# CONFIDENTIAL INSTRUCTIONS CONFIDENTIAL INSTRUCTIONS BY NICCOLO MACHIAVELLI TO RAFFAELLO GIROLAMI, ON HIS DEPARTURE, 23 OCTOBER, 1522, AS AMBASSADOR TO THE EMPEROR CHARLES V., IN SPAIN. Honorable Raffaello, — Embassies are amongst those functions in a republic that confer most honor upon a citizen; and any one incapable of filling such an office cannot be regarded as competent to take part in the government of the state. You are about to go as ambassador to Spain, a country not known to you, and materially differing in manners and customs from those of Italy; and it is moreover the first time that you are charged with such a commission. Thus, if you give good proof of yourself, as everybody hopes and believes, you will derive great honor from it, which will be the greater in proportion to the difficulties which you have to encounter. And as I have some experience in affairs of this kind, I will tell you what I know about them, not from presumption, but simply out of the love I bear to you. Every honest man knows how to acquit himself faithfully of a mission that has been confided to him; the difficulty is to do it adequately. Now he executes it adequately who knows well the character of the sovereign to whom he is accredited, and that of those who govern him, and who knows best how to adapt himself to whatever may open and facilitate the way for a favorable reception. For difficult as every enterprise is, yet gaining the ear of the sovereign renders it easy. Above all things an ambassador must endeavor to acquire great consideration, which is obtained by acting on every occasion like a good and just man; to have the reputation of being generous and sincere, and to avoid that of being mean and dissembling, and not to be regarded as a man who believes one thing and says another.   This sincerity and this frankness are of great importance; for I know some men who, from being cunning and dissembling, have so entirely lost the confidence of the prince, that they have never more been able to negotiate with him. And yet if it be sometimes necessary to conceal facts with words, then it should be done in such manner that it shall not appear; or should it be observed, then a defence should be promptly ready. Alessandro Nasi was greatly esteemed in France from having the reputation of being sincere; whilst some others, from being regarded as the contrary, were held in great contempt. I believe that you will the more easily observe this line of conduct, as it seems to me that your very nature commands it. An ambassador will also derive great honor from the information which he communicates to his government; and this embraces three kinds, relating either to matters in course of negotiation, or to matters that are concluded and done, or respecting matters yet to be done; and to conjecture rightly the issue which they are likely to have. Two of these are difficult, but one is most easy. For to know things after they are done is generally speaking most easy, unless it should happen to be that an alliance is being formed between two princes to the detriment of a third party, and that it should be important to keep it secret until the time for divulging it shall have come; as happened with regard to the league between France, the Pope, the Emperor, and Spain, concluded at Cambray, against the Venetians, which resulted in the destruction of the Venetian republic. It is very difficult to penetrate the secret of such conclusions, and it is therefore necessary to depend upon one’s judgment and conjectures. But to find out all the intrigues, and to conjecture the issue correctly, that is indeed difficult, for you have nothing to depend upon except surmises aided by your own judgment. But as the courts are generally filled with busy-bodies, who are always on the watch to find out what is going on around them, it is very desirable to be on friendly terms with them all, so as to be able to learn something from each one of them. Their good will is readily won by entertaining them with banquets and gaming. I have seen very grave gentlemen who allow gambling in their houses, for the sole purpose of having that class of men coming to see them, so as to be able  to converse with them; for what one does not know another does know, and very often it happens that amongst them all the whole affair is known. But he who wants another to tell him all he knows must in return tell the other some things that he knows, for the best means of obtaining information from others is to communicate some information to them. And therefore if a republic desires that her ambassador shall be honored, they cannot do a better thing than to keep him amply supplied with information; for the men who know that they can draw information from him will hasten to tell him all they know. I suggest to you, therefore, that you remind the Eight, the Archbishop, and the Secretaries to keep you fully advised of all that occurs in Italy, even the smallest item; and if anything of interest happens at Bologna, Sienna, or Perugia, let them inform you of it, and above all let them keep