We examine and reflect on the historical development of corporate social responsibility (CSR) and some of its variants, such as corporate citizenship, benevolence, and philanthropy, in a Kenyan context. The conceptualization and operationalization of CSR in Kenya is still in its infancy, and CSR therefore remains a largely misunderstood, misused and abused concept. This is captured in the various CSR definitions and applications that situate its contextual understanding in the Kenyan political-legal and socio-cultural nexus. Drawing parallels from the local cases of Safaricom and Delmonte, we examine CSR at the macro, meso, and micro levels, and discuss some of the perceived challenges and barriers to effective CSR. The following stakeholders are examined: Government, employees, communities, customers, and shareholders. In addition, the prospects for moving the CSR agenda forward are explored, along with the social, political, managerial, and research implications of CSR in Kenya.