Front Page Titles (by Subject) DESCRIPTION OF THE MANNER IN WHICH THE DUKE VALENTINO PROCEEDED TO KILL VITELLOZZO VITELLI, OLIVEROTTO DA FERMO, AND THE SIGNOR PAGOLO AND THE DUKE GRAVINA ORSINI. * - The Historical, Political, and Diplomatic Writings, vol. 4 (Diplomatic Missions 1506-1527)
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DESCRIPTION OF THE MANNER IN WHICH THE DUKE VALENTINO PROCEEDED TO KILL VITELLOZZO VITELLI, OLIVEROTTO DA FERMO, AND THE SIGNOR PAGOLO AND THE DUKE GRAVINA ORSINI. * - Niccolo Machiavelli, The Historical, Political, and Diplomatic Writings, vol. 4 (Diplomatic Missions 1506-1527) 
The Historical, Political, and Diplomatic Writings of Niccolo Machiavelli, tr. from the Italian, by Christian E. Detmold (Boston, J. R. Osgood and company, 1882). Vol. 4.
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DESCRIPTION OF THE
The Duke Valentino had returned from Lombardy, where he had gone to exculpate himself to King Louis XII. of France from the many calumnies that had been told of him on account of the revolt of Arezzo and other places in the Val di Chiana. He had stopped at Imola with the intention of uniting all his troops there for the purpose of attacking Giovanni Bentivogli, the tyrant of Bologna; as he wanted to bring that city under his dominion and make it the capital of his duchy of Romagna. When this project became known to the Vitelli and the Orsini and their adherents, they became apprehensive that the Duke would become too powerful; and that it was to be feared that after taking Bologna he would turn to destroy them, so as to remain alone under arms in Italy. They therefore appointed a meeting at Magione, in the Perugian territory, which was attended by the Cardinal, Pagolo, and the Duke Gravina Orsini, Vitellozzo Vitelli, Oliverotto da Fermo, Giampagolo Baglioni, tyrant of Perugia, and Messer Antonio da Venafro, envoy of Pandolfo Petrucci, chief of the government of Sienna. They discussed the aggrandizement of the Duke, and his intentions, and the necessity of checking his eager ambition, as otherwise there would be danger of their being destroyed with the rest of them. They resolved not to abandon the Bentivogli, and to endeavor to win the Florentines over to their side. Accordingly they sent agents to those places, promising help to the one, and urging the other to unite with them against the common enemy. This meeting became quickly known throughout Italy, and those peoples who were not satisfied to be under the rule of the Duke, amongst whom were the people of Urbino, took hope of a change for the better. Thus it came that, whilst minds were thus undecided, certain men of Urbino formed the plan to seize the castle of San Leo, which still held for the Duke, and availed themselves of the following opportunity. The governor was strengthening the castle, and, as he was getting some timbers brought in, the conspirators placed themselves in ambush; and whilst the drawbridge was encumbered by some beams that were being brought to the castle, so that the guard on the inside could not prevent them, the conspirators seized the opportunity and leaped upon the bridge, and thus obtained entrance into the castle. So soon as this capture became known, the whole country rose in rebellion, and recalled the old Duke; although the capture of the castle did not inspire the people with as much hope as the meeting at Magione, by means of which they hoped to obtain assistance.
So soon as the members of the assembly at Magione heard of this revolt in Urbino, they felt that they must not lose this opportunity. They at once called their troops together, for the purpose of seizing any other place that might still remain in the hands of the Duke, and sent again to Florence to solicit that republic to join them in extinguishing the conflagration that threatened her equally with themselves. They showed the Florentines how easy victory would be, and that they could never expect a more favorable opportunity. But actuated by their hatred against the Vitelli and the Orsini, from various causes, the Florentines not only declined to unite with them, but sent their secretary, Niccolo Machiavelli, to offer to the Duke Valentino shelter and assistance against his new enemies. He found the Duke at Imola, full of apprehensions because his own troops had suddenly and quite unexpectedly turned against him; so that he found himself disarmed at the very moment when war was almost upon him. But having taken courage again in consequence of the offers of the Florentines, he decided to protract the war with the few troops that he had, and to endeavor by peace negotiations to obtain assistance. This he managed in two ways: he sent to the king of France for troops, and at the same time engaged every man-at-arms, and others who followed the calling of mounted soldiers, and was careful to pay them all most exactly.
