- What are the motivations of the various FBI agents in dealing with Bulger? Compare and contrast these motivations.
- How might Whitey Bulger's criminal career have been different if he hadn't been an informant?
- What makes Fred Wyshak different from the other people who've tried to prosecute Bulger? How does he succeed where others fail?
- In what ways is Bulger shaped by the culture of South Boston? In a similar sense, how does Bulger come to shape the culture of South Boston?
- Why does John Morris reveal the truth about Bulger to The Boston Globe? What does this decision say about him as a person?
- What are the similarities and differences between Whitey and Billy Bulger?
- Where might Bulger be hiding now if he hadn't have been captured by the FBI?
- Did FBI culture and protocol in some way enable the corrupt deal with Bulger? If so, explain.