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Fair Play: The Moral Dilemmas of Spying
Revolutionary War officer Nathan Hale, one of America’s first spies, said, “Any kind of service necessary to the public good becomes honorable by being necessary.” A statue of Hale stands outside CIA headquarters, and the agency often cites his statement as one of its guiding principles. But who decides what is necessary for the public good, and is it really true that any kind of service is permissible for the public good? These questions are at the heart of James M. Olson’s book, Fair The Moral Dilemmas of Spying .
Olson, a veteran of the CIA’s clandestine service, takes readers inside the real world of intelligence to describe the difficult dilemmas that field officers face on an almost daily basis. Far from being a dry theoretical treatise, this fascinating book uses actual intelligence operations to illustrate how murky their moral choices can be. Readers will be surprised to learn that the CIA provides very little guidance on what is, or is not, permissible. Rather than empowering field officers, the author has found that this lack of guidelines actually hampers operations. Olson believes that U.S. intelligence officers need clearer moral guidelines to make correct, quick decisions. Significantly, he believes these guidelines should come from the American public, not from closed-door meetings inside the intelligence community. Fair Play will encourage a broad public debate about the proper moral limits on U.S. intelligence activities.
Olson, a veteran of the CIA’s clandestine service, takes readers inside the real world of intelligence to describe the difficult dilemmas that field officers face on an almost daily basis. Far from being a dry theoretical treatise, this fascinating book uses actual intelligence operations to illustrate how murky their moral choices can be. Readers will be surprised to learn that the CIA provides very little guidance on what is, or is not, permissible. Rather than empowering field officers, the author has found that this lack of guidelines actually hampers operations. Olson believes that U.S. intelligence officers need clearer moral guidelines to make correct, quick decisions. Significantly, he believes these guidelines should come from the American public, not from closed-door meetings inside the intelligence community. Fair Play will encourage a broad public debate about the proper moral limits on U.S. intelligence activities.
306 pages, Hardcover
First published October 24, 2006
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Displaying 1 - 30 of 61 reviews
February 10, 2023
Skim it in a library for an hour, but don't buy it.
James Olson is well-credentialed, and his work in the Agency seems to have put him in a lot of interesting situations. He brings his experiences to his writing to contemplate the moral problems of spying.
His book, Fair Play, tries to introduce the American reading public to some of the moral qualms of the spy business. Should a spy agency make up fake academic credentials for someone's child in exchange for secrets important to national security? Should a spy agency threaten to out a foreign national who is a homosexual in order to force them to trade their nation's secrets?
These questions and others are brought up in the fifty scenarios that make up the majority of the book are interesting. However, for each of these fifty scenarios, he asks others to comment on the morality of these scenarios. Some of commenters, mostly Olson's co-workers in the CIA, have interesting things to say. The majority, however, have nothing interesting to say and make the book not worth buying. Not only do I not care what the head of the Texas Christian Coalition or a middle school teacher have to say about the ethics of spying, it almost seems like they do not care either, as their responses are as deep as rain puddles and as interesting as manila envelopes.
Unfortunately, much of Olson's book is actually just the uninteresting, uninformed comments of these people. I found myself skimming the scenarios, and flipping past the bulk of the comments and reading what Olson had to say about the scenario, which was genuinely interesting.
Olson claims that he wants to start a conversation about the ethics of spying with the American people. Their tax dollars are being spent to do things that are morally problematic. If he wants to start a conversation, I would suggest that he do it by not putting anyone to sleep with the comments of people who know nothing about espionage and have never thought about the subject.
This book would have been a much better book had he simply written the scenarios and if he himself had simply discussed their moral implications in depth. These parts of the book are worth looking over in a library, but the rest of the book means that it is not worth buying.
James Olson is well-credentialed, and his work in the Agency seems to have put him in a lot of interesting situations. He brings his experiences to his writing to contemplate the moral problems of spying.
His book, Fair Play, tries to introduce the American reading public to some of the moral qualms of the spy business. Should a spy agency make up fake academic credentials for someone's child in exchange for secrets important to national security? Should a spy agency threaten to out a foreign national who is a homosexual in order to force them to trade their nation's secrets?
