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1. In the prologue O’Dea tells the story of his first day at a Catholic boy’s school. How do you think this event affects this little boy? Does keeping this secret set the tone for his later life? What effect did growing up in the Catholic Church have on O’Dea? As O’Dea describes the DEA coming to his house and ultimately his surroundings at Terminal Island, how did you feel about that eleven-year-old boy?
2. O’Dea describes his recreational, experimental drug use as a teenager in Newfoundland. Is this experimentation typical? Does he take bigger risks than others? Is this different from teenagers experimenting with alcohol and cigarettes, or the same?
3. As Brian realizes he can pay for his own drugs by selling them to his friends, we see his entrepreneurial spirit develop. Is he similar or different from his father, who owns a brewery, or the same? Is he similar or different from the Kennedy family during prohibition in the U.S., or the same?
4. Brian is in prison in Newfoundland and his first marriage fails. When he is released from prison he instinctively jumps on a plane for Colombia. What does this say about his character? What does it say about the risks he is willing to take? At what cost for O’Dea? What character traits help him survive the risks he takes?
5. When Brian focuses his entrepreneurial skills on doing legal business — the concert in Jamaica, the hair products, dinosaur bones — things don’t work out. Is it self-sabotage? Why is he not successful?
6. What motivated Brian to get out of the business? What motivated him to get clean and stay that way? If Brian were your son, brother, husband, or father, how would you have related to him over the years?
7. Brian has been married three times and divorced twice. Can you relate to his first and second wives and their reasons for getting out of the marriage? Would you have stayed or left? His current wife has been with him since he was nine months sober. She stayed through the indictment, the sentencing, prison, parole, and the years of reinventing a life. Why did she stay? Would you have stayed?
8. What kind of person is Brian O’Dea?
9. What do you think of the title of the book? What title would you give the book?
10. Currently in the U.S. murder is punishable by a sentence of three to six years in prison, but drug offenses are punishable by thirty to fifty years in prison. Do you agree with this? How do you feel as a taxpayer supporting the people serving these sentences?
11. Brian was able to survive prison and avoid any serious conflicts or confrontations. How?