Steve Coll's two-volume history of America in Afghanistan
Ghost Wars and Directorate S are really one long book split into two Pulitzer-winning halves.
Ghost Wars covers the CIA’s covert war in Afghanistan from the Soviet withdrawal to the day before 9/11: the funding, the double games, and the blind spots that let bin Laden’s network grow largely unchecked.
Directorate S picks up immediately after and follows the next twenty years: the war that followed, and the Pakistani intelligence establishment that spent two decades working both sides of it.
Neither is a quick read, since Coll reports at a level of detail that rewards patience. Back to back, they are the closest thing there is to a definitive account of how a superpower stumbled into, and never quite won, its longest war.
When the United States announced it was leaving Afghanistan this topic piqued my interest and these two books helped satisfy my curiosity. What stands out especially about Coll is style of writing. Getting through 1000+ pages without getting bored says a lot about the book.
