Front Page Titles (by Subject) LETTER VIII. - The Historical, Political, and Diplomatic Writings, vol. 4 (Diplomatic Missions 1506-1527)
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LETTER VIII. - Niccolo Machiavelli, The Historical, Political, and Diplomatic Writings, vol. 4 (Diplomatic Missions 1506-1527) 
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. 4.
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Magnificent Signori, etc.: —
If your Lordships had not been kept daily informed of every occurrence here by the Lord Lieutenant in his letters to the most reverend Legate, you might wonder at not having had letters from me for several days, and might reasonably accuse me of neglect. But I deemed it superfluous to tell you the same things that the Lord Lieutenant has written and told you. Nor have I returned yet, although the enemy has moved forward, because the Lieutenant thought that before I left he would wish to see for certain what the enemy really intended doing. And truly, before they started, and even afterwards, we were not without considerable apprehensions that they would move upon Tuscany; for we had understood that they had been so urged by the Duke of Ferrara, and that in fact it had been their own plan, as they believed that country to be more easily pillaged than any other, its inhabitants being unaccustomed to the sight of an enemy’s face. This opinion prevailed until yesterday, although it was supposed that, if they wished to enter Tuscany, they ought to have taken either the road by way of Pontremoli or by way of Garfagnana, as both these routes lead to the Lucchese territory, where they might have hoped to find provisions for some days; or they might either have had them brought here from a country that was devoted to them, or they might have been supplied from Ferrara; and once past, they might have made the attempt upon Tuscany, and if successful they could have followed up their victory, and failing they might have passed on to the Siennese territory.
But since they have gone from Modena towards Bologna, no reasonable man can suppose that they will come to Tuscany, because there are but four roads leading to it, namely, the Sasso, the Diritti, the Val di Lamona, and to pass the Alps of Crespino, or by Val di Montone, in which case they would have to pass the Alps of San Benedetto. Neither one of these roads is secure, for besides the ordinary difficulties of passing the mountains, all these passes lead into the Mugello, where they would die of hunger in two days, unless they should take either Pistoja or Prato; and as they cannot hope to do that, they cannot attempt to come by these passes. There remains one other route by which they could penetrate into Tuscany, and that is to enter into the Marecchia above Cesena, and come to the Borgo San Sepolcro. This road is easy, but it would be difficult for these troops to get to Cesena, as all the places in Romagna are fortified, and the country bare of provisions. Nevertheless, if the enemy take either of these routes, all measures are taken for our troops to arrive in Tuscany before them, in accordance with the plans which the Lord Lieutenant has communicated to the most reverend Legate; and they will, moreover, have the Duke of Urbino at their heels. We have news to-day that he is entirely well again, and that he has passed the Po with all the Venetian troops. If then it be true that the enemy has to encounter such difficulties in advancing, it follows that necessity will oblige them to attempt some enterprise nearer at hand, and which they could carry out at their ease, and which, if successful, would open the way for them to succeed in all the others.
Yesterday the impression prevailed that they would make an attempt upon Ravenna, and therefore we sent a detachment of six hundred troops there this morning. To-day it is feared their attack will be upon Bologna; the fact that the fortifications of Ravenna are in a bad state of repairs is calculated to decide them in favor of that place; whilst the reason for attempting Bologna would be its population, which is believed not to be all agreed to sustain a siege. We shall soon see which of the two it will be; and if the enemy comes here, the most important place for this game will be around the walls of this place. But I believe we may remain here quite safely, for there will be ten thousand troops here, the place is well fortified and supplied with all necessaries, and the inhabitants are united and well disposed to defend themselves.
I recommend myself to your Lordships, quæ bene valeant.
Bologna, 4 March, 1527.
P. S. — I wrote the above to your Lordships yesterday, but the letter was left behind, owing to the carelessness of the person who makes up the packages. The enemy has made no movement to-day, nor have they come to Castel San Giovanni as was expected; nevertheless we are to-day of a somewhat different opinion from yesterday. For if we were yesterday sure that the enemy would not come into Tuscany, but would attack this city, to-day we are quite in doubt, owing to the information we have that after all their real design is to enter Tuscany; and that they feigned first that they were coming here to Bologna, so that, having induced you to send all your forces here, and having thus, as it were, disarmed you, they might arrive before us and crush you at a single blow. The Lord Lieutenant therefore writes you not to send any troops into Romagna, and has ordered that the troops of the Signor Giovanni, if they are in a convenient place, shall come at once in this direction. Or perhaps the Signor Giovanni may go in person to Loglano, accompanied by a strong division of infantry, so that he may be able to return here in case the enemy should attack this city, or be in advance of them if they should attempt to move upon Florence. I said that perhaps this course might be taken, because the reasons which I alleged in my letter of yesterday for not believing that the enemy would not come into Tuscany unless he had first taken Bologna are so powerful in their nature that, notwithstanding the information received since, we remain still of the same opinion. But that which troubles our spirits is that a certain Betto, one of our own people, has related to us that, having been at the enemy’s camp to-day, the Constable de Bourbon had told him to make known to the people of Bologna that, if they would give him free passage and provisions, and become good Imperialists, he would ask nothing else of them, and would treat them as friends; but if they would not do this, they might expect to see the army before their walls. This proposition seems to us most important, for if the enemy really takes such a course, the population of the city being very great, and seeing that they can escape such great dangers on such easy terms, it is to be feared that they would eagerly accept them. It is necessary, therefore to retain a sufficient force here to keep the population firm in their good will towards us, and to be able to show them the deceit which it is intended to practise upon them, and the ease with which they can defend themselves against it.
But to do this, troops must not be sent to Loglano, unless Bologna is first relieved; and thus what might be of advantage to Florence would injure us here, and what would benefit us here might do harm to Florence. Anyhow it is supposed that all can be provided for; because, by not sending your troops into Romagna, you will find yourselves with 5,000 men, besides the 3,000 of the Signor Giovanni, which will be sent to you under any circumstances. And as for the rest of the army, excepting the troops that are with the Duke of Urbino, they will remain here to watch the enemy, who must come either by the Sasso road or by the Diritta. And we shall be prepared to come by whatever road they do not take, and shall anyhow be at Florence before them; for we shall come without artillery, whilst they must bring theirs along with them. These are the plans that have been discussed to-day; they will adopt that which is deemed the best, of which his Lordship the Lieutenant will write most fully and distinctly to the most reverend Legate.
Bologna, 5 March, 1527.