Gather initial thoughts and broad opinions about the book.

1. What was your experience reading a story with two protagonists who come from such different worlds? Did you find yourself identifying more with one than the other, and how did your perspective on them change as their secret alliance developed?

2. How did the dual-perspective narrative, written by two authors, shape your reading experience compared to other historical fiction you’ve read, perhaps even other books by Marie Benedict like The Only Woman in the Room? Did you feel the collaboration created a seamless story?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. The characters respond differently to fear, grief, and uncertainty. Which response felt most understandable to you, and what did that reaction reveal about the character’s values?

2. Polly and Eunice come from opposite ends of New York’s social hierarchy yet find themselves working toward the same goal. Have you ever formed a friendship or alliance with someone you never expected to connect with? What did that experience teach you?

3. For much of the novel, Eunice struggles to get her male colleagues to take her investigation seriously. Have you ever been in a situation where you had to fight to have your ideas or concerns recognized? What did you learn from that experience?

4. Think about the personas that Polly and Eunice adopt to survive in their respective worlds. When have you felt the need to present a particular version of yourself to navigate a challenging environment?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The story’s examination of the Combination shifts the novel’s focus from the morality of individual women to the mechanics of a criminal enterprise. How does this depiction challenge common perceptions of the sex-work industry, both in the 1930s and today?

2. What does Eunice’s experience as the only Black woman on Dewey’s task force reveal about the intersection of race and gender in professional settings during that era? Which of the barriers she faces are still present in society today?

3. Consider the role of the media in the story. Newspapers shaped public understanding of the trial partly by using a term that the press of the era applied to sex workers, “white slaves,” a label that redirected sympathy along racial lines and obscured the exploitation of women who didn’t fit that category. How does the novel treat that framing, and in what ways do you see media coverage of high-profile legal cases today performing a similar function?

Dive into the book’s structure, characters, themes, and symbolism.

1. How does the alternating chapter structure between Polly’s and Eunice’s perspectives build suspense and reinforce the theme of Subverting Patriarchal Power With Female Alliances? What key insights would have been lost if the narrative had been told from only one point of view?

2. What is the significance of Eunice’s two-toned oxford pumps,? How do the shoes function as a symbol of Eunice’s identity as she navigates the worlds of law, race, and womanhood?

3. What is the thematic significance of the secret doors and hidden passageways in the novel? How do these physical spaces reflect the clandestine nature of Polly’s business, the dangers that both she and Eunice face, and the secret alliance they must build?

4. How does the novel differentiate between the chaotic, personal violence of Dutch Schultz and the systematic, corporate menace of Lucky Luciano? What does this contrast suggest about the evolution of organized crime?

5. Think about 1930s New York City as the book’s backdrop. How do the descriptions of its glamorous hotels, gritty courtrooms, and anonymous diners contribute to the story’s atmosphere and exploration of social division and hidden power?

Encourage imaginative and creative connections to the book.

1. If you were casting a film adaptation of A Pair of Aces, which actors would you choose to play Eunice and Polly? How would you capture the way Eunice builds her case despite institutional obstruction and the way Polly manages loyalty and self-preservation simultaneously?

2. Imagine you’re a journalist covering the final day of the trial. What headline would you write for your newspaper, and what would be the opening sentence of your article to capture the significance of the verdict?