The medieval town of Dobor is located along the left bank of the Bosna River, on a small hill, with an average height of 39 meters, which represents the rim of the Vučjak mountain. Across the river lie the slopes of Mount Trebava, while four kilometers upstream lies the town of Modriča. Dobor was built at the entrance of a canyon formed by the mountains mentioned above. From the earliest times, the road from Slavonia via Usora leading into Bosnia’s interior ran through the Bosna River valley, which gave the town of Dobor enormous geostrategic importance in the defense of the Bosnian state’s northern borders. Thus, it is not surprising that this town has been referred to as the “gateway to Bosnia” in history. Dobor belonged to the county of Nenavište in Usora, mentioned in the charter of Ban Stjepan II from 1329. It is known that the feudal families Hrvatinići and Semkovići had possessions here, as well as the Bosnian bishop, and it is not excluded that a part of the county was also the king’s possession. It seems that in late feudalism, this county was divided into two districts whose seats were Dobor and Gračac. The borders of the county of Nenavište have been preserved in Ottoman registers from the 16th century, and it can be stated that they roughly correspond to the area of the present-day municipalities of Gradačac, Modriča, Orašje, Bosanski Šamac and Odžak.

Dobor’s medieval history is largely related to Bosnian-Hungarian relations, from which we can read written traces, whether it is about war or negotiations. One such episode with which the written history of Dobor begins took place in 1387, when the Horvat brothers, Zagreb bishop Pavao and Ban Ivaniš, otherwise the main opponents of the Hungarian crown, were forced to retreat to Bosnia with their ally – King Tvrtko. Mavro Orbini states that on that occasion the Bosnian king ceded certain places in Usora to the Horvat brothers, and thanks to King Sigismund’s charter dated February 17, 1401, we learn that it was Dobor that the brothers built and turned into a stronghold for further operations in Hungary. However, archaeological research indicates that there was already a fortification here, which was additionally fortified by the above-mentioned noblemen.

The Horvats paid a heavy price for not recognizing the Hungarian crown’s supremacy. King Sigismund undertook a military campaign in the summer of 1394 and broke into Usora and defeated the Horvat brothers’ army near Dobor, who had previously lost the support of Bosnian king Dabiša. The Hungarian king’s revenge was terrible, Ban Ivaniš Horvat was executed after cruel torture, and the town of Dobor was destroyed and burned. After the mighty victory, on July 20, 1394, under Dobor, Sigismund issued an act addressed to the Čazma Chapter. The Hungarian triumph completed the act of the Bosnian king Dabiša, who came to Sigismund in his camp near Dobor and submitted to him, renouncing his rights to Croatia and Dalmatia. Nevertheless, this did not diminish the Hungarian pretensions towards Bosnia. As a matter of fact, they intensified in the following period, with the clear goal of subjecting Bosnia to the Hungarian crown. In those intense Hungarian-Bosnian confrontations, the heavy defeat of the Bosnian army south of Dobor, possibly near Maglaj, in the fall of 1408, is especially memorable for its brutality. Then, according to Sigismund’s biographer Windecke, a large number of captured Bosnian nobles were cruelly executed in Dobor, whose bodies were thrown into the Bosna river, which is taken with a great deal of caution in recent historiography. Be that as it may, this defeat silenced, at least for a short time, the resistance of the Bosnian nobles towards Hungary, especially Hrvoje Vukčić, who switched from being King Sigismund’s staunchest opponent to his faithful ally.

From the events of 1408, it can be noted that Dobor was rebuilt after being burned down, but it remains unknown under whose rule it was, Bosnian or Hungarian. The town was under the control of the Hungarian king after 1408 and incorporated into the newly established Banate of Usora, whose rule most likely lasted until the famous battle of Lašva in 1415 when it passed once again into Bosnian hands. In Dobor, on November 11, 1449, at the initiative of János Hunyadi, King Stjepan Tomaš concluded an alliance with the Mačva ban Ivan II Garai directed against the Ottomans, which was not implemented in practice. Eight years later, in 1457, the papal legate Ivan Carvahal made an agreement with King Tomaš here regarding a crusade against the Ottoman Empire, which also never happened. The Venetian deputy Stjepan Tomasi stayed there with the papal legate, who informed his superiors about the results of the agreement in a letter from Dobor. Following the disappearance of the Bosnian state, Dobor became part of Hungary and was probably one of the towns that formed the Srebrenica Banate. In 1470, Dobor is mentioned in the possession of the noble family Berislavić family of Grabarje, but it remains unknown when and how it came under their control. In addition, in 1512, the county of Dobor was mentioned, which included the possessions of the Berislavić family south of the Sava. The rule of the Berislavić family was eliminated in 1536, when the warlike Husrev-bey conquered Dobor, having previously killed Stjepan Berislavić, with whom the main branch of this famous noble family died out.

Dobor is one of the most original medieval Bosnian towns in terms of its architecture. Two towers of different heights form the backbone of the town, which is surrounded by ramparts forming a small rounded space (16 x 8 meters). The larger of the two towers, which measured approximately 15 meters high, is square in shape, whereas the smaller tower, which measured no more than 12 meters high, is round in shape. The stylistic construction of Dobor exhibits Gothic characteristics. During the medieval period, the town underwent four stages of development, culminating in the development of a two-tower burg at the end of the 15th century. The Ottoman builders reduced their interventions to a minimum so that the town retained its medieval appearance. In an effort to offer the most vivid appearance of Dobor, the engraving of Višegrad in Benedikt Kuripešić’s Travelogue could serve as an analogy.

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