Caesar Borgia: A Study of the Renaissance

by John Leslie Garner

Machiavelli explained to Valentino that he had come to assure him of the friendship of the Republic and to inform him that it had refused to join his enemies. Valentino received the envoy cordially, and thanked him for the professions of friendship on the part of his Government. They discussed the political situation at great length, and Caesar appeared very anxious to conclude some sort of an agreement with Florence for their mutual support, but Machiavelli was unable to get any very definite suggestion from the Duke. The Borgia, who was then only twenty-six, showed himself a consummate diplomatist and more than a match for the Florentine secretary.

October 9th Machiavelli had another interview with Caesar, who, to strengthen the demands he had made for an alliance with Florence, produced a letter from the King of France in which aid was promised for the undertaking against Bologna. Valentino seemed much elated. “Now, you see, secretary, this letter is an answer to my request for permission to attack Bologna.”

Machiavelli did not allow himself to be deceived by Caesar’s astuteness and eloquence, but he carefully weighed the causes for the Duke’s confidence in the success of his projects; he estimated his actual military strength and the number of troops he could collect, and he found that Caesar was far from weak, but also that his enemies were much more powerful than he had represented them to be.

The Florentine was greatly impressed by Valentino’s astuteness, but he was, nevertheless, able to discern his real purpose. Caesar had boldly stated that if he effected a reconciliation with the Orsini it would be impossible for him to enter into any treaty of friendship with their enemy Florence, and Machiavelli knew that this was true, consequently he wrote the Signory that it would be well to make some sort of compact with the Duke at once.

Machiavelli’s first impressions of Caesar were vague and uncertain. The Duke was not more perspicacious than the secretary, but he had greater self-control, had a sharper insight into motives, and he possessed powers of dissimulation which Machiavelli entirely lacked. Above all else Caesar was perfect master of himself. He therefore succeeded in hiding much of his real purpose from the secretary.

The Signory of Florence, however, attached the greatest importance to Machiavelli’s report of his interviews with Caesar, and Valori wrote him, October 11th, saying his “relation was clear cut, exact, and sincere—and to be relied upon.”

Among the conspirators it had been decided that Bentivoglio should attack Romagna, while the Orsini and Vitelli should try to take Urbino. Some of the leaders had hesitated and the plan was still in abeyance when an unexpected event gave them new courage.

The Castle of San Leo, the bulwark of Urbino, was seized by a supporter of the Montefeltre early in October, and Caesar had been informed of the fact before Machiavelli reached Imola. Valentino was not disturbed by the news, and the Florentine envoy says that he expressed his pity for those who had chosen such an unfavourable moment to attack him; he made light of the loss of a State he had no intention of retaining; he could recover it any time he saw fit. He even showed Machiavelli copies of the orders he had sent his lieutenants to retire within their lines of defence.

These commanders, Ugo Moncada, Michelotto de Corella, Bartolomeo Capranica, and Giovanni de Cordova, retreated, but destroyed the villages that lay in their way, delivering them over to fire and pillage. Pergola and Fossombrone were laid waste and all their inhabitants, men, women, and children, put to the sword. The news of these crimes reached Imola October 12th, and Caesar exultingly exclaimed to Machiavelli, “The stars this year seem to be unfavourable to rebels!”

One after another the towns in Urbino revolted, but still the conspirators hesitated. Paolo Orsini announced that he would return to Caesar if he would relinquish his intention of attacking Bologna and direct his energies against Florence; Vitelli, at first the most active of the conspirators, now offered to follow Valentino if he would assure him of his safety. That all Italy was afraid of Caesar and the Pope there is no doubt.