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.

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. Ivan Shishman's reign was inextricably connected to the fall of Bulgaria under Ottoman domination.