Kaloyan took immediate advantage of his victory at Adrianople and tried to free the whole of Thrace. In 1207, the Bulgarian army besieged Salonika, but Kaloyan was dastardly murdered by a hired killer. The throne was then occupied by Tsar Boril who became famous not for his military exploits, but rather for his persecution of the Bogomils. In 1218 he was overthrown and the crown went to its legitimate heir – Ivan Assen II, son of Assen I, the founder of the Second Bulgarian Kingdom.

Ivan Assen II proved worthy of the memory of his father, and during his reign Bulgaria reached its former might. What is most remarkable about Ivan Assen II is that he, like Prince Boris before him, achieved most of his successes by peaceful means. He became guardian of the under-aged Latin Emperor Baldwin II, concluded peace with the Epirian ruler Theodor Comnenus and through well calculated dynastic marriages established lasting peaceful relations with Hungary and Serbia.

The only war of any significance waged by Bulgaria during the reign of Ivan Assen II was that with the Despot of Epirus, Theodor Comnenus, who had made it his aim to restore the past grandeur of the Byzantine Empire. Per-fidiously, he broke in L230 his peace treaty with Bulgaria and invaded South Bulgaria at the head of a numerous army. His perfidy, however, was justly punished. In the bloody battle which was fought near the village of Klokot- nitsa (northwest of the town of Haskovo) his army was routed and Theodor Comnenus himself was taken prisoner, together with his entire retinue.

The Bulgarians had not forgotten the inhuman cruelty of Basil II, but their King proved that he was a strong and wise man by displaying great magnanimity. He freed all prisoners, Theodor Comnenus included, without touching a hair of their heads. The Bulgarian state annexed new vast territories and again, as during Simeon's reign, its frontiers came out on three seas: the Black, the Aegean and the Adriatic.

The reign of Ivan Assen II was marked not only with the restoration of Bulgaria's former political might, but also with a remarkable economic and cultural upsurge. Animated handicraft and urban centres appeared, new commercial roads and public buildings were built. Ivan Assen II was the first Bulgarian king to mint his own coins. In 1253 he signed a trade agreement with the flourishing at that time Dalmatian city of Dubrovnik (Ragusa), which contributed a lot to boosting economic life in the country.

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