This chapter continues to examine how sorrow operates in Du Bois’s The Souls of Black Folk. In addition to the author’s homage to the spirituals in the final chapter, sorrow works in the text as a trope, attitude, and mode of attunement. Melancholy in Souls becomes a way to question, trouble, and render ambiguous cherished values like freedom, agency, and liberation. By offering a close reading of several chapters in the text this chapter shows how death, loss, and trauma haunt and unsettle political categories and ideals typically associated with black strivings and progress. The chapter provides a reading of “Of the Meaning of Progress,” suggesting that Du Bois’s experience in a rural Tennessee community troubles the very logic of progress. The end of the chapter asks the reader to define and measure progress by what progress excludes. This chapter also looks at Du Bois’s fictional piece, “Of the Coming of John,” a story that rejects the idea that the North is necessarily a space of freedom and progress. This story and the chapter on the death of Du Bois’s son also suggest that death is a kind of liberation from a would that prevents freedom for black bodies. The final section of this chapter examines the relationship between aesthetics and politics, in conversation with Adolph Reed’s controversial study of Du Bois.