The Mayor of Maxwell Street

Why do you think the author chose to start and end the book from Jimmy’s point of view?

When learning about the role of gossip in the Mayor’s network of associates, Nelly thinks, “every society’s foundation stood on idle chatter that spread and took like a match to fresh tinder.” What role do you see rumors and gossip playing in the story?

Discuss the function of privilege in the story. How do race, gender, and wealth impact the way characters move through the world?

As the threats around Nelly increase, she becomes more determined than ever to find the Mayor. What would you do in her shoes?

As you were reading, what theories did you develop about who the Mayor might be? What clues led you to that conclusion?

Throughout the novel, you slowly learn more about who Jay is. How did your opinion of him change as you read more?

Avery Cunningham includes a number of twists involving Jay, Elder, and Becky Harjo. Which surprised you the most?

What do you think would have happened if Nelly hadn’t chosen to run away with Jay the second time he asked?

Jay says, “I have found in my limited experience that the best defense against hate is complete, unmitigated, iridescent happiness.” Do you agree?

Every character in the story is hiding who they are in some way. Do you think anyone is truly honest, or are they all unreliable narrators in their own way?

Avery Cunningham was inspired by The Great Gatsby. What parallels do you see between the two works? What is your favorite deviation that Cunningham took from the original?

Jay is deeply affected by his upbringing in Alabama, which is explored in “The Ballad of Jimmy Blue-Eyes.” How do you see the impact (positive and negative) of his origins reflected in his new identity in Chicago?

Nelly is brought up in unprecedented privilege. In the novel, were there moments when Nelly's upbringing skewed her perspective, whether positively or negatively?