Front Page Titles (by Subject) LETTER XXVIII. - The Historical, Political, and Diplomatic Writings, vol. 3 (Diplomatic Missions 1498-1505)
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LETTER XXVIII. - 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: —
My last of the 22d was sent by Ugolino Martelli, having previously written you on the 20th in reply to your Lordships’ letter of the 15th. Since then I have nothing of interest to communicate, matters here remaining very much in the same condition as when I last wrote. For the Duke is still here, the Signor Paolo has not yet arrived, and various opinions prevail as to his coming. The treaty with Messer Giovanni Bentivogli is not yet concluded, owing to the difficulty about the old account of nine thousand ducats which Messer Giovanni was to pay the Duke within a given time. His Excellency wanted to convert this into a perpetual obligation, or into one single payment of forty thousand ducats, to be made within a few months. But Messer Giovanni will not listen to such a proposition, and wishes to terminate the annual payments in six or eight years. This dispute has been going on for four days, Messer Mino de Rossi being here as representative of Messer Giovanni, and I think from what I have heard this evening the Protonotario is expected here to-morrow. Some say that all this delay is caused by the Duke, who wishes to await the reply of Messer Romolino, whom he had sent to Rome with instructions to act in this matter only in accordance with the will of the Pope. Others give a much more sinister interpretation to the matter, notwithstanding that the most amicable relations seem to prevail between his Excellency the Duke and the Bolognese, and that there is a constant interchange of presents between them.
Many reasons are assigned for the delay in the Duke’s departure; some say that he does not wish to leave until he has concluded the agreement with the Bentivogli; others say that he is utterly without means, and is waiting for money from Rome. Others again say that it is because the Swiss have not yet arrived; although three days ago it was reported that they had passed Ferrara. But nothing certain is publicly known, though there are persons who claim to be well informed and who maintain that the Duke wants to be perfectly clear whether in going forward it will be either as the friend or the enemy of the Orsini, which, however, cannot be known until after the arrival of the Signor Paolo. Nor are there wanting persons who say that the Duke leaves for the reasons which I have indicated to your Lordships in one of my previous letters.
I have informed your Lordships that an application has been made to the Duke for a safe-conduct for one of the Duke of Urbino’s confidential persons to come here. This personage arrived here four days ago, and has suddenly left again. It is publicly reported that the object of his coming was to negotiate the exchange of certain prisoners, which is all I have heard on the subject. A couple of days since an individual returned here from Urbino, who had been made prisoner at the time when that city was in revolt, and who left there on the 19th instant. This person reports that there is a good deal of alarm felt by the people of Urbino, notwithstanding their obstiuacy; and that the cause of their alarm is the treaty now being negotiated between the Duke and the Orsini. He relates, that, two days prior to his leaving Urbino, the Duke Guidobaldi called together first the citizens and afterwards the troops, of which there were not more than some four hundred infantry under the command of Giovanni di Rossetto and two other constables; that the Duke Guidobaldi had spoken to each of them in a different manner, although the same in substance, telling them that the treaty between the Orsini and the Duke Valentino was a sure thing, and that the negotiations between that Duke and Vitellozzo were also being urged forward, and that he feared a treaty would be concluded between them, upon which matters he wanted their advice. The citizens replied that they would die with him; the soldiers, after having examined what forces the Duke of Urbino could muster, assured him that they would hold Urbino and San Leo for him during the entire winter, even though the whole world should be against them. An order was accordingly published for the evacuation of all the castles and places in the duchy; and for all the garrisons to withdraw into the cities of Urbino and San Leo. Giovanni di Rossetto had sent one of his brothers with his wife and children to San Leo. The same person from Urbino spoke also of the readiness with which the Vitelleschi had declared themselves at first against the Duke Valentino, and how much harm they would have done him if the Signor Paolo Orsino had not held them back; and how six hundred of Vitellozzo’s infantry had routed the Duke’s forces at Fossombrone, which forces consisted of one hundred men-at-arms and two hundred light cavalry, who all took to flight without having as much as put a lance in rest; — and that during the many days that they were in camp they had never seen a single penny in circulation. His Excellency the Duke has spent since the calends of October until now more than sixty thousand ducats, according to what his treasurer Alessandro has assured me not more than two days since. I take pleasure in writing this to your Lordships, so that you may see that, when others are in trouble, they spend no less than you do, nor are they any better served by their soldiers than what your Lordships are; whilst, on the contrary, he who is well armed with troops of his own will always have the same advantages whichever way things may turn.
That friend of mine whom I have mentioned before has said nothing to me touching the treaty that is about to be concluded between your Lordships and the Duke. I believe they are waiting to know the character of the instructions with which Messer Giovanni Vittorio proceeds to Rome; or rather they are awaiting the time when you shall have more need of them than at present; which I am sure your Lordships will make every effort to avoid.
I continue to pretend not to see anything, both because I have fulfilled your commission in opening the road you desired to follow, and because, not having any new propositions to make to them on your part, without which it would be difficult to accomplish anything here or at Rome. For having once made known their intentions, to which your Lordships did not agree, there is no way of making these people recede from them, except by presenting some new proposition to them; for to decline and then to remain silent would not suit men of this kind.
Your Lordships, I trust, will not charge me with presumption for having given you my opinion, seeing that in your letter of the 15th you inform me of your intention to contract an alliance with the Duke without delay. For had I not given you my views of matters as I understand them, particularly with my knowledge of the Duke’s character, I should feel that I had not done my duty.
Imola, 26 November, 1502.