I set down some thoughts a few days ago on Tim Weiner's Legacy of Ashes. Turns out that bigfoot blogger Spencer Ackerman called it "the greatest [book] ever written about the CIA." Although I haven't read that many books about the CIA, this one sounds like a stretch to me; apparently so also to Jeff Stein, proprietor of Spy Talk, and far more knowledgeable on these matters than I (link)--he's not persuaded either. Stein does move the ball downfield, though, by asking: what really is the best CIA book ever? Stein himself suggests Tom Powers' The Man Who Kept the Secrets, which seems plausible to me--I haven't read the book, but I follow Powers' stuff with great enthusiasm at the New York Review of Books. Stein's piece includes a number of alternative candidates. Remarkably, nobody mentioned Evan Thomas' The Very Best Men: Four Who Dared: The Early Years of the CIA (1995)--maybe disqualified for egregious overuse of the colon, but still an absorbing account of the "first days" at the company. And while it is not quite on point, one would want to remember Anthony Cave Brown's Wild Bill Donovan: The Last Hero (1982), about the man who built the OSS, the CIA's World War II precursor, without which the CIA as we know it is pretty much unthinkable.
But for me, a more extraordinary void was--no mention of the work of David Wise, co-author (with Thomas B. Ross) of Invisible Government (1964) which must count as the first good book about the CIA--part of a body of good work about government abuse. Wise/Ross didn't really "disclose" the history of CIA dirty tricks--the practice had been more or less an open secret for a long time. But they certainly showcased the pattern immanent in activities like the overthrow of governments in Iran and Guatamala--along with failed efforts like the attempt at a coup in Indonesia, and, closer to home, the Bay of Pigs.
Stein suggests he'll be doing "CIA novels" later, but I think he can close up shop now: the one and only candidate is Aaron Latham's Orchids for Mother (1977) about the infamous James Jesus Angelton, whose own paranoia about counterspies did as much to destroy our intelligence activities against the Soviet Union as a whole passel of moles. Have heard it said that Latham got a toehold on the project one afternoon when he got drunk with CIA director William Colby--so you know it must be true.