their hooves, making the crossing harder for the rest, who were now stepping on unstable ground. Many horses toppled over onto their riders or became stuck in the mud. When the Florentine captains saw how difficult it was to cross at this part of the river, they moved their troops higher upstream to where the riverbed was not churned up and the banks were not as steep, but there they were met by the infantry Castruccio had sent upriver. These forces were lightly armed with bucklers and spears, and with loud battle cries plunged their blades into the foreheads and chests of the Florentine soldiers. The horses, alarmed by the shouting and carnage, balked and began falling and tumbling over each other.

The clash between Castruccio’s men and the Florentines in the river was harsh and terrible. Many men fell on both sides, and both sides fought with all their might. Castruccio’s men strove to drive the Florentines back into the river, while the Florentines strove to push ahead so that those emerging from the river behind them could fight. The captains on both sides exhorted their men, Castruccio reminding his soldiers that this was the same enemy they had vanquished at Seravelle not too long ago, while the Florentines rebuked their men for allowing Castruccio’s small army to overcome their superior forces.

Castruccio saw that the battle was dragging on and that his men and the enemy were already exhausted, with many wounded and dead on both sides. So he sent forward a fresh infantry battalion of five thousand, positioning them behind the men who were fighting, and ordered the men in the fray to fan out, half retreating to the left, the other half to the right. This opened up the terrain for the Florentines, and they advanced, but when the battle-worn Florentine soldiers came upon Castruccio’s rested men, they were easily pushed back into the river.

In the meantime, neither of the two cavalries had gained the upper hand because Castruccio, aware that his was the weaker, had ordered his captains to do no more than resist the enemy. He hoped to defeat the Florentine infantry first: Once the infantry was defeated, he could rout the cavalry with greater ease. And things went according to his plan. As the enemy infantry was driven back into the river, Castruccio unleashed the rest of his infantry on the enemy cavalry, wounding them with lances and spears, and then sent in his own cavalry with greater force, putting the enemy horsemen to flight. The rest of the Florentine foot soldiers fared no better: Once the Florentine captains had seen the difficulty their horsemen had in crossing the river, they had sent the rest of their foot soldiers to cross further downstream, with the design of attacking Castruccio’s flanks. But this proved to be a mistake, for the banks there were steep and lined with enemy soldiers.

To the great honor and glory of Castruccio, the Florentine army was utterly routed. Of all the multitude of Florentine soldiers, less than one-third managed to escape. Many commanders were taken captive, while King Roberto of Naples’s son Carlo and Michelagnolo Falconi and Taddeo degli Albizzi, the Florentine commissioners, fled to Empoli. As one can imagine in such a battle, the plunder was great and the slaughter even greater. The Florentine army lost 20,231 men, Castruccio 1,570.

