Neoliberal globalization can threaten the growth of a global civil society that sanctions power-sharing arrangements. Yet, scholarship that focuses unidirectionally on global processes may in effect eviscerate the transformative power of the local. To counter this tendency, this dissertation examines the interrelationships between contextualized and historically-specific experiences in South Africa and transnational processes through a case study of social entrepreneurship, an emerging global justice movement. Drawing on a 12-months institutional ethnography of Sonke Gender Justice, a transnational social entrepreneurship NGO working to achieve gender equality, prevent gender-based violence and reduce the spread of HIV/AIDS in Southern Africa, this dissertation explores the gendered dimensions of identity construction under conditions of neoliberalism. I look at the ways in which a transnational discourse of masculinity unfolds and is confronted locally as an essential element of the neoliberal project. I argue that, in Africa, the developmentalist agenda of neoliberalism is integrally tied to the demonization of black masculinity, posed as a problem. This acts to elide the ways in which factors of oppression intersect in the manufacture of a patriarchal, sexist, racist and homophobic society, negating any effort to promote healthy gender relations. The dissertation concludes that global discourses and scholarship on African masculinity need to be informed by African women’s lived experiences, survival strategies, and aspirations for gender and racial democracy in order for the development of a truly transformative gendered democracy to occur. This can be accomplished by sound and detailed ethnographic work that engages with the messiness and fluidity of cultures, knowledges, and practices on the ground. This approach opens up spaces of possibilities and visibility for an array of local renegotiations, borrowings, and frank resistances. My conclusion acknowledges the potential for significant contributions to global civil society’s struggle for justice and for transformation when transnational solidarity projects are inserted into local formations. However, these goals can only be accomplished when there is acknowledgement and engagement of the practical ways in which local agents try to negotiate and reformulate transnational discourses and challenge neoliberal representations.