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Chlapenos Radoslabos
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Identical with Radoslav’ (Povikь?)? It is doubtful, that he is the same person as the župan Hlapen, who governed Konavle and the region of Trebinje. He died before 1385. He was a commandant of the Serbian military troops in Macedonia, 1350. He controlled a large area in Macedonia in the border region, 1357–1362. He was a relative of the Serbian Emperor Stefan Uroš IV Dušan. He married Eirene Prelumpissa in 1358 (ὅθεν καὶ γυναῖκα λαμβάνει τὴν τοῦ Πρελούμπου ἐκείνου γαμετήν). He was the father of Helena. According to a manuscript note she was married to Marko Mrnjavčević (vь dьni blagověrnago kralja Mar’ka, jegda ōdade Thodoru Grьgurovu ženu Hlapenu, a uze ženu svoju prьvověn’čan’nu Jelenu, Hlapenovu dьštere). His second daughter was the wife of Nikolaos Baldubinos Pagases [Νικόλαος Βαλδουβῖνος Παγάσης/Nikola Bagaš] (ἀπὸ τοῦ πενθεροῦ μου Ῥαδοσλάβου τοῦ Χλαπένου). The third daughter called Maria Angelina Radosthlaba married Alexios Angelos Philantropenos. Mauro Orbini, a Ragusan chronicler from 16th century, who used older sources, mentions also a son of him called Stefan-Dukas (I maschi si chiamauno Duca & Stefano). He defected in 1350 along with Tolisthlabos from the Serbian Emperor Stefan Uroš IV Dušan to the Byzantine Emperor Ioannes VI Kantakuzenos (ἧκον δὲ καὶ αὐτόμολοι δύο ἐξ αὐτῶν· ὧν ἅτερος τῶν μάλιστα ἦν ἐπιφανῶν, κατὰ γένος προσήκων Κράλῃ, Χλάπαινος ὠνομασμένος, στρατιάν τε ἔχων ὑφ’ ἑαυτὸν οὐκ εὐκαταφρόνητον καὶ πολλὴν περιουσίαν· ὁ λοιπὸς δὲ οὐ τῶν πάνυ περιδόξων ἦν, πλὴν κἀκεῖνος ἀρχάς τε πόλεων ἐγκεχειρισμένος καὶ στρατοπέδων ἡγεμονίας, ὄνομα Τολίσθλαβος). After a while he switched sides again and joined most likely the Serbian Emperor Stefan Uroš IV Dušan. He captured Beroia before 1359, probably in 1351 (Οὗτος τοίνυν ὁ Χλάπενος, εἷς ὢν τῶν Σερβικῶν σατραπῶν καὶ τινα φρούρια ἐκ τῶν Ῥωμαï κῶν ὁρίων εἰληφώς, ἀλλὰ δὴ καὶ τὴν μεγαλόδοξον πόλιν Βέῤῥοιαν, μεγάλως ἐπὶ τοὶς κατορθώμασιν ἐσέμνυνεν). He witnessed the apparently falsified charter issued by the Serbian Emperor Stefan Uroš V in 1355 for the inhabitants of the town of Kotor (Radosav Chlapene). He acted as a protector of the inheritance right of his wife and his stepson Toma Preljubović (Θωμᾶς Πρέλουμπος). Therefore he seized the Thessalian town Damasis in 1359/1360 (Τῇ Βλαχίᾳ δὲ φθάσας μετὰ τῶν στρατευμάτων καὶ φρούριον ἓν πολιορκία εἰληφώς, Δάμασιν καλούμενον, εἰς συμβάσεις μετὰ τοῦ βασιλέως Συμεὼν χωροῦσι, καὶ τὸ φρούριον τούτῳ παραχωρεῖ). He gave up the town of Damasis to Simeon Uroš (Συμεὼν Παλαιολόγος) on condition of arranging the marriage between Maria Angelina Komnene Palaiologina, the daughter of Simeon, and Toma Preljubović (Θωμᾶς Πρέλουμπος). He founded the Mesonesiotissa Monastery near Kastoria (καὶ ἂν κατὰ διαδοχὴν καὶ κληρονομίαν ἔλαβον ἀπὸ τοῦ πενθεροῦ μου Ῥαδοσλάβου τοῦ Χλαπένου σεβασμίαν καὶ ἱερὰν μονὴν, τὴν παρ’ ἐκείνου ἀνεγερθεῖσαν ἐκ βάθρων αὐτῶν τῇ ὑπερευλογημένῃ ἡμῶν δεσποίνῃ καὶ θεομήτορι, τὴν οὕτω πως καλουμένην Μεσονησιώτισσαν). Apparently his ring was found on a medieval necropolis of the Vodoča Monastery near Strumica. It bears an invocation (Izvolite raba Božija Hlapena).
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Raiko
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Maybe identical with the nephew of Momčilo, who was let in to the town of Peritheorion with 50 soldiers by its inhabitants in 1345. Mentioned in the prostagma charter of the Serbian King Stefan Uroš IV Dušan, which was issued between September and December 1345. He appears as οἰκεῖος of the Serbian King Stefan Uroš IV Dušan in the prostagma charter. He held the position of kephale (governor) of Trilision and Brontu, 1345. Rajko was asked by the Serbian King Stefan Uroš IV Dušan to not collect the toll from the 25 nomismata intented for Kyprianos, the Bishop of Pheremai. Rajko should also bring the prostagma, which was issued on this occasion between September and December 1345, to Kyprianos.
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