A Pair of Aces Book Club Questions & Discussion Guide

About this book

In 1930s New York, assistant district attorney Eunice Carter, the first Black woman to hold the role in the state, becomes convinced that the way to topple crime boss Lucky Luciano is through the one racket no other prosecutor has thought to touch. To build the case she needs an unlikely partner: Polly Adler, a celebrated madam with her own reasons to want Luciano gone. Inspired by two real women, the novel imagines the secret alliance that could have brought one of the city's most powerful mobsters to trial.

Discussion questions

1. Before you started, what did you expect from a story about taking down a mobster, and how did the novel's focus on two women working in the background change that expectation?
2. The book moves between Eunice's world and Polly's. If you set it down at any point, was it one woman's chapters that pulled you back, and what made her story stick?
3. Eunice and Polly are both outsiders who clawed their way into positions of influence. Where did you see their very different backgrounds shaping the way each of them moves through the world?
4. Their alliance asks a prosecutor to trust a woman who runs an illegal business. Was that trust earned, or did it stay partly transactional, and did your read of it change by the end?
5. The novel keeps returning to who gets believed and who gets overlooked. What did it ultimately suggest about why these two women could see an angle the men around them missed?
6. Benedict and Murray fictionalize a real case, inventing the women's secret collaboration. Did blending documented history with invention deepen the story for you, or did you find yourself wanting to know where the line fell?
7. How much was 1930s New York, with its speakeasies, courtrooms, and back rooms, a character in its own right, and what did the setting let the authors say that a modern one could not?
8. What did this remind you of, whether another work of historical fiction, a crime drama, or a real story of women fighting to be taken seriously?
9. The book is interested in justice done quietly, without credit. Has anyone at the table ever done important work that someone else was recognized for, and did this story land differently because of it?
10. Who would you hand this to next, the historical-fiction reader, the true-crime fan, or someone who loves a courtroom showdown, and who might it not be for?

Themes to listen for

• Female alliance across deep difference
• Justice pursued without credit or recognition
• Who gets believed and who gets overlooked
• The line between history and invention
• Power, vulnerability, and the women the record forgot

If your club liked this, try…

• The Personal Librarian by Marie Benedict and Victoria Christopher Murray
• The Alice Network by Kate Quinn
• The Lions of Fifth Avenue by Fiona Davis
• Lessons in Chemistry by Bonnie Garmus

Where to get it

• Check availability at your local library
• Find it on Bookshop.org
• Listen on Libro.fm

Practical notes

Best for clubs that like historical fiction, courtroom drama, or true-crime roots. The dual-protagonist structure suits a fuller, roughly two-hour discussion.

Content notes: Organized-crime violence and references to exploitation.