you advised of the affairs of the Pope, of Rome, of Lombardy, and of the kingdom of Naples. And although all these matters have nothing to do with your business, yet it is necessary and useful for you to know them, for the reasons which I have given you above. It is in this way that you have to find out the intrigues that are carried on around you; and as amongst the things you will thus learn some are true and some false, although probable, you must weigh them carefully with your judgment, and take cognizance of those that seem to you the nearest the truth, and not notice the others. When you thoroughly understand and have examined these matters, you will be able to appreciate their aim and object, and communicate your judgment to your government. But to prevent such judgment on your part from seeming presumptuous, it is well in your despatches, after discussing the intrigues that are being carried on and the men who are engaged in them, to employ phrases something like this: “Considering now all I have written, the shrewd men here judge that it will produce such or such an effect.” This plan carefully followed has, in my day, done great honor to many ambassadors, whilst the contrary course has brought shame and blame upon them. I have known others, again, who for the purpose of filling their despatches with more information make a daily record of all they hear, and in the course of eight or ten days prepare a despatch from all these notes, taking from the mass of news they have thus gathered  that which seems to them most interesting and likely to be true. I have also known wise men, who had experience in embassies, adopt the plan of placing before the eyes of their government, at least once in every two months, a complete report of the state and condition of the republic or kingdom to which they are accredited as ambassadors. Such information, when exact, does great honor to him who sends it, and is of greatest advantage to those who receive it; for it is much easier to come to a decision when fully informed upon these points, than when ignorant of them. And to enable you more precisely to understand this part of your duty, I will more fully explain it. You arrive in Spain, you present and explain your commission and office; and then write home at once and give notice of your arrival at your post, and state what you have communicated to the Emperor, and what reply he has made; leaving it for another letter to give a particular account of the affairs of the kingdom, of the character of the sovereign, and of all that a few days’ stay in the country may have enabled you to report. After that, you must note with the utmost care and industry all that concerns the Emperor and the kingdom of Spain, and you will make a full report upon it. And to come to details, I would say that you must closely observe the character of the man: whether he governs himself, or allows himself to be governed; whether he is avaricious or liberal; whether he loves war or peace; whether he has a passion for glory or for anything else; whether he is beloved by his people; whether he prefers to reside in Spain or in Flanders; what kind of men he has about him as counsellors; whether their thoughts are turned to new enterprises, or whether they are disposed to enjoy their present good fortune, and what authority they have with him; whether he changes them often, or keeps them long; whether the king of France has any friends amongst them, and whether they are likely to be corrupted. And then it will also be well to think of the lords and barons who are most around him; find out what power they have, and how far they are satisfied with him; and in case of their being malcontent, how they could injure him; and whether it be possible for France to corrupt any of them. You must also find out about his brother, how he treats him, whether he is beloved by him, and whether he is content, and whether he could cause trouble  within the kingdom, or in his other states. You must also learn the character of the people, and whether the league that took up arms is altogether quieted, or whether there is any apprehension of their rising up again, and whether France could rekindle that fire. You must endeavor to penetrate the Emperor’s projects: what his views are as to Italian affairs; whether he aspires to the possession of Lombardy, or whether he intends to leave that state for the Sforzas to enjoy; and whether he desires to come to Rome, and when; what his intentions are with regard to the Church; what confidence he has in the Pope, and whether he is satisfied with him; and, in the event of his coming into Italy, what good or what ill the Florentines may have to hope or fear. All these points carefully considered and skilfully reported to the government will do you great honor. And not only is it necessary to write it once, but it is well every two or three months to refresh the remembrance of them, adding thereto an account of any new events that may have taken place; but with such skill that it may seem prompted by wisdom and necessity, and not by presumption. The