Why Did Reality Winner Do It?

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Reality Winner stood in a county jail in rural Georgia, phone receiver pressed to her ear, staring at a brick wall and racking her brain, trying to remember the minimum sentence for violating Chapter 18, Section 793(e) of the U.S. Criminal Code. She’d signed papers acknowledging the penalty so many times — it was a requirement for anyone who handled classified information — but whatever recess of her mind the details were tucked away in, she was having trouble accessing it.

The date was June 4th, 2017. Winner was 25 years old, blonde, blue-eyed, 5-foot-5, approximately 145 pounds, according to an FBI search warrant executed the day before. She’d spent exactly one night in jail. She didn’t fully recognize it yet, but life as she knew it — her day job as a subcontractor for the National Security Agency, the yoga classes she taught in her spare time, the date she’d missed because of her arrest — was rapidly slipping away from her.

On the other end of the phone line, an automated voice repeated, “We are attempting to receive acceptance information from your called party… Please continue to hold.”

The only thing she was focusing on in that moment was getting through to her sister. She’d called before, but Brittany, who was busy finishing up her Ph.D in Michigan, didn’t recognize the jail’s number, assumed it was an aggressive telemarketer and ignored the calls. This time she picked up.

“Oh boy, Britty, I screwed up,” Reality said.

Brittany, the elder sister, knew from speaking to their mother that Reality had been arrested. “Probably not wise to tell me any details about what they think you did,” she warned. Then, to lighten the mood, she cracked a joke, asking if Reality was in trouble for something like misremembering her brother-in-law’s birthday on a government background check.

“No,” Reality replied. “I leaked a document. And they were able to trace it back to me. And it’s kind of an important one… So there’s a minimum sentence.” She just couldn’t remember what that sentence was.

Brittany was right to be cautious. The jail was recording that call, and all of Reality’s calls. Government lawyers were preparing to use them — and her emails, Facebook messages, diary entries and Internet search history — to portray her as a radical, vindictive would-be terrorist instead of a whistleblower determined to reveal the extent of the government’s knowledge of a hostile foreign power’s attempts to compromise a U.S. election.

Winner, who was sentenced to 63 months on August 23rd, should, by all rights, be the poster child of #TheResistence. While others were play acting on Twitter, she was a real life @AltNatSecAgency — a veteran who had planned to leave government service, but changed her mind when Trump was elected. She sought a job, seemingly, with the express purpose of infiltrating an administration she opposed — then she actually did it, releasing information that the government appeared intent on hiding.

The fact that her case failed to catch on as a cause célèbre for the mainstream left is a tribute, at least in part, to Department of Justice lawyers who made sure particular details — a throwaway comment that she “hate[ed] America” because of capitalism and a note she’d scribbled in her diary expressing a desire to “burn the White House down” — ultimately defined the public narrative about her.

When she spoke to her sister that night in June, Winner was still hopeful that she might be released from jail the very next day. She had a bail hearing scheduled, and her mother was driving from Texas to Georgia, ready to offer the family’s home as collateral. But she was drastically underestimating the Department of Justice’s determination to make an example of her — the first arrest they’d made in President Trump’s war on leakers.


Billie Winner-Davis, mother of Reality Winner, carries a sign in support of her daughter outside the Lincoln County Law Enforcement Center in Lincolnton, Georgia. Michael Holahan/The Augusta Chronicle/AP

About a month before Winner’s arrest, an envelope postmarked May 10th, 2017, in Augusta, Georgia — no return address — had arrived at the Manhattan offices of First Look Media, parent company of the Intercept, the online outlet founded in 2013, in part, to continue reporting on the massive trove of classified documents secretly spirited out of the NSA by Edward Snowden.

Folded inside the envelope was a five-page document. Classified as Top Secret/Special Intelligence, it contained details of Russian Military Intelligence efforts to hack at least one electronic voting software provider and more than 100 local election officials nationwide ahead of the 2016 presidential election.

Today, we know the federal government was aware as early as January 2017 that voter registration systems in at least seven states — Alaska, Arizona, California, Florida, Illinois, Texas and Wisconsin — were compromised, and systems in an additional 14 states were targeted by Russian hackers before the election. At the time, though, the government had only acknowledged the hackers’ success accessing “multiple U.S. state or local electoral boards.”