These questions and others are brought up in the fifty scenarios that make up the majority of the book are interesting. However, for each of these fifty scenarios, he asks others to comment on the morality of these scenarios. Some of commenters, mostly Olson's co-workers in the CIA, have interesting things to say. The majority, however, have nothing interesting to say and make the book not worth buying. Not only do I not care what the head of the Texas Christian Coalition or a middle school teacher have to say about the ethics of spying, it almost seems like they do not care either, as their responses are as deep as rain puddles and as interesting as manila envelopes.
Unfortunately, much of Olson's book is actually just the uninteresting, uninformed comments of these people. I found myself skimming the scenarios, and flipping past the bulk of the comments and reading what Olson had to say about the scenario, which was genuinely interesting.
Olson claims that he wants to start a conversation about the ethics of spying with the American people. Their tax dollars are being spent to do things that are morally problematic. If he wants to start a conversation, I would suggest that he do it by not putting anyone to sleep with the comments of people who know nothing about espionage and have never thought about the subject.
This book would have been a much better book had he simply written the scenarios and if he himself had simply discussed their moral implications in depth. These parts of the book are worth looking over in a library, but the rest of the book means that it is not worth buying.
December 31, 2025
A fascinating topic! I really enjoyed the scenarios and the different perspectives the author sought out to address them.
July 8, 2014
This is an interesting book, but one needs to have in mind who the author is and realize that it just can't be completely unbiased and transparent account of some of the events. However, I do like the approach of providing scenarios as an example of the (mostly moral) issues within the intelligence field. The author follows these examples with comments made by professionals (academics and practitioners) and clearly introduces variety of opinions on the subject. It is sort of a short introduction in the moral dilemmas, so it needs lots of further research. What I particularly found important, was the suggested further reading at the end of the book. I don't find it often to be the case that the authors spare time on drawing a list of "essential reading" on the subject.
The only thing which took away one star from the rating was the author's inability to remain objective and his tendency to look through the lens of an ex-CIA. But one must have this in mind even before opening the book, so...
The only thing which took away one star from the rating was the author's inability to remain objective and his tendency to look through the lens of an ex-CIA. But one must have this in mind even before opening the book, so...
June 16, 2008
I read most of this book and probably won't ever finish the rest of it. It's really nothing special. I was hoping for a real intellectual look at the ethics of spying, but the author just does not have the tools perform that analysis. Instead it farms a lot of it out to other contributors, so who have the experience to speak realistically to case studies and some who have the academic background to analyze the situation but no one who demonstrates a knowledge of real-life operations AND the ability to put that in a larger theoretical framework.
June 27, 2009
This book typifies my frustrations with "applied" ethics. They always seem to begin with a cursory survey of various ethical theories and then the remainer is given over to case study after case study. Reading interpretations of case studies does not build a solid ability to reason over ethical issues. Without taking a position on a theory any discussions of ethics becomes impossible to make a judgement on.
May 16, 2021
Fascinating scenarios from real life. Theologically interesting responses from a wide range of Americans. Difficult, difficult questions.
July 6, 2024
Interesting, but reads like a long article. Certainly informative.
June 9, 2025
Interesting look into a world of considerations that almost no one has to think about. The author suggests repeatedly that the essential nature of morality in his field comes down to considerations of both payoff and the probability of success.
January 19, 2009
It's not a profound book, but it's a novel concept. The 50 scenarios Olson provides are terrific, but not just because of the moral dilemma each poses. The book ends up being a good starting point for the countless folks who can't seem to separate the reality from the fiction in espionage. There are legal boundaries and moral limitations that aren't crossed on a daily basis, contrary to popular misconceptions. On the other hand, it's not all black and white. Cost-benefit analyses don't ignore morality, so it ends up being fascinating to see the difference of opinions among the individuals Olson selected for commentary.
It's worth reading if you're looking to build an understanding of US intelligence operations... plus, Olson was kind enough to provide a list for further reading (50 books). If used right, this book could be a valuable teaching tool in an undergrad intel course. Here's a more complete review: (just realize that it's posted on cia.gov).
Oh yeah, and there's a scenario on exploding dolphins (No. 36, I think). Olson's got all the bases covered.
It's worth reading if you're looking to build an understanding of US intelligence operations... plus, Olson was kind enough to provide a list for further reading (50 books). If used right, this book could be a valuable teaching tool in an undergrad intel course. Here's a more complete review: (just realize that it's posted on cia.gov).
Oh yeah, and there's a scenario on exploding dolphins (No. 36, I think). Olson's got all the bases covered.
