Why does South Africa underperform on benchmarks for nascent entrepreneurship? We use a contextualization framework to evaluate articles on entrepreneurship in South Africa, which appear in seven leading global entrepreneurship journals for the period 1986–2017. The literature is then discussed using a six-dimension contextualization framework. The historical and institutional dimensions of the contextualization framework unveil the path-dependent nature of entrepreneurial choice for Black South Africans. Understanding entrepreneurship in South Africa requires research designs that focus on where and when entrepreneurship developed in the country to render meaningful the why of entrepreneurial choices made by Black South Africans. This study illustrates the idiosyncratic nature of South Africa and its social, political and economic transitions, and how these have affected entrepreneurship development, particularly among previously disadvantaged Black South Africans. The nature of the South African case has broader impact and importance for developing and transitional economies.