Journalists who report on national security often spend years gaining a source’s trust before that person feels comfortable enough sharing documents that might put them at risk of prosecution. It’s unusual — even at an outlet like the Intercept, which offers detailed instructions on how to leak information to its reporters — for a classified document to arrive in the mail, out of the blue, with no indication of who provided it or why.

When the envelope showed up, reporters were skeptical of its authenticity. If real, it had major implications. The report represented the first evidence that — contrary to the Obama administration’s assurances — the Russian government penetrated systems involved in tallying the 2016 vote. Verifying the document without knowing anything about its origin, however, would be challenging.

It remains unclear how the government was first tipped off to the leak, but an FBI agent would later testify about interviewing a witness in Tampa, Florida, who was approached by an Intercept reporter attempting to authenticate the document. That person’s texts with the reporter were described in court, but prosecutors requested an exhibit containing the messages itself remain restricted, ensuring the person’s identity and any details of the conversation are still secret.

“When the identity of a source is unknown, you have to find some other way to authenticate the materials — and that process always entails risk,” Intercept editor-in-chief Betsy Reed told Rolling Stone in a statement. “The risk can be minimized, but it is always there. It is far preferable to know who has given you documents, so you can better understand the risks the source may face and also gain perspective on the authenticity and context of the materials.”

It took four Intercept reporters several weeks to verify the report and to reach out for comment from the government agencies and software vendor it mentioned.

The story was published on June 5th, 2017. Later the same day, the Department of Justice put out a press release trumpeting Winner’s arrest, which had occurred two days prior. The blowback was instant. There was fevered speculation that the Intercept — an outlet that prides itself on specializing in digital security — had burned its source, and badly. (The Intercept, which has steadfastly maintained it has no knowledge of the source who provided the report in its story, has since instituted new newsroom procedures. Its parent company, First Look Media, volunteered to help finance Winner’s defense.)

In a statement, Reed said, “It’s regrettable that the media has largely covered this case as a whodunit, bank robbery-type story, when it is really a story about a courageous whistleblower facing persecution by a vindictive and politically motivated Justice Department.”

The National Security Agency’s Utah Data Center in Bluffdale, Utah. Rick Bowmer/AP/REX/Shutterstock

The night Donald Trump was elected president, Winner was finishing out the last days of a six-year stint with the Air Force. She’d enlisted straight out of high school, turning down a full-ride to Texas A&M University, Kingsville, to pursue a dream of deploying to Afghanistan. Her father, an amateur religious scholar, ignited her fascination with both religion and religious extremists after September 11th. (He also gave her her name — as her mother, Billie Winner-Davis, tells it, he told Billie, “I want a real Winner.”)

“I just remember being 11 years old, in the reference section of the library, with the A encyclopedia. I’d draw my own maps of Afghanistan and I’d trace Arabic letters,” Winner told Rolling Stone last fall. It was only after joining that she learned the vast majority of Air Force linguists never make it overseas.

Winner spent the entirety of her career stateside, much of it eavesdropping on foreign nationals and using information gleaned from their conversations to help pinpoint drone targets abroad. She earned a commendation during her time at Maryland’s Fort Meade for, among other accomplishments, “geolocating 120 enemy combatants during 734 [air missions]… and removing more than 100 enemies from the battlefield.”

By November 2016, Winner was preparing to leave the service, and making plans to move abroad. Her mother says she hoped to put the language skills she gained in the military to work at a humanitarian organization. (Winner is fluent in Farsi, Dari and Pashto). According to a record of her Internet search history later presented in court, in the days immediately preceding the election, she was Googling flights to Erbil, the capital of Iraqi Kurdistan.

“Well. People suck. #ElectionNight,” Winner tweeted from a pseudonymous account at 10:34 p.m. on November 8th, 2016. (She’d voted absentee, in Texas, for Hillary Clinton.) Later that night, she floated the idea of a mass exodus in protest of the election. “50 million Americans defecting to #syria will end the civil war, revive real estate in the country, and defeat #ISIS w/ #starbucks #done.”

After the election, though, Winner began actively searching for government contractor  jobs in the United States — specifically jobs that could make use of her security clearance — while also retweeting accounts like @RogueNASA, @AltForestServ and @AltUSDA, that imagined an army of anonymous civil servants inside the government who were actively resisting the Trump agenda.