But Fortune proved hostile to Castruccio’s glory and took his life just when she ought to have nurtured it, cutting short the grand designs he had aimed to achieve for so many years, designs that nothing but death could hinder. Exhausted from the day-long battle, Castruccio stood above the castle gate of Fucecchio, breathless and covered in sweat, waiting for his men to return from their victory, to receive them and thank them in person. He also wanted to keep an eye out in case some of the enemy forces regrouped to attack. It was the duty of a good leader to be the first to mount his horse and the last to dismount. But standing above the gates, exposed to a wind that usually rises at midday over the Arno and is almost always pestiferous, Castruccio caught a chill. Accustomed to the rigors of battle, he paid little heed to this, but it proved the cause of his death. The following night he was seized by a strong fever that kept rising. As all the doctors judged it fatal, Castruccio called Pagolo Guinigi to him and spoke the following words:³⁸ “My son, had I believed that Fortune intended to cut me down midway to the glory I had seen was mine with so many successes, I would have tired myself less and left you a smaller state, fewer enemies, and less envy. I would have been content with ruling Lucca and Pisa and would not have subjugated the Pistoians and angered the Florentines with my many assaults. I would have made those cities my friends, and would have led my life, if not longer, then with greater tranquillity. I would have left you this state smaller, but doubtless more stable and secure. But Fortune, the arbitrator of all human affairs, did not give me sufficient judgment to understand this, nor enough time to be able to overcome what she had in store. Many have told you—and I have never denied it—that I came into your father’s house as a boy deprived of all the hopes that flourish in a young nobleman’s heart, and how your father nurtured and loved me more than if I had been of his blood. Under his tutelage I became valiant and able to grasp the gifts of Fortune, which you yourself have seen and still see. When your father died, he placed you and all he possessed in my care, and I have raised you, bound as I was and still am by a love and loyalty that have increased that wealth for you. So that you would not only inherit what your father left, but also what Fortune and my skill have gained, I never took a wife. I did not want my love for my sons to hinder me from showing to your father’s blood the gratitude I owe.³⁹ I leave you a great state, and of that I am pleased. But I am most unhappy that I leave it to you weak and unstable. You own the city of Lucca, which will never be content to live under your reign. You own Pisa, whose men are fickle and disloyal, and though over the years Pisa has been accustomed to subjugation, it will always scorn the rule of a lord from Lucca. You own Pistoia, which cannot be loyal, as it is divided and angry at your blood for the recent injuries we have inflicted on them. You have the Florentines for neighbors, whom we have offended and harmed in a thousand ways, though not destroyed. They will hear the news of my death with greater joy than if they had acquired all of Tuscany. And you cannot rely on the princes of Milan or the Emperor, as they are far away, sluggish, and slow to send help. You can only place your hopes in your own industry, in the memory of my skill and prowess, and in the standing that our present victory has afforded you. If you use it with prudence, it will bring you advantage in a treaty with the Florentines, who, alarmed at their defeat, will be eager to negotiate. Whereas I sought to make them my enemy, in the belief that such enmity would bring me power and glory, you must seek with all your strength to make them your friends, because their friendship will bring you security and benefit. In this world it is vital to know oneself, to know how to measure one’s spirit and power. He who knows that he is unable to wage war must strive to reign through the art of peace, and my counsel to you is that you would do well to master this art, and so enjoy what my toil and peril have gained. It should be easy for you to accomplish this, if you esteem what I am telling you as true. And you will be indebted to me in two ways: first, for having left you this realm, and second for having taught you how to keep it.”

Then Castruccio called to his side the men of Lucca, Pisa, and Pistoia who had fought under him, and presented Pagolo Guinigi to them. Castruccio made them swear obedience to Pagolo, and died. All who knew him and were his friends had happy memories of him, and he was mourned like no other prince. His funeral was celebrated with the greatest honors, and he was buried in the church of San Francesco in Lucca. But skill and Fortune were not as forthcoming for Pagolo Guinigi as they had been for Castruccio. He was soon to lose Pistoia and then Pisa, and with difficulty held on to power in Lucca, which remained under his family’s rule until the reign of his great-great-grandson Pagolo.⁴⁰

As I have demonstrated, Castruccio was a rare man not only in his era, but in all eras that had come before. He was taller than average, each limb in perfect harmony with the others. His features were so handsome, and he received everyone with such grace, that none who left his presence ever spoke badly of him. His hair had a reddish tint, and he wore it short above the ears, and always and in all weather—in rain or snow—he left his head uncovered.

He was kind to his friends, ruthless to his enemies, fair to those under his rule, and unfair to those who were not. If he could win through deception, he never sought to win through force. “Victory brings glory” was his motto—it mattered little how victory was achieved.

No man was bolder in encountering dangers, nor more cautious in emerging from them. He used to say that man must attempt everything and fear nothing, and that God loved strong men because one could see that God always punished the weak through the strong.

Castruccio was also admirable with his quick answers and retorts, which at times could be pointed or elegant, and because he had no misgivings about directing his wit at anyone, he also was not angered when wit was directed at him. So we know of many witticisms that he uttered, and many that he heard good-naturedly.

Castruccio had once bought a partridge for a ducat, and when a friend rebuked him at the expense, Castruccio asked him: “Why, you mean you would not have given more than a brass coin for it?” When his friend said no, Castruccio replied: “A ducat is worth far less to me.”⁴¹

Once he had spat at a flatterer in derision, upon which the flatterer said: “A fisherman will let the waves of the sea wash over him to catch a tiny fish. I, on the other hand, will gladly let myself be wetted by a little spit to catch a whale.”⁴² Castruccio not only heard him good-naturedly, but rewarded him.

