Well might it have pleased Cesare to oblige the Orsini to the letter, and to give a lesson in straight dealing to these shuffling Florentine pedlars who sent a nimble witted Secretary of State to hold him in play with sweet words of barren meaning. But there was France and her wishes to be considered, and he could not commit himself. So his answer was peremptory and condescending. He told them that, if they desired to show themselves his friends, they could set about reconquering and holding Urbino for him.
It looked as if the condottieri agreed to this, for on October II Vitelli seized Castel Durante, and on the next day Baglioni was in possession of Cagli.
In view of this, Cesare bade the troops which he had withdrawn to advance again upon the city of Urbino and take possession of it. But suddenly, on the 12th, a messenger from Guidobaldo rode into Urbino to announce their duke's return within a few days to defend the subjects who had shown themselves so loyal to him. This, the shifty confederates accounted, must be done with the support of Venice, whence they concluded that Venice must have declared against Valentinois, and again they treacherously changed sides.
The Orsini proceeded to prompt action. Assured of their return to himself, and counting upon their support in Urbino, Cesare had contented himself with sending thither a small force of 100 lances and 200 light horse. Upon these fell the Orsini, and put them to utter rout at Calmazzo, near Fossombrone, capturing Ugo di Moncada, who commanded one of the companies, but missing Michele da Corella, who contrived to escape to Fossombrone.
The conquerors entered Urbino that evening, and, as if to put it on record that they burnt their boats with Valentinois, Paolo Orsini wrote that same night to the Venetian Senate advices of the victory won. There days later on October 18 Guidobaldo, accompanied by his nephews Ottaviano Fregioso and Gianmaria Varano, re entered his capital amid the cheers and enthusiasm of his loyal and loving people.
Vitelli made haste to place his artillery at Guidobaldo's disposal for the reduction of Cagli, Pergola, and Fossombrone, which were still held for Valentinois, whilst Oliverotto da Fermo went with Gianmaria Varano to attempt the reconquest of Camerino, and Gianpaolo Baglioni to Fano, which, however, he did not attempt to enter as an enemy an idle course, seeing how loyally the town held for Cesare but as a ducal condottiero.
Fired by Orsini's example, Bentivogli also took the offensive, and began by ordering the canonists of Bologna University to go to the churches and encourage the people to disregard the excommunications launched against the city. He wrote to the King of France to complain that Cesare had broken the Treaty of Villafontana by which he had undertaken never again to molest Bologna naively ignoring the circumstance that he himself had been the first to violate the terms of that same treaty, and that it was precisely upon such grounds that Cesare was threatening him.
Thus matters stood, the confederates turning anxious eyes towards Venice, and, haply, beginning to wonder whether the Republic was indeed going to move to their support as they had so confidently expected, and realizing perhaps by now their rashness, and the ruin that awaited them should Venice fail them. And fail them Venice did. The Venetians had received a reply from Louis XII to that letter in which they had heaped odium upon the Borgia and shown the king what dishonour to himself dwelt in his alliance with Valentinois. Their criticisms and accusations were ignored in that reply, which resolved itself into nothing more than a threat that " if they opposed themselves to the enterprise of the Church they would be treated by him as enemies," and of this letter he sent Cesare a copy, as Cesare himself told Macchiavelli.
So, whilst Valentinois in Imola was able to breathe more freely, the condottieri in Urbino may well have been overcome with horror at their position and at having been thus left in the lurch by Venice. None was better aware than Pandolfo Petrucci of the folly of their action and of the danger that now impended, and he sent his secretary to Valentinois to say that if the duke would but reassure them on the score of his intentions they would return to him and aid him in recovering what had been lost.
Following upon this message came Paolo Orsini himself to Imola on the 25th, disguised as a courier, and having first taken the precaution of obtaining a safe conduct. He left again on the 29th, bearing with him a treaty the terms of which had been agreed between himself and Cesare during that visit. These were that Cesare should engage to protect the States of all his allied condottieri, and they to serve him and the Church in return. A special convention was to follow, to decide the matter of the Bentivogli, which should be resolved by Cesare, Cardinal Orsini, and Pandolfo Petrucci in consultation, their judgment to be binding upon all.
Cesare's contempt for the Orsini and the rest of the shifty men who formed that confederacy that " diet of bankrupts," as he had termed it was expressed plainly enough to Macchiavelli.
" To day," said he, " Messer Paolo is to visit me, and to morrow there will be the cardinal; and thus they think to befool me, at their pleasure. But I, on my side, am only dallying with them. I listen to all they have to say and bide my own time."
Later, Macchiavelli was to remember those words, which meanwhile afforded him matter for reflection.
As Paolo Orsini rode away from Imola, the duke's secretary, Gherardi, followed and overtook him to say that Cesare desired to add to the treaty another clause one relating to the King of France. To this Paolo Orsini refused to consent, but, upon being pressed in the matter by Gherardi, went so far as to promise to submit the clause to the others.
On October 30 Cesare published a notice in the Romagna, intimating the return to obedience on the part of his captains.
Macchiavelli was mystified by this, and apprehensive as men will be of the things they cannot fathom of what might be reserved in it for Florence. It was Gherardi who reassured him, laughing in the face of the crafty Florentine, as he informed him that even children should come to smile at such a treaty as this. He added that he had gone after Paolo Orsini to beg the addition of another clause, intentionally omitted by the duke.
" If they accept that clause," concluded Messer Agabito, " it will open a window; if they refuse it, a door, by which the duke can issue from the treaty."
Macchiavelli's wonder increased. But the subject of it now was that the condottieri should be hoodwinked by a document in such terms, and well may he have bethought him then of those words which Cesare had used to him a few days earlier.