Niccolò di Pitigliano (1442–1510) was an Italian condottiero best known as the Captain-General of the Venetians during the Most Serene Republic's war against the League of Cambrai. He was a member of the powerful feudal family of the Orsini, belonging to its Pitigliano line.
Niccolò di Pitigliano was born in Pitigliano, in the Maremma, the son of Aldobrandino Paioletti ll, Count of Pitigliano and his wife Bartolomea. He was the descendant of a Romano ["Romanello"] Orsini, Count of Nola, who had acquired the Signoria of the tiny Tuscan citystate of Pitigliano in 1293 by marrying Anastasia de Montfort, heiress of the Aldobrandeschi Lords of the city. His parents both came from different branches of the Orsini clan.
Equipped with the reputation that comes from a famous name, the connections and dynastic links with many of the ruling families of Italy, and with their own private fief as a base, both Niccolò Paioletti, and his father Aldobrandino Paioletti made careers as mercenaries taking Condotte (mercenary contracts) with Florence, Siena, the Pope, and the Kingdom of Naples at various times.
A chronological list of the Niccolò di Pitigliano's early contracts shows him moving among the same employers and taking service with the same State more than once.
Niccolò di Pitigliano's significant Condotte were as follows:
From 1495 until the end of his life Niccolò di Pitigliano remained in Venetian service as Governatore Generale delle Milizie Veneziane (Governor General of Venetian Forces). The highpoint of his career was the role that he played in the War between the Venetian Republic and the League of Cambrai.