King Ivan Shishman (1371- June 3 1395)

Ivan Shishman, Ivan Alexander's firstborn son succeeded his father to the throne in Turnovo in 1371, but the state had become a shadow of one-time great Bulgaria. Almost all ties with the other two Bulgarian states, Ivan Sratsimir's Vidin principality and the Dobroudja principality of Despot Dobrotitsa, had been severed. Ivan Shishman's struggle to survive under the pressure of the Ottoman offensive soon turned into a desperate and valiant, though hopeless fight. The Turks ravaged the Bulgarian lands, leaving terror and ruin behind them. Ivan Shishman watched them conquer Macedonia and the Rhodopes, aware that he was not strong enough to help Bulgarian strongholds in the Rhodopes against the assailants. Northern Thrace and the Zagore region also fell prey to the invader. Ivan Shishman himself, in the face of the common threat, found it hard to extend a hand to his neighbors. He was compelled to make peace and to suffer the humiliation of becoming vassal to the Sultan, even allowing the Sultan to marry his sister Kera Tamara. Soon afterwards the Turks violated the treaty. After heavy fighting, Ivan Shishman surrendered Ihtiman, Samokov and Sofia. He fought desperately to defend the western part of the Balkan range, but Murad's troops overran Nish and Prilep and headed for the heart of the Balkans. Only then did Ivan Shishman and the other Balkan rulers manage to join forces. In 1387 the allied Christian forces routed the Turks at Plocnik (Serbia), proving that the Sultan's army was not immune to defeat. However, the Turkish army, once recovered from the defeat, took the offensive again. In July 1393, after three months in siege under the courageous leadership of Patriarch Euthymius, the capital Turnovo finally fell. In the besieged stronghold of Nikopol, the Tsar heard of the massacred boyars and of the population sold as slaves. Ivan Shishman held this last piece of Bulgarian land in the ancient fortress on the Danube for months, while Turkish attempts to crush the resistance failed. But so did Ivan Shishman's efforts to form an alliance with the Hungarian King Sigismund against the Turks. He watched the principality of Dobroudja collapse and the invaders close the ring around the Vidin kingdom. The Second Bulgarian State was perishing before his eyes. In 1395 Ivan Shishman finally succumbed to the army of Sultan Murad and died in captivity.