SPOILER WARNING: These book discussion questions are highly detailed and will ruin plot points if you have not read the book.
Title: Sin in the Second City: Madams, Ministers, Playboys, and the Battle for America’s Soul
Author: Karen Abbott
Page Count: 356
Tone: Engaging, dramatic, well-researched
1. Do you see the Everleigh sisters as criminals?
2. The sisters elevated their craft. Down another path in history this elevation could have led to legalization and taxation of prostitution in Chicago. How different do you think Chicago would be were that to have happened?
3. Do you think sex work was empowering or exploitive to the butterflies? Explain. Do you think sex work was empowering for other brothel house workers?
4. Do you think more women were “white slaves” or prostitutes during this era?
5. Would you have considered becoming an Everleigh butterfly?
6. Why do you think the sisters outshined their competition so fiercely?
7. Do you think there was a stronger sister?
8. Why do you think the sisters didn’t ever (re)marry?
9. Was there a madam in this book you admired?
10. What about a madam you hated?
11. Are there any heroes in this story?
12. What about villains?
13. What do you think of the reformers’ techniques? Were they effective?
14. What do you think of Ernest Bell, the preacher? Did you find him more often in the wrong or in the right?
15. What did you think of Clifford Roe, the lawyer obsessed with white slavery?
16. Some folks believed that brothels and prostitution kept “respectable” women safe from rape and the “baser” fantasies of their husbands. What is your reaction to this?
17. Were you surprised by the caliber of patrons at the Everleigh Club? (Ex: Edgar Lee Masters, Theodore Dreiser, the Prince of Prussia, etc.)
18. How did the Everleighs handle racial issues at their club?
19. Do you think people’s sexuality has changed all that much since the Everleighs’ time?
20. Do you think the Everleigh sisters would be successful today? How do you think their business might be different?
21. Does this book mirror present day society at all?
22. Would you have wanted to live in Chicago during this era?
23. Sin in the Second City is a work of nonfiction. Do you think you would’ve enjoyed it more as a novel? Why or why not?
24. Has your perspective of sex workers changed? Elaborate.
25. What is one story you can take away from Sin in the Second City and use for cocktail party chatter?
Sin in the Second City website
Book discussion questions at Reading Group Guides
Claire Zulkey interviews Karen Abbott
Freakonomics interviews Karen Abbott
Windy City Writers interviews Karen Abbott
New York Times review of Sin in the Second City
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