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LETTER I. - Niccolo Machiavelli, The Historical, Political, and Diplomatic Writings, vol. 3 (Diplomatic Missions 1498-1505) 
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. 3.
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Magnificent Signori, etc.: —
Finding myself not well on horseback at my departure from Florence, and believing that my commission required all speed, I took the post at Scarperia and came here without loss of time, arriving to-day at about the eighteenth hour. Having left my horses and servants behind, I presented myself at once, in my travelling costume, to his Excellency, who received me most graciously. After presenting my credentials, I explained to his Excellency the object of my coming, beginning by thanking him for the restitution of the cloths. I then spoke of the defection of the Orsini, of their meeting with their adherents, how they had cunningly endeavored to induce your Lordships to unite with them, and of your disposition in regard to your friendship with the king of France and your devotion to the Church, amplifying in the best manner I could the reasons that bind you in friendship to these two powers, and caused you to avoid any alliance with their adversaries. I assured him that under all circumstances your Lordships would have every consideration for the interests of his Excellency consistent with your friendship for the king of France and your ancient devotion to the Church, as well as the affection which you had ever borne to his Excellency, regarding as you do all the friends of France as your allies and particular friends.
His Excellency made no reply to what I said respecting the restitution of the merchandise, but, passing to the other matters, he thanked your Lordships for your offers and obliging demonstrations. After that he said that he had always desired your friendship, and that, if he had failed to obtain it, it was owing more to the malice of others than to any fault of his own, — adding that he wished to relate to me what he had never before told any one respecting his coming to Florence with his army. And then he told me that ever since the taking of Faenza, and his attempt upon Bologna, the Orsini and the Vitelli had been after him trying to persuade him to return to Rome by way of Florence, which he had refused, because the Pope, by a special brief, had instructed him differently. That thereupon Vitellozzo had thrown himself at his feet, weeping, and begging him to come that way, and promising him that no harm of any kind should be done either to the country or the city. But that, still refusing to consent, they had so beset him with prayers to that effect, that he finally yielded, but under a pledge on their part that no damage should be done to the country, and that the subject of the Medici should not be mentioned.
Wishing, however, to derive some benefit from his coming to Florence, he had thought of availing of the opportunity to form a friendship with your Lordships, which is proved by the fact that he had engaged in no negotiations, or had hardly said one word respecting the Medici, a fact well known by the commissioner who had treated with him, and that he never allowed Piero de’ Medici to come to his camp. And that whilst they were at Campi the Orsini and the Vitelli had repeatedly asked permission of him to present themselves at Florence or at Pistoja, showing him how they could strike some successful blows; but that so far from consenting, he had made them understand by a thousand protests that he would rather fight them himself. That afterwards, when the treaty was concluded, the Orsini and the Vitelli, on pretence that he had consulted only his own interests and not theirs, and that his coming to Florence had been solely for his benefit and to their injury, had tried by dishonest means to break the treaty; and had committed all sorts of outrages for the purpose of giving offence to your Lordships, and to disturb the good understanding between yourselves and him. Nor had it been possible for him to remedy these outrages, because he could not be in all places at once; and also because your Lordships had not paid him the subsidies stipulated and provided for. Thus matters had remained until the month of June past, when the revolt of Arezzo occurred, respecting which he told me, the same as he had previously told the Bishop of Volterra, that he had not heard anything until then. Still he was pleased that it had occurred, for he thought the occasion might be used to render your Lordships a service that would merit your acknowledgments. But that even then nothing was done, either because of the ill-luck of both parties, or because our republic was not disposed to treat and conclude an arrangement that would have been mutually advantageous, which, however, had not caused him much uneasiness. But being disposed to render you a service, and knowing the wishes of the king, he had written and at once had sent messengers to Vitellozzo to withdraw from Arezzo. And not content with this, he had himself gone with his troops to Citta di Castello, and could easily have deprived Vitellozzo of his state, for the principal inhabitants had come to offer themselves to him; and this, he said, was the cause of Vitellozzo’s ill-will and dissatisfaction. As to the Orsini, he said that he really knew not what had given rise to their indignation and their departure from the court of Rome without leave of the Pope. Subsequently, when they saw that his Majesty the king had treated him better than the Cardinal of their name, and had bestowed great honors upon him, to which came furthermore certain reports that had been spread that he intended to deprive them of their possessions, then the Orsini abandoned him, and joined that gathering of bankrupts at Magione. And although he had received several messages from Signor Giulio Orsino, protesting that they had no intention of opposing him, etc., etc., yet he knew full well that the reason why they did not wish to declare themselves openly against him was that they had received his money. But if ever they did so declare themselves, he would look upon them as greater fools than he had ever supposed them to be, for not knowing how to choose a better moment for injuring him than the present, when the king of France was in Italy, and his Holiness the Pope still alive; two circumstances that had kindled such a fire in his favor as all the water the Orsini could command would not quench. Nor did he care much about their stirring up the duchy of Urbino, for he had not yet forgotten the way to reconquer it, in case he should lose it.
