Autobiographies present a personal view of a life that often lacks the kind of unflinching insight that a biography brings. But, the strength of the autobiography is that it presents a person’s individual view of their lives. They present stories and details that most others could not know. Frederick Douglass was never more artfully subtle or persuasive than in Narrative of the Life of an American Slave. In this memoir, Douglass – a black man who, as slavery was still in practice, engendered admiration and respect from both black and white people, including Abraham Lincoln – revealed his torturous boyhood as the work-beast of many owners of varying degrees of cruelty, though none so bad as Mr. Covey. The eloquently keen observations made by this former slave flew in the face of the conventional rationale that black people were just dumb beasts put on Earth for the use of white men. In Narrative, Douglass ultimately earns his right to be a man in a final physical and psychological showdown with his brutal master, Covey. He achieves his ‘rebellion’, by defying those who would whip him (Mr. Covey) and those who would censor his identity as a man and a human. It is the purpose of this paper to examine the psychology of the relationship between Douglass and Covey and to demonstrate how it was psychology that ultimately defeated Covey.