May 12, 2013
My high ratings reflect the book's engaging style and clarity when conveying information. This is the first source I have found that reveals at least some basic structures of CIA operations, recruitment, and training. Recommended by a fellow author for research purposes, I find this book to be informative, even fascinating. A real, retired CIA case worker wrote it, a man with covert action experience. This sort of information helps me decide which facets of my spy character are realistic and which are not. The author also recommends books and movies where writers get it "basically right," and the bibliography lists other books with relevant titles. If I start falling asleep, I'll downgrade the rating, but so far, this book is a fascinating and highly useful resource for the average fiction writer.
March 14, 2014
Without any hesitation, this is the best book on the intelligence community that I've come across to date. Olson is a fantastic writer who capably navigates the murky intersection of morality and intelligence-gathering, first with an overview of various philosophical standpoints and then with a series of deliciously compelling hypotheticals. His experience as a former CIA officer adds to the conversation but doesn't color it, as Olson's insights guide the reader through the full scope of ethical considerations facing the intelligence community today. If nothing else, Olson deftly conveys that there are no clear answers when it comes to the world of espionage. If you have even the slightest interest in intelligence work, this is a must read.
September 20, 2016
This is an excellent book for those who wish to ponder the moral elements of intelligence work amidst the competing interests of security, privacy, and civil liberty, et al. Olson specifically does a good job with creating hypothetical situations and showing the highly gray nature of the choices. The chapter that examines the different philosophical perspectives on spying is a little dry but it is valuable in the examples.
August 8, 2012
Professor Olson discusses his CIA career and poses many questions CIA personnel face every day. I found it interesting but was beginning to be bored before I finished the book. The reason may be that I read small parts of this book over an extended period of time. Olson is a great public speaker and I had the pleasure of hearing him at a county fair dinner. His presentation was great!
March 23, 2018
This was a super interesting read. This made me consider a lot of different types of situations the US government finds itself in. I would recommend this book to anyone who has any type of interest in ethics or the US government.
February 18, 2020
Pulling the trigger
Most people can commit a crime but not all can live with the consequences. This is a fascinating series of fifty scenarios with which you must decide if a CIA case officer is justified moving ahead with the facts laid out. Its not as easy as you might think
Most people can commit a crime but not all can live with the consequences. This is a fascinating series of fifty scenarios with which you must decide if a CIA case officer is justified moving ahead with the facts laid out. Its not as easy as you might think
December 4, 2021
I really like Olson’s writing, and how he tries to focus reader’s attentions on what spies have to deal with, not only physically but mentally, morally. It’s important for people to understand the dilemmas spies face in different situations.
They lie, cheat, and steal from people and governments in multiple countries. They commit acts of atrocity against other governments. They deceive, abuse, and attack people whether it be physically or in other ways. And while it’s for the good of our country, is it actually moral? What are the moral dilemmas of spying?
Spying is not considered honorable, and espionage is illegal in all countries and yet we do it…sometimes to even affect other democratic governments. If nothing else, WWII showed the need for national security and counterintelligence. Yes, espionage may prevent war, but it has some nasty repercussions.
Olson posits the question: Can we remain a truly democratic nation while staying in the business of spying and deceit? Are we putting our country in danger by going out and influencing other countries?
He gives his own brief history, the history of espionage in the United States, and then fictional yet realistic scenarios to be analyzed by the reader before being answered by people in a number of positions. He uses these to demonstrate the moral dilemmas the CIA faces and to show there is no one single correct answer.
When I read another book by Olson, I thought that other than my issue with other languages, I would be interested in the CIA sans the high levels of espionage. After this book, I realize I would be really bad in such a position, if only because I have a very high moral compass that made me say “no” to almost every situation.
Still, 50 is a lot and they take up the majority of the book. After 20 scenarios, I felt like they were becoming repetitious (even if they weren’t) and could be cut down by a lot.
They lie, cheat, and steal from people and governments in multiple countries. They commit acts of atrocity against other governments. They deceive, abuse, and attack people whether it be physically or in other ways. And while it’s for the good of our country, is it actually moral? What are the moral dilemmas of spying?
Spying is not considered honorable, and espionage is illegal in all countries and yet we do it…sometimes to even affect other democratic governments. If nothing else, WWII showed the need for national security and counterintelligence. Yes, espionage may prevent war, but it has some nasty repercussions.
Olson posits the question: Can we remain a truly democratic nation while staying in the business of spying and deceit? Are we putting our country in danger by going out and influencing other countries?
