The Castle of San Leo, the bulwark of Urbino, was seized by a supporter of the Montefeltre early in October, and Caesar had been informed of the fact before Machiavelli reached Imola. Valentino was not disturbed by the news, and the Florentine envoy says that he expressed his pity for those who had chosen such an unfavourable moment to attack him; he made light of the loss of a State he had no intention of retaining; he could recover it any time he saw fit. He even showed Machiavelli copies of the orders he had sent his lieutenants to retire within their lines of defence. These commanders, Ugo Moncada, Michelotto de Corella, Bartolomeo Capranica, and Giovanni de Cordova, retreated, but destroyed the villages that lay in their way, delivering them over to fire and pillage. Pergola and Fossombrone were laid waste and all their inhabitants, men, women, and children, put to the sword. The news of these crimes reached Imola October 12th, and Caesar exultingly exclaimed to Machiavelli, “The stars this year seem to be unfavourable to rebels!” One after another the towns in Urbino revolted, but still the conspirators hesitated. Paolo Orsini announced that he would return to Caesar if he would relinquish his intention of attacking Bologna and direct his energies against Florence; Vitelli, at first the most active of the conspirators, now offered to follow Valentino if he would assure him of his safety. That all Italy was afraid of Caesar and the Pope there is no doubt. The Duke pretended to believe in the sincerity of his captains and received them again into his favour; he even dispatched them to the support of the garrisons in Urbino that were still loyal to him. Vitelli had advanced as far as Castel-Durante, and the Baglioni were at Cagli. The Orsini were in the neighbourhood of the stronghold of San Leo, holding aloof from both Caesar and Montefeltre, who had taken refuge in Venice, where he had recruited a considerable number of troops. October 12th a courier arrived in Urbino with the news that Montefeltre was advancing to the aid of the garrison. This meant that Venice was helping the conspirators, who consequently again took heart and threw off the mask. The 15th the Orsini, who had apparently been willing to return to Caesar, fell upon the troops of Ugo Moncada and made him prisoner. Michelotto was forced to flee to Fossombrone, and a few days later the Duke of Urbino again entered his capital.