Caesar learned the existence of this league by its first effects: the Duke of Urbino, who was adored by his subjects, had come with a handful of soldiers to the fortress of San Leone, and it had yielded at once. In less than a week towns and fortresses followed this example, and all the duchy was once more in the hands of the Duke of Urbino.
At the same time, each member of the confederacy openly proclaimed his revolt against the common enemy, and took up a hostile attitude.
Caesar was at Imola, awaiting the French troops, but with scarcely any men; so that Bentivoglio, who held part of the country, and the Duke of Urbino, who had just reconquered the rest of it, could probably have either taken him or forced him to fly and quit the Romagna, had they marched against him; all the more since the two men on whom he counted, viz., Don Ugo di Cardona, who had entered his service after Capua was taken, and Michelotto had mistaken his intention, and were all at once separated from him. He had really ordered them to fall back upon Rimini, and bring 200 light horse and 500 infantry of which they had the command; but, unaware of the urgency of his situation, at the very moment when they were attempting to surprise La Pergola and Fossombrone, they were surrounded by Orsino of Gravina and Vitellozzo. Ugo di Cardona and Michelotto defended themselves like lions; but in spite of their utmost efforts their little band was cut to pieces, and Ugo di Cardona taken prisoner, while Michelotto only escaped the same fate by lying down among the dead; when night came on, he escaped to Fano.
But even alone as he was, almost without troops at Imola, the confederates dared attempt nothing against Caesar, whether because of the personal fear he inspired, or because in him they respected the ally of the King of France; they contented themselves with taking the towns and fortresses in the neighbourhood. Vitellozzo had retaken the fortresses of Fossombrone, Urbino, Cagli, and Aggobbio; Orsino of Gravina had reconquered Fano and the whole province; while Gian Maria de Varano, the same who by his absence had escaped being massacred with the rest of his family, had re-entered Camerino, borne in triumph by his people. Not even all this could destroy Caesar's confidence in his own good fortune, and while he was on the one hand urging on the arrival of the French troops and calling into his pay all those gentlemen known as "broken lances," because they went about the country in parties of five or six only, and attached themselves to anyone who wanted them, he had opened up negotiations with his enemies, certain that from that very day when he should persuade them to a conference they were undone. Indeed, Caesar had the power of persuasion as a gift from heaven; and though they perfectly well knew his duplicity, they had no power of resisting, not so much his actual eloquence as that air of frank good-nature which Macchiavelli so greatly admired, and which indeed more than once deceived even him, wily politician as he was. In order to get Paolo Orsino to treat with him at Imola, Caesar sent Cardinal Borgia to the confederates as a hostage; and on this Paolo Orsino hesitated no longer, and on the 25th of October, 1502, arrived at Imola.