1. William Outlaw, as Charles Barber writes at the end of the prologue, was able to create “an exit plan from hell”? How did he do that? Why did he do that? What might we all learn from his story about the capacity to change?
  2. As Charles Barber writes in the final chapter, he and William Outlaw come from very different backgrounds yet were able to forge a strong relationship. Is it possible for people of such very different experiences to fully understand each other?
  3. Citizen Outlaw is a story of redemption and atonement for prior misdeeds.  But is it possible for William Outlaw to fully atone for his past? Is it possible for anyone to do that?
  4. Near the end of the book, Ivan Kuzyk, the crime analyst for the State of Connecticut, says that had William Outlaw been born in different circumstances, he might have become Fortune 500 CEO? Do you agree or disagree with that opinion?
  5. Is it possible that what made Outlaw a good gang leader also makes him a good “violence interrupter”? Are the same skill sets at play?
  6. Kelefa Sanneh of The New Yorker has written that Citizen Outlaw is a “mediation on the nature of ambition”. What drove William Outlaw to be a gang leader? What drove him to be a peacekeeper?  Are those motivations different?
  7. Do you think William Outlaw’s story can be used as a model for others to turn their lives around? Or, as Stacy Spell says about him near the end of the book, is he a “one in a million character” whose story is the exception rather than the norm?
  8. What is the role of fatherhood in the story, or the lack of it? Do you think Frank James and Warren Kimbro represented substitute fathers for Outlaw? Do you think he needed a father figure to turn his life around?
  9. What did you learn from Citizen Outlaw about the prison system? Even though there are many horrors that Outlaw experienced behind bars, he still believes that federal prison saved his life. Why?
  10. Do you think the book suggests some answers to the problems of mass incarceration? What are some reforms that come to mind?