He was the recipient of the charter issued by the Serbian Emperor Stefan Uroš IV Dušan on 21th May 1349. He served as dijakь (scribe) and anagnostь (reader or lector). The father of his wife is mentioned in the document (I ōvy dijakь Dragoe sь svoimь tьsninomь). He moved in the place before the field Trěblěgrьmь, which was above Gabrovo and near the Belasica mountain, in order the erect a Church dedicated to the Holy Mother of God and to the Holy Archangels Michael and Gabriel (izide dijakь anagnostь Dragoje kako estь ulezlь više Gabrova u Belasici predь Trěblěgrьmь zidati hramь prěčistee crьkvь i besplьtnihь silь Mihaila i Gabrila). At the request of Kalinik, the Bishop of Banьska (Velbužd, Kjustendil), made the Serbian Emperor Stefan Uroš IV Dušan the endowment of Dragoje exempt from various duties and allowed Dragoje live here freely with his father-in-law. Stefan Uroš IV Dušan donated to Dragoje also a field Podь and another field beneath Gabrovo. The Serbian Emperor gave him the permission to settle people near the church.