More Discussion Questions
1 .The author says to the other Wes, "I guess it's hard sometimes to distinguish between second
chances and last chances." What do you think he means? What is each Wes's "last chance"?
Discuss the differences in how each one uses that chance and why they make the decisions they
do.
2. During their youth, Wes and Wes spend most of their time in crime- ridden Baltimore and the
Bronx. How important was that environment in shaping their stories and personalities?
3. Why do you think the incarcerated Wes continues to proclaim his innocence regarding his role
in the crime for which he was convicted?
4. The book begins with Wes and Wes's discussion of their fathers. What role do you think
fatherhood plays in the lives of these men? How do the absence of their fathers and the
differences in the reasons for their absences affect them?
5. Wes dedicates the book to "the women who helped shape [his] journey to manhood." Discuss
the way women are seen in Wes's community. What impact do they have on their sons?
6. The author says "the chilling truth is that [Wes's] story could have been mine. The tragedy is
that my story could have been his." To what extent do you think that's true? What, ultimately,
prevented their stories from being interchangeable?
7. Throughout the book, the author sometimes expresses confusion at his own motivations. Why
do you think he is so driven to understand the other Wes's life?
8. The author attributes Wes's eventual incarceration to shortsightedness, an inability to critically
think about the future. Do you agree? Why or why not?
9. Wes states that people often live up to the expectations projected on them. Is that true? If
someone you care for expects you to succeed-or fail-will you? Where does personal
accountability come into play?
10. Discuss the relationship between education and poverty. In your discussion, consider the
education levels of both Weses' mothers, how far each man got in his education, the
opportunities they gained or lost as a result of their education, and their reasons for continuing or discontinuing their studies.