In an inner-city classroom, a teacher tries to save an at-risk student by introducing him to American novelist, Horatio Alger, Jr. As the play moves across two worlds—urban America today and 19th-century New York—the conflict between fact and fiction leads to hard lessons about the American dream and the myth that we can all pull ourselves self up by our bootstraps.

English teacher Philip Johnson confronts Anthony, a 16-year-old African-American student, about plagiarizing a paper. He offers another chance, giving Anthony Horatio Alger’s 1866 juvenile novel Ragged Dick, and proposing that he write about the book’s relevance today. As Anthony begins reading, Alger introduces Ragged Dick, an uneducated but ambitious bootblack trying to achieve “respectability” in Gilded Age New York. Throughout Dick’s adventures, Alger plays a series of wealthy men who take an interest the boy and help him rise.

Anthony questions Alger’s maxims for success and challenges the device of wealthy men who help Dick without asking anything in return. In response, Philip pushes him to dig deeper and consider the enduring value of Alger’s ideas. Alone, Philip imagines conversations with Alger, investigating how writing this novel converged with his own life events, and probing Alger’s actual relationships to the boys who inspired his stories. Alger replies with platitudes but avoids honest disclosure. During these moments, Philip is haunted by the presence of Solomon Freeman, a congregant of the New England church where Alger briefly ministered before moving in New York, who warns emphatically against Alger’s influence.

Through their conversations, Philip infers troubling truths about Anthony’s home life and problems. Their exchanges become more complicated when Anthony points to the homoerotic undercurrents in Alger's writing and turns a spotlight on Philip’s sexuality. Anthony uncovers the real-life sex scandal that implicated Alger with at least two teenage boys, related in dramatic fervor by Freeman. As they investigate Alger’s motives and actions with the boys who influenced his stories, Philip and Anthony confront the boundaries of their own relationship. Ragged Dick’s tale ends in triumph; however, Philip and Anthony emerge with more complicated perspectives on how of power, privilege, sexuality are entangled in the American success story.