The purpose of the research was to indicate how strategically driven CSR in the retail sectorcan improve social and environmental well-being. A qualitative comparative case studydesign was followed. Through the literature review in the first phase, three previouslyunrelated components, namely Warren’s (2003) evolution of business legitimacy theory,Jensen’s (2001) three descriptors of the company as an agent in society; and Holmström’s(1997) social systemic Public Relations paradigm, were combined to develop a theoreticalframework against which the websites and the annual and sustainability reports of threeSouth African retailers were analysed in the second phase. Analyses were done at twolevels: the degree to which community relations and governance issues were representedat strategic level and the achievement of specific impact objectives at technical level. All threeretailers channelled CSR activities through either a foundation or a trust registered as a non-profit entity. This could be indicative of the importance assigned to their CRS initiatives.An ability to adapt to changes in the macro environment and surviving economic, politicaland social challenges was demonstrated.