Radoslav Hlapen (; 1350âÂÂ1379) was a Serbian magnate who served Emperor Stefan Duà ¡an (r. 1331âÂÂ1355) and Stefan Uroà ¡ V (r. 1355âÂÂ71) as vojvoda (military commander). He took part in the conquest of Byzantine lands, and was given a region north of Thessaly to govern in the early 1350s.
It is believed that Radoslav Hlapen is the same person as à ¾upan (count) Hlapen () who governed Konavle and the wider Trebinje region in the 1330s. He was possibly the son of à ¾upan 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. 1347âÂÂ54) mentioned him as among the most important nobles, and he was called a relative of Duà ¡an.
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.
Emperor Duà ¡an died in Devol, on 20 December 1355. Duà ¡an was succeeded by his son Stefan Uroà ¡ 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 PreljuboviÃÂ 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 Uroà ¡ NemanjiÃÂ, the brother of Duà ¡an, was appointed governor of Epirus, Aetolia and Acarnania in 1348. Following the death of Duà ¡an and subsequent invasion of Nikephoros II, Simeon Uroà ¡ retreated to Kastoria, where he proclaimed himself "Emperor of Serbs, Greeks and Albanians". Simeon Uroà ¡ acquired the support of John Komnenos Asen, Duà ¡an's brother-in-law and the appointed Despot in Valona. In response, the Serbian nobility held a council in April 1357 at Skopje, in which they vowed to support Emperor Uroà ¡ V, according to Duà ¡an's will. In the summer of 1358, Simeon Uroà ¡ advanced on Zeta but was stopped at Skadar, where his army of 5,000 men was defeated by the Serbian nobility. Simeon Uroà ¡ returned to Kastoria, and never again tried to acquire Serbia. Simeon was, however, fortunate in that Nikephoros II Orsini was slain in battle, thus giving Simeon an opportunity to rapidly seize back his former territories in Epirus, as well as former territories of caesar Preljub in Thessaly.
As Simeon was campaigning in Epirus, Hlapen invaded Thessaly on behalf of his stepson Thomas, Preljub's son. Simeon Uroà ¡ was forced to cut his losses by recognizing Radoslav Hlapen's conquests, turning over Kastoria and the region surrounding it, and marrying his daughter Maria to Thomas. Hlapen continued to recognize the suzerainty of Emperor Stefan Uroà ¡ V, and provided a buffer between him and Simeon. After the treaty between Hlapen and Simeon Uroà ¡, the latter settled in Thessaly.
In 1365, a ÃÂelnik Radoslav was mentioned, referring either to Radoslav Hlapen or Radoslav Povika, the brother of logotet ÃÂuraÃÂ.
In September 1371, the ruler of the lands around Edessa and Veria, Radoslav Hlapen, gained independence from the guardianship of brothers Vukaà ¡in and Ugljeà ¡a and sought to expand his influence into Thessaly. Around the early 1370s, John Uroà ¡, heir of the late Serbian Emperor Simeon Uroà ¡, briefly ruled Thessaly but was soon deposedâÂÂeither by the local Greek aristocracy under Despot Manuel II Palaiologos or by Radoslav Hlapen himself. John Uroà ¡ retired to the Meteora monasteries as a monk, taking the name Joasaph, but maintained some political influence in Epirus and Ioannina. Radoslav HlapenâÂÂs intervention in Thessaly underestimated the power of Manuel II Palaiologos of Thessalonica. With PalaiologosâÂÂs support, Alexios Angelos Philanthropenos, a prominent local noble, took control of Thessaly in 1373, and his family ruled the region until the Ottoman conquest. To neutralize HlapenâÂÂs heirs, Alexios married HlapenâÂÂs daughter Maria. Manuel II Palaiologos continued to attack HlapenâÂÂs territories, capturing the key city of Veria by 1375, effectively ending HlapenâÂÂs principality. Radislav Hlapen died under uncertain circumstances around 1379.
He retired as a monk in the VodoÃÂa monastery where he also was buried. His votive ring was found at the site. He also founded a church in KuÃÂevià ¡te, Skopje, a monastery in Ostrovo, and a monastery in Greece.
He married Irina (Irene) NemanjiÃÂ, the widow of caesar Preljub. They had the following issue:
Mavro Orbini (1563âÂÂ1614) called him "primo barone di Grecia" (1601).