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The Works of Niccolò Machiavelli
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The Historical, Political, and Diplomatic Writings of Niccolò Machiavelli, vol. 3: Diplomatic Missions 1498-1505
MISSIONS.
SECOND MISSION TO SIENNA.
LETTER VI.

Niccolo Machiavelli
Machiavelli, Niccolo

23 July, 1505
Sienna

LETTER VI.

Magnificent Signori, etc.: —

Your Lordships’ last letter of the 21st reached me the same day at the twenty-second hour. Having noted what your Lordships write respecting the proposition of Messer Michele de’ Ricci, I called on Pandolfo and executed your Lordships’ commission in such manner as seemed to me proper. Pandolfo replied that he had not had any conversation with Messer Michele on the subject; and that, if the latter had made that proposition, it was done doubtlessly because he desired that an agreement should be concluded, and because it probably seemed to him the best thing to be done. And when I asked him what he thought of it, he said that he would have to confer with some of his citizens on the subject; but if he had to give his individual opinion about it, without further reflection, he would say that he saw no security in it for the people of Sienna. We discussed this matter for a while, and although I thought I perceived clearly what his sentiments were, yet it seemed to me well not to write immediately to your Lordships, for I imagined that possibly, on further reflection, Pandolfo might assent in part to the proposition. Nor could I yet write differently to your Lordships yesterday, not having had any further answer from Pandolfo, who has been occupied with the citizens of Sienna in a solemn festivity in honor of the return of the Nine. He excused himself on this ground, and deferred his reply until this morning.

Having gone therefore at a suitable hour to the Duomo, I found Pandolfo there with four of his leading citizens; and having joined them, Pandolfo said to me in few words that he would leave me with Messer Antonio da Venafro, who would inform me of their conclusion. Being thus left alone with Messer Antonio, he said to me that he saw no security for the Siennese in this proposition of Messer Michele, for he noticed

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that it exposed them to two dangers; the one, in case the king for some reason should or could not decide; and the other, that if he did he might adjudge Montepulciano to your Lordships. And although it was believed here that your Lordships would cheerfully accede to a relinquishment of it, in case the king, after having restored Pisa to you, were also to adjudge Montepulciano to you; yet as but one of two results is possible, they would be left in doubt, and would therefore never consent, unless means should first be found to dissipate that uncertainty; and for this he knew of no better way than to do as had been proposed in the beginning. For to try and have the king do some act to reassure the people of Sienna would be a protracted affair, whilst there is hardly time to make suitable preparations for resisting those who desire to destroy Tuscany.

And thus Messer Antonio talked much more at length than what I have written. In reply I said all that seemed to me proper for the justification of your Lordships’ course, whilst he with his utmost ability neglected nothing to prove how much Pandolfo desired this agreement with your Lordships, and as he wished to conclude it with a good will, so he purposed to execute it even with a better will. Antonio added, that it would be so manifestly for your advantage that, knowing your wisdom, he was astonished at the difficulties made in deciding to conclude it; and that he could not comprehend whence this reluctance arose. And as he went so far in this matter I could not help pointing out to him that the difficulty lay more with others than with your Lordships, and was more particularly caused by those who wanted to take a greater share of things than what belonged to them; and that the impediments in the way of such a treaty were not so much the separation of Montepulciano, although that involved both loss of honor and advantage, as the proceedings of certain private persons here, which had caused a mistrust in the minds of many persons, and made them doubt whether even the cession of Montepulciano would be of any use; for they seem to think that others wish to subject them to their will both by insults and violence. The reason for their believing this was, amongst other things of the past which I will not now repeat, the rupture of the agreement with Lucca, and the breaking of the engagement of Giovanpaolo, and the present movement of

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Bartolommeo d’ Alviano, with which we are threatened at the same time that we are solicited to favor it. He knew well that enmities were engendered by injuries, and friendships by benefits; and that it was a great error to attempt to make any one a friend by beginning with injuring him; and that therefore I had said several times to Pandolfo, to him, and to many other citizens, that to conclude this agreement easily it would be necessary for them to remove this mistrust that had sprung up, and to do this the greatest efforts must be made by those who were most to blame for its existence; and that it was the business of the Siennese to show themselves ready and united, and with a single purpose to resist Bartolommeo. That such a proof of good will would promptly produce friendship, and would assuredly put an end to all mistrust; otherwise, there being no time to build up such a friendship, I feared we should see the whole business get into such confusion as to fill every one with fear, and that within a short time here I had seen many people who would laugh in the summer but cry in the winter. That I had said on former occasions, and would now again remind him, that it was generally the feeble who had most to fear and least to gain from disorders.

Messer Antonio nevertheless maintained his case, and lacked neither words nor reasons to demonstrate to me that, Sienna not having any agreement with Florence, you could not reasonably desire nor expect any benefits at their hands; and that this had been the cause of the rupture of the agreement with Lucca, and of the breaking of Gianpaolo’s engagement, and of their doing nothing to remedy the present evil. For unless you became their shield, they could not draw the sword against others. But if a treaty were once concluded between you, you would at once become masters of Tuscany. And then he enlarged anew upon the great advantages that would result to you in consequence, saying to me several times, “Believe me, Niccolo, he who blames Pandolfo may give you many reasons, but will not tell you all that he has in his heart.” I combated him the best I could, but could get nothing else out of him.

Pandolfo tells me that he has no news from D’ Alviano’s camp, and presumes, from the fact that Cornelio has not written him, that the army did not move yesterday as he had written. He promises to let me know so soon as he hears anything.

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This rests entirely with him, as I have no means of obtaining information on the subject from any other source.


Servitor
Niccolo Machiavelli.
Sienna,
23 July, 1505.

Your Lordships will please have Francesco del Nero reimbursed fifteen carlini for despatching this letter at the seventeenth hour.