This paper is intended to analyze the contributions of Contextual Theology and Contextual theologians to dismantling the South African apartheid system. It is intended to demonstrate that the South African churches failed to effectively politicize and radicalize to confront the government until the advent of Contextual Theology in South Africa. Contextual Theology provided the Christian clergy the theological justification to unite with anti-apartheid organizations. Its very concept of working with the poor and oppressed helped the churches gain favor with the black masses that were mostly Christian. Its borrowing from Marxist philosophy appealed to anti-apartheid organizations. Additionally, Contextual theologians, who were primarily black, began filling prominent leadership roles in their churches and within the ecumenical organizations. They were mainly responsible for radicalizing the churches and the ecumenical organizations. They also filled an important anti-apartheid political leadership vacuum when most political leaders were banned, jailed, or killed.