The second embassy, Baldelli tells us, was to Francesco degli Ordelaffi, in October, 1350, "after the sale of Bologna on the 14th of that month." This again is pure conjecture, the only document which supports it being that quoted above, discovered by Mehus. We have, however, reason to suppose that Baldelli may be right here,[399] and may possibly have been in possession of a document or documents since lost to us, which unfortunately he has not quoted or even named. We know at least that Boccaccio was ambassador in Romagna before November 11, 1350. Now until late in 1349 we have seen him in Naples, and in January and February, 1350, in Florence. In October, 1350, we know him to have been in Florence again, for he there entertained Petrarch, as he did in December. What was he doing between February and October in that year? Well, in September he was in Romagna, in Ravenna fulfilling his mission from the Or San Michele to the daughter of Dante. It seems likely, therefore, that it was at this time he was acting as Florentine ambassador at the court of the Ordelaffi of Forlì.
As to the third embassy of which Baldelli speaks, that to Bernardino da Polenta "a few months after" the second, we know nothing of it, and it remains absolutely in the air--a mere conjecture.[400]
Putting aside Baldelli's assertion, we may take it on the evidence as most probable that Boccaccio was the ambassador of Florence in Romagna at some time between March and October, 1350. If we are right in thinking so, his mission was of very great importance. What Florence feared, as we have seen, was the growing power of Milan, and, after the sale of Bologna, the loss of her trade routes north, and finally perhaps even her liberty. Already, in the latter part of 1349,[401] she had offered again and again to mediate between the Pope and Bologna and Romagna, fearing that in their distraction Milan would be tempted to interfere for her own ends. In the first months of 1350 she had written to the Pope, to Perugia, Siena, and to the Senate of Rome, that they should send ambassadors to the congress at Arezzo to form a confederation for their common protection.[402] In September she wrote the Pope more than once explaining affairs to him; but he had touched Visconti gold, and far away in Avignon cared nothing and paid but little heed. The sale of Bologna, however, brought things to a crisis so far as the policy of Florence was concerned, and having secured Prato, Pistoia, and the passes, her ambassadors in Romagna had apparently induced the Pepoli to replace Bologna under the protection of the communes of Florence, Siena, and Perugia, till the Papal army was ready to act. But the Papal army was not likely to be ready so long as Visconti was willing to pay,[403] and we find the Pope, while he thanks Florence effusively, refusing to acknowledge the claim of the League to protect Bologna. The sale of Bologna to Milan, its seizure by the Visconti, brought all the diplomacy of Florence to naught for the moment, and in another letter, written on November 9, 1350,[404] she returns once more to plead with the Pope and to point out to him the danger of the invasions of the Visconti in Lombardy and in Bologna, which placed in peril not only the Parte Guelfa, but the territories of the Church and the Florentine _contado_. By the time that letter was written Boccaccio was back in Florence, and it must have been evident to the Florentines that the Pope had no intention of giving them any assistance and that they must look elsewhere for an ally.