December 31st the army left Fano with Don Michele and two hundred lances in the van, followed by Caesar with the men-at-arms. When they reached the bridge crossing the Misa just before Sinigaglia, Don Michele halted the light horse to allow the infantry to pass and enter the town.
Oliverotto da Fermo had remained in the city, but Paolo and Francesco Orsini and Vitellozzo Vitelli, who had taken possession of some of the neighbouring castles, came to meet Caesar, who received them graciously, shook hands with them in the “French fashion” and kissed them. According to Machiavelli, seeing that Oliverotto was not with them, Caesar made a sign to Michele to go and find him, which he did and told him to come with him to Caesar.
Valentino entered Sinigaglia on horseback, riding between Vitellozzo Vitelli and Francesco Orsini, and on arriving at the palace the four prepared to take leave of him, but he asked them to go in with him to confer—or perhaps to have luncheon. This they did, but no sooner had they passed the portals than they were seized by Valentino’s guard. The accounts differ in some unimportant details but the above is the generally accepted one.
That evening when Machiavelli reached Sinigaglia he found the streets filled with soldiers and the place in a tumult. As he was about to enter the palace he saw the Duke come forth, armed from head to foot, mounted on his charger. Caesar called the Ambassador to him and told him of the arrest of the Orsini and Vitelli. The Florentine secretary was dazzled by this masterpiece of treachery which he described as il bellissimo inganno—“the most beautiful piece of deception.”
When news of the capture reached the troops of Vitelli and Orsini they at once realised their danger, and rallying about Fabio Orsini and Vitelli’s nephew, withdrew from the town. Encountering no further opposition, Caesar’s men overran the place, robbing, plundering, violating, until he himself issued from the palace with a guard and hanged a number of the rioters in the public square.
Caesar decided to take Orsini to Rome, while Oliverotto and Vitelli were condemned to death after a semblance of a trial, the Duke apparently desiring to give his action an appearance of right. The order was given for them to be executed the same night. It is related that the youthful and proud Oliverotto tried to stab himself to avoid the shame of death at the hands of the executioner. As to Vitelli—“in his last hour he showed himself unworthy of his past life, for he begged to be allowed to plead with the Pope for forgiveness—and Oliverotto turned his back on him.” At the tenth hour of the night they were strangled.
Immediately after the execution Caesar wrote all his friends among the Italian princes telling them what he had done; his officers had conspired to destroy him, and although he had forgiven them they had met at Sinigaglia expressly for the purpose of again entering into a compact to secure his overthrow; having learned of this, he himself had gone to that place with his troops and seized the traitors, who had been duly tried and condemned. The letter to Venice concludes with the remark, “I am certain your Serenità will be pleased.” To the Romagnols he wrote: “All the world ought to be pleased, and especially Italy, seeing that by their death the country is relieved of a dangerous pest,” and he urges them to “thank God for putting an end to the calamities the country suffered owing to these misguided ones,” who, it may be observed, had until recently been among his most capable commanders.
Many of the princes congratulated Caesar, and Isabella d’Este sent him a present of some masks, and in her letter referred to the “favourable progress you are making.”
During the night of January 2, 1503, news was brought the Pope of the capture of Sinigaglia, and the next morning he sent a messenger to Cardinal Orsini to inform him that he desired his presence.
According to the Master of Ceremonies, when the cardinal and his suite reached the apostolic palace their horses and mules were led away to the Pope’s stables, and when Orsini entered the Chamber of the Papagalli he found himself surrounded by armed men and—says Burchard—was frightened.