Front Page Titles (by Subject) LETTER XIV. - The Historical, Political, and Diplomatic Writings, vol. 3 (Diplomatic Missions 1498-1505)
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LETTER XIV. - 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: —
By mine of the 23d, which I retained until the 24th, I have replied to yours of the 21st. Yesterday, the 25th, Signor Paolo Orsino arrived here and presented himself to the Duke, dressed like a courier, and stated that the Cardinal Borgia had placed himself as a hostage for his security in the hands of the Orsini. The coming of Signor Paolo is in great part due to that gentleman, at whose request he has come here to excuse and justify what has occurred, and to learn more nearly the intentions of his Excellency; and to communicate them to the others. He has to-day despatched a courier to them in the neighborhood of Fano to learn their final resolution. I have not been able to learn any particulars of the interview between Signor Paolo and the Duke, nor do I believe that I shall be able to obtain any, as that gentleman is very reticent, and talks with but few persons. At one time an arrangement was under consideration, and Messer Giovanni Bentivogli has sent several messengers to the Bishop of Euna; but now, since the arrival of Messer Paolo, he often receives a chancellor sent by Messer Annibale Bentivogli, who is at Castel San Piero. All the booty taken by the Bolognese three days ago is being restored. The Orsini have not laid siege to Fano, as had been reported, nor are the Bentivogli before Doccia, which I wrote you yesterday had been currently reported here. And thus nobody stirs; and we now see that the negotiations for an arrangement are favorable to the Duke, and that he entertains them willingly; but I will not pretend to judge what his real intentions are.
To-day is the 27th, and yesterday evening at the fourth hour I received your Lordships’ letter of the 25th. So soon as his Excellency the Duke had arisen this morning I went to see him, and as it seemed to me proper to communicate your despatch to him, I read him the greater part of it. He thanked your Lordships according to his wont for your firm disposition, and for the communication made to him through the mission of Messer Gino di Rossi. He assured me that he could not but believe you, as your words and your letters agreed so entirely. Then, referring to the arrival of Signor Paolo and the proposed treaty, he said: “These men merely want that I should secure them, and it only remains to find the way of doing it, which mustbe according to fixed stipulations, for which they look to the Cardinal Orsino.” And without giving me a chance to say a word, he added: “It is enough for you to know in general that I shall never conclude anything contrary to the interests of your Signoria; I will not permit them to be wronged to the extent of a single hair.” He seemed pleased that an envoy had been sent to Rome, and yet he did not refer to that matter, but passed it over. I did not fail to recommend to him Salvestro di Buosi in the terms suggested to me by your Lordships. His Excellency replied: “Your Signoria desires that I should set Salvestro at liberty, he being their friend. To which I reply, that all my subjects are their friends and servants; and your Signoria should rather interest itself for the great number of my subjects, who would suffer by the liberation of Salvestro, than for him alone. Suffice it for the present that no harm shall come to him, and so soon as I can set him free without irritating my people, I will comply most cheerfully with the request of your Signoria.”
Your Lordships desire me to give them a fresh account of the condition of things as I find them here, having already done so in my last, which I presume was received by you on the 24th; I therefore do not repeat it. Matters are very much as when I wrote you, excepting that the booty taken by the Bolognese is being restored, and neither Fano nor Doccia is besieged, as had been reported. It is true, we have the news to-day that the Vittelleschi have taken the castle of Fossombrone, which held to the Duke. Paolo Orsino expressed his dissatisfaction at it, and spoke very severely of those who caused it to be done. As to the terms of any arrangement that may be concluded between them, they are not sufficiently known; but one may augur favorably regarding it. If we examine the characters of both the one and the other party, we shall find in the Duke a daring and fortunate man, full of hope, favored by a Pope and a king, and who finds himself assailed by the others, not only in a state that he wishes to acquire, but also in one that he has already acquired. The other party will be seen to fear for their own states, and to have been afraid of the Duke before they provoked him. Having done so now, their fears are increased, and it is impossible to see how the latter can pardon the offence, or how the former can dismiss their apprehensions; and consequently how either the one can yield in his attempt against Bologna, or the others in theirs upon the duchy of Urbino. It is argued that an amicable arrangement between them would be possible only if they could unite their joint forces against some third party, in which case neither the Duke nor the confederates need reduce their forces, and both would rather gain in renown and in real advantages.
However, if such an arrangement could be brought about, there would be no other power for them to turn against except Florence or Venice. An attack upon Florence is judged to be the easier of the two, so far as Florence itself is concerned, but more difficult on account of the king of France; whilst an attempt upon Venice would be easier so far as the king of France is concerned, but more difficult as regards Venice itself. The latter would be the most agreeable to the Duke, and the former more acceptable to the confederates. Still it is not believed that either one or the other will be undertaken, although spoken of as a possible thing. And thus I can find no one who can definitely suggest a way for an agreement between the two. But such as nevertheless form some definite idea to themselves on the subject believe that the Duke will succeed in causing a division amongst the confederates, and having thus broken up their alliance he will have nothing more to fear from them, and may then pursue his own enterprises. I am rather disposed to believe this from some mutterings that have fallen from the lips of his ministers; and moreover I have evidence that the Bentivogli are quite uneasy on account of the coming here of Paolo Orsino. The league, however, is so recent, that it is difficult to believe in its being broken up.
Your Lordships, having now been apprised of the various reports current here, will, with your greater wisdom and experience, form a better judgment of the state of things here, respecting which I have thought it my duty to write all I have heard.
A considerable part of the Gascons have arrived at Castello in the Bolognese territory, and the quartermasters of the French troops are expected here from day to day.
I entreat your Lordships again to accord me my recall, for the public weal requires no further temporizing; and if anything definite is to be concluded, then it will be necessary to send some one of greater authority. My own affairs at home are falling into the greatest disorder, and moreover I cannot remain here any longer without money, which it is necessary to spend here.
I recommend myself to your Lordships.
Imola, 27 October, 1502.