He gives his own brief history, the history of espionage in the United States, and then fictional yet realistic scenarios to be analyzed by the reader before being answered by people in a number of positions. He uses these to demonstrate the moral dilemmas the CIA faces and to show there is no one single correct answer.
When I read another book by Olson, I thought that other than my issue with other languages, I would be interested in the CIA sans the high levels of espionage. After this book, I realize I would be really bad in such a position, if only because I have a very high moral compass that made me say “no” to almost every situation.
Still, 50 is a lot and they take up the majority of the book. After 20 scenarios, I felt like they were becoming repetitious (even if they weren’t) and could be cut down by a lot.
May 8, 2023
This is an interesting and thoughtful book. It is essentially a plea for clear guidelines for what it is acceptable for American intelligence officers to do. It starts out by giving an overview of American spying and how it developed, but the bulk of the book is scenarios that American intelligence officers may face and asking about the morality of certain actions. He then gets a variety of people to answer. It doesn't offer any conclusions, although the author does make notes comparing the hypothetical scenario to an actual one.
There is a lot to like in this book. The writing style is easy to follow and it provides a lot of perspectives. There were some trends that I thought were very interesting. The first is that when more than one former CIA officer was presented with the same scenario, they didn't always come to the same conclusion on the morality of an action. Another was how ofter the respondents dodged the question of morality by only looking at the efficacy or insisting that there was another way to achieve the objective.
There were also some specifics I thought interesting. Olson says that the CIA has never (to his knowledge) broken a deal with an agent, not because of morality, but because it is good business to be known as trustworthy. Another was that the CIA doesn't use honeypot agents. The issue of assassination was particularly murky because it is illegal but we have targeted specific terrorist leaders for drone strikes.
If you are interested in espionage or ethics, this is worth a read.
There is a lot to like in this book. The writing style is easy to follow and it provides a lot of perspectives. There were some trends that I thought were very interesting. The first is that when more than one former CIA officer was presented with the same scenario, they didn't always come to the same conclusion on the morality of an action. Another was how ofter the respondents dodged the question of morality by only looking at the efficacy or insisting that there was another way to achieve the objective.
There were also some specifics I thought interesting. Olson says that the CIA has never (to his knowledge) broken a deal with an agent, not because of morality, but because it is good business to be known as trustworthy. Another was that the CIA doesn't use honeypot agents. The issue of assassination was particularly murky because it is illegal but we have targeted specific terrorist leaders for drone strikes.
If you are interested in espionage or ethics, this is worth a read.
July 17, 2021
Spying creates a host of ethical and moral dilemmas. Depending on your worldview and code of ethics, it can be easy to indulge or forbid certain actions on a personal or institutional level. I was surprised to learn how few guidelines American spies and intelligence officials are given. They are expected to stay out of sight, get the job done, and not draw unfavorable attention to the US government. I've certainly come to the conclusion that more explicit rules are needed. Intelligence officials need to know what's in-bounds and out-of-bounds for their operations, while the American people need to have a broad understanding of what intelligence agencies do.
This was quite the intellectual workout. I really enjoyed going through the 50 semi-fictitious scenarios that Professor Olson uses. It pushed me to think through what I would be comfortable and uncomfortable authorizing/doing, and then to compare that with how Olson and the experts view the situations. Some were clearly unethical and immoral, but many were rife with gray areas. It gives me respect for men and women tasked with making these challenging situations.
This was quite the intellectual workout. I really enjoyed going through the 50 semi-fictitious scenarios that Professor Olson uses. It pushed me to think through what I would be comfortable and uncomfortable authorizing/doing, and then to compare that with how Olson and the experts view the situations. Some were clearly unethical and immoral, but many were rife with gray areas. It gives me respect for men and women tasked with making these challenging situations.
March 8, 2024
I would give this 3.5 ⭐️
The author provides a helpful framework for ethics at the beginning of the book. He then walks readers through 50 scenarios that present ethical dilemmas. The author also quotes various commentators who come from various backgrounds (defense, intelligence, religion, diplomacy, education, etc.). The result is a robust discussion of the scenarios and good, practical applications of ethical principles.
The appendix is very helpful in defining terms of art and giving historical background.
The author provides strong guidance on some of the scenarios, but others are more open ended. Ultimately this work is a call to Americans to think of these issues and define an acceptable operating standard.
