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1230 Battle of Klokotnitsa ★ ★ ★ ★ ★
Outcome: A crushing defeat of the Byzantines of Epirus by the Bulgarians 9 March 1230
War  &  Enemy: Enemy:
Bulgarians
War:
Epirote-Bulgarian Wars
Battle Type:
Pitched Battle
The Battlefield Klokotnitsa Location:
In Klokotnitsa, near modern Khaskovo in south Bulgaria
Modern Country:
Bulgaria
  The Byzantines(emperor:  John III Doukas Vatatzes) The Enemies
Commander: Emperor Theodore Komnenos Doukas of Epirus Tsar Ivan Asen II
Forces: A large army Unknown (outnumbered)
Losses: Heavy, only a few escaped Unknown
Background story: Initially in the service of Emperor Theodore I Laskaris of Nicaea, Theodore Komnenos Doukas joined his half-brother Michael I in Epirus in c. 1210. Michael had founded the so called Despotate of Epirus in 1205. The Despotate was one of the Byzantine Greek successor states of the Byzantine Empire which were formed after the conquest of Constantinople by the "Latin" crusaders in 1204.
When Michael was murdered, Theodore took his place and embarked on a policy of aggressive expansion after allying himself with Serbia and the Albanian clans. Taking advantage of the temporary weakness of Bulgaria and the Latin Kingdom of Thessalonica, Theodore seized most of Macedonia and Thessaly in c. 1216. In 1217, when the new Latin Emperor Peter II of Courtenay attempted to cross through Epirus to reach his lands, Theodore defeated and captured him.

Around 1221–1222 the Bulgarian Tsar Ivan Asen II made an alliance with Theodore . Secured by the treaty, Theodore managed to conquer Thessalonica from the Latin Empire and he was crowned Byzantine Emperor, although he was not recognized by the rest of the Greeks.
After the death of the Latin emperor Robert of Courtenay in 1228, Ivan Asen II had the ambition to become regent of the new Latin Emperor Baldwin II. Theodore, on the other hand, considered the Bulgarians the last obstacle on his way to the throne of Constantinople and in the beginning of March 1230 he invaded Bulgaria, breaking the peace treaty.
The Battle:
Klokotnitsa
Theodore Komnenos gathered a large army including western mercenaries. He was so confident for his victory that he took the whole royal court with him including his wife and children. His army moved slowly and plundered the villages on its way. When the Bulgarian tsar learned that the state was invaded, he gathered a few thousand men and quickly marched southwards.
On 9 March, the two armies met near the village of Klokotnitsa. Ivan Asen II applied clever tactics and managed to surround the enemy who was surprised to meet the Bulgarians so soon. The battle continued until sunset. The Byzantines of Epirus were completely defeated, only a small force under the despot's brother Manuel managed to escape the battlefield. The rest were killed in the battle or captured.
Noteworthy: Ivan Asen II ordered the broken treaty to be stuck on his spear and used as a flag.
Aftermath: Theodore was taken prisoner and was blinded. He remained a prisoner for 7 years and was released when Ivan Asen married his daughter Irene. He soon took the rule of Thessalonica back from his brother Manuel.