He was told by someone that his extravagant way of life was evil, to which he replied: “If that were a vice, then we should not dine so lavishly on the feast days of our saints.”⁴³

Walking down the street, Castruccio saw a young man coming out of a prostitute’s house, the young man blushing with shame at being seen. But Castruccio said: “There is no need to be ashamed when you come out of there, only when you go in.”⁴⁴

A friend handed him a complicated knot to untie, to which Castruccio said: “You fool, do you think I wish to untie something that gives me so much trouble tied?”⁴⁵

Castruccio said to a man whose trade was philosophy: “You are made of the stuff that dogs are, always following behind those who feed them.” The philosopher replied: “In fact, we are more like doctors who go to the houses of those who need us most.”⁴⁶

On his way by ship from Pisa to Livorno there was a sudden tempest that made Castruccio quite anxious. A man in his entourage reproved him for his faintheartedness, saying that he himself feared nothing, to which Castruccio replied that he was not surprised, as every man valued his soul at what it was worth.⁴⁷

Castruccio was once asked by a man what he should do to gain respect, and he replied: “When you go to a banquet, be sure that one block of wood is not sitting on another.”⁴⁸

A man prided himself for having read much, to which Castruccio said: “It would be better to pride yourself if your mind had retained much.”⁴⁹

A man expressed pride at being able to drink a great deal without becoming drunk, to which Castruccio said: “An ox can do the same.”⁵⁰

Castruccio was living with a young woman and was reproached by a friend who told him that it was bad to be taken in by her. “You are mistaken,” Castruccio replied, “I have taken her, not she me.”⁵¹

Someone blamed him for eating food that was too sumptuous, to which Castruccio replied: “So you do not spend as much as I do?” The man replied that this was true. “Then,” Castruccio said, “you are more miserly than I am gluttonous.”⁵²

Castruccio was invited to dinner by Taddeo Bernardi of Lucca, a very rich and ostentatious man. When Castruccio arrived at his house, Taddeo showed him a room beautifully draped, its floor composed of elegant stones interwoven in an array of colors representing flowers, leaves, and foliage. Suddenly Castruccio cleared his throat and spat in Taddeo’s face, and seeing that Taddeo was taken aback, said: “I was not sure where my spitting would offend you less.”⁵³

Asked how Caesar died, Castruccio remarked: “God wanted me to die as he did!”⁵⁴

One night, Castruccio was at the house of one of the gentlemen of his entourage where many ladies had gathered for a ball. There he danced and amused himself more than was seemly for a man of his position, and when a friend called him to account, he replied: “He who is considered wise during the day will never be considered foolish at night.”⁵⁵

A man came to ask Castruccio for a favor, and when Castruccio pretended not to hear, the man threw himself on his knees. When Castruccio reproved him, the man answered: “You are the reason why I am kneeling, as your ears are in your feet.” At this, Castruccio granted him twice the favor he asked.⁵⁶

Castruccio used to say that the path to hell was easy, since you went downward with your eyes shut.⁵⁷

A man was bothering Castruccio for a favor with a stream of words, to which Castruccio said: “The next time you want something from me, send someone else.”⁵⁸

A similar man, having annoyed Castruccio with a long speech, concluded by saying: “I have perhaps tired you with speaking too much.” “Not at all,” Castruccio replied. “I haven’t listened to a word you said.”⁵⁹

Castruccio used to say about a handsome man who had been a handsome boy that he was quite destructive, having first taken husbands from their wives, and then wives from their husbands.⁶⁰

To an envious man who laughed, he said, “Are you laughing because you are doing well, or because someone else is doing badly?”⁶¹

While he was still in the care of Messer Francesco Guinigi, one of his companions said to him: “What can I give you in exchange for letting me give you a blow on the nose?” “A helmet with a visor,” Castruccio replied.⁶²

Castruccio put to death a citizen of Lucca who had been instrumental in his rise to greatness. When people said that he had done a bad thing in killing an old friend, he replied that they were wrong, as he had put to death a new enemy.

Castruccio greatly praised men who chose a bride but then did not marry her, as he praised those who prepared to go on a sea voyage but then did not go.

Castruccio expressed surprise that a man who bought a clay or glass pot would tap it first to see if it was good, but in taking a wife was content just to look at her.

As Castruccio was dying, someone asked him how he wished to be buried, to which he replied: “Face down, as I know that once I am dead everything in this land will be upside down.”⁶³

When asked if he had ever thought of taking up the cloth to save his soul, he replied that he had not, because it seemed strange to him that Brother Lazarus should go to Heaven while Uguccione della Faggiuola should go to Hell.⁶⁴

When he was asked at what time it was best for a man’s health to eat, he replied: “If you are rich, eat when you are hungry. If you are poor, eat when you can.”⁶⁵

When he saw a gentleman in his retinue have one of his servants button him up, he said, “I hope to God that you also have him feed you.”

