Kenya’s recent democratic challenges have not only questioned its commitment to the democratic process, but the economic development course as well. While Kenya has made some important strides in its development, questions of inequality and marginalization still linger. What features of Kenya’s political culture threatens democracy and inclusion? Can Ghana’s democratic experiences offer any insights or serve as guideposts to Kenya’s political course? Through the conceptual overview of democracy and development in Africa, this chapter analyzes Kenya’s democratic trajectory in historical, political, and economic contexts, and assesses the features of the country’s sociopolitical challenges in its democratization path.