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| 1218–41 |
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| JOHN ASEN II, whose reign marked the apogee of the Second Bulgarian Empire. John was a mild and generous ruler, much beloved even by the Greek population. | 1 |
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| 1228–30 |
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| Owing to the youth of Emperor Baldwin II, a number of Frank nobles at Constantinople proposed making John Asen emperor, thereby securing themselves against the aggression of Theodore of Epirus (See 1230). The scheme was opposed by the Latin clergy and ultimately came to nothing. | 2 |
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| 1230 |
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| John Asen defeated Theodore of Epirus at Klokotnitsa and captured him. He then occupied all of western Thrace, Macedonia, and even northern Albania, leaving Thessalonica and Epirus to Theodore's brother Manuel, who became his vassal. | 3 |
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| 1235 |
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| Alliance of John with the Greek emperor of Nicaea against the Franks. The Bulgars broke with Rome, their church became independent, and the Greeks recognized the patriarch of Tirnovo. Together the allies besieged Constantinople, which was relieved by a fleet and forces from Achaia. | 4 |
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| 1236 |
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| The Hungarians, instigated by the pope, began to threaten the Bulgarians and forced John to withdraw from operations against the Latin Empire. | 5 |
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| 1241–46 |
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| Kaliman I, the son of John Asen II. His reign was distinguished chiefly by the great incursion of the Mongols, returning from the expedition into central Europe (1241). | 6 |
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| 1246–57 |
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| Michael Asen, the youngest son of John, and a mere child. The Nicaean emperor, John Vatatzes, took advantage of the situation to conquer all southern Thrace and Macedonia, while Michael of Epirus appropriated western Macedonia. | 7 |
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| 1254 |
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| On the death of John Vatatzes, Michael Asen attempted to recover the lost territories, but he was badly defeated by Theodore II Lascaris at Adrianople and later (1255) in Macedonia. | 8 |
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| 1256 |
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| Kaliman II, who, with support of the boyars, drove out Michael Asen, only to be deposed and expelled in his turn. (See The Byzantine Empire) | 9 |
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