Ivan Shishman of Bulgaria (b. 1350)
Ivan Shishman (Bulgarian: Иван Шишман) ruled as emperor (tsar) of Bulgaria in Tarnovo from 1371 to 3 June 1395. The authority of Ivan Shishman was limited to the central parts of the Bulgarian Empire.

In the wake of the death of Ivan Alexander, the Bulgarian Empire was subdivided into three kingdoms among his sons, with Ivan Shishman taking the Tаrnovo Kingdom situated in central Bulgaria and his half brother Ivan Sratsimir holding the Vidin Tsardom. Although his struggle to repel the Ottomans differentiated him from the other rulers on the Balkans like the Serbian despot Stephan Lazarevic who became a loyal vassal to the Ottomans and paid annual tribute and participated in all of the Ottoman campaigns subsequent to the battle of Kosovo, contributing a 5,000 strong contingent of christian knights. Although Ivan Shishman has been categorized as indecisive and inconsistent in his policy in the past, this was done with little regard for an understanding of the context of the conditions and limited resources that this ruler had at his disposal. It is notable that Ivan Shishman is the only Balkan ruler for whom there is no evidence of tribute paid to the Ottoman empire or any military aid provided. Based on historical evidence and the numerous folk songs of the region glorifying his struggle against the Ottoman invaders, the image of Ivan Shishman is one of fierce and concerted resistance to the Ottoman incursions.

Regardless, in 1393 the Ottoman Turks seized the capital Tarnovo. Two years later, Sultan Bayezid I captured Nicopolis with a surprise approach from the north of the fortress after two failed campaigns in Hungary and Wallachia, summoning Ivan Shishman on the false pretense of a discussion and had him executed by beheading.

Despite the military and political weakness, during his rule Bulgaria remained a major cultural center and the ideas of Hesychasm dominated the Bulgarian Orthodox Church. Patriarch Evtimiy of Tarnovo became the most prominent cultural figure of the country. A number of texts were written or translated and an orthographic reform of the Bulgarian language was issued with synchronised rules. After the fall of Bulgaria, a number of scholars found refuge in the other Orthodox countries and brought the achievements of the Bulgarian culture to them.

His reign was inextricably connected to the fall of Bulgaria under Ottoman domination. In Bulgarian folklore Ivan Shishman is portrayed as a legendary and heroic ruler who desperately fought against the overwhelming Ottoman forces. There are numerous sites, geographical features and fortresses named after him throughout Bulgaria.