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Updated: May 31, 2025
As for the condottieri, Vitelli and Oliverotto were dealt with that very night. There is a story that Oliverotto, seeing that all was lost, drew a dagger and would have put it through his heart to save himself from dying at the hands of the hangman. If it is true, then that was his last show of spirit.
Andrea Doria did not remain to make formal surrender of the citadel of Sinigaglia to the duke for which purpose, be it borne in mind, had Cesare been invited, indirectly, to come to Sinigaglia. He fled during the night that saw Vitelli and Oliverotto writhing their last in the strangler's hands.
Lastly, Vitelli was bidden to prepare quarters within the new town for the troops that would accompany Cesare. To do this it was necessary to dispose the soldiers of Oliverotto da Fermo in the borgo. These were the only troops with the condottieri in Sinigaglia; the remainder of their forces were quartered in the strongholds of the territory at distances of from five to seven miles of the town.
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.
But the duke's soldiers, not being content with having pillaged the men of Oliverotto, began to sack Sinigalia, and if the duke had not repressed this outrage by killing some of them they would have completely sacked it. Night having come and the tumult being silenced, the duke prepared to kill Vitellozzo and Oliverotto; he led them into a room and caused them to be strangled.
Vitellozza Vitelli in particular, who knew Caesar the best, never ceased to tell the other condottieri that so prompt and easy a peace must needs be the cover to some trap; but since Caesar had meanwhile collected a considerable army at Imala, and the four hundred lances lent him by Louis XII had arrived at last, Vitellozzo and Oliverotto decided to sign the treaty that Orsino brought, and to let the Duke of Urbino and the lord of Camerino know of it; they, seeing plainly that it was henceforth impassible to make a defence unaided, had retired, the one to Citta di Castello and the other into the kingdom of Naples.
In our times, during the rule of Alexander the Sixth, Oliverotto da Fermo, having been left an orphan many years before, was brought up by his maternal uncle, Giovanni Fogliani, and in the early days of his youth sent to fight under Pagolo Vitelli, that, being trained under his discipline, he might attain some high position in the military profession.
To celebrate his home-coming, Oliverotto invited his uncle and the principal citizens of Fermo to a banquet, and at table contrived to turn the conversation upon the Pope and the Duke of Valentinois; whereupon, saying that these were matters to be discussed more in private, he rose from table and begged them to withdraw with him into another room.
But the duke noticing that Oliverotto, who had remained with his band in Sinigalia, was missing for Oliverotto was waiting in the square before his quarters near the river, keeping his men in order and drilling them signalled with his eye to Don Michelle, to whom the care of Oliverotto had been committed, that he should take measures that Oliverotto should not escape.
Neither of them used words in keeping with their past lives: Vitellozzo prayed that he might ask of the pope full pardon for his sins; Oliverotto cringed and laid the blame for all injuries against the duke on Vitellozzo.
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