The plight of marginalized people in former colonies is an important theme in Naipaul’s novels. His early short story One Out of Many focuses on the protagonist Santosh’s life between “freedom” and “unfreedom”, which mirrors the spiritual dilemma of immigrants living in the center of West and their difficulties in freeing themselves from their inner shackles of constraints. Based on Erich Fromm’s Freedom Theory and Freud’s Psychoanalysis, this paper explores the complex game among Santosh’s “id”, “ego” and “superego” and his pursuit of “freedom”. Santosh gains a better understanding of both “self” and “freedom”, yet he still finds it difficult to break through constraints of “superego”. His belief in Hinduism from his motherland encourages his resistance to pursuing fame and high status in American society, so he chooses to pray for religious forgiveness and inner peace in an “unfree” state. By such an ironic image, Naipaul effectively critiques alienation by American civilization and modernity, delivering his profound humanism.