Inter alia, it was agreed between them that Bologna should supply Cesare with 100 lances and 200 light horse for one or two enterprises within the year, and that the condotta of 100 lances which Cesare held from Bologna by the last treaty should be renewed. The terms of the treaty were to be kept utterly secret for the next three months, so that the affairs of Urbino and Camerino should not be prejudiced by their publication.

The result was instantaneous. On November 27 Paolo Orsini was back at Imola with the other treaty, which bore now the signatures of all the confederates. Vitelli, finding himself isolated, had swallowed his chagrin in the matter of Florence, and his scruples in the matter of Urbino, abandoning the unfortunate Guidobaldo to his fate. This came swiftly. From Imola, Paolo Orsini rode to Fano on the 29th, and ordered his men to advance upon Urbino and seize the city in the Duke of Valentinois’s name, proclaiming a pardon for all rebels who would be submissive.

Guidobaldo and the ill-starred Lord of Faenza were the two exceptions in Romagna—the only two who had known how to win the affections of their subjects. For Guidobaldo there was nothing that the men of Urbino would not have done. They rallied to him now, and the women of Valbone—like the ladies of England to save Coeur-de-Lion—came with their jewels and trinkets, offering them that he might have the means to levy troops and resist. But this gentle, kindly Guidobaldo could not subject his country to further ravages of war; and so he determined, in his subjects’ interests as much as in his own, to depart for the second time.

Early in December the Orsini troops are in his territory, and Paolo, halting them a few miles out of Urbino, sends to beg Guidobaldo’s attendance in his camp. Guidobaldo, crippled by gout and unable at the time to walk a step, sends Paolo his excuses and begs that he will come to Urbino, where he awaits him. There Guidobaldo makes formal surrender to him, takes leave of his faithful friends, enjoins fidelity to Valentinois and trust in God, and so on December 19 he departs into exile, the one pathetic noble figure amid so many ignoble ones. Paolo, taking possession of the duchy, assumes the title of governor.

The Florentines had had their chance of an alliance with Cesare, and had deliberately neglected it. Early in November they had received letters from the King of France urging them to come to an accord with Cesare, and they had made known to the duke that they desired to reoccupy Pisa and to assure themselves of Vitelli; but, when he pressed that Florence should give him a condotta, Macchiavelli—following his instructions not to commit the Republic in any way—had answered “that his Excellency must not be considered as other lords, but as a new potentate in Italy, with whom it is more seemly to make an alliance or a friendship than to grant him a condotta; and, as alliances are maintained by arms, and that is the only power to compel their observance, the Signory could not perceive what security they would have when three-quarters or three-fifths of their arms would be in the duke’s hands.” Macchiavelli added diplomatically that “he did not say this to impugn the duke’s good faith, but to show him that princes should be circumspect and never enter into anything that leaves a possibility of their being put at a disadvantage.”(1)

1 See the twenty-first letter from Macchiavelli on this legation.

Cesare answered him calmly (“senza segno d’alterazione alcuna”) that without a condotta, he didn’t know what to make of a private friendship whose first principles were denied him. And there the matter hung, for Macchiavelli’s legation had for only aim to ensure the immunity of Tuscany and to safeguard Florentine interests without conceding any advantages to Cesare—as the latter had perceived from the first.

On December 10 Cesare moved from Imola with his entire army, intent now upon the conquest of Sinigaglia, which State Giuliano della Rovere had been unable to save for his nephew, as king and Pope had alike turned a deaf ear upon the excuses he had sought to make for the Prefetessa, Giovanna da Montefeltre—the mother of the young prefect—who had aided her brother Guidobaldo in the late war in Urbino.

On the morrow Valentinois arrived in Cesena and encamped his army there for Christmas, as in the previous year. The country was beginning to feel the effects of this prolonged vast military occupation, and although the duke, with intent to relieve the people, had done all that was possible to provision the troops, and had purchased from Venice 30,000 bushels of wheat for the purpose, yet all had been consumed. “The very stones have been eaten,” says Macchiavelli.

To account for this state of things—and possibly for certain other matters—Messer Ramiro de Lorqua, the Governor-General, was summoned from Pesaro; whilst to avert the threatened famine Cesare ordered that the cereals in the private granaries of Cesena should be sold at reduced prices, and he further proceeded, at heavy expense, to procure grain from without. Another, less far-seeing than Valentinois, might have made capital out of Urbino’s late rebellion, and pillaged the country to provide for pressing needs. But that would have been opposed to Cesare’s policy, of fostering the goodwill of the people he subjected.