Tsar Ivan Shishman

Ivan Shishman was tsar of Bulgaria from 1371 to 1395. He was the son of Tsar Ivan Alexander and the Jewish woman Theodora.

Early in his reign, Tsar Ivan Alexander proclaimed his firstborn son Michael Asen co-ruler and heir. After Michael Asen died in battle with the Turks, the question of succession to the throne arose. Because Ivan Shishman had been born after his father's accession, he was designated heir to the throne. In early 1371, immediately after his father's death, Ivan Shishman was crowned tsar.

During his reign, Bulgaria experienced a difficult period. The Battle of Chernomen took place in 1371, and the united Christian forces suffered defeat at the hands of the Ottoman Turks. After this defeat, Tsar Ivan Shishman withdrew behind the Balkan Mountains.

The Ottomans continued their raids and conquered territories in Thrace, reaching Kostenets and Ihtiman in 1378. The tsar of Tarnovo was required to acknowledge Turkish vassalage and give his sister Kera Tamara of Bulgaria as a wife for the sultan's harem. Between 1380 and 1385, Lala Shahin, an Ottoman commander of Greek origin, besieged and captured Sofia.

In 1387, the Bulgarians, united with Serbian and Bosnian forces, defeated the Turks at the Battle of Pločnik. However, around 1388–1389, the Ottoman army, led by Grand Vizier Ali Pasha, captured territories in Dobruja, including the towns of Preslav, Shumen, Pliska, Cherven and others.

Ivan Shishman moved his capital to Nikopol and submitted as a vassal to Sultan Bayezid I. In 1393, after a siege, Tarnovo was conquered by the Ottomans. In the following years, Ivan Shishman ruled Nikopol and was formally the sultan's vassal.

On 3 June 1395, after Nikopol had been captured by the Ottomans, Ivan Shishman was killed. He sought refuge in an alliance with the Hungarians and participated actively in the battle at Rovine in Wallachia, where the Ottomans suffered defeat. As a result of treachery in Tarnovo, the city was conquered by the Ottomans, and Tsar Ivan Shishman perished. One of the last Bulgarian rulers, he ruled until 1395, when Bulgaria fell under Ottoman rule.