Once he saw that someone had written above a door in Latin: “May God preserve this house from the wicked,” to which he said: “In that case, the head of that household had better not go in.”⁶⁶

Walking down the street, he saw a small house with a big door, to which he said: “That house will escape through its own door.”⁶⁷

On being told that a certain foreigner had ruined a boy he said: “That man must be from Perugia.”⁶⁸

When asked which city was renowned for cheaters and frauds, he replied: “Lucca, where all men are cheaters and frauds, except for Bonturo.”⁶⁹

Castruccio was in discussion with an emissary of the King of Naples concerning the property of some exiles, and voices were raised. At which the ambassador said: “But are you not afraid of the king?” Castruccio replied: “Is this king of yours good or bad?” When the emissary replied that he was good, Castruccio said, “Then why do you think that I should be afraid of a good man?”⁷⁰

I could relate many other things that Castruccio said—both witty and serious things—but I think these are a sufficient testimony to his great qualities. He lived for forty-four years and remained a great prince in good and bad fortune. Since much has been said about his good fortune, I have wanted to present as well moments when his fortune was bad. The manacles with which he was chained in prison can still be seen today in the tower of his home, where he had them put so they would always bear witness to his adversity. In his life he was in no way inferior to Philip of Macedon, Alexander’s father, nor Scipio of Rome, and he died at the same age they did. Had he not been born in Lucca, but in Macedonia or Rome, he would doubtless have surpassed both of them.

1. This is a fictitious account. Castruccio Castracani was born in 1281 to Gerio Castracani of the wealthy and influential Antelminelli family that was exiled from Lucca in 1301 when Castruccio was twenty.

2. The Guinigi of Lucca were a prominent mercantile family. Machiavelli, however, invented Messer Francesco.

3. The Ghibellines, for the most part feudal aristocrats and their partisans, were supporters of the Holy Roman Emperor, and their opponents, the Guelphs, wealthy merchants, supported the papacy. Throughout the Middle Ages, the two factions vied for power in Italian cities. The Castracani were Ghibellines.

4. Machiavelli’s account is fictitious. In 1301 Castruccio and his family were banished from Lucca. On his father’s death that year, Castruccio went to the court of King Edward I in England, after which he was said to have moved to Flanders before returning to Italy, where he worked as a mercenary captain.

5. The Obizi family had been instrumental in the exiling of the Castracani and the other Ghibelline families in 1301.

6. Lucca and other Tuscan cities had sought the protection of King Roberto I of Naples in 1311, when Henry VII of Germany marched against the Italian states in his mission to be crowned Holy Roman Emperor. The Guelph faction in Lucca were supporters of King Roberto, while Castruccio, a Ghibelline, supported the Holy Roman Emperor.

7. Uguccione della Faggiuola (c. 1250–1319) was one of the most influential members of the Ghibelline faction of Tuscany. He had been elected chief magistrate of Pisa, then commander of the army, and in 1314, already in his late sixties, seized power and became tyrant of Pisa. Machiavelli is moving events back in time to fit the plot of his narration, as Castruccio was in fact in his mid-thirties and an experienced mercenary by the time of these events. See also Florentine Histories, Book II, chapter 25.

8. Giovanni Villani’s Nuova Cronaca (New Chronicles), which Machiavelli used as a source, lists the Antelminelli (Castruccio’s clan) joining with the Quartigiani, the Pogginghi, and the Onesti in this conspiracy.

9. Montecatini is a town eighteen miles northeast of Lucca, and Montecarlo seven miles.

10. Machiavelli invented Uguccione’s illness and departure for Montecarlo in order to place Castruccio in the foreground of the action. Castruccio did participate in this battle, but not in the role of a military leader.

11. Though Villani’s chronicles and other accounts of the battle describe the tactics Uguccione used, Machiavelli is describing the methods that Livy attributed to Scipio in his battle with Hannibal.

12. Carlo d’Anjou and his father, Filippo d’Anjou, Prince of Taranto and Acaia.

13. This account is fictitious. Castruccio, outside his jurisdiction, had put to death some thirty men in Lunigiana, which historians believe Uguccione perceived as a challenge to his authority.

