A new documentary reveals the FBI interrogation of jailed whistleblower Reality Winner. 'I cried through most of it,' her mother told Insider.
By Charles Davis
"United States vs. Reality Winner," is about the whistleblower the Trump administration imprisoned.
Reality Winner, an Air Force veteran, leaked evidence of Russian interference in the 2016 election.
Her mother told Insider she hopes the documentary will increase pressure to pardon her daughter.
When 11 FBI agents showed up with a search warrant in 2017, the 25-year-old Air Force veteran — a poet, animal lover, and the owner of a pink AR-15 — initially professed her innocence.
Reality Leigh Winner would later tell her sister in a phone call from jail that she feared if she did not keep calm then one of the men might end up shooting her dog or cat dead.
"Oh boy, Brittany, I screwed up," Winner, now 29 and behind bars, told her older sibling. "I leaked a document. And they were able to trace it back to me. And it's kind of an important one."
Winner was arrested and prosecuted under the Espionage Act for leaking a document about the Russian government's efforts to undermine American democracy and help elect President Donald Trump.
"United States vs. Reality Winner," a documentary premiering this week at the SXSW Online film festival, explores the whistleblower's years-long tribulations, which began in 2017 when the US Department of Justice, eager to fight Trump's war on leaks, threw the book at her.
The filmmakers shared a bonus footage clip exclusively with Insider:
UNITED STATES VS. REALITY WINNER Bonus Scene "Middle America" from on Vimeo.
The USA v. Reality Winner
"To release information about foreign election interference — that is information that is threatening our democracy," Sonia Kennebeck, the film's director, said in an interview with Insider. "It impacts all of us. It impacts everyone who votes or has the right to vote."
Born in Texas, and given her uncommon name by her now-deceased father, Winner was always a little bit different. As a child, she read at a level far more advanced than her age, her teenage angst manifesting itself in fandom for the emo-punk band AFI — and an impatience for adulthood.
When she graduated college, she forwent an engineering scholarship and enlisted in the US Air Force, uninterested in four more years of an extended adolescence spent in dorm rooms and at frat parties. She worked as a cryptolinguist, becoming fluent in Farsi, Darsi, and Pashto, helping the military translate eavesdropped conversations — and target people for drone strikes.
It was not the sort of work suited for a peace-loving free spirit. When she got the chance, she got out, collecting a fat paycheck working as a contractor for the National Security Agency. No longer a soldier, she could speak more freely; on Twitter, in 2016, she called the newly elected commander-in-chief a "fascist."
That was a sign, perhaps, that she was still in the wrong field. Though no longer enlisted, she did have top-secret security clearance, and continued to help serve the execution of a foreign policy she did not support. Prosecutors would later cite a Facebook chat with her sister, one where she said "I hate America," to call into question her love of country.
Winner was arrested two days before the story broke in The Intercept, the federal government charging her under the same law used for those who provide intelligence to foreign governments. She was ultimately handed the longest sentence anyone has ever received for leaking classified information to a media outlet: five years and three months, with three years of state supervision to follow her release in November 2021.
One aspect of Russia's interference was well established at that point: Russian military intelligence hacked the Democratic National Committee and provided the emails it stole to Wikileaks and sympathetic journalists. But the top-secret document Winner came across detailed how Russian hackers had also targeted state election officials with the apparent aim, which was unsuccessful, of disrupting voter-registration rolls.
It was a leak motivated by serving the public. No sources or methods of spycraft were revealed. But it was, nonetheless, very much illegal. Only a president can unilaterally declassify intelligence — and there was no interest, back then, in revealing anything more about an attack on the 2016 election.
Journalism in the crosshairs
It's not clear why Winner chose The Intercept. The publication was well known as sympathetic to national-security whistleblowers, founded in part to publish the government secrets that NSA contractor Edward Snowden revealed about mass surveillance.
But its founders also showed skepticism of all this Russia stuff: its own writers collaborated with Guccifer 2.0 even after most experts had decided the hacker persona was a creation of Russian military intelligence.
Whatever her reason for printing out an NSA report and mailing it to The Intercept's office in New York, the decision would change her life. Hindsight is 20/20, but many have been baffled by what the publication itself did next: It provided the document to the federal government for comment. The government was then able to determine that it had been printed out; from there it did not take long to discover who had done that.
In an interview featured in the documentary, Betsy Reed, The Intercept's editor in chief, profusely apologizes for what happened. "I'm so incredibly sorry about everything that she had to go through," Reed said, "and I feel a lot of sadness about that, and regret."
She and others at the outlet were afraid that they were the targets of a "hoax" and the government, Reed said, would only agree to comment on the authenticity of the report if they were provided an original copy. But a journalist at The Intercept also told an employee at Pluribus, the NSA contractor where Winner had worked, that the report had been mailed from Augusta, information that then made its way to the government. ("What the heck?" Thomas Drake, another NSA whistleblower, comments in the film.)
