Enos John Nganani Mabuza‟s life and work is used as a case study to highlight the conceptual and methodological theories and challenges in academic biographical writing regarding history, memory and legacies. This thesis answers the question: Who was Mabuza and what is his place or relevance in South Africa‟s history? We over-simplify and stereotype people because it is convenient. We judge others but there is no saint without a past or a sinner without a future. Mabuza reconciled with the main liberation movements and moved from a maligned position on the political fringes to a respectable one within the emerging black economic elite. History, like reference systems and values is not calcified or static. It is prone to interpretation, adaptation, modification, invention, manipulation, decomposition and re-composition. Bourdieu‟s habitus-field analysis, theory or logic of practice, notions of capital (symbolic, political, social, cultural and economic) is used together with Latour‟s actor-network theory as the basis of analysis of the social contracts and trust bonds that Mabuza was able to create and which enabled him to navigate South Africa‟s socio-political and economic milieus during apartheid and the transition in the early 1990s. As people or actors, we believe in the mantra, nothing ventured, nothing gained. We exercise agency and take risks every day. We make choices and those choices have consequences. Mabuza‟s choices in the fields of education, politics and business had implications for how he is perceived or has been written into history. His choices put notions of identity, citizenship, power, legitimacy, ambition, elite accommodation, class, personal and professional networks, popular struggles, agency and structure under the spotlight. Mabuza‟s involvement in Bantustan politics, for instance, is contextualised in terms of a historical overview of the unpopular role played by traditional authorities in South Africa before and during colonialism and apartheid. His later foray into the world of business, however, was facilitated in part, by the personal and professional contacts that he made whilst he was in politics and the opportunities which opened up during the country‟s political transition. Mabuza adapted to changing circumstances and demonstrated a level of versatility which other Bantustan functionaries did not or could not exercise.