Notwithstanding all this, his enemies advanced and moved upon Fossombrone, where some of his troops had made a stand, but were routed by the Vitelli and the Orsini. This induced the Duke to try and stop these hostile attempts against him by peace negotiations; and being thoroughly skilled in the art of dissembling, he lost no chance of making his enemies understand that they were making war upon a man who was willing that they should have possession of all he had acquired, and that he merely wanted the title of prince, leaving them to have the principality. And so thoroughly did he persuade them of this that they sent the Signor Pagolo to him to negotiate a peace, and meantime they put up their arms.
But the Duke did not for a moment stop his preparations, and made every effort to increase both his infantry and his mounted force; and to prevent these preparations from being noticed, he distributed his troops separately through all the places of the Romagna. Meantime some five hundred French lances had come to him, and although he felt strong enough to revenge himself upon his enemies by open war, yet he thought it would be safer and more advantageous for him to keep up his deception, and not to stop his peace negotiations. And so well did he manage this matter, that he concluded a peace with them, according to which he confirmed to each of them their old engagements; he paid them four thousand ducats at once, and promised them not to disturb the Bentivogli. He also concluded a matrimonial alliance with Giovanni, and consented that none of them should ever be constrained to appear in person before him, except so far as it might suit themselves to do so. On the other hand, they promised to restore the duchy of Urbino to him, as well as all the other places which they had taken up to that day, to serve him in all his expeditions, and not to make war upon any one without his permission, nor to engage themselves in the service of any one else.
After the conclusion of this treaty, Guido Ubaldo, Duke of Urbino, fled again to Venice, having first caused all the fortresses in his state to be dismantled; for having full confidence in the population, he did not want these fortresses, which he believed he could not defend, to fall into the enemy’s hands, who might use them to restrain and oppress his friends. But the Duke Valentino, after having concluded this convention, and having distributed all his troops and the French lances throughout the Romagna, suddenly left Imola, about the end of November, and went to Cesena, where he remained many days, negotiating with the agents of the Vitelli and of the Orsini, who happened to be with their troops in the duchy of Urbino, as to what new enterprises were to be undertaken. But as nothing was concluded, Oliverotto da Fermo was sent to make him the offer, that, if he were disposed to undertake the conquest of Tuscany, they were ready to co-operate with him; but if not, then they would go and endeavor to capture Sinigaglia. To which the Duke replied, that he had no intention of carrying the war into Tuscany, as the Florentines were his friends; but that he should be well pleased that they should take Sinigaglia.
Very soon after that, news came that the place had capitulated, but that the citadel had refused to surrender to them, the governor being unwilling to give it up to any one except to the Duke in person; and therefore they urged him to come there at once. The opportunity seemed favorable to the Duke, and his going not likely to give umbrage, as he had been called by them, and did not go of his own accord. And to make things the more sure, he dismissed all the French troops, who returned to Lombardy, except the one hundred lances under the command of Monseigneur de Caudales, his brother-in-law; and having left Cesena about the middle of December, he went on to Fano. There he employed all the cunning and sagacity that he was capable of; he persuaded Vitelli and the Orsini to await him at Sinigaglia, assuring them that mistrust could not make the agreement between them more sincere nor more durable, and that, so far as he was concerned, he only wanted to be able to avail himself of the arms and advice of his friends. And although Vitellozzo remained very reluctant to accept the invitation, his brother’s death having taught him that a prince whom you have once offended is not to be trusted, yet he yielded to the persuasion of Pagolo Orsino, who had been corrupted by presents and promises of the Duke to wait for him at Sinigaglia. The Duke thereupon, before leaving for Fano, on the 30th of December, communicated his plan to eight of his most trusty followers, amongst whom were Don Michele and Monseigneur d’Enna, who afterwards became Cardinal. He directed them that so soon as Vitellozzo, Pagolo Orsino, the Duke Gravina, and Oliverotto came to meet him, each two of them should take one of these four between them, mentioning specially by name each one of the four which each two of them were to take between them; they were to entertain them until their arrival at Sinigaglia, and were not to permit them to leave until they had reached the Duke’s lodgings, where they were to make them prisoners. After that he ordered that all his armed force, consisting of more than two thousand horse and ten thousand infantry, should be at the break of day on the Metauro, a river five miles from Fano, and there to wait for him. Having met them there on the morning of the last day of December, he sent about two hundred of his mounted men ahead towards Sinigaglia, and then he started his infantry, after which he came himself with the remainder of his mounted force.