14. Today San Giuliano Terme, about four miles from Pisa and five miles from Lucca. Machiavelli is closely following Giovanni Villani’s Nuova Cronaca (IX, 78): “Uguccione had not yet reached the mountain of San Giuliano, when the populace of Pisa rose […] and ransacked the building of the Signoria where Coscetto dal Colle was magistrate, and ran with arms and fire to the palace where Uguccione and his family lived, shouting ‘Death to Uguccione the tyrant!’ They robbed and killed his entire family.”

15. Gaddo della Gherardesca, Count of Donoratico, also a prominent member of the Ghibelline faction, overthrew Uguccione in 1316.

16. Cangrande della Scala, Lord of Verona, was the leader of the Ghibelline League. Uguccione, however, did not die in poverty, but after an unsuccessful attempt to regain Pisa and Lucca, became chief magistrate of Vicenza, where he died in 1319.

17. Machiavelli is rearranging the sequence of events for effect. Castruccio built the Fortezza di Sarzanello in 1322 on the site of a tenth-century fortress.

18. In April, 1320, Castruccio was elected Dominus Generalis of Lucca for life.

19. In 1320 Frederick III appointed Castruccio as his governor, or Imperial Vicar General of Lucca, Versilia, and Lunigiana.

20. Gaddo della Gherardesca, a moderate ruler who was an ally of Castruccio’s, in fact died in 1320.

21. Matteo I the Great, 1250–1322.

22. Valdarno is the Arno River valley, and Fucecchio and San Miniato important strategic castles on the Arno, approximately equidistant from Lucca, Florence, Pisa, and Pistoia. San Miniato had been the seat of the Holy Roman Emperors, and Frederick II had fortified the town extensively in the mid—thirteenth century.

23. Machiavelli has recast the incident. One of the junior members of the Poggio clan, Stefano di Poggio, had killed one of Castruccio’s officials. Castruccio, on his immediate return to Lucca, invited the heads of the Poggio family to his house to discuss what should be done about Stefano. When they came, he had them seized and executed.

24. Giovanni Villani in Nuova Cronaca (IX) writes: “Fearing that the populace of Lucca would revolt, Castruccio ordered a wondrous castle to be built within the city, taking up almost a fifth part of the town facing Pisa. He reinforced the mighty walls with twenty-eighty towers.”

25. Pistoia, surrounded by hills that form part of the Apennine Mountains, lies about eighteen miles northwest of Florence.

26. The Whites (Bianchi) and Blacks (Neri) were feuding factions within the Guelph party that did much to destabilize Pistoia, and later Florence too. Machiavelli, however, invented the names of the faction leaders.

27. This account of Castruccio’s seizing power in Pistoia is fictitious. Machiavelli closely follows a tale from Xenophon’s Cyropaedia (7.4.4), in which Adusius, Cyrus’s general, tricks two warring Carian factions and so takes over the city of Caria. “[Adusius] arranged a meeting with both factions for the same night, each without the other’s knowledge. On the night in question he entered and took possession of the strongholds of both factions.”

28. In 1309, when Pope Clement V moved the papal residence to Avignon in France, Rome suddenly lost its lucrative role as the center of the Catholic world and faced escalating turmoil triggered by the factional fighting of the Orsini and Colonna families.

29. According to Villani’s Nuova Cronaca, Arrigo d’Ostericchi (Henry of Austria), the emperor’s brother.

30. In 1320 the Holy Roman Emperor Frederick III had made Castruccio his “imperial vicar” of Lucca, Versilia, and Lunigiana. Four years later, Emperor Louis IV appointed Castruccio Duke of Lucca and Count of Latran. Beside this debt, which Castruccio felt he had to repay, it was strategically vital for him to keep Roberto of Naples, the champion of the Guelph cause and the enemy of the Holy Roman Emperor, out of Rome and Ghibelline territory.

31. Giovanni Villani describes Castruccio’s pomp, commenting on the arrogant words of the toga: “And thus he himself prophesied the future judgment of God.”

32. A city eight miles northwest of Florence.

33. A cavalry of three hundred that King Roberto had sent in December 1325 had proved insufficient to curb the increasing raids of Castruccio’s soldiers on the Florentine countryside. Carlo of Calabria, King Roberto’s oldest son, was then officially proclaimed Lord of Florence for ten years in January 1326, though he did not serve the full term.

