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Our current read is Agent Zigzag: A True Story of Nazi Espionage, Love, and Betrayal by Ben McIntyre. Agent Zigzag is the improbable, but completely true, story of a small-time criminal and ladies-man named Eddie Chapman in pre-WW2 Britain who became a double agent during the war for both the Nazi regime’s Abwehr intelligence organizatrion, and Britain’s MI5.

Click this link Agent Zigzag Background and Questions to get a printable PDF file of the contents of this page.

Agent Zigzag was highly regarded in many reviews including The New York Times, The Guardian, and Kirkus Reviews.

Here is a list of suggested discussion questions from LitLovers.com

What kind of character traits make for a good spy—and how does Eddie Chapman reflect those traits? Is he typical of other successful spies you might have read about previously? Are the qualities it takes to become a spy present in your make-up?
Follow-up to Question #1: What in Chapman’s character, if anything, would you say is admirable? One reviewer has commented that “there is something about a democracy that makes a spy untrustworthy to the public and unworthy of its respect…. Chapman was no exception.” Do you agree…or disagree? Where does the author come down on this question? Does he attempt to convince readers, one way or another? Or does he let you make your own determination?
How does did Chapman convince the Nazis to use him as their spy—what enables him to convince them? Same with the British—how does he persuade the Allies to use him as a double agent?
What have you learned about how the secret intelligence services operated during World War II—both the Abwehr and MI5? What do you find most interesting…or disturbing? Same questions regarding the techniques used to train spies.
Talk about the relationship between spies and their “handlers.” How would you describe Ryde and his handling of Chapman? Does Ryde run Chapman…or the other way around? Also, what role does class play in the relationship of spies to handlers?
Should agents’ lives be considered expendable—or promises negotiable—in the overwhelming necessity of winning a war?
Talk about the dangers Chapman faced in Germany. How vulnerable was his position as a spy?
We rightfully herald the heroism of armed forces in World War II. Yet the story of intelligence gathering and analysis remained untold for years. (The story of the Ultra secret, for instance, wasn’t written about till the 1970s.) Discuss role of intelligence operations—including code-breaking as well as spying—in the Allies’ ultimate success? Would the war have been won in 1945 without their efforts?
Follow-up to Question #8: Overall, how vital was Chapman’s role to the Allied victory? Did his work make a critical difference?
What in this story do you find humorous? The episode, for instance of Bobby the Pig? Any others? What about the hapless German agents in Britain? Were Nazi spies truly bunglers?
Chapman was dead by the time Macintyre wrote his book. Having read Agent ZigZag, do you feel you have a fairly complete picture? Or are there still unanswered questions—more you would like to know?

Two questions that I find especially thought provoking are these:

To what extent did Chapman’s lower-class origins affect his British handlers’ ability to trust him and value his work?
Was Eddie Chapman a genuine sociopath? And, is a sociopathic personality an advantage or disadvantage for a spy? Here are some characteristics of the sociopath taken from sociopathicstyle.com.
1. GLIB and SUPERFICIAL CHARM — the tendency to be smooth, engaging, charming, slick, and verbally facile. Sociopathic charm is not in the least shy, self-conscious, or afraid to say anything. A sociopath never gets tongue-tied. They have freed themselves from the social conventions about taking turns in talking, for example.
2. GRANDIOSE SELF-WORTH — a grossly inflated view of one’s abilities and self-worth, self-assured, opinionated, cocky, a braggart. Sociopaths are arrogant people who believe they are superior human beings.
3. NEED FOR STIMULATION or PRONENESS TO BOREDOM — an excessive need for novel, thrilling, and exciting stimulation; taking chances and doing things that are risky. Sociopaths often have low self-discipline in carrying tasks through to completion because they get bored easily. They fail to work at the same job for any length of time, for example, or to finish tasks that they consider dull or routine.
4. PATHOLOGICAL LYING — can be moderate or high; in moderate form, they will be shrewd, crafty, cunning, sly, and clever; in extreme form, they will be deceptive, deceitful, underhanded, unscrupulous, manipulative, and dishonest.
5. CONNING AND MANIPULATIVENESS- the use of deceit and deception to cheat, con, or defraud others for personal gain; distinguished from Item #4 in the degree to which exploitation and callous ruthlessness is present, as reflected in a lack of concern for the feelings and suffering of one’s victims.
6. LACK OF REMORSE OR GUILT — a lack of feelings or concern for the losses, pain, and suffering of victims; a tendency to be unconcerned, dispassionate, coldhearted, and un empathic. This item is usually demonstrated by a disdain for one’s victims.
7. SHALLOW AFFECT — emotional poverty or a limited range or depth of feelings; interpersonal coldness in spite of signs of open gregariousness.
8. CALLOUSNESS and LACK OF EMPATHY — a lack of feelings toward people in general; cold, contemptuous, inconsiderate, and tactless.
9. PARASITIC LIFESTYLE — an intentional, manipulative, selfish, and exploitative financial dependence on others as reflected in a lack of motivation, low self-discipline, and inability to begin or complete responsibilities.
10. POOR BEHAVIORAL CONTROLS — expressions of irritability, annoyance, impatience, threats, aggression, and verbal abuse; inadequate control of anger and temper; acting hastily.
11. PROMISCUOUS SEXUAL BEHAVIOR — a variety of brief, superficial relations, numerous affairs, and an indiscriminate selection of sexual partners; the maintenance of several relationships at the same time; a history of attempts to sexually coerce others into sexual activity or taking great pride at discussing sexual exploits or conquests.
12. EARLY BEHAVIOR PROBLEMS — a variety of behaviors prior to age 13, including lying, theft, cheating, vandalism, bullying, sexual activity, fire-setting, glue-sniffing, alcohol use, and running away from home.
13. LACK OF REALISTIC, LONG-TERM GOALS — an inability or persistent failure to develop and execute long-term plans and goals; a nomadic existence, aimless, lacking direction in life.
14. IMPULSIVITY — the occurrence of behaviors that are unpremeditated and lack reflection or planning; inability to resist temptation, frustrations, and urges; a lack of deliberation without considering the consequences; foolhardy, rash, unpredictable, erratic, and reckless.
15. IRRESPONSIBILITY — repeated failure to fulfill or honor obligations and commitments; such as not paying bills, defaulting on loans, performing sloppy work, being absent or late to work, failing to honor contractual agreements.
16. FAILURE TO ACCEPT RESPONSIBILITY FOR OWN ACTIONS — a failure to accept responsibility for one’s actions reflected in low conscientiousness, an absence of dutifulness, antagonistic manipulation, denial of responsibility, and an effort to manipulate others through this denial.
17. MANY SHORT-TERM MARITAL RELATIONSHIPS — a lack of commitment to a long-term relationship reflected in inconsistent, undependable, and unreliable commitments in life, including marital.
18. JUVENILE DELINQUENCY — behavior problems between the ages of 13-18; mostly behaviors that are crimes or clearly involve aspects of antagonism, exploitation, aggression, manipulation, or a callous, ruthless tough-mindedness.
19. REVOCATION OF CONDITION RELEASE — a revocation of probation or other conditional release due to technical violations, such as carelessness, low deliberation, or failing to appear.
20. CRIMINAL VERSATILITY — a diversity of types of criminal offenses, regardless if the person has been arrested or convicted for them; taking great pride at getting away with crimes.