December 10th Valentino departed for Forli and from there he went to Cesena, where he made preparations to go to Rome by way of Ancona.
It had been decided to make war on Sinigaglia, Cardinal Giuliano della Rovere having failed to convince the Pope and the King that he had not aided Guidobaldo di Montefeltre in the last rebellion. The Cardinal exerted himself to save his nephew’s estates but failed.
The day before Caesar left Cesena for Pesaro a terrible sight met the eyes of the peasants as they entered the town in the early morning bringing supplies. Thrown in the public square was a bleeding and headless corpse clothed in a rich costume; near by, impaled on a pike, was the head, which the inhabitants of the capital of Romagna immediately recognised as that of their Governor, Don Remiro de Lorca. One of Caesar’s political maxims was: leniency for small offenders, severity for great ones. Numerous charges of malfeasance in office—among others that of having sold for his own profit grain which Valentino had imported—had been made against the Governor and he had been tried “to satisfy justice and our honour, and that of those he had injured—and as a salutary example for all public officials present and to come,” condemned, and executed.
Machiavelli, who saw the body exposed in the public square, observes: “It is not clearly known what was the cause of his death—unless it was simply the pleasure of the prince, who shows that he knows how to make and unmake men according to their deserts.” There were rumours, however, that Don Remiro had been plotting with Caesar’s enemies.
The 29th of the month, while in Fano, which had remained faithful to him, Valentino received a delegation from the citizens of Ancona, who had come to assure him of their loyalty. With them was a messenger from Vitelli, bringing news of the capture of Sinigaglia, after a feeble resistance, about the end of December, 1502.
Caesar’s commanders, to prove their good faith, had not only offered their services for his movement against Sinigaglia but several of them had gone there in person. Paolo Orsini and his son Fabio, Francesco Orsini, Duke of Gravina, and Oliverotto da Fermo were there, and Vitellozzo Vitelli and one of his nephews appeared on the 30th. The only ones absent were Giampaoli Baglioni, who, distrustful of Caesar, had sent him word from Perugia that he was ill; and Giulio Orsini, who was in Rome under the protection of the all-powerful head of the house, Cardinal Orsini.
How astute men, living in an age of unparalleled duplicity, when every man’s hand was against his neighbour, when treachery and assassination were regarded as fine arts, and poison and poignard perfectly proper tools in political machinations, could have rushed into such a trap is difficult to understand. Caesar’s character was known to all of them; he was more than a match for any one of them in cunning, intellect, astuteness, determination, and what is of still more importance, he had even less moral sense; he had frequently shown that mercy, compassion, pity, were no part of his nature, and these men, having betrayed him, conspired to destroy him, ruin him, rob him of the estates he regarded as his own, deliberately placed themselves in his power! It would not have been surprising if one or two had been deceived, but there were seven or eight; in fact, there was only one, Baglioni, who had not fallen into the trap.
The only explanation is that the conspirators were utterly panic-stricken; they found their coalition was gradually being weakened by Valentino—in fact, that he was “eating the artichoke leaf by leaf” as he said—and that they were doomed; they perhaps thought that by surrendering and again entering his employ there would be at least a chance of being forgiven; with many men this would have been the case, but they had failed to grasp what was perhaps Caesar’s chief characteristic, his utter implacability, which, in conjunction with his extraordinary powers of dissimulation, made him the most dangerous of the Italian despots. All the members of his own family, not excepting his father, the Pope, feared him. He possessed all the characteristics of all the other Italian condottieri but in a more highly developed form. Caesar immediately saw that the hour for vengeance had arrived—all the rebels were together.
The conspirators informed the Duke that the territory had surrendered to them, but that the stronghold still held out because, as the warder said, he would relinquish it only to the Duke in person.
The 30th of December Caesar sent them word from Fano that he would be in Sinigaglia the next day with the artillery to reduce the castle in case it still refused to yield.