Tsar Ivan Shishman was the last ruler of the Second Bulgarian Empire, reigning from 1371 to 1395. He came to power during a turbulent time when the empire faced threats from the Ottoman Empire and internal strife. His reign was marked by efforts to defend Bulgaria against foreign invasions and maintain its independence. Despite his efforts, Ivan Shishman ultimately could not prevent the fall of Bulgaria to the Ottomans. In 1393, the capital, Tarnovo, was captured, and he was forced to flee. His reign is often remembered for the challenges faced by Bulgaria during this period of decline.