His Excellency then added, that now was the moment to oblige him, if your Lordships really wished to be his friends, for he could now form an alliance with you regardless of the Orsini, which he had never before been able to do. But if your Lordships were to defer it, and he in the mean time should make up with the Orsini, which they sought by all means to bring about, then he would be bound again by the same considerations as before. And as no arrangement would satisfy the Orsini that did not re-establish the Medici, your Lordships would be exposed to the same difficulties and jealousies as before. He therefore thought that your Lordships should anyhow declare yourselves at once either his friends or theirs, as delay might bring about an agreement between him and the Orsini, that would be prejudicial to you. For in the case of victory of either party, the successful one would either remain your enemy, or would anyhow be under no obligations to your Lordships. And his Excellency says that when you come to decide upon this matter, which of necessity you will have to do, he does not see how you can take a different course from that in which his Majesty the king of France and his Holiness the Pope concur; adding, at the same time, that it would be most agreeable to him, in case that Vitellozzo or any other should make an attempt upon any of his states, that you should cause whatever troops you have to advance either towards the Borgo or to the frontiers of his states, for the purpose of sustaining his cause.
I listened with the utmost attention to the above remarks of his Excellency, and have given you in full, not only their substance, but his very words, so that your Lordships may be able to form a better judgment of it all. Not deeming it important, I shall not relate what I answered, but I was careful not to go outside of my instructions. In relation to the subject of the troops I made no reply at all, but merely said that I would report to your Lordships his excellent disposition, which I had no doubt would give you signal pleasure. And although, as you will perceive, his Excellency manifested a great desire that a treaty between yourselves and him should be promptly concluded, yet notwithstanding my efforts to get at his real thoughts, he always avoided the subject, so that I did not succeed in getting more from him than what I have written.
But having heard on my arrival here that there had been some disturbances in the duchy of Urbino, and his Excellency having said in the course of his remarks that he did not attach any importance to the troubles in that duchy, it seemed to me not amiss, in the course of my reply, to ask him how this matter had occurred. To this his Excellency made answer: — “My clemency and disregard of these things have done me harm. You are aware that I took that duchy in three days without hurting a hair of any one’s head, with the exception of Messer Dolce and two others, who had made open opposition to his Holiness the Pope. And what is more, I had even confided the public offices of that state to many of its principal citizens, and had placed one of them in charge of a certain wall which I had ordered to be built in the citadel of San Leo. A couple of days ago, under pretence of raising a beam, this individual concerted a plot with certain peasants, that enabled him to obtain possession of that citadel by force, and thus I lost it. Some say that they raised the cry of St. Mark, others say that of the Vitelli or the Orsini; but up to the present, neither one nor the other have openly declared themselves. Now, although I give up that duchy for lost, it being a weak and feeble state, and its inhabitants dissatisfied in consequence of my having burdened them heavily with my troops, yet I hope to put all this matter right again. And you must write to your Signori to look well to their own affairs, and to let us hear from them promptly; for if the Duke of Urbino returns to his duchy from Venice, it will not be for their advantage, and still less for ours; and this should cause us to have more confidence in each other.”
This is all I am at present able to communicate to your Lordships; and although my duty would require me to write you how many troops the Duke has, and where they are stationed, as well as many other particulars respecting the state of things here, yet, having arrived only to-day, it is impossible for me to ascertain the exact truth, and I therefore reserve all that for another time, and recommend myself to your Lordships.
7th October, 1502.
P. S. — I have kept this letter until the sixteenth hour of this morning, because my courier had no horse and was not able to find one until now. I have to add, that, in the course of conversation last evening, his Excellency told me that Pandolfo Petrucci had sent a disguised messenger to him on the previous evening to assure him that he would not countenance any one that opposed his Excellency, and that he had given him the most positive assurances to that effect. On my way here yesterday, I met Messer Agapito* about two miles from here with some seven or eight cavaliers; and, recognizing me, he asked where I was going, and who it was that sent me. He gave me a cordial welcome, but after having gone on his way a short distance he turned back. This morning I have learnt that said Messer Agapito was on his way to Florence, being sent on a mission to your Lordships by his Excellency the Duke, and that my coming caused him to return.
8th October, 1502. — I have given the bearer of this two ducats, so that he might be at Florence by to-morrow, the 9th, before daylight. I beg you will have that sum reimbursed to Ser Agostini Vespucci.
[* ]Messer Agapito de’ Gherardi da Amelia, several times mentioned in these despatches, was one of the principal secretaries of the Duke Valentino.