FBI interrogators citing the fact — "It made its way to an online news source that you subscribe to. Getting really specific." — is what prompted Winner to give up on denying.
"There wasn't enough checks and balances in the newsroom," Reed explained in the film. The Intercept would later go on, as amends, to pay for a high-powered legal team to defend Winner.
But Reed also insisted that what happened was inevitable. "She would have been caught," Reed said in the documentary, "even if we had disguised certain aspects of the document. Because the way the government surveils its contractors and employees would lead them to know who accessed it. Not only who printed, but who looked at it, and who had a reason to look at it, and who was in contact with The Intercept in any way."
Jeannie Kedas, a spokesperson for The Intercept's parent company, First Look Media, said Reed's statement in the film "is not new."
"It is consistent with previous statements from The Intercept as well as the findings of other media outlets who reported on the case," Kedas told Insider, citing a 2017 editoriall from The Washington Post's media critic, Erik Wemple, who wrote that "the mistakes of the leaker before the Intercept received the document would likely have sealed her fate."
'Why can't this be public?'
Kennebeck's first documentary "National Bird" detailed the stories of three military service members who blew the whistle on US drone wars.
When Winner's story broke, the Malaysian-born filmmaker, who has a master's degree in international affairs from American University, flew down to Georgia almost immediately. She knew it was "extremely rare": someone within the national security apparatus deciding to make Americans privy to the same information as the national security establishment. She met with Reality's family, who judged her to be someone they could work with.
The film details the lead-up to Winner's sentencing and the family's efforts to drum up public support for their daughter. But Kennebeck's latest work rests upon an exclusive linchpin: audio from June 3, 2017, when black SUVs rolled up to Winner's home and agents with the FBI confronted her with the fact they knew exactly what she had done.
The FBI did not want to hand this audio over. Kennebeck and her team had to sue, finally obtaining it in February 2021. In it, Reality Winner, in her own words, in her own voice, can be heard explaining why she did it.
"I saw the article and was like, 'I don't didn't understand why this isn't a thing,'" Winner says on the recording. "It made me very mad. It's right there. And I guess I didn't care about myself at that point. I felt really hopeless. Seeing that information, that had been contested back and forth, back and forth, in the public domain for so long, trying to figure out, with everything else that keeps getting released and keeps getting leaked, why isn't this out there?"
"Why can't this be public?" she added.
The film brought Winner's mom Billie Winner-Davis to tears
Billie Winner-Davis, Reality's mother, told Insider from her home in Texas that she was deeply affected by hearing her daughter, in her own voice, explain why she did what she did.
"I cried throughout most of it," she said, just after seeing the film for the first time. It was painful, she said, to relive the pretrial period. It also made her furious.
She was struck by the apparent hypocrisy of government officials condemning her daughter as they publicly discussed what she shared with them and the public.
"This was the first time that I heard [former Sen.] Claire McCaskill so strongly… say that she condemns the leak. She condemns the leaker," Winner-Davis said. "And yet she used the information that my daughter leaked."
Indeed, back in 2017, McCaskill, the former Democratic senator from Missouri, described that information as "an earthquake," albeit one overshadowed by the constant controversies of the Trump years.
"We now have in the public domain verified information that the Russians made an aggressive attempt to access not only a vendor of voter software in this country," McCaskill said, "but also a number of states, the voter-file databases in the month prior to the election."
Winner-Davis is pleased the film is now a historical artifact that lauds her daughter's actions. But she is not interested in a moral victory or the judgment of history. She wants justice for Reality — an acknowledgement of public service.
"For her, justice looks like clemency — release her, right now. Every single day she spends in prison is a day of suffering."
This is 'not just about Reality Winner's story but also a reflection of… Trump's legacy'
It would be easier to never do any national-security reporting; to never do any original journalism.
Kennebeck told Insider there is much to reflect on when it comes to why a publication's source got jailed, but she does not want that to be what people take away from her film — that Winner is the victim of a media outlet and not the administration that escalated the war on leakers and chose to pursue a lengthy prison sentence.
Snowden, interviewed for the film in Russia, where he is under de facto house arrest, said history will judge Winner as a prisoner of conscience. What stood out to him about the case, he said, was the over-the-top prosecution by the Trump Justice Department, which was eager not just to enforce the law but to make an example out of Winner, using out-of-context journal entries to paint a military veteran as an enemy of the state.
"There's an absence of shame that is, for me as an American, honestly embarrassing to watch," Snowden said in the film.
Indeed, that is what the filmmakers hope viewers take away from the documentary.
This is
"not just about Reality Winner's story," Kennebeck said,
"but also a reflection of… Trump's legacy, which is going after whistleblowers and journalists and really suppressing the freedom of the press."
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