Black Hopes/Black Woes begins by delving into the contrasting mindsets of postbellum African Americans and their twenty-first-century counterparts, aiming to elucidate the shift from early black optimism to present-day black pessimism. It then focuses on the rationale behind Afro-pessimism, a contemporary school of thought with an inconspicuous yet potent influence on mainstream culture.

The first part of the book focuses on Frederick Douglass's and WEB Du Bois's interpretations of slave songs, establishing a link between the Negro, freedom, and democracy. This optimistic view is juxtaposed with Saidiya Hartman's, who, with a hundred years' hindsight, condemns Du Bois's reformist spirit and efforts to tackle black poverty as supercilious and damaging. The book then scrutinizes Afro-pessimism through the work of Frank B. Wilderson III, who posits that the stability of civil society hinges on anti-black violence. Accordingly, he argues that any analogy between black and non-black experiences is flawed and that Marxism, which privileges labor over racial issues, is inadequate to grasp blackness. Additionally, the book explores the essentialist discourse of Afro-pessimism through David Marriott's analysis of Frantz Fanon, which theorizes the non-beingness of blackness despite Fanon's focus on being colonized rather than black. Finally, the book demonstrates how Afro-pessimism overlaps with postcolonialism and conflicts with Fanon's universalism, his rejection of identity politics, and his advocacy for transracial and transnational dialogue.

While the radical nature of Afro-pessimism may seem to manifest an unresolved national trauma, Black Hopes/Black Woes situates this ideology in the larger contemporary philosophical and critical discourse, shedding light on its propensity to foster a culture of resentment and cynicism. Once confined to a niche academic audience, Afro-pessimism has percolated the mainstream, stoking the fire of racial antagonism.