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He began his military career in the service of Braccio da Montone, who at that time was waging war against Perugia on his own account, and at the death of his chief, shortly followed by that of the latter's son Oddo, Piccinino became leader of Braccio's condotta. After serving for a short period under the Florentine Republic, he went over to Filippo Maria Visconti, duke of Milan (1425), in whose service together with Niccolò Fortebraccio he fought in the wars against the league of Pope Eugenius IV, Venice and Florence.
He defeated the papal forces at Castel Bolognese (1434), but another papal army under Francesco Sforza having defeated and killed Fortebraccio at Fiordimonte, Piccinino was left in sole command, and in a series of campaigns against Sforza he seized a number of cities in Romagna by treachery. In 1439 he again fought in Lombardy with varying success against Sforza, who had now entered the Venetian service.
Piccinino then induced the duke of Milan to send him to Umbria, where he hoped, like so many other condottieri, to carve out a dominion for himself. He was defeated by Sforza at Anghiari (1440), but although a number of his men were taken prisoners they were at once liberated, as was usually done in wars waged by soldiers of fortune. Again the war shifted to Lombardy, and Piccinino, having defeated and surrounded Sforza at Martinengo, demanded of the visconti the lordship of Piacenza as the price of Sforza's capture.
The duke by way of reply concluded a truce with Sforza; but the latter, who, while professing to defend the Papal States, had established his own power in the Marche, aroused the fears of the pope and the king of Naples, as well as of the viscenti, who gave the command of their joint forces to Piccinino. Sforza was driven from the Marche, but defeated Piccinino at Montelauro, and while the latter was preparing for a desperate effort against Sforza he was suddenly recalled to Milan, his army was beaten in his absence, and he died of grief and of his wounds in 1444.
Short of stature, lame and in weak health, he was brave to the point of foolhardiness, wonderfully resourceful, and never overwhelmed by defeat. He was cruel and treacherous, and had no aim beyond his own aggrandizement. Piccinino left two sons, Jacopo and Francesco, both distinguished condottieri.
A good account of Piccinino is contained in vol. iii of E Ricotti's Storie della compagnie di ventura (Turin, 1845); GB Poggio, Vita dl N. Piccinino (Venice, 1572); see also the general histories of the period.
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