The House of Orsini is an Italian noble family that was one of the most influential princely families in Medieval Italy and Renaissance Rome. Members of the Orsini family include five popes:George L. Williams, Papal Genealogy (London 2004). Stephen II (752–757), Paul I (757–767), Celestine III (1191–1198), Nicholas III (1277–1280), Richard Sternfeld, Der Kardinal Johann Gaëtan Orsini (Papst Nikolaus III.) (Berlin 1905). and Benedict XIII (1724–1730). The family also included 34 cardinals, numerous condottieri, and other significant political and religious figures. The Orsini are part of the Black nobility who were Roman aristocratic families who supported the Popes in the governance of the Papal States.

Origins According to their own family legend, the Orsini are descended from the Julio-Claudian dynasty of ancient Rome. They attribute their origin to an individual named Ursus, who served as count of Tivoli, probably in the 9th century.Ferdinand Gregorovius, The History of Rome in the Middle Ages, vol. 5, pp. 39, 214 The Orsini carried on a political feud with the Colonna family for centuries in Rome, until it was stopped by Papal Bull in 1511. In 1571, the heads of both families married nieces of Pope Sixtus V as an act of reconciliation.

The Orsini descend from Cajo Orso Orsini who lived c. 600 AD. Five popes are descended from him: Stephen II, Paul I, Celestine III, Nicholas III and Benedict XIII.George L. Williams, Papal Genealogy (London 2004). Some members used the surname of Bobone-Orsini. One member by the name Bobone, lived during the early 11th century, father of Pietro, who was in turn father of Giacinto Bobone (1110–1198), who in 1191 became pope as Celestine III. One of the first great nepotist popes, he made two of his nephews cardinals and allowed his cousin Giovanni Gaetano (Giangaetano, died 1232) to buy the fiefs of Vicovaro, Licenza, Roccagiovine and Nettuno, which formed the nucleus of the future territorial power of the family.

The Bobone surname was lost with his children, who were called de domo filiorum Ursi. Two of them, Napoleone and Matteo Rosso the Great (1178–1246), considerably increased the prestige of the family. The former was the founder of the first southern line, which died out with Camillo Pardo in 1553. He obtained the city of Manoppello, later a countship, and was gonfaloniere of the Papal States. Matteo Rosso, called the Great, was the effective lord of Rome from 1241, when he defeated the Imperial troops, until 1243, holding the title of Senator. Two of his sons, and Napoleone, were also Senators. Matteo ousted the family's traditional rivals, the Colonna family, from Rome and extended the Orsini territories southwards down to Avellino and northwards to Pitigliano. During his life, the family was firmly in the Guelph faction. He had some ten sons, who divided the fiefs after his deaths: Gentile (died 1246) originated the Pitigliano line and the second southern line, Rinaldo that of Monterotondo, Napoleone (died 1267) that of Bracciano, and another Matteo Rosso that of Montegiordano, from the name of the district in Rome housing the family's fortress. The most distinguished of his sons was Giovanni Gaetano (died 1280): elected pope as Nicholas III, he named his nephew Bertoldo (d. 1289) as count of Romagna, and had two nephews and a brother created cardinals.

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 13 August 1379; Dean of Salisbury, Archdeacon of Leicester and Archdeacon of Durham) 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.

Pitigliano line This line was initiated by Guido Orsini, second son of Romano, who inherited the county of Soana, on the western side of Lake Bolsena in southern Tuscany.Giuseppe Bruscalupi, Monografia storica della Contea di Pitigliano (Firenze 1906). He and his descendants ruled over the fiefs of Soana, Pitigliano and Nola, but in the early 15th century wars against the Republic of Siena and the Colonnas caused the loss of several territories. Bertoldo (died 1417) managed to keep only Pitigliano, while his grandson Orso (died July 5, 1479) was count of Nola and fought as condottiere under the Duke of Milan and the Republic of Venice. Later he entered the service of Ferdinand I of Naples, but, not having taken part in the Barons' conspiracy, he was rewarded with the fiefs of Ascoli and Atripalda. He took part in the Aragonese campaign in Tuscany and was killed at the siege of Viterbo.

