Ordelaffi, Manfredi, and Alidosi were legally dependent only on the Popes. But they were just the families who caused perpetual strife. The Malatesta had established themselves in Rimini in the latter part of the thirteenth century, and in the following century enlarged their possessions by talent and skilful use of circumstances, but had again weakened their power by dividing into several lines. The three sons of Galeotto Malatesta, of whom the history of the wars of Visconti and Albornoz has much to relate, formed the lines of Rimini, Cesena, and Fano, the second of which expired in 1465 with Malatesta Novello; while Sigismondo, the legitimised son of the lord of Fano, had after the death without children of his uncle Carlo lord of Rimini, become his successor, and Rimini remained the centre of the dominions of this family. Sigismondo is a prototype of the city tyrants of the fifteenth century—talented, active, enterprising, a good warrior, the patron of intellectual effort, but passionate and untrustworthy, and stained with faithlessness and cruelty in a measure unusual even in those wild times. In 1447 and again in 1451 he fought in the pay of Florence against the Neapolitan Aragonese, then shared in Anjou’s enterprise against Naples, and was so pressed by Federigo of Montefeltro that only the republic of Venice, which he had served in the Morea, saved for him the remnant of his possessions. Pope Pius II. prevented Rimini from falling into the hands of the Venetians by investing Sigismondo with the sovereignty of the town and a little territory, reserving its lapse to the Holy See in case of his decease without rightful heirs, as had happened at Cesena in 1464. In 1466 Pope Paul II. endeavoured to persuade Sigismondo, on his return from the Morea, to relinquish Rimini, offering him the government of Spoleto and Fuligno—certainly a rich compensation, had not the intention too evidently been to weaken the Malatesta by detaching them completely from their native country and from the sea. His son Roberto, born like himself out of wedlock, but legitimised by Pope Nicholas V., had taken possession of Cesena in 1464, but was unable to retain it against the Papal strength, as the inhabitants, tired of the endless oppressions of the violent dynasties, rather surrendered themselves to the direct rule of the Church, which allowed them greater freedom in their movements and did not annoy them with taxes.
Confusion enough prevailed in the house of the Ordelaffi, who had taken a firm footing in Forli in the last decades of the thirteenth century, and at times ruled over Cesena. Albornoz had no worse opponent than Cecco (Francesco) Ordelaffi, whom only Venetian protection saved from complete ruin. His son Sinibaldo had returned by means of Florentine support in 1375 to Forli, where he fell, ten years later, a victim to a conspiracy of his two nephews. Antonio, the son of one of the latter, had joined the Florentines during the wars of the last Visconti in Romagna, and in 1441 they received him into their Accomandigia, and obtained for him the investiture of Forli from Pope Nicholas V. His two sons Cecco and Pino ruled at first together, but the latter in 1466 rid himself by violence of the former, who had been as bitter an enemy of Florence as Cecco was an ardent friend of the Republic. With the Manfredi too, who ruled in Faenza from 1314, there was nothing but quarrels and repeated changes of party. The towns of Faenza and Imola belonged in common to the different members of the family, and in such a manner that the eldest always conducted the government. But at the death of Guido Antonio, Taddeo Manfredi took possession of Imola in 1448, to the prejudice of his uncle Astorre, to whom the administration should have passed, and a contest arose which Pope Pius II., Francesco Sforza, and Florence tried to appease, without however procuring a real peace. Taddeo passed from one side to another, fought first in Florentine, then in Aragonese, and then again in Florentine pay. His uncle was not more constant. He had taken up arms for the Visconti in 1440, had been taken prisoner in the battle of Anghiari, and brought to Florence. Freed from prison, he had murdered him into whose power he had fallen in the battle at Bologna, for which Francesco Sforza set a price of a thousand gold florins on his head. Yet he succeeded in reconciling himself with the Republic, in whose service he fought against the Neapolitans in the Chiana valley in 1452. Florence had repeatedly concluded defensive alliances with both lines of the Manfredi since the year 1384. The Alidosi, once reigning in Imola, which they lost now to the Church, now to the Visconti, and now to the Manfredi, had been obliged to content themselves with the little Castel del Rio in the territory of Imola, towards the mountains, with which in 1392 they had joined the Florentine Accomandigia. A younger family had associated itself with these elder dynasties. Alessandro Sforza, brother of the Duke of Milan, had in 1445 acquired the lordship over Pesaro, by the cession of Galeazzo Malatesta, maternal grandfather of his wife Costanza da Varano, and maintained it under many changes of fortune. Pope Nicholas V. had invested him with the government; he had been an essential support to his brother in the contest for Milan, and he afterwards performed mercenary service for King Ferrante and for Venice.[144]