In December 2016, she accepted what she would later tell FBI agents was “the only job I could get” — as a linguist for Pluribus International Corporation, an NSA contractor at Fort Gordon in Augusta, Georgia. She started on February 9th, three weeks after Trump’s inauguration.

Over the past 20 years, the NSA’s outpost at Fort Gordon has transformed from a small 50-person operation into one of the agency’s most important hubs, with a workforce of several thousand focused on intercepting communications from Europe, the Middle East and North Africa. (It was a pair of whistleblowers from Fort Gordon who, in 2008, provided one of the earliest indications that the agency was eavesdropping on U.S. citizens living abroad.)

As a contractor, Winner was required to go through a security orientation that warned new employees to be on the look-out for insider threats. She’d later tell Brittany on Facebook, “It was hard not to laugh when he was like, ‘Yeah, so, uh, we have guys like Edward Snowden who, uhh, thought they were doing the right thing, but you know, they weren’t so, uh, we, uh, have to keep an eye out for that insider threat, especially with contractors…”

In chats that were later introduced as evidence by the prosecution, Winner spoke of her admiration for Snowden and Wikileaks’ Julian Assange; discussed how “awesome” it was that Wikileaks’ published Vault 7 (internal documents that detailed the CIA’s cyber warfare capabilities) and joked to her sister, “I have to take a polygraph where they’re going to ask if I’ve ever plotted against the govt. #gonna fail.”

Presumably, she passed the polygraph and background checks, because she was soon assigned to the Iranian Aerospace Forces office, on the second floor of the Whitelaw Building at the Georgia Cryptologic Center inside Fort Gordon, translating documents from Farsi to English. Security at the building was so tight that every day Winner had to open her bag and allow the guard to inspect her lunchbox.

Nonetheless, on May 9th — the day Donald Trump fired James Comey — Winner printed the report on Russian hacking. She folded it in half, stuck it down her pantyhose and smuggled it out of the building undetected. Later that day, parked at a shopping center across the street from the studio where she taught yoga, Winner looked up the news outlet’s mailing address on her phone. (It took “three minutes of scrolling” she’d later say, which “felt like an eternity sitting in my car.”) She took a stamp out of her glove box, applied it and dropped the envelope in a mailbox.

A month later, after she confessed, FBI agents asked her why she did it. The best Winner could offer was: “It was just that day, that week — it was too much. And [to] just sit back, and watch it, and think, ‘Why do I have this job if I’m just going to sit back and be helpless?’…I just thought that was the final straw.”

This past Thursday, Reality Winner shuffled out of the Lincoln County jail handcuffed, in a standard-issue orange jumpsuit, to learn her fate. Her light-blonde hair had darkened and her features had softened since her arrest, but Winner smiled and flashed a peace sign as she climbed into a van that would transport her to the federal courthouse an hour away in Augusta.  

It had been 446 days since she’d come home from grocery shopping to find a cadre of federal agents waiting in her driveway, handed over her cell phone, the keys to her white Nissan Cube covered in bumper stickers and voluntarily answered the agents’ questions.

On her phone, the FBI would gain access to her messages and find a screenshotted list, made by @Anonymous, about how to securely leak documents to several news outlets, including the Intercept; in her car, they’d find a box of envelopes and stamps; in her house, the diaries prosecutors would introduce as evidence in court.

“I did not even think about the consequences for, like, a second,” Winner told her sister by phone after that first night in jail. “I wish there was a reset button.”

Winner was denied bail the next day, deemed a flight risk and a threat to national security. She was denied again in October 2017. “I thought I was going to get out of here,” she told Rolling Stone back in the fall. “And then it kind of sunk in that I am not getting out of here. They’re not going to let me go back to my life. Now it’s just been a battle of trying to keep the smallest portion of who I am.”

In court on Thursday, Winner, who admitted to leaking a single document, apologized “profusely” for the “undeniable mistake I made.” She was formally sentenced to 63 months in prison with three years of supervised release. Her sentence — the longest ever handed down for an “unauthorized disclosure to the media” — was intended, prosecutors said, to deter other would-be leakers inside the government.

The next morning, President Trump tweeted, “Ex-NSA contractor to spend 63 months in jail over ‘classified’ information. Gee, this is ‘small potatoes’ compared to what Hillary Clinton did! So unfair Jeff, Double Standard.”