Gianpaolo Baglioni warned those attending the conference that they all risked being ‘devoured one by one by the dragon’ if they did not act against Cesare. Yet so long as not only France but also Florence and Venice declined to help them, the majority of the members of the conference were reluctant to face up to the danger that confronted them. On October 7, however, there was an uprising against the Borgias in the fortress of San Leo in Urbino; and, with this encouragement, agreement was reached; it was settled that Cesare was to be attacked simultaneously by Giovanni Bentivoglio in the Romagna and by the members of the Orsini family, who were to encourage the revolt in Urbino.
When he heard of this threat, which seemed for a time to weaken his hold on his state, Cesare withdrew his forces to Imola and the security of the Romagna. When Machiavelli joined him there, to offer the support of Florence, he found the duke to be quite unperturbed, even indifferent. He accepted the loss of Urbino with apparent nonchalance and prepared for war with evident confidence in victory, raising troops and money, and appointing new condottieri captains, many of whom were Spanish, to replace the conspirators. He also spent such large sums on his intelligence services that Machiavelli thought that he ‘laid out as much on couriers and special messengers in two weeks as anyone else would have spent in two years.’
At first the military operations did not go well for Cesare; and toward the end of October, the duchy of Urbino fell to the conspirators, who, according to Burchard, after having assembled some five hundred cavalry and two thousand troops, restored the city of Urbino and all its territory to the illustrious Guidobaldo da Montefeltro, rightful Duke of Urbino.
But as more money came in and more troops were enlisted, the tide, as Machiavelli said, began to turn. His enemies were ‘tardy in pressing him’; they had failed to seize the moment, as he himself undoubtedly would have done, and, as they began to lose heart in opposing him, were eventually persuaded to come to terms with him.
As Machiavelli was later to write in The Prince, Cesare ‘overcame the revolt of Urbino, the uprisings in the Romagna, and the countless threats with the help of the French’ to which he added his own not inconsiderable political skills:
His former standing in Italy was restored, but he no longer trusted the French or the forces of others, and in order to avoid the risk of doing so, he resorted to stratagems. His powers of dissimulation were so impressive that even the Orsini, through Lord Paolo [of Palombara] reconciled themselves with him. The Duke used every device of diplomacy to reassure Paolo Orsini, giving him gifts of money, clothes and horses.
The general desire now to regain the good opinion of Cesare was, so Machiavelli said, reflected in the submissive letter addressed to him by Vitellozzo Vitelli, who excused himself for having joined the alliance against the duke and saying that if he ever had the opportunity to speak to him personally, he had no doubt he would be able to justify himself completely.
Receiving no reply to his letter, and denied a personal interview with Cesare, Vitelli could but guess what Cesare intended to do next. Machiavelli was also kept in the dark. ‘I have not tried to speak to the Duke, having nothing new to tell him,’ he reported to Florence, ‘and the same things would bore him; you must realise that he talks to nobody other than three or four of his ministers and various foreigners who are obliged to deal with him about important matters and he does not come out of his study until late at night; and so there is no opportunity to speak to him except when an audience has been appointed.
‘Besides,’ continued Machiavelli, ‘he is very secretive. I do not believe that what he is going to do is known to anyone other than himself. His secretaries have told me often that he does not reveal his plans until they are ready to be carried out. So I beg your Lordships will excuse me and not put it down to my negligence if I do not satisfy your Lordships with information, because most of the time I do not even satisfy myself.’
So Machiavelli could not by any means discover what Cesare intended to do next. Then, just before Christmas, there was news; Cesare had summoned all the French officers in his army to come to see him and had told them that he no longer needed them; their upkeep in idleness was an expense that he no longer wished to afford. On the day of their departure, a ball was held in Cesare’s honour at Cesena. The pretty wife of one of these officers attracted his attention, and he danced with her several times, closely watched by her husband.
While he was apparently enjoying this ball, the military governor of the Romagna, the fierce, aggressive Ramiro de Lorqua, was immediately arrested on his return from Pesaro and cast into prison. At dawn three days later, he was beheaded in the piazza at Cesena. His decapitated body was left on the block, his head displayed on a lance.
No explanation was given for this sudden execution other than that Ramiro had been guilty of corruption in the exercise of his office; but this solution to the mystery was not generally accepted. There was a rumour that Ramiro had been in correspondence with the conspirators, notably in some kind of plot with Giovanni Bentivoglio, Vitelli, and members of the Orsini family. ‘The reason for his death is not known,’ Machiavelli commented, ‘but perhaps it pleased the Prince who likes to show that he knows how to make and unmake men at his will.’
Certainly Cesare’s occupying troops had been ill-disciplined at first, while the Spanish officers, like the unpopular and corrupt Ramiro de Lorqua, who were installed as administrators, had dealt most harshly with recalcitrant people. But, in time, Italians replaced Spaniards; and, to the general satisfaction, a peripatetic court of appeal was established under the direction of a lawyer of good reputation, Antonio del Monte.
What at least seemed certain after Ramiro’s execution was that Cesare was preparing some kind of move against the condottieri captains who had been plotting his own murder. In the meantime they agreed to take in Cesare’s name the small town of Senigallia on the Adriatic coast south of Fano. Senigallia had been the fief of Giovanni della Rovere, brother of Cardinal Giuliano, but he had died in November 1501, leaving his wife, Giovanna, sister of Guidobaldo da Montefeltro, acting as regent for his young son. Cardinal Giuliano della Rovere, mindful of the fate of Astorre Manfredi, had arranged for his twelve-year-old nephew, Francesco Maria, to be smuggled out of the area to the safety of his own palace in Savona. And, knowing Cesare’s reputation for cruelty, the cardinal had warned Giovanna not to offer any resistance.
The town fell without a struggle, but its military commander refused to surrender the citadel to anyone other than Cesare Borgia himself. Wearing full armour, Cesare rode toward Senigallia on December 31, 1502, at the head of his army, the condottieri captains coming out to meet him and following him back into the town, the gates of which were closed behind them.
Cesare now called upon his captains to attend a conference in the house he chose to occupy as his headquarters. Responding to his invitation to join him at table, they entered the courtyard of this house as Cesare, according to one account, was mounting a staircase in order, so he said, to ‘answer a call of nature.’ When he was halfway up the stairs, he turned to nod to Miguel de Corella. And in obedience to this signal, the condottieri were suddenly surrounded by armed soldiers; only Vitelli had time to draw his sword and wound several of the soldiers, before they were all arrested and disarmed.