askew sign that says please stay on the path

Reality Winner was only 25 when she leaked a single NSA intelligence report to the media. The report was about Russia’s attempt to influence the 2016 U.S. Presidential election. She was arrested on June 3, 2017, and convicted on August 23, 2018. She was released from prison on June 2, 2021.

Kerry Howley, the author of Bottoms Up and the Devil Laughs, has the following theory about Reality Winner:

“Reality was intellectual but she had not been raised in an intellectually sophisticated household. . . . An intellectual orphan comes to knowledge absent the social pressure to conform to a particular set of ideas. Reality would not have known which theories were fashionable or which to be slightly ironic about. It takes such a person, in their conceptual innocence, far longer to ably sort through the tangle of established human thought. But you cannot be subject to blind acceptance of received wisdom you have never received. She took ideas in their fullness, ignorant of their social context, and therefore radically open to argument. It did not matter to Reality that working for the drone program while teaching yoga and loudly moralizing about climate change would strike many people as bizarre. She was not on a team. Had not been invited to join one.”

First of all, I want to say, what a fabulously written paragraph. Strangely enough, I find Howley’s writing similar to Nikolai Gogol’s in that I have no idea where Howley is going most of the time. Each sentence is layered on top of the next like lasagna. You don’t know whether the ricotta is coming next or the noodles, or maybe it will be the bolognese—but then she throws in a layer of zucchini, and then olives, and you’re baffled until you sort it all out.

I find Howley’s theory persuasive. But, honestly, the more I think about this topic, the more I find my own mind caught up in “the tangle of established human thought.” I don’t normally quote from Amazon reviews, but one reviewer named Randall Peelen left a 5-star review that perfectly encapsulates how I feel about Howley’s book. They wrote, “I’m a little tongue-[tied] regarding how to describe this book.” And then, “The author has raised some questions that do not have black or white answers. . . . Regarding the author’s use of Reality Winner as an illustration of her narrative, ‘there but for the grace of God go I.’”

Randall—you nailed it. Those were exactly my feelings as I read. Most of our society’s discussions of Reality Winner and other whistleblowers center around the politics of questions like “Should she have leaked the document or should she have not leaked the document?” But Howley blows past all that and delves into Winner’s psychology: what it’s like to be an “intellectual orphan,” and what it’s like to be young.

I remember being 25. I remember being consumed by the grand ideas of the books I loved, while also being quite socially unaware. This combination of traits resulted in me getting into trouble at work. I tried to stand up for what I believed in, but I did not understand what I was doing, nor did I understand the consequences. I did things I later regretted. But don’t lots of people in their 20s do things that they later regret? Oh, Reality—”There but for the grace of God go I.”

Do you know the rules?