Chapter 5 begins with the dual reactions of both the white and African-American communities upon the Emancipation Proclamation going into effect on January 1, 1863. Oakes then backtracks to discuss the final steps that lead up to the historic day, specifically the ways in which Lincoln managed to position himself so as to free the slaves with what otherwise could have seen to be either a kingly executive degree or an act of Northern desperation.

Still, there was much debate and concern, especially among Democrats, centered around the question: “What shall be done with the slaves?” (179). In this regard, Oakes does not gloss over the fact that Lincoln did contemplate the idea of colonization, even having his subordinates look into suitable locations in Africa and Latin America, which enraged Douglass, who “had always equated the struggle for racial equality with the struggle against slavery” (195). For Douglass, emancipation was only the first step in proving that blacks and whites could live side by side in a productive and peaceful society.

To this end, Chapter 5 continues with Douglass attempting to convince the federal government of the United States that emancipation should logically lead to opportunity and advancement for black people, and there was no better example than the chance for the newly freedmen to serve in the Union Army.