Historical Works The Historical Works St. Peter’s Square, Vatican City, Rome — in the early 1500’s Machiavelli carried out several diplomatic missions, most notably to the Papacy in Rome. From 1502 to 1503, he witnessed the brutal reality of the state-building methods of Cesare Borgia (1475–1507) and his father, Pope Alexander VI, who were then engaged in the process of trying to bring a large part of central Italy under their possession. Unknown Portrait of a man traditionally believed to be Cesare Borgia by Altobello Melone, c. 1520 A DESCRIPTION OF THE MANNER IN WHICH DUKE VALENTINO PUT VITELLOZZO VITELLI, OLIVEROTTO DA FERMO, LORD PAGOLA AND THE DUKE OF GRAVINA TO DEATH A DESCRIPTION OF THE MANNER IN WHICH DUKE VALENTINO PUT VITELLOZZO VITELLI, OLIVEROTTO DA FERMO, LORD PAGOLA AND THE DUKE OF GRAVINA TO DEATH Translated by W. K. Marriott This short text describes the methods used by Cesare Borgia to suppress members of the Orsini family, a princely family of Renaissance Rome. Both Vitellozzo Vitelli and Oliverotto da Fermo were strangled on the night of their arrest on 31 December 1502. Unknown Vitellozzo Vitelli by Luca Signorelli DESCRIPTION OF THE METHODS ADOPTED BY THE DUKE VALENTINO WHEN MURDERING VITELLOZZO VITELLI, OLIVEROTTO DA FERMO, THE SIGNOR PAGOLO, AND THE DUKE DI DESCRIPTION OF THE METHODS ADOPTED BY THE DUKE VALENTINO WHEN MURDERING VITELLOZZO VITELLI, OLIVEROTTO DA FERMO, THE SIGNOR PAGOLO, AND THE DUKE DI The Duke Valentino had returned from Lombardy, where he had been to clear himself with the King of France from the calumnies which had been raised against him by the Florentines concerning the rebellion of Arezzo and other towns in the Val di Chiana, and had arrived at Imola, whence he intended with his army to enter upon the campaign against Giovanni Bentivogli, the tyrant of Bologna: for he intended to bring that city under his domination, and to make it the head of his Romagnian duchy. These matters coming to the knowledge of the Vitelli and Orsini and their following, it appeared to them that the duke would become too powerful, and it was feared that, having seized Bologna, he would seek to destroy them in order that he might become supreme in Italy. Upon this a meeting was called at Magione in the district of Perugia, to which came the cardinal, Pagolo, and the Duke di Gravina Orsini, Vitellozzo Vitelli, Oliverotto da Fermo, Gianpagolo Baglioni, the tyrant of Perugia, and Messer Antonio da Venafro, sent by Pandolfo Petrucci, the Prince of Siena. Here were discussed the power and courage of the duke and the necessity of curbing his ambitions, which might otherwise bring danger to the rest of being ruined. And they decided not to abandon the Bentivogli, but to strive to win over the Florentines; and they send their men to one place and another, promising to one party assistance and to another encouragement to unite with them against the common enemy. This meeting was at once reported throughout all Italy, and those who were discontented under the duke, among whom were the people of Urbino, took hope of effecting a revolution. Thus it arose that, men’s minds being thus unsettled, it was decided by certain men of Urbino to seize the fortress of San Leo, which was held for the duke, and which they captured by the following means. The castellan was fortifying the rock and causing timber to be taken there; so the conspirators watched, and when certain beams which were being carried to the rock were upon the bridge, so that it was prevented from being drawn up by those inside, they took the opportunity of leaping upon the bridge and thence into the fortress. Upon this capture being effected, the whole state rebelled and recalled the old duke, being encouraged in this, not so much by the capture of the fort, as by the Diet at Magione, from whom they expected to get assistance. Those who heard of the rebellion at Urbino thought they would not lose the opportunity, and at once assembled their men so as to take any town, should any remain in the hands of the duke in that state; and they sent again to Florence to beg that republic to join with them in destroying the common firebrand, showing that the risk was lessened and that they ought not to wait for another opportunity. But the Florentines, from hatred, for sundry reasons, of the Vitelli and Orsini, not only would not ally themselves, but sent Nicolo Machiavelli, their secretary, to offer shelter and assistance to the duke against his enemies. The duke was found full of fear at Imola, because, against everybody’s expectation, his soldiers had at once gone over to the enemy and he found himself disarmed and war at his door. But recovering courage from the offers of the Florentines, he decided to temporize before fighting with the few soldiers that remained to him, and to negotiate for a reconciliation, and also to get assistance. This latter he obtained in two ways, by sending to the King of France for men and by enlisting men-at-arms and others whom he turned into cavalry of a sort: to all he gave money. Notwithstanding this, his enemies drew