In The Pilgrim’s Progress (1678) John Bunyan describes the Flatterer as a “man black of flesh.” This depiction sets the course for the reception and adaptation of his work as a spiritual classic to enact, perpetuate, and even deepen a racist vision. Alternatively, theological awareness of racism and racialization finds expression in critique and correction. The history of the illustration of the Flatterer raises particularly acute questions. Bunyan’s own scripturally informed concern for monuments allows illustrated adaptations, such as Little Pilgrim’s Progress, to be brought into conversation with Ryan Newson’s theological treatment of confederate monuments. Given that so many adaptations of The Pilgrim’s Progress come from within evangelicalism, both racist and racially aware representations of Bunyan’s work are weighed in light of Vincent Bacote’s race-centered, constructive critique of evangelical theology.