A Pair of Aces Reading Guide

1. As an assistant district attorney for the City of New York and Manhattan's first Black female prosecutor, Eunice Hunton Carter achieved incredible success. What personality traits led her to achieve this success?
2. Polly Adler became the most infamous madam of her time. What life circumstances led her to that position? What qualities led her to thrive in that role? How does her profession reflect the limitations imposed on immigrant women in the early twentieth century, as well as the attitudes about them?
3. Eunice Hunton Carter and Polly Adler were well-known figures in 1930s New York. Were you familiar with either of them before reading A Pair of Aces?
4. Lucky Luciano was the most notorious mobster of his time, known as the boss of all bosses. Had you heard of him before reading A Pair of Aces? Lucky, Eunice, and Polly were all prominent figures in their time. Who do you think is the best known of the three of them today? Why do you think that is?
5. Both Eunice and Polly had to sacrifice a lot to achieve their positions. What trade-offs did they have to make? Do you think it was worth it?
6. Eunice and Polly both faced a lot of challenges in their lives. How were their struggles similar and different?
7. Eunice and Polly formed an alliance to achieve a common goal even though they were on opposite sides of the law. What characteristics helped them to set aside their differences and work together?
8. Do you think Eunice and Polly influenced each other's lives? Do you think they learned anything from one another? How did their relationship change over the course of the book? What factors led to this transformation?
9. At one point in the book, Eunice and Polly discuss whether race or class shaped their hardships more profoundly. Did you better understand each woman's perspective after this conversation? Did it shift your own view of race and class?
10. Special Prosecutor Thomas Dewey gave Eunice incredible career opportunities, like appointing her to his team, but he also initially didn't give her the same level of responsibility as the other lawyers on the team. How did you feel about Eunice's working relationship with Thomas Dewey? What did you think of his decisions throughout the book? Do you think his view of Eunice changed by the end? Do you think Eunice would face the same sorts of issues if she was in this role today?
11. How did you feel about Eunice's relationship with her mother? In what way did her mother's accomplishments influence Eunice's life choices? Did she inspire her? Or did Eunice feel more pressure to succeed because of her mother's achievements?
12. How would you describe Polly's relationship with her parents? Was her relationship different with her mother than with her father, and if so, how? Why did she feel more animosity toward her father, and do you feel that was justified?
13. Polly had a complicated relationship with the women, like Virginia, who worked for her. How did her relationship with these women influence Polly's decision to work with Eunice? Do you think the women like Virginia felt like they were family to Polly?
14. What did you think of Polly's relationship with the Lion? Why do you think the two women were so close?
15. How did you view Eunice's relationship with her husband? Why do you think there was so much tension in their marriage?
16. Did anything surprise you about the trial of Lucky Luciano? Why do you think Dewey didn't want to prosecute Luciano for running a prostitution ring? Do you think this perspective would still be in evidence today?
17. Eunice and Polly formed an unlikely alliance to take down Lucky Luciano. What qualities are required to make these kinds of alliances successful? Can you think of other situations where women from different backgrounds came together to achieve a common goal? What lessons can we derive from Eunice and Polly's relationship, and how can we apply them today? Have you ever formed this type of strategic alliance in your life? Can you envision a reason or issue that might inspire you to do so?

Unless otherwise stated, this discussion guide is reprinted with the permission of Berkley Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.