1. Why do you think that Wes Moore, the author, begins the book by
writing about the fathers of Wes and Wes? What significance did fathers play in
the lives of both Wes Moores? How was that different from the relationship with
2. What are some of the similarities of the neighborhoods where Wes and Wes
spent their childhoods?
3. How well does Moore describe the culture of the streets, where young boys
grow up believing that violence transforms them into men? Why do you think so
many young men find it attractive?
4. In writing about the Wes Moore who is in prison, Wes Moore the author says, “The
chilling truth is that his life could have been mine. The tragedy is that my
story could have been his.” Do you think he’s right? Why or why not?
5. You are all about to attend college with the expectation it will in some way
make you and your life better. What does education have to do with the life
path on which each Wes Moore landed?
6. Oprah Winfrey has said that “when you hear this story, it’s going to turn
the way you think about free will and fate
upside down.” So, which is it...freedom or determinism? If determinism, what
kind of determinism—God, cosmic fate,
environment, biology, psychology? Or if free will, to what degree are we free
to choose and create our own destiny?
7. Author Wes Moore states, “Later in life I learned that the way many
governors projected the numbers of beds they’d need for prison facilities was
by examining the reading scores of third graders.” How did reading this make
you feel? Why?
8. Wes Moore (the author) attended four elite educational institutions –
Riverdale Country School, Valley Forge Military College, Johns Hopkins
University, and the University of Oxford. How important do you think education
was to his future? The other Wes Moore (incarcerated) attended various public
schools in the greater Baltimore area, which have significantly below-average
graduation rates & numerous budgetary problems. How important do you think
education was to his future?
9. Wes Moore (the author) had a strong family support system, both emotionally
& financially. How important do you think family was to his future? The
other Wes Moore had a difficult family situation, frequently lacking in
oversight and discipline. How important do you think family was to his future?
10. Wes Moore (the author) distinguished himself in both military school and
active-duty combat. How important do you think the military was to his future?
The other We Moore had difficulty finding regular employment, even after
earning his GED & completing vocational training via the Job Corps. How did
this general lack-of-opportunity affect his future?
11. Wes Moore’s (the author’s) life changed significantly after moving from the
Bronx to rural Pennsylvania. How much of his current life would you attribute
to personality vs. luck vs. the situation? The other Wes Moore’s life changed
significantly after becoming a father & entering the drug trade. How much
of his current life would you attribute to personality vs. luck vs. the
12. Wes Moore (the author) experienced instability at an early age, with the
death of his father (in 1982), a cross-country move (from southern Maryland to
the Bronx in 1984), and living in various impoverish neighborhoods. How do you think
these experiences shaped his personality? The other Wes Moore experienced
instability at an early age, with barely knowing his father, frequently moving
(within the greater Baltimore area), and living in various impoverish neighborhoods.
How do you think these experiences shaped his personality?
13. The book is written as part autobiography, part biography. What are the
benefits and challenges of this genre?
14. Consider the language and tone of the work. Does the author use different
words, language, phrasing, to distinguish between the two different lives?
15. What imagery in the text struck you as most memorable? Why?
16. Has this book left you with any ideas for improving the conditions that led
directly and indirectly to the imprisonment of the other Wes Moore? What can be
done to ensure a more productive life for the many young men who grow up on the
streets of Muncie and other Indiana cities?
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