This paper will analyze the objectives, policies, and strategies of the four North Caucasus rulers who submitted both to the Ottoman sultan and the Muscovite tsar either simultaneously or at different times during the second half of the sixteenth century. The local chiefs to be examined are Solokh of the Kabardinians, Kansavuk and Sibok of the Janeys, and Urus of the Greater Nogays. Since no sources written in the local languages of the North Caucasus are extant, any study of these regional actors and their strategies has to be based on Ottoman and Muscovite sources. This presentation, therefore, relies on the Ottoman mühimme defters (registers of important affairs), materials of the Muscovite Posol’skii prikaz (Ambassadorial Office), and Ottoman and Russian chronicles. A comparative analysis of these sources allows us to achieve a more precise understanding of the internal mechanisms and functioning of the North Caucasus polities in relation to the expanding imperial powers. The prevailing scholarly opinion has held that the North Caucasus rulers—be they Adyghe, Kabardinian, or Daghestani chiefs—tried to gain utmost advantage out of the imperial rivalry over their territories among the Ottomans, Muscovites, and Safavids. They were “greedy” and “needy” and consequently always in pursuit of higher salaries, loftier titles, and more gifts from the rival powers. Pledges of allegiance meant little to these rulers who broke their promises easily and even changed their religion whenever that promised greater reward. The paper proposed, however, will challenge this interpretation. The perceived “greediness” should be understood as a reflection of the Ottomans, Muscovites, and Safavids trying to outbid each other by offering the North Caucasus rulers titles, salaries, and gifts. The “neediness” of North Caucasus polities is clearly contradicted by the fact that they occupied a strategically advantageous location controlling several important trade routes and were the source of slaves, renowned swords, and many other goods and raw materials. This paper will argue that the North Caucasus polities under discussion were largely self-sufficient economically, but they had no choice but to play double in order to preserve their power and authority in the face of the imperial rivalry between the Ottomans and Muscovites. The paper will also explore the meaning of the Ottoman-Muscovite imperial rivalry from the perspective of the North Caucasus rulers and ruling families.