The author provides a helpful framework for ethics at the beginning of the book. He then walks readers through 50 scenarios that present ethical dilemmas. The author also quotes various commentators who come from various backgrounds (defense, intelligence, religion, diplomacy, education, etc.). The result is a robust discussion of the scenarios and good, practical applications of ethical principles.
The appendix is very helpful in defining terms of art and giving historical background.
The author provides strong guidance on some of the scenarios, but others are more open ended. Ultimately this work is a call to Americans to think of these issues and define an acceptable operating standard.
April 18, 2025
Very interesting book in which the author poses a variety of very specific scenarios involving the development of intelligence leads such as blackmail, inserting someone under cover at a news organization, etc. and presents the opinions of professionals in and out of the intelligence sector, including clergy and legal experts. Finally, the author reveals historical occurrences of similar scenarios and how they were approached by intelligence services around the world. This is not by any means a cross sector representation of views, and definitely leans biased towards the defense sector, but is nonetheless a great read.
May 5, 2025
This was a really eye-opening read. I've often thought of the CIA as doing a decent amount of morally suspect things, and I am certain those morally suspect things happen, but this book changed by view of the organization as a whole. I used to think the CIA was very "no holds barred" and would do literally anything -- no matter how immoral -- to accomplish a mission, but after reading this it seems clear that there's a lot of wrestling with morality and that many people in the CIA do have strong limits on what is acceptable and what is not, and refuse to cross those lines.
December 2, 2024
Great book if you’re interested on seeing how your moral compass aligns in regards to human rights and an engaging read in general as the situations are well written and really make you think. The fictional scenarios in the book are very realistic and possibly very similar to real scenarios. It was interesting to see how others quoted in the book felt about some of the scenarios(the CIA operatives quoted in the book had a surprising amount of moral reservations). Overall, good read.
June 13, 2025
3.5 stars. A little dry at times but a very important and thought-provoking book.
My favorite quote: “If you pick the right theologian or philosopher, you can defend almost any position, from moral absolutism to unconstrained utilitarianism to everything in between.” I believe this highlights the pivotal importance of contemplating the morality of our actions. Especially in the government and defense fields.
My favorite quote: “If you pick the right theologian or philosopher, you can defend almost any position, from moral absolutism to unconstrained utilitarianism to everything in between.” I believe this highlights the pivotal importance of contemplating the morality of our actions. Especially in the government and defense fields.
July 4, 2018
Olson’s book is an excellent resource for those serious about the practical and ethical challenges inherent in espionage. Well written, informative, and full of insights from multiple sectors. The Spying 101 notes alone are worth the purchase price of the book. They contain a treasure trove for espionage writers and enthusiasts.
July 30, 2018
Had to give it back before I finished. Over all, I don't think the play is fair at all. The author seems to say that the ends justify the means and it's ok to lieb cheat, steal and murder for your country because all the other countries are doing it. Doing things "for the greater good" is a very slippery slope. I guess I wouldn't make a good spy.
September 5, 2021
This was a very good book, but also very disturbing. I appreciated Olson's openness about his consequentialism, but it was nevertheless disturbing that this is what most American Christian ethics boil down to. I loved that he gave a bunch of real world scenarios and then had a number of people assess them to see the range of viewpoints and rationales.
December 19, 2021
I found the first part of the book fascinating, I have a long on going conversation with some friends about jobs a Christian can’t do, spy/espionage is on that list. I am not sure I was convinced otherwise, but I did get a lot of food for thought. The case studies section was immensely concerning given that poverty of actual ethical reasoning among the respondents.
May 2, 2022
A really fascinating exploration of the ethics of spying. The introductory materials are great for a theoretical background. The meat of the book is 50 scenarios in which the dilemma is given and then the author had people comment on what should be done. That was really fascinating. I am going to use this in a course on human intelligence.
April 7, 2025
Very interesting book. Plenty of seemingly grey area scenarios to challenge one’s thinking. For the most part, if the reader adheres to utilitarian ethics, most of the scenarios will be straightforward. For those that do not, most of the scenarios will also be straightforward. For those who are unsure, lots of challenging decisions. 3.5 stars.
March 3, 2021
An insightful look at morality in our intelligence services. Olson gathers opinions on 50 different scenarios from individuals from various backgrounds and poses questions on the morality of spying and the ethical dimensions that present themselves across a variety of issues.
Displaying 1 - 30 of 61 reviews