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 is the second or the third-largest cosmopolitan city inhabited by Bulgarians, after Sofia and possibly Varna. According to the 2001 census, out of a population of 338,224 inhabitants, the Bulgarians numbered 302,858 (90%). Stolipinovo in Plovdiv is the largest Roma neighbourhood in the Balkans, having a population of around 20,000 alone; further Roma ghettos are Hadji Hassan Mahala and Sheker Mahala. Therefore, the census number is a deflation of the number of Roma people, and they are most likely the second-largest group after the Bulgarians, most of all because the Muslim Roma in Plovdiv claim to be of Turkish ethnicity