The “nephew” — that is, son — of Pope Alexander VI, Cesare resigned a cardinalcy in 1498 to follow his true passion, bloodshed, and set up as one of the Italian peninsula’s warring dukes. He had many a martial adventure before getting ambushed by a party of Spanish knights in 1507. Machiavelli considered him an able leader compromised by owing his temporal power to the pope’s territorial allotment. In The Prince, Machiavelli remarks on the lesson of Borgia’s reign, that “he who has not first laid his foundations may be able with great ability to lay them afterwards, but they will be laid with trouble to the architect and danger to the building” — and yet Cesare Borgia’s own fall months after his patron paterfamilias passed “was not his fault, but the extraordinary and extreme malignity of fortune.”
Cesare went from victory to victory in the first years of the sixteenth century, enough so that he threatened to make himself hegemonic in Italy. Several of his own allies, of which our day’s principals Vitellozzo Vitelli (his family ruled Citta di Castello) and Oliverotto da Fermo* (lord of Fermo) were two, began plotting against him and sent out feelers to build an anti-Borgia alliance among small powers who fretted the prospective domination of Cesare. (Though Borgia had them killed on a separate occasion, the others of note for purposes of this post are two members of the powerful Orsini family — Francesco Orsini, known as the Duke di Gravina; and, Cardinal Pagolo.)
As Florence’s own representative to Borgia’s court during the events in question, Machiavelli had a first-person view of events and recorded them in some detail. Taken on the back foot momentarily, Borgia stalled, firmed up his relations with friendly cities like Florence, and beat a momentarily tactical retreat. He came to terms with his friends-cum-rivals, who once more resumed campaigning on Borgia’s side.
Putatively back on the same team, several of the plotters soon found themselves at a stalemate besieging Senigallia, which refused to surrender to any but Borgia himself. They were therefore required to summon the dangerous prince from Lombardy. True to his name, Borgia did not miss the opportunity of an innocent invitation to destroy his foes.
Borgia marched into Seniallia with 10,000 infantrymen and 2,000 cavalry for a friendly little reunion. According to Machiavelli (who in this passage refers to Borgia as Duke Valentino, or simply as “the duke”),
Vitellozzo, Pagolo, and the Duke di Gravina on mules, accompanied by a few horsemen, went towards the duke; Vitellozo, unarmed and wearing a cape lined with green, appeared very dejected, as if conscious of his approaching death — a circumstance which, in view of the ability of the man and his former fortune, caused some amazement. And it is said that when he parted from his men before setting out for Sinigalia to meet the duke he acted as if it were his last parting from them. He recommended his house and its fortunes to his captains, and advised his nephews that it was not the fortune of their house, but the virtues of their fathers that should be kept in mind. These three, therefore, came before the duke and saluted him respectfully, and were received by him with goodwill; they were at once placed between those who were commissioned to look after them.
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. Therefore Don Michele rode off and joined Oliverotto, telling him that it was not right to keep his men out of their quarters, because these might be taken up by the men of the duke; and he advised him to send them at once to their quarters and to come himself to meet the duke. And Oliverotto, having taken this advice, came before the duke, who, when he saw him, called to him; and Oliverotto, having made his obeisance, joined the others.
So the whole party entered Sinigalia, dismounted at the duke’s quarters, and went with him into a secret chamber, where the duke made them prisoners; he then mounted on horseback, and issued orders that the men of Oliverotto and the Orsini should be stripped of their arms. Those of Oliverotto, being at hand, were quickly settled, but those of the Orsini and Vitelli, being at a distance, and having a presentiment of the destruction of their masters, had time to prepare themselves, and bearing in mind the valour and discipline of the Orsinian and Vitellian houses, they stood together against the hostile forces of the country and saved themselves.
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. 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. Pagolo and the Duke di Gravina Orsini were kept alive until the duke heard from Rome that the pope had taken the Cardinal Orsino, the Archbishop of Florence, and Messer Jacopo da Santa Croce. After which news, on 18th January 1502, in the castle of Pieve, they also were strangled in the same way.
* Machiavelli also wrote up Oliverotto in The Prince.