The duke learned the news of this decision, so much desired, when he arrived at Fano on the 20th of December 1502. At once he summoned eight of his most faithful friends, among whom were d'Enna, his nephew, Michelotto, and Ugo di Cardona, and ordered them, as soon as they arrived at Sinigaglia, and had seen Vitellozzo, Gravina, Oliveratta, and Orsino come out to meet them, on a pretext of doing them honour, to place themselves on the right and left hand of the four generals, two beside each, so that at a given signal they might either stab or arrest them; next he assigned to each of them his particular man, bidding them not quit his side until he had reentered Sinigaglia and arrived at the quarters prepared for him; then he sent orders to such of the soldiers as were in cantonments in the neighbourhood to assemble to the number of 8000 on the banks of the Metaurus, a little river of Umbria which runs into the Adriatic and has been made famous by the defeat of Hannibal.
The duke arrived at the rendezvous given to his army on the 31st of December, and instantly sent out in front two hundred horse, and immediately behind them his infantry; following close in the midst of his men-at-arms, following the coast of the Adriatic, with the mountains on his right and the sea on his left, which in part of the way left only space for the army to march ten abreast.
After four hours' march, the duke at a turn of the path perceived Sinigaglia, nearly a mile distant from the sea, and a bowshot from the mountains; between the army and the town ran a little river, whose banks he had to follow for some distance. At last he found a bridge opposite a suburb of the town, and here Caesar ordered his cavalry to stop: it was drawn up in two lines, one between the road and the river, the other on the side of the country, leaving the whole width of the road to the infantry: which latter defiled, crossed the bridge, and entering the town, drew themselves up in battle array in the great square.
On their side, Vitellazzo, Gravina, Orsino, and Oliverotto, to make room for the duke's army, had quartered their soldiers in little towns or villages in the neighbourhood of Sinigaglia; Oliverotto alone had kept nearly 1000 infantry and 150 horse, who were in barracks in the suburb through which the duke entered.
Caesar had made only a few steps towards the town when he perceived Vitellozzo at the gate, with the Duke of Gravina and Orsina, who all came out to meet him; the last two quite gay and confident, but the first so gloomy and dejected that you would have thought he foresaw the fate that was in store for him; and doubtless he had not been without same presentiments; for when he left his army to came to Sinigaglia, he had bidden them farewell as though never to meet again, had commended the care of his family to the captains, and embraced his children with tears—a weakness which appeared strange to all who knew him as a brave condottiere.
The duke marched up to them holding out his hand, as a sign that all was over and forgotten, and did it with an air at once so loyal and so smiling that Gravina and Orsina could no longer doubt the genuine return of his friendship, and it was only Vitellozzo still appeared sad. At the same moment, exactly as they had been commanded, the duke's accomplices took their posts on the right and left of those they were to watch, who were all there except Oliverotto, whom the duke could not see, and began to seek with uneasy looks; but as he crossed the suburb he perceived him exercising his troops on the square. Caesar at once despatched Michelotto and d'Enna, with a message that it was a rash thing to have his troops out, when they might easily start some quarrel with the duke's men and bring about an affray: it would be much better to settle them in barracks and then come to join his companions, who were with Caesar. Oliverotto, drawn by the same fate as his friends, made no objection, ordered his soldiers indoors, and put his horse to the gallop to join the duke, escorted on either side by d'Enna and Michelotto. Caesar, on seeing him, called him, took him by the hand, and continued his march to the palace that had been prepared for him, his four victims following after.
Arrived on the threshold, Caesar dismounted, and signing to the leader of the men-at-arms to await his orders, he went in first, followed by Oliverotto, Gravina, Vitellozzo Vitelli, and Orsino, each accompanied by his two satellites; but scarcely had they gone upstairs and into the first room when the door was shut behind them, and Caesar turned round, saying, "The hour has come!" This was the signal agreed upon. Instantly the former confederates were seized, thrown down, and forced to surrender with a dagger at their throat. Then, while they were being carried to a dungeon, Caesar opened the window, went out on the balcony and cried out to the leader of his men-at-arms, "Go forward!" The man was in the secret, he rushed on with his band towards the barracks where Oliverotto's soldiers had just been consigned, and they, suddenly surprised and off their guard, were at once made prisoners; then the duke's troops began to pillage the town, and he summoned Macchiavelli.
Caesar and the Florentine envoy were nearly two hours shut up together, and since Macchiavelli himself recounts the history of this interview, we will give his own words.
"He summoned me," says the Florentine ambassador, "and in the calmest manner showed me his joy at the success of this enterprise, which he assured me he had spoken of to me the evening before; I remember that he did, but I did not at that time understand what he meant; next he explained, in terms of much feeling and lively affection for our city, the different motives which had made him desire your alliance, a desire to which he hopes you will respond. He ended with charging me to lay three proposals before your lordships: first, that you rejoice with him in the destruction at a single blow of the mortal enemies of the king, himself, and you, and the consequent disappearance of all seeds of trouble and dissension likely to waste Italy: this service of his, together with his refusal to allow the prisoners to march against you, ought, he thinks, to excite your gratitude towards him; secondly, he begs that you will at this juncture give him a striking proof of your friendliness, by urging your cavalry's advance towards Borgo, and there assembling some infantry also, in order that they may march with him, should need arise, on Castello or on Perugia. Lastly, he desires—and this is his third condition—that you arrest the Duke of Urbino, if he should flee from Castello into your territories, when he learns that Vitellozzo is a prisoner.
"When I objected that to give him up would not beseem the dignity of the republic, and that you would never consent, he approved of my words, and said that it would be enough for you to keep the duke, and not give him his liberty without His Excellency's permission. I have promised to give you all this information, to which he awaits your reply."