In this paper, I show the complex and fluid relationship between the colonial administration, the chiefs and headmen and the local communities of Turkana, in Northwestern Kenya. I focus on how the chiefs navigated the colonial contact zone; the dilemmas and challenges they faced, and how they over time appropriated the structure of chieftaincy and learned the language and practices of the colonial system, and used them to meet their own ends. The act of negotiating the local and administrative demands and expectations was a delicate balancing act for the chiefs. Representing the interests of the local communities and fulfilling colonial duties were at times polar opposites, and decisions about loyalties were crucial matters of life and death. To illustrate these dynamics the paper presents the cases of two Turkana chiefs, Abong and Ekadille, who both negotiated the politics of power relations in Turkana, however in different ways. They imbued the colonial structure of chieftaincy with meaning, concrete actions, words, and silences vis-á-vis the European officers and the local communities. This was done in a dynamic dialectic process between the local communities, the colonial administration, and the chiefs’ own ambitions.