Guidobaldo da Montefeltre was a good prince. None in all Italy was more beloved by his people, towards whom he bore himself with a kindly, paternal bonhomie. He was a cultured, scholarly man, a patron of the arts, happiest in the splendid library of the Palace of Urbino. It happened, unfortunately, that he had no heir, which laid his dominions open to the danger of division amongst the neighbouring greedy tyrants after his death. To avoid this he had adopted Francesco Maria della Rovere, hereditary Prefect of Sinigaglia, his sister's chilc and a nephew of Cardinal Giuliano della Rovere's. There was wisdom and foresight in the adoption, considering the favour enjoyed in Rome and in France by the powerful cardinal.
From Nocera Cesare sent Guidobaldo a message calculated to allay whatever uneasiness he may have been feeling, and to throw him completely off his guard. The duke notified him that he was marching upon Camerino which was at once true and untrue and begged Guidobaldo to assist him in this enterprise by sending him provisions to Gubbio, which he should reach on the morrow since he was marching by way of Cagli and Sassoferrato. Further and obviously with intent that the Duke of Urbino should reduce the forces at his disposal he desired Guidobaldo to send Vitelli the support of a thousand men, which the latter had earlier solicited, but which Guidobaldo had refused to supply without orders from the Pope. Cesare concluded his letter with protestations of brotherly love the Judas' kiss which makes him hateful to us in this affair.
It all proved very reassuring to Guidobaldo who set his mind at ease and never bethought him of looking to his defences, when, from Nocera, Cesare made one of those sudden movements, terrible in their swiftness as the spring of a tiger enabling him to drive home his claws where least expected. Leaving all baggage behind him, and with provisions for only three days, he brought his troops by forced marches to Cagli, within the Urbino State, and possessed himself of it almost before the town had come to realize his presence.
Not until the citadel, taken entirely by surprise, was in Cesare's hands did a messenger speed to Guidobaldo with the unwelcome tidings that the Duke of Valentinois was in arms, as an enemy, within the territory. Together with that message came others into the garden of the Zoccolanti monastery that favourite resort of Guidobaldo's where he was indulging his not unusual custom of supping in the cool of that summer evening. They brought him word that, while Valentinois was advancing upon him from the south, a force of 1,000 men were marching upon Urbino from Isola di Fano in the east, and twice that number through the passes of Sant' Angelo and Verucchio in the north all converging upon his capital.
The attack had been shrewdly planned and timed, and if anything can condone the treachery by which Guidobaldo was lulled into his false security, it is the circumstance that this conduct of the matter avoided bloodshed a circumstance not wholly negligible, and one that was ever a part of Cesare Borgia's policy, save where punishment had to be inflicted or reprisals taken.
Guidobaldo, seeing himself thus beset upon all sides at once, and being all unprepared for resistance, perceived that nothing but flight remained him; and that very night he left Urbino hurriedly, taking with him the boy Francesco Maria, and intending at first to seek shelter in his Castle of S. Leo a fortress that was practically impregnable. But already it was too late. The passes leading thither were by now in the hands of the enemy, as Guidobaldo discovered at dawn. Thereupon, changing his plans, he sent the boy and his few attendants to Bagno, and, himself, disguised as a peasant, took to the hills, despite the gout by which he was tormented. Thus he won to Ravenna, which was fast becoming a home for dethroned princes.
Urbino, meanwhile, in no case to resist, sent its castellan to meet Cesare and to make surrender to him whereof Cesare, in the letter already mentioned, gives news to the Pope, excusing himself for having undertaken this thing without the Pope's knowledge, but that " the treachery employed against me by Guidobaldo was so enormous that I could not suffer it."
Within a few hours of poor Guidobaldo's flight Cesare was housed in Urbino's splendid palace, whose stupendous library was the marvel of all scholars of that day. Much of this, together with many of the art treasures collected by the Montefeltri, Cesare began shortly afterwards to transfer to Cesena.
In addition to publishing an edict against pillage and violence in the City of Urbino, Cesare made doubly sure that none should take place by sending his soldiers to encamp at Fermignano, retaining near him in Urbino no more than his gentlemen at arms. The capital being taken, the remainder of the duchy made ready surrender, all the strongholds announcing their submission to Cesare with the exception of that almost inaccessible Castle of S. Leo, which capitulated only after a considerable resistance.
From Urbino Cesare now entered into communication with the Florentines, and asked that a representative should be sent to come to an agreement with him. In response to this request, the Republic sent him Bishop Soderini as her ambassador. The latter arrived in Urbino on June 25 and was immediately and very cordially received by the duke. With him, in the subordinate capacity of secretary, came a lean, small headed, tight lipped man, with wide set, intelligent eyes and prominent cheek bones one Niccolo Macchiavelli, who, in needy circumstances at present, and comparatively obscure, was destined to immortal fame. Thus did Macchiavelli meet Cesare Borgia for the first time, and, for all that we have no records of it, it is not to be doubted that his study of that remarkable man began then in Urbino, to be continued presently, as we shall see, when Macchiavelli returns to him in the quality of an ambassador himself.