In 1220, Engelberto d'Ugo Piccolomini received the fief of Montertari in Val d'Orcia from the Holy Roman Emperor Frederick II as a reward for the services rendered. The family acquired houses and towers in Siena as well as castles and territories in the republic, including Montone and Castiglione; the latter sold to the comune in 1321.[3]
They obtained great wealth through trade, and established counting-houses (merchant banks) in Venice, Genoa, Trieste, Aquileia, and in various cities of France and Germany. Supporters of the Guelph cause in the civil broils by which Siena was torn, they were driven from the city during the time of King Manfred of Sicily. Their houses were demolished but they returned in triumph after the victory of the Angevin Kings. They were expelled once more during the brief reign of King Conradin, and again returned to Siena with the help of King Charles of Anjou. But through their riotous political activity, the Piccolominis lost their commercial influence, which passed into the hands of the Florentines, although they retained their palaces, castles and about twenty fiefs, some of which were in the territory of Amalfi, to a great extent.[3]
Another branch of the family obtained great success in the Kingdom of Naples, becoming one of the "seven great houses"[5] of the Kingdom.
In the 17th century, two Piccolomini brothers, from the Modanella branch, were about to make a large family tree of the family. To seal their ancient genealogy with a legal certification, they commissioned a notary, Alessandro Rocchigiani, to put in order the various sources that disserted the family's origin. Evidently the fascination of myth, mixed with the reverence due to the illustrious patrons, instead of eliminating the legendary components ended up increasing them. Horatius Cocles was indicated with certainty, by the zealous notary, as the new progenitor of the family. Undoubtedly some coincidences arouse astonishment. Indeed, in the column that adorned the Campidoglio, his enterprise, was a coat of arms identical to that of the Sienese family, stood out carved in the shield of the ancient Roman.[6] Once attached to Horace, the Piccolomini lineage had, in ancient Rome, the name of Parenzi, and from there one of its members chose the Sienese colony as his new residence, became Podestà (chief magistrate), and abandoned his name, Chiaramontese, and changed it to Piccholuomo.[7]
The civil discords that agitated Rome in those times favored Siena because of their previous affiliation with the members of the Horatia gens, of which Chiaramontese belonged to.[8] Having left from his homeland in Rome and also his surname, he came to live in the jurisdiction of Siena, and just as it is customary for men from one city when they move to another to take a different name from the usage of their native country, so it happened, Rocchigiani explained, that the Roman exile named Chiaramontese, took on in his new homeland the nickname Piccoluomo (Piccholuomo) from which the surname Piccolomini was later derived.[9] The Piccolominis also descended from a certain Iulius Piccolomini Amideis, a member of the Amidei family, who was also of Roman descent.[10][11]Pope Pius II, his full name being Enea Silvio Bartolomeo Piccolomini, was named in relation to his Roman ancestry and refers to Aeneas Silvius, King of Alba Longa, from which the Amideis also claimed descent through the gens Julia.[12]
^Penny cyclopaedia, Vol. 18, citing Niccolò Machiavelli. (1532). Historie fiorentine (History of Florence and of the affairs of Italy: from the earliest times to the death of Lorenzo the Magnificent).
^Le "Serenissime Sette Grandi Case del Regno di Napoli" comprendevano: Acquaviva, Celano, Evoli, Marzano, Molise, Ruffo, Sanseverino; estintesi le famiglie d'Evoli, Marzano e Molise, queste furono sostituite da quelle dei d'Aquino, del Balzo e Piccolomini (in merito si vedano: Archivio di Stato di Napoli scheda famiglia SanseverinoArchived 2013-12-24 at the Wayback Machine; B. Filangieri di Candida Gonzaga, op.cit, ad voces; Spreti, op.cit, ad voces).
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