Further Stability Problems and External Conflicts
At home Ivan Alexander compromised the internal stability of his realm by divorcing his first wife Theodora of Wallachia (in about 1349) and marrying a converted Jew, also named Theodora. The new marriage produced new sons, whom Ivan Alexander proceeded to crown co-emperors, Ivan Šišman in about 1356 and Ivan Asen V by 1359. Ivan Alexander's last surviving son from his first marriage, the co-emperor Ivan Sracimir, became effectively independent around 1356; and Ivan Alexander's control over other powerful vassals, such as the rulers of Wallachia and Dobruja, who pursued their own foreign policies, was hardly stronger.
From the middle of the 14th century, Bulgaria fell prey to the aspirations of the Angevin king Louis I of Hungary, who annexed Moldavia in 1352 and established a vassal principality there, before conquering Vidin in 1365, and taking Ivan Sratsimir and his family into captivity.
In the meantime Bulgarians and Byzantines had clashed again in 1364. In 1366, when Emperor John V Palaiologos was returning from his trip to the west, the Bulgarians refused to let him pass through Bulgaria. This stance backfired, as another Byzantine ally, Count Amadeus VI of Savoy, leading the Savoyard crusade, captured several Bulgarian maritime cities in retaliation, including Ankhialos (Pomorie) and Mesembria (Nesebǎr), though he failed to take Varna. Outmanoeuvred, Ivan Alexander was forced to make peace.
The captured cities were turned over to the Byzantine Empire, while Emperor John V Palaiologos paid the sum of 180,000 florins to Ivan Alexander. The Bulgarian emperor used this sum and territorial concessions to induce his at least de jure vassals Dobrotica of Dobruja and Vladislav I of Wallachia to reconquer Vidin from the Hungarians. The war was successful, and Ivan Sracimir was reinstalled in Vidin in 1369, although the Hungarian king forced him to acknowledge his overlordship.
The relatively successful resolution of the crisis in the northwest did nothing to help recover the losses in the southeast. To make matters worse, in 1369 (the date is disputed), the Ottoman Turks under Murad I conquered Adrianople (in 1363) and made it the effective capital of their expanding state. At the same time, they also captured the Bulgarian cities of Philippopolis and Boruj (Stara Zagora). As Bulgaria and the Serbian princes in Macedonia prepared for united action against the Turks, Ivan Alexander died on February 17, 1371. He was succeeded by his sons Ivan Sracimir in Vidin and Ivan Šišman in Tǎrnovo, while the rulers of Dobruja and Wallachia achieved further independence.
Read more about this topic: Ivan Alexander Of Bulgaria
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