Into the Post-Privacy Digital Age: A Look at Bottoms Up and the Devil Laughs: A Journey Through the Deep State by Kerry Howley

Layne Barr ‘27

Visual by Lily Gottschling ‘27.

The moment I read the title of Kerry Howley's book, Bottoms Up and the Devil Laughs, I was reminded of a viral YouTube video from 2014 in which a middle-aged woman at a Christian conference breaks down the purportedly satanic symbolism on a Monster Energy drink can. In her well-rehearsed two-minute speech (complete with visual aids), she confidently assures her audience that the letter "O" in the word "Monster" on the can becomes an inverted crucifix—a Satanic anti-Christian message—when the can is turned upside down to drink from.

After three days on YouTube, the video amassed more than 5.7 million views. 

How fitting a title for Howley's consuming exploration into the post-privacy digital age of today. Her book is both a question and a warning about the real-world impacts of our often very distorted online identities. "Who are you? You are data about data. You are a map of connections—a culmination of everything you have ever posted, searched, emailed, liked, and followed," writes Howley early on in her book. Through just over two hundred pages of polished prose, Kerry Howley examines what it means to be living in the era of the indelible.

Following the story of the acclaimed whistleblower, Reality Winner, Howley’s book descends into a rabbit hole of government agencies' secret and potentially unauthorized networks. 

In 2016, Winner was a twenty-five-year-old Air Force veteran. She had served for six years working as a cryptologic linguist assigned to the drone program where she listened in on intercepted foreign dialogue to provide intelligence to U.S. forces. After being honorably discharged, Winner packed her belongings and moved to Augusta, Georgia, where she found a job working as a translator for the National Security Agency, Pluribus International. At Pluribus, Winner was one of the 1.4 million Americans with top-secret clearance. 

On May 9th, 2017, Winner opened a classified report on a Russian cyberattack. The report read, "Russian General Staff Main Intelligence Directorate actors executed cyber espionage operations against a named U.S. company in August 2016, evidently to obtain information on elections-related software and hardware solutions." 

The document was marked "TOP SECRET", meaning it was supposedly classified information that the government deemed highly sensitive and required protection. It was a report that Winner had no reason to be accessing. She was not supposed to be reading it in her spare time. She was not supposed to be printing it out on her work printer. In the summer of 2017, Winner was, however, frustrated with the current political climate. It bothered her that Fox News always played on the televisions at Pluribus. It irritated her that questions of whether Russia had interfered in the 2016 election were being debated right in front of her. There was evidence available to Winner. 

She printed the document, stuffed it in her pantyhose and left the building. Later, in an interview with 60 Minutes, Winner told correspondent Scott Pelley that she knew the risk she was taking when she anonymously mailed the report to The Intercept two days later. "I knew it was a secret," she said. "I also knew that I had pledged service to the American people. And at that point in time, it felt like they were being led astray."

On June 3rd, 2017, less than a month after Winner mailed the document to The Intercept, two FBI officers approached her as she unloaded groceries from her bumper-sticker-covered Nissan Cube. They told her they had a warrant to enter and search her house. Winner told them she had a rescue dog that did not like men. They asked for her cell phone. Winner gave it to them, despite realizing she had not set up any security – not even a passcode. They asked if she had any weapons in the house. "Yes," she replied, "a Glock under the bed, a fifteen gauge, and an AR-15 (and yes, it is pink)." Nine more FBI officers showed up. In her living room, they checked for anything hidden behind her framed posters of Billy Joel and The Beatles and her pencil sketches of Gandhi and Martin Luther King Jr.. 

The officers maneuvered around Winner's extensive collection of workout equipment (she taught Crossfit and Yoga, depending on the day of the week). They found and confiscated her four laptops and second cell phone. They asked her about the leak, her intentions, and how she smuggled a classified document out of Pluribus. Winner said she was "definitely here to comply." She did not request to consult a lawyer. The FBI officers failed to inform her of her right to one.

Winner was detained hours later, and on June 8th, she pleaded not guilty to a charge of “willful retention and transmission of national defense information.” She was denied bail. During Winner’s trial, prosecutor and U.S. Assistant Attorney Jennifer Solari used evidence from Winner’s Twitter. Her feed (inactive since February when she became an NSA contractor) contained tweets denouncing Donald Trump as “the orange fascist we let into the white house” and mocked Attorney General Jeff Sessions as being a “Confederate.” Solari suggested this was evidence of Winner’s motive for leaking the document. 

Solari questioned Winner’s mother and step-father during the first day of her trial. She asked them if they knew what their daughter did in terms of her job. They said that she carried a top secret clearance and therefore could not discuss the details of her job with them. Solari said this was further evidence of Winner’s “fractured personality.” 

Winner told her older sister, Brittany Winner, in a phone call she made from jail that she did not want to spend the rest of her life in jail and that she was going to “play that card being pretty, white, and cute; braid my hair and all, gonna cry.” Solari used this phone call as evidence of the “defendant’s poor character” in her prosecution against Winner. Winner, a woman who spent years eavesdropping on conversations for the U.S. military failed to assume that someone might be listening to her call. It was a fatal assumption.

There is a significant anxiety among those living in the era of the indelible – an apprehensive sense that we are leaving pieces, traces, of ourselves on our smartphones. The possibility that these fragments of our lives could be reassembled to form an identity that looks like us, but actually is not us—what Howley calls “a fantasy built on solid ground”—is illustrated through Reality Winner’s story.

In a Facebook chat between Winner and her sister a couple of months before her trial, Winner wrote, "Look, I only say I hate America like three times a day, I'm no radical. It's mostly just about Americans' obsession with air conditioning." Her sister wrote back, "But you don't actually hate America, right?" Winner replied, "I mean, yeah I do, it's literally the worst thing to happen on the planet. We invented capitalism and the downfall of the environment." 

Prosecutor Solari used this text along with several other pieces of Winner’s online identity to illustrate her as a dangerous terrorist. Her strategy worked. Reality Winner was sentenced to 63 months in prison—the longest sentence ever imposed upon someone for an unauthorized release of government information.