“Naive as a word to describe me feels a lot better than idiot, but both equally apply,” says Reality Winner, explaining the series of decisions that led FBI agents to descend upon her home in Augusta, Georgia, on June 3, 2017. In what she calls a “four-hour chess game for my life,” the then 25-year-old military contractor was interrogated and ultimately confessed to leaking a classified National Security Agency report on Russian interference in the 2016 elections. In a call made to her sister Brittany shortly after her arrest, Winner lamented a date she’d miss that night, and the yoga class she’d have to skip the next day. “I know it’s stupid,” Winner said then. “But that’s my whole life.”

Footage from that interrogation, Winner’s first calls to loved ones, and an unvarnished perspective on the single piece of folded paper that uprooted her life are captured in the new documentary Reality Winner, a Codebreaker Films production, which premiered in select theaters October 11 and be released via VOD on October 31. Winner, now 31, tells Vanity Fair that the project’s five-year production, completed largely while she was behind bars, offered “a sense of hope that someday the public would be given the whole story.”

Director Sonia Kennebeck, who covered similar whistleblowing terrain in 2016’s National Bird and 2020’s Enemies of the State, and her producing partner Ines Hofmann Kanna first discovered the story of Reality Winner as most people did: the day that Winner’s arrest was announced by the Justice Department as the first criminal leak case under Donald Trump. Struck by Winner’s story, Kennebeck flew to Georgia for one of her pretrial hearings.

She was expecting to be wedged between reporters covering the proceedings. That didn’t happen. “I met Reality’s mom, Billie, and I was a bit shocked how few journalists were there,” says Kennebeck. “We decided to document [it], because no one else was really doing it.”

Winner, whose trust of the media had understandably fractured, was relieved to learn that her mother wasn’t alone. “I always had so much anxiety anytime she would come back to Georgia [from Texas] for the hearings, because I knew the emotional burden that it would have on her,” says Winner. “But when I would call her from jail to see how she was doing those weeks, I would also get to hear these funny stories of what it was like filming with Sonia.”

Kennebeck felt she was just biding her time until Winner was released on bail and could participate firsthand in the film—a day that never came. Says the filmmaker, “I had a sense of what she and her family were up against, even though it turned out to actually be worse than I had expected.”

“I just wanted to settle a national debate and quietly accept the consequences,” Winner says in the documentary about the aftermath of her 2017 arrest. Due to her peculiar name (bestowed by her father, Ronald, who died about six months before Reality’s arrest), an administration eager to establish itself as tough on national security, and the cherry-picking of messages between Reality and her sister, Winner became the headline—overshadowing the information she risked everything to release. “The punishment and the prosecution that I receive is the message,” says Winner, who was denied bail as she awaited trial.

Her case was complicated by its entanglement with The Intercept, which published the document Winner leaked, and may have made it easy for the government to learn her identity. Winner says in the documentary that her legal team was not allowed to name The Intercept or its tagline, “If you see something, leak something,” in court. (In response to a request for comment, Betsy Reed, who was The Intercept’s editor in chief at the time of the leak, says she is “not aware of any limitations on Reality’s ability to name the Intercept in her court case.”)

The outlet did help pay for Winner’s lawyers—but “paying for my legal fees for the fire that they started, that doesn’t make me any more grateful to them,” Winner says in the doc. The film also includes what Kennebeck calls a “tense” interview with Reed.

While Reed apologizes onscreen for the “terribly unjust” way that the legal system has treated Winner, Winner still finds it hard to forgive The Intercept. “Very basic source-protection errors were made that basically gave me no time to prepare or even expect the FBI would come,” Winner tells VF. “The storm that was headed my way, they sent them to me. It wasn’t the other way around. The [FBI] interrogated me and had me in jail before The Intercept even published” the leaked document.

Winner notes that there are four people, including herself, who suffered serious consequences after leaking material to The Intercept or its founders. “[Edward] Snowden’s in Moscow still. Terry Albury went to jail in 2018. Daniel Hale is finishing his sentence, and I’m still on probation.”

