Isaac II Angelos’s Failed Retaliations
After the passing of the Third Crusade, Isaac II Angelos decided to deal with the Bulgarians decisively. The expedition was planned on a grand scale and reached Tărnovo before besieging it for a protracted period. By this time Peter IV had crowned Ivan Asen I as co-emperor in 1189 and, without abdicating, retired to Preslav. In charge of the defense of the Tărnovo, Ivan Asen I incited the Byzantine emperor to hastily retreat by spreading rumors of the arrival of a great Cuman army to the relief of the besieged city. The retreating Byzantine army was ambushed by Ivan Asen I in the Balkan passes and Isaac II barely escaped with his life in 1190.
Success now definitely swung in favor of the Bulgarians, who captured the areas of Sredec (Sofia) and Niš in 1191, of Belgrade in 1195, of Melnik and Prosek in 1196, while raiding parties reached as far south as Serres. When the Bulgarian emperor Ivan Asen I was murdered, his successor Kaloyan continued an aggressive policy against the Byzantine Empire by making an alliance with Ivanko, the murderer of Ivan Asen I, who had entered Byzantine service in 1196 and had become governor of Philippopolis (Plovdiv). Another ally of Kaloyan was Dobromir Hriz (Chrysos), who governed the area of Strumica. The coalition was quickly dissolved, as the Byzantines overcame both Ivanko and Dobromir Hriz. Nevertheless, Kaloyan conquered Konstanteia (Simeonovgrad) in Thrace and Varna from the Byzantine Empire in 1201, and most of Slavic Macedonia in 1202.
Read more about this topic: Byzantine–Bulgarian Wars
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