34. Machiavelli is transposing a Pisan plot that had occurred three years earlier, in 1323. Lanfranchi was in fact a supporter of Castruccio who was conspiring to kill Nieri della Gherardesca, the governor of Pisa. Lanfrachi was actually executed by della Gherardesca.

35. Bonifacio Cerchi and Giovanni Guidi, exiles from Florence, had been the co-conspirators who betrayed Lanfranchi’s 1323 plot.

36. Castles and their communities near Florence along the Arno River. Machiavelli is combining elements from three major campaigns.

37. The castle, about twenty-five miles from Florence, stands on a two-hundred-foot hill.

38. Machiavelli invented the speech, taking elements from Villani’s Nuova Cronaca, in which Villani reports the advice and suggestions Castruccio gave to his actual son and heir Arrigo and to his closest supporters.

39. In fact Castruccio had a wife and nine children, four of whom were sons, which Machiavelli would have known from his sources.

40. Castruccio’s empire in fact fell apart within a few weeks of his death on September 3, 1328. After the people of Lucca revolted on October 7, Holy Roman Emperor Ludwig IV removed Arrigo Castracani from office. According to Giovanni Villani’s Nuova Cronaca (X, 104): “Castruccio’s sons were deprived of their ducal title and were exiled to Pontremoli with their mother.”

41. Machiavelli took or adapted most of the sayings in this section from Diogenes Laertius, Lives of Eminent Philosophers (c. third or fourth century CE). This saying comes from “Aristippus” (Book 2:66): “It is said that Aristippus ordered a partridge to be bought for fifty drachmas. When he was admonished, he asked: ‘Would you yourself not have bought the partridge for an obol?’ When the man who had reproached him said that he would, Aristippus replied: ‘Well, fifty drachmas are no more to me.’”

42. From Diogenes Laertius (Book 2:67): “Dionysius once spat at Aristippus, without Aristippus reacting with a single word. When Aristippus was reproached for his silence he replied, ‘Fishermen are patient at being sprayed by the sea in order to catch a tiny gudgeon, so why should I not endure being sprayed with a little wine to catch a whale.’”

43. From Diogenes Laertius (Book 2:68): “Upbraided for living extravagantly, Aristippus said: ‘If extravagance were bad, we wouldn’t have so much of it during the feasts of the gods.’”

44. From Diogenes Laertius (Book 2:69): “Aristippus once entered the house of a hetaera. When one of the young men accompanying him blushed, Aristippus said, ‘It is not going into such a house that is bad, but not being able to leave.’”

45. From Diogenes Laertius (Book 2:70): “Someone asked Aristippus to solve a riddle, to which Aristippus replied: ‘You fool, why would you have me unknot something that vexes us so much even when it is safely tied up?’”

46. From Diogenes Laertius (Book 2:70): “When someone said that he always saw philosophers at the doors of the rich, he replied: ‘One also always sees physicians at the doors of the sick. And yet nobody would choose to be a sick man above being a physician.’”

47. From Diogenes Laertius (Book 2:71): “Aristippus was once sailing to Corinth when a violent storm arose and he became perturbed. Somebody said, ‘We simple folk are not afraid, but you philosophers tremble.’ To which Aristippus replied: ‘That is because we are not trembling over the same kind of soul.’”

48. From Diogenes Laertius (Book 2:72): “When a man asked him in what way his son would be better once he had completed his education, he replied: ‘If nothing else, he won’t sit at the theater like one stone on another’”

49. From Diogenes Laertius (Book 2:71): “Seeing a man who prided himself on the extent of his erudition, he said, ‘Those who eat and exercise without limit are in no better health than those who do so within limits. Likewise, it is not those who read much, but those who read what is useful who excel.’”

50. From Diogenes Laertius (Book 2:73): “A man boasted of being able to drink a great deal without becoming drunk, to which Aristippus said: ‘A mule can do the same.’”

51. From Diogenes Laertius (Book 2:74): “Reproached for living with a hetaera, he said, ‘Does it make a difference whether one chooses a house where many have lived or one where no one has lived before?’”

