Legacy of Ashes: The History of the CIA by Tim Weiner
Summary: A history of the CIA from its origins in US military intelligence units up to right after 9/11. Based only on primary sources (released CIA documents, interviews with insides, etc.; no rumors or unconfirmed theories), Weiner shows how the CIA has routinely failed to meet its goals and has often made bad situations worse. All of this despite filling the organization with intelligent men ready to die to defend their country by providing military intelligence to the president and engaging in covert operations.
Lessons: There are many small lessons you can learn from the episodes of the history, but the big lesson you'll find is that when an organization has a culture of secrecy, to the point that not even the people in charge with the highest clearance have access to all the secrets, you open the door for mismanagement and abuse. But because the CIA was designed to be opaque, even to the president, it had no accountability or oversight, became inbred with bad ideas, and began to operate independently of US policy by receiving money from Congress and hiding its operations, even from units within itself. The CIA is a case study of the tremendous damage that a few men with power, money, and secrecy can do, where only luck prevented what could have been disastrous consequences.
Followup to: Unteachable Excellence
As previously observed, extraordinary successes tend to be considered extraordinary precisely because it is hard to teach (relative to the then-current level of understanding and systematization). On the other hand, famous failures are much more likely to contain lessons on what to avoid next time.
Books about epic screwups have constituted some of my more enlightening reading. Do you have any such books to recommend?
Please break up multiple recommendations into multiple comments, one book per comment, so they can be voted on and discussed separately. And please say at least a little about the book's subject and what sort of lesson you learned from it.