near to him, and approached Fossombrone, where they encountered some men of the duke and, with the aid of the Orsini and Vitelli, routed them. When this happened, the duke resolved at once to see if he could not close the trouble with offers of reconciliation, and being a most perfect dissembler he did not fail in any practices to make the insurgents understand that he wished every man who had acquired anything to keep it, as it was enough for him to have the title of prince, whilst others might have the principality. And the duke succeeded so well in this that they sent Signor Pagolo to him to negotiate for a reconciliation, and they brought their army to a standstill. But the duke did not stop his preparations, and took every care to provide himself with cavalry and infantry, and that such preparations might not be apparent to the others, he sent his troops in separate parties to every part of the Romagna. In the meanwhile there came also to him five hundred French lancers, and although he found himself sufficiently strong to take vengeance on his enemies in open war, he considered that it would be safer and more advantageous to outwit them, and for this reason he did not stop the work of reconciliation. And that this might be effected the duke concluded a peace with them in which he confirmed their former covenants; he gave them four thousand ducats at once; he promised not to injure the Bentivogli; and he formed an alliance with Giovanni; and moreover he would not force them to come personally into his presence unless it pleased them to do so. On the other hand, they promised to restore to him the duchy of Urbino and other places seized by them, to serve him in all his expeditions, and not to make war against or ally themselves with any one without his permission. This reconciliation being completed, Guido Ubaldo, the Duke of Urbino, again fled to Venice, having first destroyed all the fortresses in his state; because, trusting in the people, he did not wish that the fortresses, which he did not think he could defend, should be held by the enemy, since by these means a check would be kept upon his friends. But the Duke Valentino, having completed this convention, and dispersed his men throughout the Romagna, set out for Imola at the end of November together with his French men-at-arms: thence he went to Cesena, where he stayed some time to negotiate with the envoys of the Vitelli and Orsini, who had assembled with their men in the duchy of Urbino, as to the enterprise in which they should now take part; but nothing being concluded, Oliverotto da Fermo was sent to propose that if the duke wished to undertake an expedition against Tuscany they were ready; if he did not wish it, then they would besiege Sinigalia. To this the duke replied that he did not wish to enter into war with Tuscany, and thus become hostile to the Florentines, but that he was very willing to proceed against Sinigalia. It happened that not long afterwards the town surrendered, but the fortress would not yield to them because the castellan would not give it up to any one but the duke in person; therefore they exhorted him to come there. This appeared a good opportunity to the duke, as, being invited by them, and not going of his own will, he would awaken no suspicions. And the more to reassure them, he allowed all the French men-at-arms who were with him in Lombardy to depart, except the hundred lancers under Mons. di Candales, his brother-in-law. He left Cesena about the middle of December, and went to Fano, and with the utmost cunning and cleverness he persuaded the Vitelli and Orsini to wait for him at Sinigalia, pointing out to them that any lack of compliance would cast a doubt upon the sincerity and permanency of the reconciliation, and that he was a man who wished to make use of the arms and councils of his friends. But Vitellozzo remained very stubborn, for the death of his brother warned him that he should not offend a prince and afterwards trust him; nevertheless, persuaded by Pagolo Orsini, whom the duke had corrupted with gifts and promises, he agreed to wait. Upon this the duke, before his departure from Fano, which was to be on 30th December 1502, communicated his designs to eight of his most trusted followers, among whom were Don Michele and the Monsignor d’Euna, who was afterwards cardinal; and he ordered that, as soon as Vitellozzo, Pagolo Orsini, the Duke di Gravina, and Oliverotto should arrive, his followers in pairs should take them one by one, entrusting certain men to certain pairs, who should entertain them until they reached Sinigalia; nor should they be permitted to leave until they came to the duke’s quarters, where they should be seized. The duke afterwards ordered all his horsemen and infantry, of which there were more than two thousand cavalry and ten thousand footmen, to assemble by daybreak at the Metauro, a river five miles distant from Fano, and await him there. He found himself, therefore, on the last day of December at the Metauro with his men, and having sent a cavalcade of about two hundred horsemen before