Alexios Angelos Philanthropenos
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Alexios Angelos Philanthropenos was a Byzantine Greek
Byzantine Greeks
Byzantine Greeks or Byzantines is a conventional term used by modern historians to refer to the medieval Greek or Hellenised citizens of the Byzantine Empire, centered mainly in Constantinople, the southern Balkans, the Greek islands, Asia Minor , Cyprus and the large urban centres of the Near East...

 nobleman who ruled Thessaly
Thessaly
Thessaly is a traditional geographical region and an administrative region of Greece, comprising most of the ancient region of the same name. Before the Greek Dark Ages, Thessaly was known as Aeolia, and appears thus in Homer's Odyssey....

 from 1373 until ca. 1390 (from ca. 1382 as a Byzantine
Byzantine
Byzantine usually refers to the Roman Empire during the Middle Ages.Byzantine may also refer to:* A citizen of the Byzantine Empire, or native Greek during the Middle Ages...

 vassal) with the title of Caesar
Caesar (title)
Caesar is a title of imperial character. It derives from the cognomen of Julius Caesar, the Roman dictator...

.

The Angeloi of Thessaly rose to prominence during the rule of Simeon Uroš
Simeon Uroš
Simeon Uroš Nemanjić, nicknamed Siniša , also known in Greek as Symeōn Ouresēs Palaiologos , was the Despot of Epirus from 1359 to 1366, and of Thessaly from 1359 until his death in 1370. He governed Epirus and Acarnania under his half-brother Emperor Dušan the Mighty Simeon Uroš Nemanjić,...

 (1359–1370), as they were related to his wife. When Simeon died in 1370, he was succeeded by his son John Uroš
John Uroš
Jovan Uroš or John Ouresis Doukas Palaiologos was the ruler of Thessaly from c. 1370 to c. 1373, died 1422/3.John Uroš was the son of Emperor Simeon Uroš Palaiologos by Thomais Orsini. His maternal grandparents were John II Orsini and Anna Palaiologina Angelina.Between 1369 and 1372 he succeeded...

. John cared more for religious pursuits than the governance of the state, and entrusted the affairs of state to the Caesar
Caesar (title)
Caesar is a title of imperial character. It derives from the cognomen of Julius Caesar, the Roman dictator...

Alexios. Eventually, probably in 1372/1373, he retired altogether to a monastery, leaving Alexios as the ruler of Thessaly. Alexios was married to Maria Angelina Radoslava, a daughter of the Serbian general Radoslav Hlapen
Radoslav Hlapen
Radoslav Hlapen was a Serbian voivode in the service of Emperor Dušan the Mighty . He took part in the operations into the south, Macedonia, and was given a region north of Thessaly to govern in the early 1350s.-Life:Radoslav was born around 1322...

 and was supported by the powerful local magnates. In ca. 1382, Alexios sought the protection of the Byzantine Empire
Byzantine Empire
The Byzantine Empire was the Eastern Roman Empire during the periods of Late Antiquity and the Middle Ages, centred on the capital of Constantinople. Known simply as the Roman Empire or Romania to its inhabitants and neighbours, the Empire was the direct continuation of the Ancient Roman State...

, recognizing the suzerainty of Manuel Palaiologos
Manuel II Palaiologos
Manuel II Palaiologos or Palaeologus was Byzantine Emperor from 1391 to 1425.-Life:...

, who at the time governed Thessalonica as an appanage
Appanage
An apanage or appanage or is the grant of an estate, titles, offices, or other things of value to the younger male children of a sovereign, who would otherwise have no inheritance under the system of primogeniture...

. Alexios is lastly recorded in 1388, and must have died by ca. 1390, when he was succeeded by his son (or perhaps brother), Manuel
Manuel Angelos Philanthropenos
Manuel Angelos Philanthropenos was a Byzantine Greek nobleman who ruled Thessaly from ca. 1390 until it was conquered by the Ottoman Turks in 1393, as a Byzantine vassal with the title of Caesar....

. It is recorded that in 1389 the "Caesar of Thessaly" sent aid to the ruler of Ioannina
Ioannina
Ioannina , often called Jannena within Greece, is the largest city of Epirus, north-western Greece, with a population of 70,203 . It lies at an elevation of approximately 500 meters above sea level, on the western shore of lake Pamvotis . It is located within the Ioannina municipality, and is the...

, Esau de' Buondelmonti
Esau de' Buondelmonti
Esau de' Buondelmonti, ruler of Epirus in Ioannina from 1385 to his death in 1411.Esau was the son of the Florentine nobleman Manente Buondelmonti and Lapa Acciaiuoli, sister of Niccolò Acciaiuoli of Corinth and the grandson of the great Χρηστόφορxοςστασία XXIV...

 against the Albanian
Albanians
Albanians are a nation and ethnic group native to Albania and neighbouring countries. They speak the Albanian language. More than half of all Albanians live in Albania and Kosovo...

 tribes of Epirus
Epirus
The name Epirus, from the Greek "Ήπειρος" meaning continent may refer to:-Geographical:* Epirus - a historical and geographical region of the southwestern Balkans, straddling modern Greece and Albania...

, and that their joint forces scored a major victory over them, but it is unclear if by that date Alexios was still alive. Either he or, more plausibly, Manuel, was the grandfather of the Serbian ruler Mihailo Anđelović
Mihailo Anđelović
Mihailo Anđelović was a 15th century Serbian governor of Serbia briefly in 1458.After the Ottoman conquest of Thessaly in 1394, the ruling Angeloi Philanthropenoi family took refuge in Serbia...

 and the Ottoman Grand Vizier
Grand Vizier
Grand Vizier, in Turkish Vezir-i Azam or Sadr-ı Azam , deriving from the Arabic word vizier , was the greatest minister of the Sultan, with absolute power of attorney and, in principle, dismissable only by the Sultan himself...

 Mahmud Pasha Angelović.

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