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Byzantines, Crusaders, and Bulgars. Frederick Barbarossa occupied the city in 1190 and from there negotiated a treaty with Constantinople. The Bulgarian Kalojan defeated the Latins at Adrianopolis in 1205, although the conflict continued for several subsequent years, with the Latins evidently maintaining control of the city. In 1225, Adrianopolis passed from the Latins to John III Dukas Vatatzes of Nicaea but fell in the same year to Theodore of Epiros. In 1230, the Bulgarians once again took the city, but John III reestablished Nicaean rule in 1242-46. In 125556, Theodore II Laskaris used Adrianopolis as his base for a campaign against the Bulgars. With the reestablishment of Byzantine rule in Constantinople in 1261, Adrianopolis became the strategic center on the border with Bulgaria. The Catalan Grand Company besieged the city during their westward march in 1307. Adrianopolis played an important role during the civil wars of the fourteenth century. In 1346, John VI Kantakouzenos was crowned in Adrianopolis by the Patriarch of Jerusalem. Shortly thereafter, the city and its district were given as a fiefdom to his son Matthew Kantakouzenos. In the subsequent conflict with John V Palaiologos, John VI brought Turkish troops to his aid. The city seems to have been seized by Turkish begs in or around 1369, and in 1376-77, Murad I established his residence there. The city subsequently was developed as the Ottoman capital, serving as such prior to the conquest of Constantinople in 1453. The fifteenth and sixteenth centuries witness major architectural investment in the city by the Ottomans.
Monuments Little survives in modern Edirne to bear witness to the important Byzantine history of the city. Continually ravaged by war during the Byzantine period and dramatically rebuilt in the early Ottoman period, the historic core of the city was devastated by fire and earthquake and suffered additional damage during the Russian siege and occupation of 1877-78 in the Balkan Wars of 1912-13. An inventory compiled by I. Saraphoglou in 1929 lists one Byzantine church, ten postByzantine churches, four churches that had burned in the seventeenth or eighteenth centuries, 163