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Updated: July 31, 2024


The protection of France and the lack of decision on the part of his enemies, however, saved the Duke of Romagna from the danger which threatened him. December 31st he relieved himself of the barons by the well-known coup of Sinigaglia. This was his masterstroke.

This union, though a happy one, was never blessed with children; and in the certainty of barrenness, the young Duke thought it prudent to adopt a nephew as heir to his dominions. He had several sisters, one of whom, Giovanna, had been married to a nephew of Sixtus IV., Giovanni della Rovere, Lord of Sinigaglia and Prefect of Rome.

The pope had barely learned that Caesar had his enemies in his power, when, eager to play the same winning game himself, he announced to Cardinal Orsino, though it was then midnight, that his son had taken Sinigaglia, and gave him an invitation to come the next morning and talk over the good news. The cardinal, delighted at this increase of favour, did not miss his appointment.

Caesar's reply was that he did not desire to war upon Tuscany, because the Tuscans were his friends; but that he approved of the lieutenants' plan with regard to Sinigaglia, and therefore was marching towards Fano.

But the daughter of Frederic, the former Duke of Urbino, who held the town of Sinigaglia, and who was called the lady-prefect, because she had married Gian delta Rovere, whom his uncle, Sixtus IV, had made prefect of Rome, judging that it would be impossible to defend herself against the forces the Duke of Valentinais was bringing, left the citadel in the hands of a captain, recommending him to get the best terms he could for the town, and took boat for Venice.

The Sinigaglia trials were followed by similar prosecutions at Ancona, Jesi, Pesaro, and Funa, where unhappy groupes of citizens, indicted for political offences, waited the tender mercies which the "Holy Father" dispenses to his figli by the hands of Swiss and Austrian carabiniers. Let us state the result at Ancona.

Immediately upon the arrest of the condottieri Cesare had issued orders to attack the soldiers of Vitelli and Orsini, and to dislodge them from the castles of the territory where they were quartered, and similarly to dislodge Oliverotto's men and drive them out of Sinigaglia. This had been swiftly accomplished. But the duke's men were not disposed to leave matters at that.

Under pretence of assisting him in the taking of Sinigaglia, whither it was known that he was going, they had assembled there in their full strength, but displaying only one-third of it, and concealing the remainder in the castles of the surrounding country.

Besides, Oliverotto was so simple as to fall at last into the snare of Cesare Borgia at Sinigaglia. Cesare himself supplies Machiavelli with a notable example of the way in which cruelty can be well used. Having found the cities of Romagna in great disorder, Cesare determined to quell them by the ferocity of a terrible governor.

The terrible way in which Ferdinand of Naples handled the conspiracy of the nobles of his kingdom made him, in the eyes of Italy, not horrible but great; and Macchiavelli speaks of the trick with which Cæsar Borgia outwitted his treacherous condottieri at Sinigaglia as a "masterstroke," while the Bishop Paolo Giovio called it "the most beautiful piece of deception."

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