In South Africa, the response to HIV and TB epidemics is complex, varied, and contextually defined. “Task-shifting” and a movement toward a decentralized model of care have led to an increased reliance on community health workers (CHWs) providing health care services to residents of impoverished, peri-urban areas. Public health policy tends to present CHWs as a homogeneous group, with little attention paid to the nuances of experience, motivation, and understanding, which distinguish these care workers from one another and from other kinds of health workers. An exploration of the layered meanings of providing community health care services under financially, politically, and socially difficult conditions reveals clear distinctions of experience across the generations. Many older CHWs say that ubuntu, a notion of shared African humanity, is being “killed off” by the younger generation, whereas younger CHWs often describe older women as being “jealous” of the opportunities that this younger generation has for education, training, and employment. The structure of the South African health system, past and present responses to disease epidemics, and the legacy of apartheid’s structural violence have amplified these generational differences among CHWs. Using ethnographic data collected from approximately 20 CHWS in a peri-urban settlement in Cape Town, South Africa, I explore how CHWs experience and understand legitimacy in the moral economy of care. A call for closer attention to the experiences of CHWs is critical when designing public health policies for the delivery of health care services in impoverished communities in South Africa.