him, he then moved forward the infantry, whom he accompanied with the rest of the men-at-arms. Fano and Sinigalia are two cities of La Marca situate on the shore of the Adriatic Sea, fifteen miles distant from each other, so that he who goes towards Sinigalia has the mountains on his right hand, the bases of which are touched by the sea in some places. The city of Sinigalia is distant from the foot of the mountains a little more than a bow-shot and from the shore about a mile. On the side opposite to the city runs a little river which bathes that part of the walls looking towards Fano, facing the high road. Thus he who draws near to Sinigalia comes for a good space by road along the mountains, and reaches the river which passes by Sinigalia. If he turns to his left hand along the bank of it, and goes for the distance of a bow-shot, he arrives at a bridge which crosses the river; he is then almost abreast of the gate that leads into Sinigalia, not by a straight line, but transversely. Before this gate there stands a collection of houses with a square to which the bank of the river forms one side. The Vitelli and Orsini having received orders to wait for the duke, and to honour him in person, sent away their men to several castles distant from Sinigalia about six miles, so that room could be made for the men of the duke; and they left in Sinigalia only Oliverotto and his band, which consisted of one thousand infantry and one hundred and fifty horsemen, who were quartered in the suburb mentioned above. Matters having been thus arranged, the Duke Valentino left for Sinigalia, and when the leaders of the cavalry reached the bridge they did not pass over, but having opened it, one portion wheeled towards the river and the other towards the country, and a way was left in the middle through which the infantry passed, without stopping, into the town. Vitellozzo, Pagolo, and the Duke di Gravina on mules, accompanied by a few horsemen, went towards the duke; Vitellozo, unarmed and wearing a cape lined with green, appeared very dejected, as if conscious of his approaching death — a circumstance which, in view of the ability of the man and his former fortune, caused some amazement. And it is said that when he parted from his men before setting out for Sinigalia to meet the duke he acted as if it were his last parting from them. He recommended his house and its fortunes to his captains, and advised his nephews that it was not the fortune of their house, but the virtues of their fathers that should be kept in mind. These three, therefore, came before the duke and saluted him respectfully, and were received by him with goodwill; they were at once placed between those who were commissioned to look after them. But the duke noticing that Oliverotto, who had remained with his band in Sinigalia, was missing — for Oliverotto was waiting in the square before his quarters near the river, keeping his men in order and drilling them — signalled with his eye to Don Michelle, to whom the care of Oliverotto had been committed, that he should take measures that Oliverotto should not escape. Therefore Don Michele rode off and joined Oliverotto, telling him that it was not right to keep his men out of their quarters, because these might be taken up by the men of the duke; and he advised him to send them at once to their quarters and to come himself to meet the duke. And Oliverotto, having taken this advice, came before the duke, who, when he saw him, called to him; and Oliverotto, having made his obeisance, joined the others. So the whole party entered Sinigalia, dismounted at the duke’s quarters, and went with him into a secret chamber, where the duke made them prisoners; he then mounted on horseback, and issued orders that the men of Oliverotto and the Orsini should be stripped of their arms. Those of Oliverotto, being at hand, were quickly settled, but those of the Orsini and Vitelli, being at a distance, and having a presentiment of the destruction of their masters, had time to prepare themselves, and bearing in mind the valour and discipline of the Orsinian and Vitellian houses, they stood together against the hostile forces of the country and saved themselves. But the duke’s soldiers, not being content with having pillaged the men of Oliverotto, began to sack Sinigalia, and if the duke had not repressed this outrage by killing some of them they would have completely sacked it. Night having come and the tumult being silenced, the duke prepared to kill Vitellozzo and Oliverotto; he led them into a room and caused them to be strangled. Neither of them used words in keeping with their past lives: Vitellozzo prayed that he might ask of the pope full pardon for his sins; Oliverotto cringed and laid the blame for all injuries against the duke on Vitellozzo. Pagolo and the Duke di Gravina Orsini were kept alive until the duke heard from Rome that the pope had taken the Cardinal Orsino, the Archbishop of Florence, and Messer Jacopo da Santa Croce. After which news, on 18th January 1502, in the castle of Pieve, they also were strangled in the same way.