Plovdiv

Philippopolis was a great Byzantine city in the heart of Thrace, on the road from Sredets to Adrianople and Constantinople. In the eleventh century it was known for its many Paulicians — dualist heretics whom the Byzantine authorities long tried to bring to heel. In 1083 open conflict broke out between the close-knit Paulician communities of the city and its surroundings and the imperial government, and around 1073–1078 the Paulician Leka of Philippopolis, married to a Pecheneg woman, raised a revolt and killed the bishop of Sredets. The heretics of Plovdiv would play a decisive part in the first wars of the restored Bulgarian tsardom as well.

In the very first years of the revolt Asen raided the villages around Philippopolis and wore the Byzantines down with his mobile tactics: whenever the emperor arrived at one place, the Bulgarians were already riding for another. In the autumn of 1190 Isaac II Angelos led his army to Philippopolis in person, beating off the attacks of Vlachs and Cumans along the way.

The emperor entrusted the defence of the city to his cousin Constantine Angelos, duke of the fleet. The new commander managed to repel Bulgarian attacks on Plovdiv and Beroe, but success went to his head: he rebelled against the emperor, was captured and blinded. In 1193 the Byzantines beat off a Cuman raid on the district of Philippopolis, but the Bulgarians kept striking the great Thracian cities — Sredets, Plovdiv, Adrianople.

After Asen's murder in 1196 his killer Ivanko fled to the Byzantines and was given a command at Philippopolis. Until 1199 he served the empire well — stopping raids, recovering a number of small forts and training his troops — but then he tried to carve out a principality of his own around Plovdiv and later along the Struma. The empire put an end to his ambitions only in 1200–1202.

After the Fourth Crusade Philippopolis was assigned to the crusader Renier de Trit, who took it early in 1205. After his victory at Adrianople in April Kaloyan marched on Thessaloniki, and on his way back to "his own country", as Villehardouin puts it, he made contact with the "Popelicans" of Plovdiv — Paulicians and probably Bogomils — who offered to hand the city over to him. The frightened Renier abandoned Plovdiv in June 1205 and shut himself up in Stanimaka.

The city was not surrendered without a fight, however: the local Greeks, led by Alexios Aspietes, resisted the Bulgarians. Kaloyan besieged and took Plovdiv — the most important city in Thrace — and destroyed it. Retribution for Greek treachery was harsh: according to Nicetas Choniates, after the events at Plovdiv the enraged tsar condemned to death the Greek nobles he was holding in the dungeons of Tarnovo. The events at Plovdiv marked the end of the short-lived Bulgarian-Greek alliance against the Latins.

The fate of the city immediately after Kaloyan's death is unclear; most likely the local Greek notables took control again. In the summer of 1208, after the indecisive clash at Beroe, the Latin emperor Henry of Flanders withdrew south-west towards Plovdiv, and Tsar Boril pursued him. According to Henri de Valenciennes, Boril came to the battlefield with 33,000 men divided into 36 detachments.

The battle of Philippopolis on 31 July 1208 ended in a complete Latin victory. The chronicler credits the knights' escape to the personal bravery of the knight Liénard and of the emperor himself, but the Latins' withdrawal behind the walls of Plovdiv shows the victory was not an easy one. The Latins held the city until 1230. Shortly after the battle the despot Alexius Slav appeared in Henry's camp at Krichim, acknowledged himself his vassal and asked for his daughter's hand.

Under Latin rule some of the Greeks of Plovdiv emigrated. Several hundred refugees — senior officials, soldiers and monks — settled at Melnik under the despot Slav and created there the Greek intellectual climate of his court. As late as 1228 a draft agreement between the barons of Constantinople and John of Brienne still speaks of "the whole duchy of Philippopolis".

In April 1230 Ivan Asen II defeated Theodore Komnenos at the village of Klokotnitsa on the Maritsa, near Philippopolis on the road to Adrianople. The victory opened Thrace to the Bulgarians and Plovdiv passed under their rule once more. From 1255, though, the city was Byzantine again. In 1262 Constantine Tikh attacked Thrace and took Stanimaka and Philippopolis, but the very next year a second Byzantine army recovered them — at the same time, Pachymeres says, as Mitso surrendered Mesembria.

Plovdiv went on changing hands. In 1322, exploiting the civil war between the two Andronikoi, Tsar George II Terter advanced into Thrace and took the city. After the young tsar's sudden death at the end of the year, Andronikos III and Voysil, brother of Tsar Smilets, besieged Philippopolis. Michael Shishman managed to recover most of the lost fortresses, but Plovdiv fell to the Byzantines in circumstances that Božilov calls absurd.

At the start of his reign Ivan Alexander exploited the Byzantine civil wars to recover Plovdiv and several towns in the northern Rhodopes. In 1344, when Anne of Savoy's regency was threatened by John Kantakouzenos, the empress asked the Bulgarian tsar for help. As his price Ivan Alexander demanded nine fortresses at the foot of the Rhodopes and in the Upper Thracian plain — among them Plovdiv, Stanimaka, Tsepina, Krichim and Perushtitsa. The empress agreed readily, since these towns might at any moment have gone over to Kantakouzenos anyway.

Bulgarian rule did not last long. Having taken Didymoteichon, the second city of Thrace, the Ottomans advanced up the Maritsa. The assault was led by Lala Shahin, a comrade-in-arms of Suleyman Pasha, who took Plovdiv in 1363 and made it his headquarters. According to tradition he was rewarded with the title of beylerbey of Rumelia — the name the Turks gave to the empire's European provinces. From here the campaigns against Sredets and northern Bulgaria would later set out.