The Many Betrayals of Reality Winner 1

In March of last year, Andrea Circle Bear was transferred from a South Dakota jail to FMC Carswell, an all-female prison for those with special medical needs in Fort Worth, Texas. Circle Bear, a member of the Cheyenne River Sioux Tribe, was serving out a 26-month sentence for conducting a pair of drug deals totaling $850. She was also heavily pregnant. On March 31, Circle Bear began experiencing symptoms of COVID-19—dry fever, heavy cough—and was placed on a ventilator. The following day, she delivered her baby via C-section. Three days after that, she tested positive for COVID-19. She was dead three weeks later, becoming the first federal prisoner to die of the coronavirus.

Around this time, another inmate at FMC Carswell, Reality Winner, requested compassionate release due to the rapid spread of COVID-19 amongst the prison population. Due to her history of respiratory illness and bulimia, the virus posed a heavy risk for the 28-year-old. But federal prosecutors blocked Winner’s request to commute the remaining 19 months of her sentence. Three months later, she contracted COVID-19. Of the 1,625 incarcerated women at FMC Carswell, over 500 ended coming down with the coronavirus, the second most cases of any federal prison in the country. Six of the women died.

“She has been under tremendous pressure,” says Sonia Kennebeck. “She has also been sexually harassed, and a bunch of other things. It’s completely inhumane and entirely disproportionate.”

Kennebeck, a filmmaker and investigative journalist, has been documenting Winner’s case for the better part of three years, trailing her family members and friends, filing FOIA requests, and conducting a phone interview with the whistleblower from prison. The result is The United States vs. Reality Winner, a documentary feature making its (virtual) premiere at SXSW.

Reality Winner’s case is a complicated one, to say the least. She was given her name—and that is her real, government name—by her father after he’d observed a woman in Lamaze class with a T-shirt that read “I COACHED A REAL WINNER.” He wanted her to succeed, and she in turn worshipped him. The September 11th attacks had a profound effect on her father, who instilled in 9-year-old Winner the curiosity to learn what happened, and why. In addition to her academic prowess, Winner was possessed of an almost innate desire to help others, donating to volunteer groups, rescuing cats and dogs, and pushing wheelchair-bound kids in half-marathons as part of Athletes Serving Athletes. She served as an Air Force cryptolinguist from 2010 to 2016, translating communications that would inform drone operators who they should target. When she was honorably discharged in October of 2016, she received a commendation stating she was responsible for “removing more than 100 enemies from the battlefield.”

One month later, she moved to Augusta, Georgia, in search of work at an NGO. She was a bit disenchanted by her work in the drone program, and felt she’d lost sight of the reason she joined the military in the first place—to help others. She taught at a yoga studio and CrossFit gym, and, despite being fluent in Persian, Pashto, and Dari, couldn’t seem to find work at a nonprofit due to her lack of a college degree. Then her father passed away. In February of 2017, she landed a job at Pluribus International Corporation, an NSA contractor, translating documents related to Iran’s aerospace program.

But Winner, a Libertarian-minded Texan armed with a bright-pink AR-15, soon became disgusted with President Trump. Following his “Muslim ban,” she tweeted, “the most dangerous entry to this country was the orange fascist we let into the white house.” And as the chatter began heating up about possible Russian interference in the 2016 presidential election, Winner was puzzled. She had top-secret clearance and had seen with her own two eyes documented evidence that Russia had conducted an elaborate cyberattack on a key U.S. voting software supplier, thereby accessing voter rolls, and sent a series of spear-phishing emails to over 100 election officials just prior to the election. Why was the U.S. government suppressing this information?

On May 9, 2017, the day President Trump fired FBI Director James Comey—who was heading an investigation into Russian interference in the 2016 election—Winner printed out a document from her computer, folded it up, stuffed it in her pantyhose, and left the building. She then sent copies of the documents via snail mail to The Intercept’s New York office and another unnamed publication. Then, The Intercept—thinking the document was perhaps fake—did something highly unusual. As New York Magazine reported:

On May 30, according to court filings, an unnamed reporter sent pictures of the document to a contractor for the U.S. government and told the contractor that they’d been postmarked in Augusta. The contractor initially said that the documents were fake but, after checking with someone at the NSA, reported that they were real.

A journalist sending copies of a leaked U.S. government document back to the U.S. government is almost unheard of.

A journalist sending copies of a leaked U.S. government document back to the U.S. government is almost unheard of. The copies of the document sent by The Intercept reporter eventually made it to the NSA and then the FBI, and the move ended up giving Winner away to the authorities. According to The Guardian:

A visible crease in the document told officials that the Intercept must have received a hard copy in the mail, according to prosecutors… Information security analysts also pointed out that the printout handed to the NSA by the Intercept appeared to feature a unique microdot pattern, a security feature intended to allow the document’s owner to keep track of precisely when and where it was printed. Investigators reviewed a log of who had printed the file. Six names, including Winner’s, showed up. A search of Winner’s computer system also allegedly turned up two emails that she had previously sent to the Intercept from her personal account about a podcast published by the site. Investigators had their target.

On June 3, 2017, eleven mostly armed federal agents descended on Winner’s home and, without reading her Miranda rights, interrogated her for over an hour in a back room, eventually coaxing a confession out of her.

While a transcript of the FBI interrogation of Winner has leaked, forming the basis for the stage play Is This a Room, the audio of the strange encounter had never seen the light of day. So, Kennebeck filed a FOIA request for the audio two years ago. After the FBI denied the request, she appealed the decision to Trump’s Department of Justice, which sided with the filmmaker. “And the FBI still didn’t release the material, so we sued them—my small production company, with some pro bono help from the Reporters Committee for Freedom of the Press,” says Kennebeck.

