This paper investigates the impact of narratives from English witnesses of Ivan IV’s – the Russian Tsar also known as “the Terrible”—violent expansionism into the Muslim khanates of Central Asia during the 1550s and 1560s. In particular, the subjugation of the Muslim khanates situated in the border zone between the predominately Christian regions west of the Volga and the predominately Muslim regions eastwards marks the beginnings of Ivan’s expansion into Central Asia. Populated by various Tatar tribes, they became a target for Ivan due to accelerating Ottoman expansion into the Balkans and around the Black Sea after their conquest of Constantinople in 1453, which until that time had been the center of the Orthodox Christian world. When Ivan took up that mantle, he also aggressively occupied the khanates of Kazan (1552) and Astrakhan (1556), which he had managed prior through puppet rulers and a policy of assimilating (converted) Tatars. The first Englishman to land in Russian territories, Richard Chancellor, arrived in the midst of these bloody campaigns (1553). Subsequent travelers, most notably Anthony Jenkinson, who became an “ambassador” of sorts between Queen Elizabeth and the Russian, Central Asian, and Persian rulers he met on his several voyages, also deplored this expansionist violence. Jenkinson witnessed the aftermath of this violence on his eastward journey of 1558, where he observed “[h]eaps of dead Nagayans [Nogai Tatars] lay unburied over the island on which Astrakhan is built, and many of the survivors were offered as slaves” for the price of “a loaf of bread.” Jenkinson and the other early English travellers' accounts are important as often the only extant records of these events. Furthermore, these accounts from the 1550s and 1560s were subsequently published in Richard Hakluyt’s The Principal Navigations, Voyages, Traffiques and Discoveries of the English Nation (1599–1600), which sought to provide precedents to spur the “sluggish” English onto imperialist efforts similar to the Iberians and, as he suggests by commencing his collection with “the worthy Discoveries, &c. of the English toward the North and Northeast by Sea,” the Russians. This paper thus proposes to show, using the model of “frontier orientalism” for European regions that had experienced Islamic imperialism in the past even as they sought to participate in the modern Western European imperialist project, how the accounts of the English merchants who witnessed the impact of Ivan’s massacres introduces dissonance into Hakluyt’s proto-imperialist “epic of the English nation.”