Valentinois listened to the specious compliments, and replied by similar protestations and by reminding Florence how he had curbed the hand of those very condottieri who had now rebelled against him as a consequence. He showed himself calm and tranquil at the loss of Urbino, telling Macchiavelli that he “had not forgotten the way to reconquer it,” when it should suit him. Of the revolted condottieri he contemptuously said that he accounted them fools for not having known how to choose a more favourable moment in which to harm him, and that they would presently find such a fire burning under their feet as would call for more water to quench it than such men as these disposed of.
Meanwhile, the success of those rustics of Urbino who had risen, and the ease of their victories, had fired others of the territory to follow their example. Fossombrone and Pergola were the next to rebel and to put the Borgia garrisons to the sword; but, in their reckless audacity, they chose their moment ill, for Michele da Corella was at hand with his lances, and, although his orders had been to repair straight to Pesaro, he ventured to depart from them to the extent of turning aside to punish the insurgence of those towns by launching his men-at-arms upon them and subjecting them to an appalling and pitiless sack.
When Cesare heard the news of it and the details of the horrors that had been perpetrated, he turned, smiling cruelly, to Macchiavelli, who was with him, and, “The constellations this year seem unfavourable to rebels,” he observed.
A battle of wits was toward between the Florentines’ Secretary of State and the Duke of Valentinois, each mistrustful of the other. In the end Cesare, a little out of patience at so much inconclusiveness, though outwardly preserving his immutable serenity, sought to come to grips by demanding that Florence should declare whether he was to account her his friend or not. But this was precisely what Macchiavelli’s instructions forbade him from declaring. He answered that he must first write to the Signory, and begged the duke to tell him what terms he proposed should form the treaty. But there it was the duke’s turn to fence and to avoid a direct answer, desiring that Florence should open the negotiations and that from her should come the first proposal.
He reminded Macchiavelli that Florence would do well to come to a decision before the Orsini sought to patch up a peace with him, since, once that was done, there would be fresh difficulties, owing, of course, to Orsini’s enmity to the existing Florentine Government. And of such a peace there was now every indication, Paolo Orsini having at last sent Cesare proposals for rejoining him, subject to his abandoning the Bologna enterprise (in which, the Orsini argued, they could not bear a hand without breaking faith with Bentivogli) and turning against Florence. Vitelli, at the same time, announced himself ready to return to Cesare’s service, but first he required some “honest security.”
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 11 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. Three 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.