Among all the towns of this province, Bologna was the largest, richest, and most powerful, and would have been destined to exercise the greatest influence on the fate of Romagna, had not irreconcilable factions weakened her internally, and robbed her of the fruits of that heroic time in which she so gloriously conquered the Emperor Frederick II., and the lion of San Marco. The supremacy of the Church, which obtained greater authority here in proportion to the weakening of the civil constitutions of Lombardy and the bordering countries, was not able to suppress the factions which in 1337 brought the Pepoli to power, and thirteen years later gave the city into the hands of the Visconti, from whom Cardinal Albornoz wrested it after a possession of ten years. Even then the quarrels did not cease, which in the beginning of the fifteenth century brought the Visconti back again, who were again expelled by Cardinal Baldassar Cossa, to return a third time in 1438 and assume the position beside the Bentivogli (who had risen to the first rank among the contending native families) which belonged to the Popes. The evident endeavour of Filippo Maria Visconti to convert this relation into unlimited power, soon led to war. Supported by Florence and Venice, who fought here in their own cause as well as in that of Bologna, Annibale Bentivoglio completely defeated the Milanese army, August 14, 1443, on the plain of San Giorgio, only to fall two years afterwards beneath the dagger of murderers of high rank who were in league with the Duke. It was especially important for the Florentines not to let a party serviceable to their hereditary enemy rise to power in a city which they rightly regarded as a protection against the power of the Visconti. The members of the Bentivoglio family were, however, either too young, or not in a position, or not inclined to take the lead. Under these circumstances they hit upon a peculiar idea. The exiled Count of Poppi, Francesco da Guidi, then in Bologna, is said to have related that a cousin of Annibale Bentivoglio had had a love affair with a girl in the above mentioned castle of Casentino, and had a son who lived there with his maternal relatives. Cosimo de’ Medici, and, at his suggestion, Neri Capponi, who knew more about Casentino than anyone, took up the matter, and the end was that Sante, the nephew of Antonio da Cascese, was recognised as Sante Bentivoglio, waited upon in Florence most respectfully by deputies from Bologna, who escorted him to their city, where he succeeded in maintaining himself till his death by prudence, not unmixed with acts of violence towards his opponents.
As the Florentines had done the most in enabling Sante Bentivoglio to seize on the power, so they made it easier for him to preserve it. The Bolognese ambassadors had represented how the position of the city was such that they must throw themselves into the arms of the Duke of Milan if the Holy See did not deal mercifully with them. ‘Beg his Holiness,’ so wrote the Signoria on February 3, 1446, to their ambassador to Pope Eugenius IV., Paolo da Diaceto,[145] ‘to be gracious towards the poor Bolognese people, who have been so afflicted by oppression and misery, by fierce civil discord and strife, that it must move everyone to pity. The Bolognese hope from the gentleness of his Holiness, and the authority of the Republic of Venice, that it may be possible to discover some decent form of paying the Pope a reasonable tribute; but remaining otherwise in their present freedom, without Papal legates or other officers in the name of the Church. Do you make the observation that with people who are accustomed to bloodshed and full of suspicion, violence does not suffice; and that one must rather temporise in order to attain from them afterwards by love what violence cannot effect.’ So much, indeed, Bologna did not attain in the agreement concluded at Rome with Pope Nicholas V. on August 24, 1447, for she was obliged to receive a legate who shared the administration with the senate and the city magistrates. But the choice of these bodies was free; the city had its own militia and unrestricted power over its revenue, while the Papal troops were bound to protect her from foreign enemies. It is clear that such a relation might easily afford an opportunity for difficulties, and it is to be accounted a merit in Sante Bentivoglio