The Second Southern Line
The rise of the Orsini did not stop after Nicholas' death. Bertoldo's son, Gentile II (1250–1318), was two times Senator of Rome, podestà of Viterbo and, from 1314, Gran Giustiziere ("Great Justicer") of the Kingdom of Naples. He married Clarice Ruffo, daughter of the counts of Catanzaro, forming an alliance of the most powerful Calabrian dynasty. His son Romano (1268–1327), called Romanello, was Royal Vicar of Rome in 1326, and inherited the countship of Soana through his marriage with Anastasia de Montfort, Countess of Nola. Romano's stance was markedly Guelph. After his death, his two sons divided his fiefs, forming the Pitigliano and the second southern line.
Roberto (1295–1345), Gentile II's grandson, married Sibilla del Balzo, daughter of the Great Senechal of the Kingdom of Naples. Among his sons, Giacomo (died 1379) was created cardinal by Gregory XI in 1371, while Nicola (August 27, 1331 – February 14, 1399) obtained the counties of Ariano and Celano. The latter was also Senator of Rome and enlarged the family territories in Lazio and Tuscany.
His second son, Raimondello Orsini del Balzo, supported Charles III' coup d'état in Naples against Queen Joan I. Under king Ladislaus he was among the few Neapolitan feudataries who were able to maintain their territorial power after the royal war against them. However, at his death in 1406 the southern Orsini fiefs were confiscated. Relationships with the royal family remained cold under Joan II; However, when Raimondello's son Giannantonio (1386–1453) sent his troops to help her against the usurpation attempt of James of Bourbon, he received in exchange the Principality of Taranto.
The links with the court increased further under Sergianni Caracciolo, Joan's lover and Great Senechal. A younger brother of Giannantonio married one of Sergianni's daughters. However, the Orsini changed side when Alfonso V of Aragon started his conquest of the Kingdom of Naples. Giannantonio was awarded with the duchy of Bari, the position of Great Connestable and an appanage of 100,000 ducati. Giannantonio remained faithful to Alfonso's heir, Ferdinand I, but was killed during a revolt of nobles. Having died without legitimate sons, much of his possessions were absorbed into the Royal Chamber.
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