52. From Diogenes Laertius (Book 2:75): “When someone reproached him for buying expensive food, he asked, ‘Wouldn’t you have bought all this for three obols?’ The other said that he would, to which Aristippus replied: ‘In that case, I am not as much of a glutton as you are a miser’”

53. From Diogenes Laertius (Book 2:75): “One day Dionysius’s steward Simos, a Phrygian and a contemptuous fellow, showed Aristippus a lavish house paved with mosaics. Suddenly Aristippus cleared his throat and spat in Simos’s face. Simos was outraged, but Aristippus said: ‘I couldn’t find a more suitable place to spit’”

54. From Diogenes Laertius (Book 2:76): “Asked how Socrates died, he said, ‘The way I hope that I shall die.’”

55. This is a conflation of two different anecdotes. The opening line is from Diogenes Laertius (Book 2:76).

56. From Diogenes Laertius (Book 2:79): “He was once asked a favor of Dionysius for a friend, but as Dionysius would not listen, he fell at his feet. When someone made fun of him for this, he replied: ‘It’s Dionysius’s fault I am doing this, as his ears are in his feet’”

57. From Diogenes Laertius (Book 4:49): “Bion used to say that the road to Hades is an easy one. One goes downhill with one’s eyes shut.”

58. From Diogenes Laertius (Book 4:50): “To an idle prattler harrying him for aid, Bion said: ‘I will do what I can for you, as long as you send mediators instead of coming yourself.’”

59. From Diogenes Laertius (Book 5:20): “An idle prattler who had poured a stream of words over him asked Aristotle: ‘I hope I haven’t been boring you.’ To which Aristotle replied, ‘By Zeus you haven’t, I wasn’t even listening’”

60. From Diogenes Laertius (Book 4:49): “Bion used to reproach Alcibiades, saying that as a boy he had taken husbands from their wives, and as a young man wives from their husbands.”

61. From Diogenes Laertius (Book 4:51): “Bion said to a despondent envious man: ‘I do not know whether you are sad because something bad has happened to you, or because something good has happened to someone else.’”

62. From Diogenes Laertius (Book 6:54): “When Diogenes was asked what he would take in exchange for a blow on the head, he replied: ‘A helmet’” The sources of the three anecdotes that follow are unidentified.

63. From Diogenes Laertius (Book 6:31): “When Xeniades asked Diogenes how he wanted to be buried, he replied, ‘On my face.’ When asked why, he said, ‘Because soon enough everything will be turned upside down.’”

64. From Diogenes Laertius (Book 6:39): “When the Athenians asked him why he would not become initiated, as those initiated were accorded the best place in Hades, he replied: ‘It would be ridiculous if Agesilaus and Epaminondas remain in the mud, while men of no importance, just because they are initiated, will live on the Isles of the Blessed.’” Machiavelli juxtaposes Lazarus the beggar at the rich man’s banquet from the New Testament, who receives his reward in Paradise, to the heroic but unreligious Uguccione della Faggiuola.

65. From Diogenes Laertius (Book 6:40): “Asked when it was the best time for a man to eat, he replied, ‘For a rich man, whenever he wants to; for a poor man, whenever he can.’” The source of the anecdote that follows is unidentified.

66. From Diogenes Laertius (Book 6:39): “An odious eunuch had written above his door: ‘Let no evil enter.’ To which Diogenes said: ‘But then how will the master of house get inside?’”

67. From Diogenes Laertius (Book 6:57): “Arriving at Myndus, where he saw large gates but a small city, he said: ‘Men of Myndus, shut your gates or your city will escape through them.’”

68. From Diogenes Laertius (Book 6:61): “He was once asked where a certain depraved boy was from, to which he replied: ‘He is from Tegea’” (a pun on the city of Tegea and tegos, “brothel”). In Boccaccio’s Decameron (Fifth Day), Pietro, a man from Perugia, catches his wife with a youth, whom he then seduces.

69. A witty reference to Dante’s Inferno (Canto XXI) which Machiavelli’s readers would have recognized, where a devil says that Lucca is well furnished with sinners, as “Every man is a fraud, except Bonturo.” Merchant and demagogue Bonturo Dati had in fact gone down in history as a politician who was particularly corrupt.

70. From Diogenes Laertius (6:68): “Alexander once stopped Diogenes and asked, ‘Are you not afraid of me?’ To which Diogenes replied: ‘Are you good or evil?’ ‘I am good,’ Alexander replied. To which Diogenes said: ‘So why should anyone fear what is good?’”