Literarily, Peter Abrahams’ endeavours to capture the dilemma of Black man in South Africa as a critical problem. From the context of corruption, deceit, injustice, insecurity, insincerity, indiscipline and cheap popularity, the novelist portrays how the economic, social, political and host of other state systems have been bastardized. Most African leaders oppress and rule through the force of arms; instances could be seen in Empror Bukasa of Central African Republic (CAR), Sese-Seko of Congo, Abacha of Nigeria, Samuel Doe of Liberia, Gaddafi of Libya just to mention a few. These people became oppressive in their different countries. Moreso, this paper attempts to analyze and critically examine the two texts in view of the above topic: TELL FREEDOM AND MINE BOY would be examined from two approaches that is, empirical and descriptive. Finally, this paper concludes that Black man in South Africa has lost his essence (then) from his groaning under the cobweb of the white man. In view of this, the way out would be critically examined.