In a statement to Vanity Fair, a spokesperson for The Intercept said: “The Intercept has reported on a great number of significant stories involving unauthorized leaks, and we take source protection very seriously. We recognize the courage of whistleblowers. Without these brave individuals, government misconduct will remain hidden. The weaponization of the Espionage Act should concern us all and these laws must be rewritten to grant First Amendment protections to those who reveal information of significant public concern.”

“The Intercept and its previous editor Betsy Reed have acknowledged errors were made in attempting to authenticate an NSA document that was mailed to us from an anonymous source. However, as all news organizations have experienced, it is impossible to protect sources from the vast power of the US surveillance state in all cases.”

Snowden himself appears in the doc as well, sitting for a rare interview from Moscow, where he has been living for more than a decade after leaking classified NSA documents. Snowden thinks that whistleblowers like Winner and himself are “some kind of unusual,” but Winner doesn’t agree with that characterization. “My father taught me to hold contradictory ideas in my mind simultaneously and believe them to both be true,” she says. Releasing information illegally was “an unethical act. But to be sitting on that information when our country was torn apart by a question that nobody at a higher rank was willing to answer…was also unethical. I could see both at the same time.”

Winner battled intense depression and an eating disorder while in jail. She pleaded guilty, and in 2018 was sentenced to more than five years in prison—the longest sentence ever imposed for an unauthorized release of government information to the media.

In an unsettling twist, Trump now faces his own 37 felony counts related to top-secret documents seized from Mar-a-Lago. But Winner isn’t gloating. “I understand that he’s being treated much better than I was,” she says, “but I also read that [indictment] and wonder how many of these documents actually did damage national security.” When she was being prosecuted under the Espionage Act, she says, “they exaggerated everything. All they had to do was use all the buzzwords, say I gravely endangered national security in a way that was irreparable, and they never had to prove that to get a conviction.”

Winner was released from prison in June 2021, after serving four years. Kennebeck captures an emotional reunion with her mother and stepfather, Gary Davis, as well as Winner’s first meeting with her infant niece. “I don’t even remember seeing a camera that day,” Winner tells me.

As her three-year supervised release draws to a close, Winner is looking forward to what’s next. She dreams of opening a CrossFit gym, but has no intention of watching Reality, an HBO film about her case starring Sydney Sweeney, or even Kennebeck’s documentary. “There is this residual trauma of being in a jail cell and watching things about you on a TV screen that I physically can’t recover from,” Winner says. “If I see or hear myself on any screen, I start shaking really bad because of that first year of seeing myself on the local news. I’m excited that the attention from the HBO film, the theatrical interpretation of my actual interrogation, is only going to leave more and more people who want the full story. My DMs are full of people who want to know more, and so this documentary should answer all those questions.”

Yet the reality of Winner’s guilty plea is that her life may never look the way she hoped it would. “My identity as a convicted felon, being bound to this plea deal, is forever going to be tied to what I can do financially with my life,” she says. “I can’t really use any type of notoriety to generate any income. My story can make movies and books, but I’m always going to be applying for Walmart at Kingsville, Texas, and getting turned down because of my felony status.”

Winner and Kennebeck didn’t officially meet until after her release. But they remained connected throughout her imprisonment. Kennebeck repeatedly tried to interview Winner from prison; for weeks, Winner would be summoned by prison authorities to be told that Kennebeck’s requests were denied. Winner’s frequent visits to the lieutenant’s bench became the talk of the prison yard. “Everyone thought I was constantly in trouble,” Winner says. “Everybody was like, ‘Damn, Winner, what are you doing?’”

Kennebeck apologizes to Winner with a weary smile, before stating with steely conviction: “I really feel comfortable saying that Reality was silenced during this time and that’s why it was so important that this film is told in her voice. Reality is really telling her story now—beginning to end.”