If there is a single analytical frame that over the past 15 years or more has acquired a degree of consistent use amongst analysts of foreign policy, it is the notion that South Africa is an emerging middle power. As a concept, it appeared for the first time in 1997 amid a zeitgeist of hope and renewal both in South Africa and the rest of the world. The assumed universalist triumphalism in 1989 about the supremacy of the Anglo-American model of capitalism had been replaced by a resurgence of scepticism about globalization and what it supposedly offered. Part of this process included a renewed recognition of the role of the developing world, and in particular some of its major economies or ‘emerging markets’, as key drivers of global growth. Coinciding with geo-strategic concerns, the reconfiguration of who mattered in world politics, circulated in American foreign policy circles as ‘pivotal states’ (Chase et al. 1996). Clearly the table was set to popularize the idea of ‘emerging middle powers’ in both scholarly and policy-making circles. Yet unlike traditional middle powers, identity questions complicate the extent to which emerging middle powers can affect outcomes at both the regional and international levels. To illustrate these complexities, this chapter provides a broad overview of South Africa’s past role as a middle power. Drawing on a Coxian understanding of middle power activism, I argue that this role orientation is not without contradictions and dilemmas. While there are sound reasons to believe that such a role appears to have become relatively entrenched, the demand of playing middle power in the developing world remains a daunting task. The process requires a fine balance at the intersection of four polar positions. At the international level, a normative commitment to pan-Africanism on the one hand, versus cosmopolitanism on the other. Rationalizing a middle power role domestically also entails engaging the international system in order to effect a balance between redistributive demands on the one hand, versus market-led expectations on the other. Finding means of overcoming the tensions between these positions will determine the extent to which Pretoria successfully sustains its middle power role.