The Republic of South Africa has long been celebrated by global audiences because of the peaceful transition from Apartheid rule to multiparty democratic and non-racial rule. The African National Congress and President Nelson Mandela came to symbolize the best of this post-1994 moment. Yet, two decades removed from this momentous occasion the ANC government finds itself unable to generate the type of economic development needed to address historical problems such as mass unemployment (especially among black youth) and poor spatial planning. This chapter seeks to explore why despite having some of the most vaunted constitutional and liberal policies and institutions, the ANC-led government is failing to effect the requisite economic development policies to address mass unemployment among black citizens. Moreover, why have township areas failed to be transformed into geographic areas of economic excellence? This chapter puts forward that in order to address this lack of economic development in township areas, the ANC-led government needs to utilize economic entrepreneurship as the catalyst for improving South Africa’s dire economic situation. In perusing this objective, the South African government might have to do this by renegotiating some of its core liberal constitutional ideals and practices.