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Updated: May 31, 2025
The tale of that happening is graphically told by the pen of the admiring Macchiavelli, who names the affair "Il Bellissimo Inganno." That he so named it should suffice us and restrain us from criticisms of our own, accepting that criticism of his. To us, judged from our modern standpoint, the affair of Sinigaglia is the last word in treachery and iscariotism.
"Who were they?" "Among others, Amparito's father and Don Calixto Garcia Guerrero." "If they wish to give security, tell our broker, and I will sell them anything they want to buy." "Really?" "Really. I have my reasons for doing it." "This time we are all going to make, except you." "Dear Ignacio, I am at Sinigaglia." "What does that mean?"
Here, then, is Macchiavelli's story of the event: On the morning of December 31 Cesare's army, composed of 10,000 foot and 3,000 horse, was drawn up on the banks of the River Metauro some five miles from Sinigaglia in accordance with his orders, awaiting his arrival.
The duke, leaving instructions with Michelotto, set off for Sinigaglia as soon as the first execution was over, assuring Macchiavelli that he had never had any other thought than that of giving tranquillity to the Romagna and to Tuscany, and also that he thought he had succeeded by taking and putting to death the men who had been the cause of all the trouble; also that any other revolt that might take place in the future would be nothing but sparks that a drop of water could extinguish.
What were the final aims of the latter? Even in the last months of his tyranny, when he had murdered the Condottieri at Sinigaglia, and was to all intents and purposes master of the ecclesiastical State , those who stood near him gave the modest reply that the Duke merely wished to put down the factions and the despots, and all for the good of the Church only; that for himself he desired nothing more than the lordship of the Romagna, and that he had earned the gratitude of all the following Popes by ridding them of the Orsini and Colonna.
"I intend to leave very early to-morrow morning," he said, "for Sinigaglia, with the Abbe Vilmarcati, but I expect to return for supper the day after to-morrow." I wished him a happy journey, saying that we would most 'likely meet on the road, as I should probably leave Ancona myself on the same day, after paying a visit to my banker.
It was not till the seventh century of the city that the coast-district from Sinigaglia to Rimini, and not till the eighth that the basin of the Po, became incorporated with Italy. The ancient boundary of Italy on the north was not the Alps but the Apennines.
Many chroniclers set forth how the Lord Vitellozzo Vitelli and his associates were barbarously strangled by Cesare's orders at Sinigaglia, and wilfully for I cannot believe that it results from ignorance are they silent touching the reason, leaving you to imagine that it was done in obedience to a ruthlessness of character beyond parallel, so that you may come to consider Cesare Borgia as black as they were paid to paint him.
Then he fell upon the Pentapolis, seized Sinigaglia, Jesi, Urbino, Gubbio, S. Leo, and other "Roman" cities, and indeed possessed himself of everything save only Ravenna and Rimini, and proceeded upon a raid into the duchy of Rome. The answer of the pope was mild but firm: mild, for the hour was not yet come; firm, for it would strike ere long.
It was at this juncture that Alexander VI received his answer from Bajazet II: the reason of so long a delay was that the pope's envoy and the Neapolitan ambassador had been stopped by Gian della Rovere, the Cardinal Giuliano's brother, just as they were disembarking at Sinigaglia.
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