Orlando (or Roland) (1296–1361) was the second-eldest illegitimate son of Frederick II of Sicily by his concubine Sibilla di Sormella. During his father's reign, he lived in the shadows, but he rose to influence in the courts of his half-brother Peter II and his nephews,

Louis Louis may refer to: * Louis (coin) * Louis (given name), origin and several individuals with this name * Louis (surname) * Louis (singer), Serbian singer * HMS ''Louis'', two ships of the Royal Navy See also Derived or associated terms * Lewis (d ...

and Frederick IV, especially as the leader of the

Catalan Catalan may refer to: Catalonia From, or related to Catalonia: * Catalan language, a Romance language * Catalans, an ethnic group formed by the people from, or with origins in, Northern or southern Catalonia Places * 13178 Catalan, asteroid #1 ...

party after the death of his brother

Giovanni of Randazzo John, Duke of Randazzo (1317–1348) was duke of Randazzo, Athens, and Neopatria, Count of Malta and regent of Sicily (1342–1348). The fourth son of Frederick III of Sicily and Eleanor of Anjou, he was the most powerful nobleman in Sicily dur ...

. In 1339, he was present fighting the Angevins then trying to conquer

Lipari Lipari (; scn, Lìpari) is the largest of the Aeolian Islands in the Tyrrhenian Sea off the northern coast of Sicily, southern Italy; it is also the name of the island's main town and ''comune'', which is administratively part of the Metropolit ...

. Taken captive, he was freed in November 1340 through the interference of a

Sienese Siena ( , ; lat, Sena Iulia) is a city in Tuscany, Italy. It is the capital of the province of Siena. The city is historically linked to commercial and banking activities, having been a major banking center until the 13th and 14th centuri ...

widow, Camiola Turinga, a woman he promised to marry. He never did and was considered highly ungrateful by contemporaries, including Boccaccio. From 1343 to 1345, he was governor of

Palermo Palermo ( , ; scn, Palermu , locally also or ) is a city in southern Italy, the capital (political), capital of both the autonomous area, autonomous region of Sicily and the Metropolitan City of Palermo, the city's surrounding metropolitan ...

and in 1345, ''

strategos ''Strategos'', plural ''strategoi'', Linguistic Latinisation, Latinized ''strategus'', ( el, στρατηγός, pl. στρατηγοί; Doric Greek: στραταγός, ''stratagos''; meaning "army leader") is used in Greek language, Greek to ...

'' of

Messina Messina (, also , ) is a harbour city and the capital of the Italian Metropolitan City of Messina. It is the third largest city on the island of Sicily, and the 13th largest city in Italy, with a population of more than 219,000 inhabitants in ...

. He supported the duke of Randazzo as

regent A regent (from Latin : ruling, governing) is a person appointed to govern a state '' pro tempore'' (Latin: 'for the time being') because the monarch is a minor, absent, incapacitated or unable to discharge the powers and duties of the monarchy ...

during the reign of Louis and then supported his sister-in-law

Elisabeth of Carinthia Elizabeth of Carinthia (1298–1352) was Queen of Sicily by marriage to Peter II of Sicily. She was the regent of Sicily during the minority of her son Louis, King of Sicily from 1348 until her death in 1352. The daughter of the Otto, the penu ...

after the duke's death. He was sent as an ambassador to

Sardinia Sardinia ( ; it, Sardegna, label=Italian, Corsican and Tabarchino ; sc, Sardigna , sdc, Sardhigna; french: Sardaigne; sdn, Saldigna; ca, Sardenya, label=Algherese and Catalan) is the second-largest island in the Mediterranean Sea, after ...

on behalf of

Peter IV of Aragon Peter IV, ; an, Pero, ; es, Pedro, . In Catalan, he may also be nicknamed ''el del punyalet'': "he of the little dagger". (Catalan: ''Pere IV''; 5 September 1319 – 6 January 1387), called the Ceremonious (Catalan: ''el Cerimoniós''), w ...

in 1353. He continued to help Elisabeth into the reign of his other nephew Frederick the Simple. He was a soldier and a general during the last wars between the houses of Barcelona and Anjou for possession of

Trinacria Trinacria may refer to: *the ancient Name of Sicily **Sicily in the classical Greek period, see History of Greek and Hellenistic Sicily **Name for the Kingdom of Sicily during the 1300s **Name for the emblem of Sicily (the triskeles with the Go ...

. He distinguished himself in the

Battle of Aci A battle is an occurrence of combat in warfare between opposing military units of any number or size. A war usually consists of multiple battles. In general, a battle is a military engagement that is well defined in duration, area, and force ...

and in defending Messina from the Angevins. In 1358, he reconquered the area from Vizzini to

Avola Avola (; scn, Àvula/, becoming / if preceded by vowel; la, Abola) is a city and in the province of Syracuse, Sicily (southern Italy). History The foundation of the city in an area previously inhabited by the Sicani and invaded by the Si ...

. He died in a spring skirmish at Caltanissetta, during the war between

Federico Chiaramonte Federico (; ) is a given name and surname. It is a form of Frederick, most commonly found in Spanish, Portuguese and Italian. People with the given name Federico Artists * Federico Ágreda, Venezuelan composer and DJ. * Federico Aguilar Alcuaz, r ...

and

Francesco Ventimiglia Francesco, the Italian (and original) version of the personal name "Francis", is the most common given name among males in Italy. Notable persons with that name include: People with the given name Francesco * Francesco I (disambiguation), sever ...

. Orlando married Maria de Stromoncourt, and had four children: Alfonso, Federigo, Juan, and Sybilla. All boys were Barons of Avola, Sicily only Juan had issue and their descendants,genealogy.eu while Sybilla married into Maltese nobility Michele de Bava, Baron de Djar-il-Bniet in Dingli, Rabat, on the island of Malta and had issue.

Sources

*Giunta, Francesco
"Aragona, Orlando d'."
In Alberto M. Ghisalberti, ed. ''Dizionario Biografico degli Italiani''. Rome, 1961. {{refend 1296 births 1361 deaths Italian nobility House of Barcelona (Sicily) Military personnel killed in action