Fano and Sinigaglia are two cities of the Marches, situated on the shore of the Adriatic, and some fifteen miles distant from each other. Any one going to Sinigaglia has the mountains on his right hand; their base in some places stretches close down to the sea, so as to leave but a narrow space between, and at the widest place the distance between the mountains and the sea is barely two miles. The city of Sinigaglia is but little more than a bowshot’s distance from the foot of the mountains, and less than a mile from the shore. By the side of the city runs a little stream, which bathes that part of the walls of the city that looks up the road towards Fano. On approaching Sinigaglia the road runs for a considerable distance by the mountains; but on arriving at the stream that bathes the walls of Sinigaglia, the road turns to the left, and follows the banks of the stream for about a bowshot’s distance, until it comes to a bridge that spans the stream almost in face of the gate by which you enter Sinigaglia, not in a straight line, but obliquely. Before the gate there is a suburb composed of some houses and a square, one side of which is formed by the bank of the little stream.
The Vitelli and the Orsini, having given orders to await the coming of the Duke, had, by way of personally showing him honor, and for the purpose of lodging his troops, sent their own away to some castles about six miles distant from Sinigaglia, and had only left Oliverotto with his men in Sinigaglia; these consisted of one thousand infantry and one hundred and fifty mounted men, who were quartered in the above-mentioned suburb. Matters being thus arranged, the Duke Valentino went towards Sinigaglia; and when the head of his cavalry had reached the bridge, they did not pass it, but halted, and one half faced the river, and the other half fronted towards the country, leaving a space between them for the infantry to pass through, who entered the place without halting. Vitellozzo, Pagolo and the Duke Gravina, mounted on mules, and accompanied by a few horsemen, came to meet the Duke. Vitellozzo was without arms, and wore a cloak lined with green; he seemed very sad, as though he had a presentiment of the death that awaited him, which caused some astonishment, as his valor and former fortune were well known. It was said that, when he parted from his troops to come to Sinigaglia for the purpose of meeting the Duke, it seemed as though he bade them good by forever. He recommended his house and fortune to his captains, and admonished his nephews not to remember the fortune of their house, but only the valor of their fathers.
When the three arrived before the Duke, they saluted him courteously, and were graciously received by him; and those to whom the Duke had committed their charge took them at once between them. But when the Duke noticed that Oliverotto was not with them, (he having remained with his troops at Sinigaglia, whom he kept arrayed in line in the square opposite his lodgings by the river, where he made them go through their exercises,) he gave a wink to Don Michele, to whose charge Oliverotto had been confided, to see that Oliverotto should not escape. Don Michele therefore rode ahead, and having found Oliverotto he told him that this was not the time to keep the troops out of their quarters, which might otherwise be taken from them by the troops of the Duke; and therefore he advised him to let the troops go into their quarters, and come himself with him to meet the Duke. Oliverotto followed this advice, and went to join the Duke, who so soon as he saw him called him; and after having duly saluted the Duke, he joined the others.
When they had entered Sinigaglia they all dismounted at the Duke’s lodgings, and, having entered with him into an inner chamber, they were all made prisoners. The Duke immediately mounted his horse and ordered the troops of Oliverotto and the Orsini to be disarmed and stripped. Oliverotto’s troops, being near by, were completely stripped, but those of the Vitelli and the Orsini, being at a distance and having apprehended the destruction of their masters, had time to unite, and, recalling the valor and discipline of the Orsini and the Vitelli, drew together, and succeeded in saving themselves despite of the efforts of the people of the country and the hostile troops. The Duke’s soldiers, not satisfied with plundering the troops of Oliverotto, began to sack Sinigaglia, and they would have completely pillaged the town, if the Duke had not repressed their rapacity by having a number of them put to death.
But when night came and the disturbances were stopped, the Duke thought it time to make way with Vitellozzo and Oliverotto; and having them both brought into the same chamber, he had them strangled. Neither of them before death said a single word worthy of their past lives. Vitellozzo conjured those who put him to death to implore the Pope to grant him a plenary indulgence for all his crimes. Oliverotto, weeping, cast all the blame for the injuries done the Duke upon Vitellozzo. Pagolo and the Duke Gravina Orsini were left alive until Duke Valentino heard that the Pope had seized the Cardinal Orsino, the Archbishop of Florence, and Messer Jacopo da Santa Croce. After having received this intelligence, the Signor Pagolo and the Duke Gravina were strangled in the same way as the others, at Castel della Pieve, on the 18th of January, 1503.
[* ]This description is contained in an official letter written by Machiavelli to the Magistracy of the Ten at the very time when he was the Florentine envoy to the Duke Valentino. The slight difference between that letter and the description, is one of words only, and not of facts. The beginning of the letter is as follows: —