The most outstanding member of the Pitigliano line was Niccolò, one of the major condottiere of the time. His son Ludovico (died January 27, 1534) and his nephew Enrico (died 1528) participated in the Italian Wars at the service of both France and Spain, often changing side with the typical ease of the Italian military leaders of the time. Two of Ludovico's daughters married relevant figures: Geronima to Pier Luigi Farnese, illegitimate son of Pope Paul III and Marzia to Gian Giacomo Medici of Marignano, an important general of the Spanish army.

The line started to decay after the loss of Nola by Ludovico, who was also forced to accept the Sienese suzerainty over Pitigliano. Under his son Giovan Francesco (died May 8, 1567) the county entered the orbit of the Grand Duke of Tuscany. Later, the attempt of Alessandro (died February 9, 1604) to obtain the title of Monterotondo was thwarted by Pope Gregory XIII. His son Giannantonio (March 25, 1569 – 1613) sold Pitigliano to Tuscany, in exchange for the marquisate of Monte San Savino.

The line became extinct in 1640 with the death of Alessandro.

Monterotondo line This line was founded by Rinaldo, third son of Matteo Rosso the Great. His son, Napoleone, became a cardinal in 1288 and remained a prominent member of the Curia until his death at Avignon in 1342.

This branch of the family was often involved in the baronial struggles of the Late Middle Ages Rome, at least three members of the family being elected as Senators, while others fought as condottieri. Francesco in 1370 took part to the war of Florence against the Visconti of Milan. Orso (died July 24, 1424) died fighting for the king of Naples in the Battle of Zagonara against the Milanese. His sons Giacomo (died 1482) and Lorenzo (1452) battled for the Papal States, Naples and Florence. One of Giacomo's daughters, Clarice (1453–July 30, 1488) became Lorenzo de' Medici's wife. Franciotto Orsini was created cardinal by Leo X in 1517.

The most important member of the Monterotondo Orsinis was Giovani Battista Orsini, who became cardinal under Sixtus IV (1483). He was probably among the promoters of the failed plot against Cesare Borgia in 1502, being assassinated on February 22 of 1503 as retaliation, together with other members of the family: Giulio survived captivity under Cesare, but Paolo and Francesco 4th Duke of Gravina were strangled to death on 18 January 1503.

The line decayed from the late 16th century, when several members were assassinated or lost their lands for various reasons. Its last representatives Enrico (died September 12, 1643) and Francesco (1592 - September 21, 1650) sold Monterotondo to the Barberini in 1641.

Bracciano line Napoleone, another son of Matteo Rosso the Great, received Bracciano, Nerola and other lands in what is now northern Lazio. In 1259 he was Senator of Rome. Thanks to the strategic positions of their fiefs, and to their famous castle built in Bracciano in 1426, they were the most powerful Orsini line in the Lazio. Count Carlo (died after 1485), son of another Napoleone (died October 3, 1480), was Papal Gonfaloniere. By his marriage with a Francesca Orsini of Monterotondo was born Gentile Virginio Orsini, one of the most prominent figures of Italian politics in the late 15th century. After Carlo's death, he enlarged the family's tenure with lands inherited by his wife, another Orsini from Salerno, and most of all he was amongst the favourites of Ferdinand I of Naples, who appointed him as Great Constable of Naples. Together with his cousin, the Cardinal Giovanni Battista, he was among the fiercest opponents of popes Innocent VIII and Alexander VI. In 1492 Gentile Virginio bought the county of Anguillara from Franceschetto Cybo.

During Charles VIII of France's descent into Italy, he managed to keep Bracciano. Ferdinand II had his fiefs confiscated and imprisoned him in Castel dell'Ovo, where he was poisoned in 1497. The family recovered this setback under the more friendly Medici popes of the early 16th century. His son Gian Giordano was Prince Assistant to the Papal Throne. His nephew Virginio was a famous admiral for the Papal States and France, but in 1539 he had his fiefs confiscated under the charge of treason.