Radoslav Hlapen (; 1350–1383) was a Serbian magnate who served
Serbian Emperor Stefan Dušan (r. 1331–1355) and
Stefan Uroš V (r. 1355–71) as ''
vojvoda'' (military commander). He took part in the conquest of
Byzantine lands, and was given a region north of
Thessaly
Thessaly ( ; ; ancient Aeolic Greek#Thessalian, Thessalian: , ) is a traditional geographic regions of Greece, geographic and modern administrative regions of Greece, administrative region of Greece, comprising most of the ancient Thessaly, a ...
to govern in the early 1350s.
Origin
It is believed that Radoslav Hlapen is the same person as ''
župan'' (count) Hlapen () who governed
Konavle and the wider
Trebinje region in the 1330s. He was possibly the son of ''župan''
Radoslav, and thus named Radoslav after his father. Another theory is that he was the son of
Syrgiannes Palaiologos.
Byzantine Emperor
John VI Kantakouzenos (r. 1347–54) mentioned him as among the most important nobles, and he was called a relative of Dušan.
Service under Stefan Dušan
Serres was captured in September 1345,
Veria in the first half of 1346. Veria and the surrounding towns were recuperated by John VI Kantakuzenos. After the military conquests, perhaps by spring 1351, Hlapen returned the city to Serbian rule, with many cities and towns in the area. He was appointed governor of
Edessa (Voden) and
Veria (Ber), just north of
Thessaly
Thessaly ( ; ; ancient Aeolic Greek#Thessalian, Thessalian: , ) is a traditional geographic regions of Greece, geographic and modern administrative regions of Greece, administrative region of Greece, comprising most of the ancient Thessaly, a ...
.
Emperor Dušan died in
Devol, on 20 December 1355. Dušan was succeeded by his son
Stefan Uroš V.
Service under Stefan Uroš V
After the death of the governor of Thessaly ''
kesar''
Preljub (1356), Preljub's son
Thomas' claim to the region was asserted by the widow Irene. The Preljubović family was forced to flee to Serbia after the advance of
Nikephoros II Orsini in 1356. Irene married Radoslav Hlapen, who adopted Thomas.
''Despot''
Simeon Uroš, the brother of Dušan, was appointed governor of
Epirus
Epirus () is a Region#Geographical regions, geographical and historical region, historical region in southeastern Europe, now shared between Greece and Albania. It lies between the Pindus Mountains and the Ionian Sea, stretching from the Bay ...
and
Acarnania in 1348. Following the death of Dušan and subsequent invasion of
Nikephoros II, Simeon Uroš retreated to Kastoria, where he proclaimed himself "Emperor of Serbs, Greeks and Albanians". Simeon Uroš acquired the support of
John Komnenos Asen (the brother-in-law of Dušan). In response, the
Serbian nobility held a council in April 1357 at
Skopje
Skopje ( , ; ; , sq-definite, Shkupi) is the capital and largest city of North Macedonia. It lies in the northern part of the country, in the Skopje Basin, Skopje Valley along the Vardar River, and is the political, economic, and cultura ...
, in which they vowed to support Emperor Uroš, according to Dušan's will. In the summer of 1358, Simeon Uroš advanced on Zeta but was stopped at
Skadar, where his army of 5,000 men was defeated by the Serbian nobility. Simeon Uroš returned to Kastoria, and never again tried to acquire Serbia. During the absence of Simeon Uroš in Epirus (1359), Hlapen invaded Thessaly on behalf of his stepson Thomas. Simeon Uroš was forced to cut his losses by recognizing Radoslav Hlapen's conquests, turning over Kastoria to him, and marrying his daughter Maria to Thomas. Hlapen continued to recognize Uroš' suzerainty, and provided a buffer between Uroš V and Simeon Uroš. After the treaty between Hlapen and Simeon Uroš, the latter settled in Thessaly.

In 1365, a ''
čelnik'' Radoslav was mentioned, referring either to Radoslav Hlapen or
Radoslav Povika, the brother of ''
logotet''
Đurađ.
Fall of the Serbian Empire
After the
Battle of Maritsa (1371) he became one of the most powerful provincial lords.
Last years
He retired as a monk in the
Vodoča monastery where he also was buried. His votive ring was found at the site. He also founded a church in
Kučevište,
Skopje
Skopje ( , ; ; , sq-definite, Shkupi) is the capital and largest city of North Macedonia. It lies in the northern part of the country, in the Skopje Basin, Skopje Valley along the Vardar River, and is the political, economic, and cultura ...
, a monastery in Ostrovo,
and a monastery in Greece.
Family

He married Irina (Irene)
Nemanjić, the widow of ''caesar''
Preljub.
They had the following issue:
*Maria Angelina Radoslava, married
Alexios Angelos Philanthropenos
*Jelena, married
Marko Mrnjavčević
*Unnamed, married
Nikola Bagaš
*Unnamed, married
John Uroš
*Stefan
Legacy
Mavro Orbini (1563–1614) called him "primo barone di Grecia" (1601).
See also
*
Nobility of the Serbian Empire
References
Sources
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{{DEFAULTSORT:Hlapen, Radoslav
Year of birth unknown
1380s deaths
14th-century Serbian nobility
Medieval Serbian military leaders
Medieval Macedonia
People from the Serbian Empire
Medieval Serbian magnates
Generals of Stefan Dušan
Boyars of Stefan Dušan