This paper entitled “Suffering as a Route to Freedom: Challenging the Problem of Evil Through the Poetry of Dennis Brutus” discusses the traumatizing experiences South Africans endure during the period of Apartheid and the raison d’être for inflicting such inhumane treatment on fellow human beings. We Investigate the cause of this problem of evil as well as the means the subjugated victims use to cope with the traumatizing experiences within confined prisons as well as those out of prison. From a philosophical and psychological perspective, we investigate how man strives to give a meaning to his life by finding a “why” and a “how” to live through suffering. We question how long one can be ascetic in the face of suppression and what happens when man reaches the level of apathy where he no longer fears death? Does he retaliate against the oppressor? against his own fellowman who is also a victim? Or against both the oppressor and his fellowman? This research will establish that Brutus and the South Africans who survive the horrifying experiences of Apartheid succeed because they identify the problem and individually as well as collectively chose a “why” and “how” to live through it.