Discussion Questions (BKMT Reading Guide)
From the author:


• The Everleigh sisters were technically criminals, yet they genuinely believed they were helping the girls in the Club. What do you think about the Everleigh sisters’ business practices? Why were they so successful?

• Did you identify with either Everleigh sister? If so, which one? How are Minna and Ada alike, and how are they different? Who was the stronger sister, in your opinion? How were they able to perpetuate so many lies for so long?

• On the surface it seems that there are only two sides in Sin in the Second City—the reformers and the sisters—but there are actually a few more: the politicians, the Levee gangsters and the rival madams. Who are the heroes in Sin in the Second City, and who are the villains? Who did you sympathize with? Did you find your loyalties shifting at any point along the way?

• At the time the Everleighs ruled Chicago, what other choices did women have? Did you judge the women who became “sporting girls”? Did you judge the madams? What path do you think you would have chosen if you’d been alive during the turn of the century?

• Sin in the Second City follows the careers of two reformers, Ernest Bell and Clifford Roe. How were Bell and Roe alike, and how were they different? What do you think motivated each man? Whose tactics were more effective? Do you think they exaggerated or accurately represented the “white slavery” situation?

• At one point, the boxing champion Jack Johnson shows up at the Club, and his presence becomes quite a commotion. What did his visit tell you in terms of race and America at the turn of the century? And was the Levee different from the rest of the country in this regard?

• How did America’s sexual culture change during the Everleighs’ reign? Who was primarily responsible for these changes, the reformers or the underworld?

• Chicago is as much a character in Sin in the Second City as the gangsters and the madams. Why do you think the Everleigh sisters chose to settle in Chicago? Would they have been as successful in another city, or was Chicago particularly conducive to their success?

• Many reformers cited strong religious convictions as a reason for fighting the red-light districts. How do you think the religious tenor of the times compares to that of today?

• The politicians in Sin in the Second City argued that the segregated vice district was necessary to protect “respectable” neighborhoods and “respectable” women. Do you agree with their reasoning? Or with the reformers’ belief that the Levee needed to be destroyed entirely?

• Aside from the reformers, there were others in the Levee who were trying to take down the Everleigh sisters. Madams like Vic Shaw and Ed and Louis Weiss. Why, do you think, were the Everleighs able to so successfully foil their attempts?

• The Everleighs had very strict rules when it came to their clientele, yet they admitted their fair share of eccentric characters. What was your favorite Everleigh Club anecdote?

• What satisfaction can be derived from a nonfiction book like Sin in the Second City that can’t be from novels? In what ways is the book like a novel?

• What is the total picture of early 20th century America that emerges from Sin in the Second City? How is that time both like and unlike contemporary America? What are the most significant differences? In what ways does that time mirror the present?

• Neither Everleigh sister had a serious relationship during her adult life. Do you think they chose to remain unattached? If so, why?

• Abbott stumbled upon the story of the Everleigh sisters while researching a long-lost relative. How much do you know about your own family’s history and ancestry? Do you know where they were and what they were doing from 1900 to 1911, when the Everleigh Club was in business?