Plovdiv city was possibly at times a vassal of Bulgaria or Venice. Ivan Asen II conquered the duchy finally in 1230 but the city had possibly been conquered earlier. Afterwards, Plovdiv was conquered by Byzantium. According to some information, by 1300 Plovdiv was a possession of Theodore Svetoslav of Bulgaria. It was conquered from Byzantium by George Terter II of Bulgaria in 1322. Andronikos III Palaiologos unsuccessfully besieged the city, but a treaty restored Byzantine rule once again in 1323. In 1344 the city and eight other cities were surrendered to Bulgaria by the regency for John V Palaiologos as the
Plovdiv the Turks and Greeks. Prior to the population exchange, as of 1 January 1885, the city of Plovdiv had a population of 33,442, of which 16,752 were Bulgarians (50%), 7,144 Turks (21%), 5,497 Greeks (16%), 2,168 Jews (6%), 1,061 Armenians (3%), 151 Italians, 112 Germans, 112 Romani people, 80 French people, 61 Russians and 304 people of other nationalities. The vast majority of the inhabitants are Christians, mostly Eastern Orthodox, Catholics, Eastern Catholics, and Protestant trends (Adventists, Baptists and others). There are also some Muslims and Jews. In Plovdiv there are many churches, two mosques and one synagogue (see Plovdiv