Ivan Asen II of Bulgaria
During the existence of the Latin Empire of Constantinople, the Crusaders were decisively defeated by the Bulgarian Emperor Kaloyan in the Battle of Adrianople (1205). In 1206 Adrianople and its territory was given to the Byzantine aristocrat Theodore Branas as a hereditary fief by the Latin regime. Theodore Komnenos, Despot of Epirus, took possession of it in 1227, but three years later was defeated at Klokotnitsa by Emperor Ivan Asen II of Bulgaria.