Book Club Discussion Questions for A Gentleman and a Thief by Dean Jobb

1. Was Barry a born criminal, or do you think circumstances forced him into a life of crime?
2. What skills and methods made him such a successful jewel thief?
3. "I know he's terrible," said one socialite Barry robbed, "but isn't he charming?" What were some of the characteristics that made him so likeable?
4. Were you on Barry's side? If so, why do we root for polite, gentlemanly crooks like Barry?
5. Barry prided himself on stealing only from the rich and never resorting to violence during robberies. Do you think this lessens the seriousness of his crimes?
6. "It was that kind of time. Why not live well?" Barry said of his free-spending gambler's lifestyle. In what ways was he a product of the Roaring Twenties?
7. Why was it so hard for the police and private detectives to catch Barry?
8. What mistakes did he make that ensured he would be arrested and imprisoned?
9. Do you think Anna Blake knew at least on some level that her husband was breaking the law or was she an innocent victim? And if she didn't know, should she have at least suspected?
10. How do you feel about Anna risking arrest to help Barry after his prison escape , and living with him as a fugitive?
11. Why did Barry deserve a second chance after his release from prison?

Unless otherwise stated, this discussion guide is reprinted with the permission of Algonquin Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.