Regional integration has manifested itself historically in Africa as institutional anchors of economic and political development. In Southern Africa, attempts to achieve regional integration using the Southern African Development Community (SADC) and the Southern African Customs Union (SACU) are riddled with contradictions. Highlighting these contradictions, the paper shall indicate that while regional integration presupposes complementary economic policies and productive structures in Southern African, economic nationalism, mono-cultural production of raw materials, widespread poverty, low productivity, belligerent conflicts, unjust international economic structures; chronic debt; lack of infrastructure, uneven distribution of the benefits of integration, multiple membership to regional organizations among others militate against regional integration resulting in so much inertia but little progress. Compounding these challenges are the failure to adequately address certain conceptual, strategic and practical issues by the SADC, which has led to lack of commitment and political will among member states, as well as the dynamics of globalization which provides the context within which the SADC operates. The paper equally indicates that the role of South Africa in the integration process is ambiguous, with limited inclination to come to terms with the rest of the region. Development cooperation can contribute to deep integration in the region only if member countries have the political resolve to transfer substantial sovereign powers to the regional institutions. Secondly, there is need for a fundamental change in the SADC’s strategies of economic development from being mere producers of raw materials and passive consumers of manufactured goods to dynamic and industrially diversified economies. Keywords: Regionalism, Regional Integration, Southern African Development Community, Southern African Customs Union, Economic Political development.