Legacy of Ashes: The History of the CIA

This is a red book cover with the title in big white text across the front.

Book written by Tim Weiner

Book review by Rick Howard 

Bottom Line

I don't recommend this nonfiction book for the Cybersecurity Canon Hall of Fame, but if you are interested in the topic, this is a good one to read.


As I've gotten older, I've started to notice things. I've noticed that the ideas and beliefs that I had about my country's institutions and purported democratic way of life may not be supported by the actual facts on the ground; that these same institutions (FBI, NSA, DOJ, the CIA, etc) have a history of acting counter to those aspirational ideals not as the exception but as the norm; that although we talk a big game in our promotional materials (as in President Reagan's recurring speech metaphor that the United States is the "shining city upon a hill), in the worst cases, we often act in ways that are even more devious and evil  then our hated enemies, and in the best cases, we act like a car full of clowns with no long term thoughts, or a bull in a china shop unaware or apathetic regarding the consequences of our actions. I've had to accept the idea that Americans may not be the good guys in the world as much as I would like that to be true. If you're like me, then Weiner's book, Legacy of Ashes: The History of the CIA might cause you to lose all faith in our liberal democracy. I hope not, but I could understand that reaction.

I initially chose this book for a potential Cybersecurity Canon candidate because of the intelligence angle. A subset of all intelligence operations is cyber intelligence and I was hoping to glean some tips and tricks from the professionals. I knew the book was going to be a takedown of how the CIA has operated over the last 70 years,  but I was hoping to learn from their mistakes. Unfortunately, the only lesson I learned in terms of intelligence operations is "don't do what they do."

In the United States, there are 17 official intelligence agencies. They all have the mission to gather secret intelligence through espionage but the CIA, as well as several of the military intelligence agencies, also have the mission of taking battle to the enemy through covert action. According to Dr. Amy Zegart in her Spies, Lies, and Algorithms: The History and Future of American Intelligence, a covert action is “an activity or activities of the United States Government to influence political, economic, or military conditions abroad, where it is intended that the role of the United States Government will not be apparent or acknowledged publicly ... Covert action is active; its aim is to produce or affect outcomes. Espionage is more passive; its purpose is acquiring information."

Since its inception, the CIA has leaned on that covert action lever a lot, and in the early days (late 1940s through the 1990s), they were the only organization conducting covert operations. That started to change after 9/11 when the military, and the supporting contractor commercial companies, took on more of those tasks.

But for the bulk of its history, it feels like the CIA had no long range strategy for the nation, used tactics that were "Extra-legal" (Overthrowing legitimate governments, assassinations, torture),  had little supervision (mostly only the President and sometimes CIA leaders lied to them), and had no strategic metrics to decide if what they were trying do was working let alone deciding if the United States should be engaged in that activity in the first place. Their list of operations reminds me of that scene from the 2008 movie The Dark Knight when the Joker explains to Harvey Dent that he doesn't really have a plan. "Do I really look like a guy with a plan? You know what I am? I'm a dog chasing cars. I wouldn't know what to do with one if I caught it. You know, I just... do things." That is the CIA in a nutshell in the early days.

They focused on the Russians almost exclusively and knew hardly anything about the rest of the world. When the Berlin wall came down, they were lost. They were horrible spies because they couldn't assimilate into native cultures and thus relied on recruiting locals for their intelligence collection which they weren't very good at. After 9/11, the CIA couldn't stop the massive brain drain as experienced operatives left the agency in favor of exponential salary increases working for the beltway bandits. According to Weiner, at the time of the book's publishing (2007), the CIA was just a shell of what it once was.

To be fair, the CIA has had some successes. We should acknowledge that and Weiner covers them. But the fact of the matter is that covert action, by its very nature, is risky. According to Dr. Zegart, they give Presidents a third option to influence the political landscape that is short of an all out war but better then giving your enemies a stern talking to. Still, even in the best circumstances, most have a low probability of success. It stands to reason that most of them turn out to be failures. But Presidents on both sides of the political aisle can't resist them and haven't.

Don't get me wrong, the book is a fascinating account of CIA history and how it functions. Just for that alone, it is well worth the read. But it’s depressing. The United States has always been a mixed bag of aspirational ideas and horrible actions in the real world that contradict each other. This book is a bag of those mostly horrible actions (and there are a lot of them) conducted by the CIA . Like I said in the beginning of this review, the book can cause you to lose faith in the United States' version of democracy. I hope not. I'm trying not to let that happen for me. I believe that it's up to all American citizens to be aware of these bad histories so that we can avoid them in the future; so that when we are presented with difficult choices in the future, we can choose the aspirational path. That’s a fantastic reason to read Weiner's Legacy of Ashes: The History of the CIA.