Tsar Ivan Alexander was the tsar with the unhappy fate of watching the medieval Bulgarian state fade away. The Despot of Lovech Ivan Alexander took the throne triumphantly in 1331, having ousted Tsar Ivan Stefan, Anna-Neda's son.
The first decade of the reign of Mihail Shishman's nephew showed no sign of the impending decline of his state. He was successful in his battles with Bulgaria's eternal enemy, Byzantium, and a number of fortresses in Thrace and the Khodopes came under his rule. In the summer of 1332, the Bulgarians defeated the Byzantine army at Kusocastro, south of the Balkan range, and the Byzantine emperor was compelled to sue for peace. Ivan Alexander wisely interfered in the power struggle in Byzantium, seeking a middle road between the mighty Serbian King Stefan Dusan and the Basileus.
Bulgaria's involvement in the civil war in Byzantium in 1341-1347 restored Bulgaria's sovereignty over nine towns and strongholds in Thrace and the northern side of the Rhodopes. However, Bulgaro-Byzantine relations worsened. Distrust was poisoning the relations with Serbia. Indeed, the tsar did not possess outstanding talents as a politician and a diplomat.
However, Ivan Alexander was the patron of artists and men of letters and he commissioned the construction of many churches and monasteries. In intellectual pursuits, he was comparable to Simeon the Great. He followed closely the conflicts between the different religious schools. He was responsible for the establishment of the educational center in Turnovo, which along with the monasteries became a focal point of the literary activity of some of Bulgaria's most outstanding men of letters at that time. Religious literature thrived, as did apocrypha. Craftsmen and artists portrayed the tsar in gospels and chronicles, among which two manuscripts of extreme beauty have been preserved: the London Gospel and the Vatican copy of the Chronicle of Manasses.
However, Ivan Alexander failed to cope with the ambitions of his boyars to rule independently in their lands. Dobroudja was about to break away from the state. The despots in southwestern Bulgaria were constantly waging wars among themselves. With his father's blessing, Ivan Sratsimir, Ivan Alexander's son from his first marriage, was crowned Tsar in Vidin. There were no large and strong towns to lend the tsar support against his external enemies and against the internal struggles. The continual internecine fights and the wars with Byzantium exhausted the state's economic and defence potential. In a fragmented and declining state the power of Tsar Ivan Alexander was waning.
It was then that the threat of the crescent impended over the Balkans and Bulgaria. The Turkish invasion of the Balkans took an agonizing decade to complete, and the Bulgarians were among the first to face the infidels' onslaught. In 1352 the invaders took the fortress of Zimpe, establishing an important forepost in Europe. The same year Ottoman hordes raided and pillaged southeastern Bulgaria, while Tsar Ivan Alexander was unable to put up serious resistance. Two years later they raided the country again and Ivan Alexander's son Mihail Assen was killed in battle.
Ivan Alexander's men were crossing swords with the Turks every year now. At the beginning they were raiding mainly Byzantine towns and villages and only occasionally clashed with the Bulgarian army, mostly in the border areas. The tsar was desperately trying to avert the threat by entering short-lived alliances and by cautious diplomacy.
In 1335 the son of the Byzantine Emperor Andronicus V Paleologus was engaged to the Bulgarian Tsar's daughter Keratsa. The betrothal document issued by the patriarchate said that "it would be beneficial to the Christians: Byzantines and Bulgarians, and pernicious to the infidels (the Turks)". But the alliance between the two Christian states was not durable and strong enough to ward off the advance of Sultan Murad's troops. In 1364 the centuries long enmity between Bulgaria and Byzantium led to another brief clash. Meanwhile, the Byzantine empire was collapsing under Ottoman pressure. Bulgaria's turn was next, as it had become the major obstacle to Ottoman advancement to Central Europe.
Against the most dangerous and destructive force during the Middle Ages, Ivan Alexander could only offer the resistance of a country torn by internecine strife. Neither he, nor the rulers of the neighboring Christian states realized the importance of unity against the common enemy. The Balkan rulers were too selfish and shortsighted to unite their efforts.
Thus the energetic Sultan Murad easily conquered almost the whole of Thrace. A temporary agreement with Ivan Alexander only postponed the inevitable. The Bulgarian tsar warred with Byzantines and Savoy knights for the Black Sea fortresses, with varying success. Then Bulgaria was hit by another calamity: the Hungarian king seized the north-western lands. The death of Tsar Ivan Alexander in early 1371 seemed to be a sign that the Second Bulgarian state was coming to an end.