This paper considers the conceptual framework underlying Fanon’s claim in Black Skin, White Masks that Black Americans and Black Antilleans are living different dramas. A dramaturgical analysis of Fanon’s critique of racial and colonial domination in Black Skin, White Masks and The Wretched of the Earth, reveals this claim to be motivated by Fanon’s unfolding decolonial conception of humanism and how to achieve the ideals of this humanism through specific forms of anti-colonial action, mainly national struggles. As such, this paper finds Fanon’s American-Antillean distinction in Black Skin, White Masks to be a prefiguration of his later notions concerning national culture and humanist praxis expressed in The Wretched of the Earth. This discussion endeavors to shed light on and contribute to decolonial processes—especially within Western philosophy—by briefly reflecting upon the critical necessity of scholarly flexibility and the conceptual limitations presented by subjective experience.