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Empire of Thessalonica, Thedore Comnenus-Ducas, 1224 - 1230
In 1217, Theodore, then Despot of Epirus, captured the Latin Emperor of Costantinople, Pierre II of Courtenay, while he attempted to pass through Epirus on his return from his coronation by the Pope in Rome. In 1220 Theodore took Beroia, and in 1221 Serres and Drama. In 1224 Theodore completed his conquest of the Kingdom of Thessalonica by taking its capital. Elated by his success, Theodore had himself crowned as the Byzantine emperor and set his sights on Constantinople. Theodore's forces advanced through the Aegean coast of Thrace and in 1225 seized Adrianople and the surrounding portions of Thrace from the Nicaeans. Worried by the alliance of Ivan Asen II of Bulgaria with the Latin Empire of Constantinople, Theodore broke his own treaty with Ivan Asen and invaded Bulgaria with a large army reinforced by Western mercenaries in 1230. Allegedly affixing the text of the broken treaty to one of his spears as a flag, Ivan Asen II rallied his troops and defeated Theodore in the Battle of Klokotnitsa on March 9, 1230. Theodore was captured and remained a prisoner in the Bulgarian capital Tarnovo for seven years. At some point during his captivity he became involved in a conspiracy and was blinded. Theodore's lands were divided between Ivan Asen II (who took over Thrace, Macedonia, and Albania), Theodore's brothers Manuel (who took Thessalonica) and Constantine (who took Acarnania), and Theodore's nephew Michael II (who took Epirus).