Decisions regarding livelihoods, land and natural resource management are embedded in the traditional institutions and societal structures of the Maasai communities that have been in dynamic interaction with hegemonic forms of state-building during the colonial and post-colonial periods in Kenya. The Maasai's fraught interaction with and cautious response to change, often portrayed and interpreted as being conservative and repugnant to modernization and/or maendeleo (development), is critical in understanding their response to contemporary mega-development enterprises now mushrooming in the erstwhile marginal frontiers of Kenya. This study examines these larger dynamics in the context of the nexus between development, conservation and community livelihoods in the contested landscape of Olkaria. By locating this study in a historically significant site but also an area of large-scale international and state investment in natural resource extraction, I analyze the historical and current threads that intricately but fractiously weave together geothermal development, wildlife conservation, and community well-being as well as claims and struggles of belonging. Four villages - Olomayiana, RAPland and Mt. Suswa- were purposefully selected for the study. A mixed method approach that entailed ethnographic methods such as focus group discussions, interviews and participant observation were employed to collect data. The data was qualitatively analyzed in a thematic scale using enkishon (well-being)-based Maasai philosophy as a frame to deeply understand the extent to which decision making/leadership (erikore), environmental governance (eramatare) and rights-based development (esipata) have been shaped by geothermal development in the area of study. The findings of this study show that geothermal development and wildlife conservation are incompatible as the former is privileged over the latter to the detriment of wildlife well-being. The study shows how the Kenyan government, investors, and donors promote geothermal as environmentally friendly, while documenting how local Maasai consider the environmental effects of wastewater, fumes and noise at the local scale to be harmful to their health, wildlife and livestock. Additionally, the study shows that geothermal fields require expansive space hence dispossession and displacement leading to heightened human rights violation, limited employment and little economic returns at the local scale culminating in compromised livelihoods that destabilize the Maasai enkishon of well-being.