Having spent the majority of the book discussing the ways in which Lincoln and Douglass publicly disagreed with each other over the way in which the issue of slavery should be handled by the federal government, Chapter 6 brings the two leaders face to face. With the issue of slavery settled, the freedoms afforded to Lincoln have become a bit broader, as he no longer needs to appear one way or another for the state of his constituents. Moreover, with Lincoln now firmly in his corner, Douglass can act less as a reformer and more of an ally to the president, especially in his bid for re-election in 1864.

Oakes highlights how Lincoln and Douglass turn out to realize that they have much more in common than their public positions would initially show, and Oakes’s portrayal of their meetings expressed the mutual respect the two men did have and further develop toward each other.

Apart from detailing the three meetings that Lincoln and Douglass engaged in, Chapter 6 also discusses the challenges faced by Lincoln in his bid to win re-election in 1864 and the fear that should he lose, it would risk the North concluding a compromise peace with the South that would jeopardize all that Lincoln and Douglass had striven to achieve.