This book is meant as an exploration of the National Security infrastructure and whether it is overreaching into everyday people's lives. The author starts with the case of John Walker Lindh who fought in Afghanistan for the enemy and served time back in the United States. This leads to a discussion of enemy torture. Then the cases of Julian Assange and Edward Snowden, both of whom leaked government documents.

The main thrust of the book follows the case of Reality Winner. She was recruited at age eighteen into the military and taught various languages from the countries the United States was engaged in war with. After she left the military, she got top secret clearance and worked as a translator. Bored, she wanted to go to Afghanistan and interact directly with people as a translator. In that state, she found a top secret document that she thought showed evidence of Russian interference in American elections. She sneaked it out of the office and sent it to a whistleblowing site, which released it. Winner was arrested and eventually served time for her offense.

Kerry Howley is a journalist and writing professor whose articles and short stories have been published in various publications and magazines. This book was a National Book Critics Circle Award finalist and a New York Times Top Ten Book of the Year but it felt unorganized to me. Howley seems to flit from topic to topic and never really settle on a uniting theme. Various topics include the use of enhanced interrogations, the cases of other whistleblowers, a long discussion of Winner's trial and eventual plea deal and the concept that we are all just data points and have no privacy. A more focused discussion on any of these themes would have made for a better book. This book is recommended for nonfiction readers.

BOTTOMS UP AND THE DEVIL LAUGHS by Kerry Howley is subtitled "A Journey Through the Deep State" and the author, a feature writer at New York magazine, discusses several whistleblower cases. In particular, she looks at the issues involving young, twenty somethings like Reality Winner, Chelsea Manning, or Edward Snowden. Although Howley's writing seems a bit too sophisticated to hold the interest of our high school students, this title was recently one of twelve books on a New York Times' list, "What Book Should You Read Next?," of 2023's Best Books. Plus, BOTTOMS UP AND THE DEVIL LAUGHS received a starred review from Publishers Weekly.

Link: https://www.nytimes.com/article/best-books.html

I basically knew nothing of this world. I was familiar with Julian Assange and Chelsea Manning but that’s about it. Howley really approached this book with a style that is both informative and conversational which I appreciated. Mostly because whenever anyone brings up the deep state my eyes gloss over and I zone out. That held true in my reading of BOTTOMS UP AND THE DEVIL LAUGHS but a lot less so than I expected due to Howley’s skill.
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The heart and soul of this book is Reality Winner, a woman convicted of leaking confidential documents. I think I would’ve liked the book more if it stuck with just her story versus tying in so many elements because I kept getting confused on the multiple timelines and agencies involved in the overlapping stories.
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Overall I liked, but didn’t love, this book. I read on audio and thought the narrator was engaging. If the idea of a book on the deep state interests you, read this book, if not you can skip.

This was riveting from start to finish. Potential readers should not let its opaque subject matter or bizarre title deter them (In case you forgot, as I did: it's a meme from 2014 featuring a Christian woman earnestly explaining how Monster energy drinks are a Trojan Horse of Satanism).

This is actually a very wise book about many things: the War on Terror, the Internet, surveillance in all its forms -- and how these factors have converged over the last 20 years to change how we collectively make sense of reality, remember, and are remembered. The people Howley has selected to profile in this book -- John Walker Lindt, John Kiriakou, Reality Winner, and more -- are all fascinating subjects, rendered with precision and authenticity. Like all great narrative nonfiction authors, Howley herself is a measured guide who does not insert herself unnecessarily, and steadfastly avoids deifying or condemning her subjects. I particularly enjoyed reading the interviews with Reality Winner and her family, which make up the second half of the book. Overall, this is a subject that I've been very interested in for years -- and Hawley successfully captures its nuances.