She kept on editing The United States vs. Reality Winner and locked the picture in early February, including voiceover work from Stranger Things star Natalia Dyer as Winner. Then, on February 10, she learned that they’d won their suit and would be receiving the audio of the grilling. “It was quite dramatic,” recalls Kennebeck. “When we actually won the court order, it was the same day that the SXSW world premiere was announced, so we had already finished the film and recorded the voiceovers with Natalia Dyer, and we just reopened the entire film.”

The audio of the interrogation reveals how the FBI agents engaged Winner in a bizarre, entrapment-y “talk” (their words), repeatedly insisting that she was there “voluntarily”—even though the armed agents had cornered her in a tiny room with no window—and vacillating between jokey and threatening.

All the while, Winner was absolutely terrified. “I couldn’t hold it anymore, but at the same time I was like, if I take one step out of line they’re gonna think… oh, well, let’s put her down,” she tells Kennebeck during a prison interview in the film. “Or if my cat… tried to get out or if she got scared, I don’t know what I was going to do if something was going to happen to her. So, I was afraid that my reaction would warrant lethal force… I was really afraid to even put one foot out of line.”

On June 5th, two days after she was arrested, The Intercept released their story with the headline, “TOP-SECRET NSA REPORT DETAILS RUSSIAN HACKING EFFORT DAYS BEFORE 2016 ELECTION.” There were four authors bylined on the piece: Matthew Cole, Richard Esposito, Sam Biddle, and Ryan Grim. Sources tell The Daily Beast that Biddle and Grim were not heavily involved in the reporting process, which fell on the shoulders of Cole and Esposito. In The United States vs. Reality Winner, a pair of fellow whistleblowers raise questions about the conduct of Cole and Esposito, the latter of whom left journalism after the publication of the Winner story to work in the communications department of the NYPD, in essence working for the state after revealing a source to the state. Perhaps even more egregious than the microdots oversight was the decision to supply a government contractor with where the Winner missive came from.

“Not only did they give them the content, they gave them the envelope information and where it came from. What the heck?” NSA whistleblower Thomas Drake says in the film. “The last thing you’re going to do is take a disclosure and take the raw version of it and give it to the government for review. Unfortunately, and I have to say this now, it begs some really uncomfortable questions about what was the intent of The Intercept reporters of record? What did they actually share, or what didn’t they protect?”

Those same two journalists got me arrested, and because of their carelessness—subterfuge might be a better word—I spent two years in prison.

WikiLeaks founder Julian Assange called the journalist that sent a copy of the document to the federal government—who is either Cole or Esposito—a “menace” to sources, and offered a $10,000 reward for information “leading to the public exposure & termination” of the reporter. John Kiriakou, a CIA whistleblower who disclosed information on torture, also points the finger squarely at Cole and Esposito in the film: “Those same two journalists got me arrested, and because of their carelessness—subterfuge might be a better word—I spent two years in prison.”

Neither Cole nor Esposito responded to requests for comment; a spokesperson for The Intercept issued a statement to The Daily Beast that read, in part: “We have acknowledged our mistakes, and we made changes to our editorial process after a comprehensive internal review. As other journalists have noted, our errors were not singularly responsible for her arrest, but our organization supported her legal defense and we have continued to cover her ordeal while other media outlets moved on.”

The Intercept gave Kennebeck access to their newsroom for the documentary, and both editor-in-chief Betsy Reed and national security reporter James Risen are featured. While Kennebeck is thankful for their participation, including what she characterizes as “a very tense interview” with Reed, as a journalist who’s reported on national security and who gives source-protection workshops, she’s highly critical of their methods with the Winner story. “I would have loved to talk to these journalists personally,” she says. “I even spoke to a third person who says he was revealed as a source, who worked with one of them. Now, do humans make mistakes? Yes, they do. Should they be in this job if they make them repeatedly?”

Reality Winner pleaded not guilty to the charge of “willful retention and transmission of national defense information,” and was repeatedly denied bail by the judge. During pre-trial hearings, the government tried to smear her as someone who “hates” America, pointing to a clearly sarcastic Facebook exchange she’d made with her sister Brittany about hating America, and a diary entry where she joked about burning down the White House. But Winner did not hate America; on the contrary, she cared deeply about it, having not only served her country but taken active steps to improve it, including meeting with her state senator to discuss the effects of climate change.

“They made her sound so devious and evil,” Reality’s mother, Billie Winner-Davis, says in the film. “That’s probably the reason why [her stepfather] and I decided that we had to speak out.”

Winner eventually accepted a plea deal of five years and three months behind bars for violating the Espionage Act. Once the sentence was passed down, Kennebeck repeatedly requested to interview Winner; each request was denied.

Though Winner’s family and friends have made appeals to the Trump and Biden administrations, their pleas have fallen on deaf ears. Winner is expected to be released on November 23, 2021, though she is still struggling from the aftermath of COVID. To make matters worse, in February, winter storm Uri knocked out power at FMC Carswell, leaving inmates—many of whom had COVID-19—without heat and hot water. “We’re in a cinder block building with no insulation,” an inmate told the Fort Worth Star-Telegram. “We have to go outside to get our meals, and it’s snow and icy everywhere and we’re freezing.”

Winner is the eighth whistleblower to be charged under the Espionage Act, which dates back to 1917, and received the longest sentence ever imposed in federal court for leaking government documents to the press. And the question remains: Who was harmed by Winner’s disclosure?

“Because it was so important to the integrity of our elections, and our whole election system and our democracy, aka what our country built on, you would think somebody who blew the whistle to expose the damage that a foreign adversarial nation did to us, you would think she’d be released,” Reality’s sister Brittany says in the film. “You’d think that they would actually probably say thank you for the information she made available for, really, the people who needed to know it.”