Front Page Titles (by Subject) LETTER XLIV. - The Historical, Political, and Diplomatic Writings, vol. 3 (Diplomatic Missions 1498-1505)
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LETTER XLIV. - 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: —
I wrote you two letters yesterday in relation to the events that have taken place here since the Duke’s arrival in Sinigaglia; how he had Signor Paolo and the Duke di Gravina Orsini, and Vitellozzo, and Oliverotto, arrested. In my first I simply announced the event, but in the second I gave you all the particular details, and moreover what the Duke had said to me, and the opinion expressed here as to the Duke’s proceedings. I should repeat all this at length, if I did not suppose that these letters have reached you safely. Having sent these two despatches by express messengers, the first by a Florentine at an expense of six ducats, and the other by a man from Urbino at a cost of three ducats, I feel confident of their arrival. Yet by way of extra care I will summarily repeat the whole. His Excellency left Fano yesterday morning with his entire army for Sinigaglia, which town with the exception of the citadel had been occupied by the Orsini and Messer Oliverotto da Fermo. Vitellozzo had arrived there the evening before from Castello. One after the other these persons came out to meet the Duke, and then accompanied him into the town and into his house. As they entered his apartment, the Duke had them seized as prisoners; he then had their infantry disarmed, which was in the suburbs outside of the city; and the Duke sent half of his forces to disarm also the men-at-arms who were quartered in certain castles some six or seven miles from Sinigaglia. At two o’clock in the night the Duke had me called, and with the most serene air in the world expressed to me his delight at his success; saying that he had spoken to me of this matter the day before, but had not then told me the whole. He then spoke in a most suitable and affectionate manner as to his conduct towards our republic, adducing all the motives that made him desire your friendship, provided these feelings were reciprocated by your Lordships, so that I was quite astonished. I do not repeat all he said, having already written it in my letter of yesterday evening.
Finally he concluded by requesting me to write to your Lordships upon three points. The first, that you rejoice with him at his having destroyed the chief enemies of the king of France, of himself, and of the republic of Florence; and at his having thus removed all seeds of trouble and dissension calculated to ruin Italy, for which your Lordships ought to be under great obligations to him. The next is, that I should request and beg your Lordships on his behalf to be pleased to give to the whole world a proof of your friendship for him, by ordering your cavalry towards Borgo, and to collect infantry there, so that they might march together with his forces upon Castello or Perugia, as might be required; saying that he intended at once to take that route, and that he would have started the evening before, if he had not feared that his departure would have exposed Sinigaglia to being sacked. His Excellency then reiterated to me his request that I should write and ask you to make every demonstration of friendship for him, saying that at present there was no occasion for your being restrained by any fear or mistrust of him, seeing that he was well provided with troops, and that your enemies were prisoners. And, lastly, he begged me to write to your Lordships that it was his particular desire that you should have the Duke Guido, who is at Castello, arrested, in case he should take refuge on Florentine territory upon learning that Vitellozzo was prisoner. Upon my replying to him that it would not comport with the dignity of our republic to deliver the Duke Guido to him, and that you would never do it, he answered, that “he approved of my remarks, and that it would suffice that you should detain the Duke Guido, and not set him at liberty without his consent.” I promised to write you all this, and his Excellency awaits your reply.
In my letter of yesterday I wrote you also that a certain number of well-informed persons and friends of our republic have suggested to me that the present is a most favorable opportunity for your Lordships to do something for the readjustment of the affairs of Florence. They all think that you can rely upon France, and that it would be most opportune to send here one of your most distinguished citizens as an ambassador on the occasion of this event, and that you should not delay in doing so. For if a personage of high position were to come here with orders to establish friendly relations with the Duke, he would he met half-way. This has been suggested to me again and again by those who are well-wishers to our republic; and I communicate it to your Lordships in the same spirit of devotion with which I have ever served you. This is in brief what I wrote you more fully in my despatch of yesterday. Since then the Duke has had Vitellozzo and Oliverotto da Fermo put to death at the tenth hour of the night. The others are still alive; and it is supposed that the Duke is only waiting to know whether the Pope has the Cardinal Orsino, and the others who were in Rome, safely in his hands, and that, if so, he will dispose of the whole band at the same time.*
The citadel of Sinigaglia surrendered to the Duke at an early hour this morning, and is now in his possession. His Excellency left there this same morning, and has come here with his army. It is certain that they will go in the direction of Perugia and Castello, and possibly to Sienna. The Duke will then move to Rome, and according to popular opinion will settle the Orsini castles there. He also intends taking Bracciano by force, and then all the rest will be as easy as to burn straw. We shall remain here all to-morrow and next day, and then go into quarters at Sassoferrato, the season being as unfavorable for war as can possibly be imagined. You would not believe it were I to describe the condition of the army and its followers; for a man who has the chance of sleeping under cover is deemed fortunate.
Messer Goro da Pistoja, a rebel and enemy of our republic, was with Vitellozzo, and is now prisoner here in the hands of certain Spaniards. I believe that, with a couple of hundred ducats, should your Lordships feel disposed to spend that much, it could be managed that he should be delivered to one of your Rectors. Be pleased to think of this matter, and advise me whether you think it worth while to do anything in the matter.
I recommend myself to your Lordships, quæ bene valeant.
Conrinaldo, 1 January, 1503.
[* ]The capture and death of these corresponds with what Machiavelli himself states in his description of the proceedings adopted by the Duke Valentino in putting to death of Vitellozzo Vitelli, Oliverotto da Fermo, the Signor Paolo and the Duca di Gravina Orsini. Burchard in his well-known Diary says: “The Duke Valentino had written to the Pope to hold the Cardinal Orsino. When Adriano Castellense da Corneto, the Pope’s secretary and treasurer, had read this letter of the Duke Valentino to the Pope, he would not leave the Pope’s chamber that night, lest he should be inculpated if ever the Cardinal Orsino should get a hint of it. The Pope thereupon had the Cardinal Orsino and Jacopo da S. Croce informed that the Duke had taken the castle of Sinigaglia. That Cardinal thereupon rode, on the 3d of January, 1503, to the pontifical palace to congratulate the Pope. With him was the Governor, who feigned to accompany him by chance. When the Cardinal had dismounted and had entered the palace, his horses and mules were taken to the Papal stables. The Cardinal had scarcely entered the chamber of the Parrot, when he found himself surrounded by armed men and became alarmed. He was conducted to prison, and after him the Protonotario Orsino, Jacopo da S. Croce, and Bernardino, Abbot of Alviano, where they were all confined.”