Orsini

The Orsini of Pitigliano were the Tuscan branch of the Roman Orsini family, tracing descent from Gentile Orsini, a son of Matteo Rosso the Great. In 1293 Romano Orsini married Anastasia de Montfort, heiress of the Aldobrandeschi counts of Sovana, and acquired the signoria of Pitigliano.

Guido Orsini, the first count to style himself from the town, died after 1348; his heirs fought roughly 150 years of intermittent wars with Siena, accepting its suzerainty in 1455. The branch's most famous son was Niccolò di Pitigliano, a condottiero who became captain-general of the Venetian army and commanded it at the defeat of Agnadello in 1509 during the War of the League of Cambrai.

In the following century the county slipped into the orbit of the Grand Duchy of Tuscany. In 1604 Giannantonio Orsini sold Pitigliano to Grand Duke Ferdinando I de' Medici; the line became extinct in 1640.