Darman and Kudelin

The Bulgarian lands in the late 13th century: Darman and Kudelin's semi-independent domain is in the northwest

Darman (Bulgarian: Дърман; also Drman, Dǎrman, Durman, Dorman) and Kudelin (Куделин) were two Bulgarian nobles who jointly ruled the region of Braničevo (in modern Serbia) as independent or semi-independent autocrats in the late 13th century (1273–1291). Regarded by historians to be "probably Bulgarians of Cuman origin", the two brothers used the weakened state of centralized administration in the region to become independent from the Second Bulgarian Empire or the Kingdom of Hungary in 1273. The capital of their domains was the fortress of Zhdrelo (Ždrelo, "gorge"), on the Mlava river. Relying on their army that consisted of people of various ethnicities, but mostly Bulgarians, Tatars and Cumans, the brothers were "very independent-minded and afraid of no one".

They regularly attacked their western neighbour, the Hungarian vassal Stefan Dragutin's Syrmian Kingdom, in Mačva, an area previously under the sovereignty of Elizabeth of Hungary. The Hungarian queen had sent troops to claim Braničevo in 1282–1284, but her forces were repelled and her vassal lands plundered in retaliation. Another campaign, this time organized by both Dragutin and Elizabeth, failed to conquer Darman and Kudelin's domains in 1285 and suffered another counter-raid by the brothers. It was not until 1291 when a joint force of Dragutin and Serbian king Stefan Milutin managed to defeat the brothers and, for the first time ever, the region came under the rule of a Serb, as it was annexed by Dragutin. The brothers were most likely killed in this campaign, as they disappear from the historical sources thereafter.

Darman and Kudelin were relatives or close associates of the Bulgarian despotēs Shishman of Vidin, the founder of the Shishman dynasty of Bulgarian rulers, as he proceeded to attack the Serbian domains to his west, presumably as a response to Dragutin's annexation of the neighbouring Braničevo.