Reality Winner Is Hollywood’s New Muse. And She Won’t See a Dime

Reality Winner has been out of prison since June 2021, but she’s still under lockdown. The whistleblower’s travel is confined to the Southern District of Texas and she must abide by a 10 p.m. curfew. If all goes according to plan — and it really, really hasn’t for most of her hellish ordeal — her probation will be lifted Nov. 24. And right now, she’s cautiously optimistic. The 31-year-old is hard at work on her memoir, was recently the subject of the critically acclaimed HBO movie Reality with actress Sydney Sweeney playing her, and next year will bring Winner, a more expansive film on her life starring Emilia Jones of CODA fame. She’s become a cause célèbre of sorts in Hollywood, yet is still coming to terms with her years of torment at the hands of the government.

Her story is also captured in a new documentary, Reality Winner, directed by Sonia Kennebeck and hitting digital and on-demand services Oct. 31. The nonfiction film chronicles the former Air Force linguist and NSA contractor’s decision to smuggle five classified documents out of the offices of Pluribus in her pantyhose that revealed Russian attempts to interfere in the 2016 U.S. presidential election via a cyberattack on a U.S. voting software supplier and spear-phishing emails sent to over 100 local election officials in the days leading up to the Nov. 8 election. Winner mailed the classified material to The Intercept who published their piece on the leaked documents two days after FBI agents visited her Texas home, interrogated her for four grueling hours, and detained her. The Intercept had been sloppy — sending the original documents to the NSA for verification, whose printer tracking dots identified Winner as the leaker. The outlet also informed the government of the address on the envelope in which they were mailed. Winner is one of three whistleblowers to be apprehended after leaking classified material to The Intercept, along with Daniel Hale and Terry Arbury, and she is not happy about it.

After over a year in pre-trial detention, on August 23, 2018, Winner was sentenced to 63 months in federal prison at FMC Carswell for violating the Espionage Act — the longest amount of time ever imposed on someone for leaking government secrets to the media, and the first whistleblower to be jailed under then-President Trump. In an ironic twist, Trump himself is currently facing 31 charges under the Espionage Act.

Kennebeck, whose previous doc National Bird highlighted three people who blew the whistle on the U.S. drone program (Hale being one of them), proves a reliable steward of Winner’s story, capturing the tense FBI interrogation with audio and dramatic recreations, trailing her mother Billie and sister Brittany’s efforts to free her, detailing her cruel and inhumane treatment behind bars, and using interviews with other whistleblowers like Edward Snowden and Hale to provide context. The backbone of the film is Winner herself, who sits down for a number of interviews where she calmly and courageously guides viewers through that which befell her.

Winner opened up to Rolling Stone about the film(s) and life after government persecution.

What has life been like for you out of prison? Did you experience culture shock?
I never thought that in a million years the transition from being incarcerated to just being on home confinement would be so difficult. But what actually happened was the last year and a half of my incarceration, with the start of the Covid-19 pandemic, and going into the summer of 2020 with the George Floyd protests, and January 6^th and the Inauguration of President Biden, there were five separate times that we were put on a very severe lockdown for things that we had nothing to do with. The final straw was twenty-three days locked in one room and I wasn’t even getting fed most meals because they kept purposefully forgetting to bring vegetarian options to that room. My own release date was pushed back almost a full week because of the Covid quarantine guidelines. I was institutionalized and disruptive to the point where when they told me I would be released six days later, my outlook was, “You mean I could have gotten into a fight that was worth something over those six days, and instead they took them from me for nothing?”

Delaying your release date like that is twisted.
Any time I needed something, whether it was a vegetarian meal, access to religious services, health care, or post-assault counseling — because an officer assaulted me — or just being released on the terms that they set out, I needed an attorney to fight for that. By the time I got home I was a psychological wreck. I felt like I was against everybody, even my family. I’m still working to this day to feel like I’m not fighting people or getting one step ahead of any obstacle that comes my way. I’m still in that headspace where I’m fighting for basic resources and respect. I never imagined that they could take away being at home with my parents and feeling good again. You walk out of prison and things still aren’t OK. Now, I coach CrossFit full-time, have my own puppy, and take care of my parents’ other dogs, a horse, and chickens. Doing CrossFit and taking care of a small farm has been the therapy I needed.

Can you talk a little about the officer you say assaulted you? What happened?
In March 2020, during a 3 a.m. count, an officer touched me while I was waiting in my bunk. I waited two days and then I filed a Prison Rape Elimination Act (PREA) report to the DOJ OIG email, and it wasn’t until things had boiled over in December 2020, when that officer said she was “coming for my blood” in front of 200 inmates and a lieutenant, that I realized I needed to contact prison staff at Carswell and left them know I was being threatened, that I had made a report to the Bureau of Prisons in Washington, D.C., and that I didn’t feel safe. When I contacted a staff member from our actual prison, they said they had never seen the sexual assault report, that it was my fault because I didn’t report it properly, and that if I wanted something to happen, I would have reported it to prison staff — even though everywhere you go in prison there are these posters everywhere with the Prison Rape Elimination Act and how to report, and the very first option says to email the DOJ’s inspector general. That still didn’t warrant removing the officer from our unit. It took a completely separate incident in which that officer violated a Covid quarantine to bring other inmates from Covid quarantine units into our unit, which had active cases of Covid-19 in it, for the purpose of inciting violence between inmates to get that officer removed from our unit, because sexual harassment or sexual assault claims weren’t enough.

Watch an exclusive clip of Edward Snowden in Reality Winner:

You open up in the film about how difficult prison was with your bulimia battle, and that you considered taking your own life but thinking about your mother stopped you.
So, in October 2017, we were reaching a point where I would not be released pre-trial — meaning I could not participate in my own legal defense — and yet there was no way we could mount anything worthy of going to trial anytime soon. What I had been surviving up until that point was bulimia in a really enclosed space. I had run out of ways to cope with that. When it became apparent that there was truly no end in sight, and there would be no scenario where my conditions would be better, something shifted in my brain where I understood that there was no longer any surviving bulimia in those conditions. It just felt like the choice was: Do I die fast, or do I die slow? That was my only decision left because there was no life after that moment.

The only thing I had left in my control was how my mother would hear the news. That in and of itself was the waiting game. How could I get my mom out of Georgia because I knew that I wasn’t going to make it? There was a moment where I absolutely snapped, and it involved my ability to go outside that day — and my ability to compose myself and envision a future for myself, which is what outside yard call meant for me. When I missed it one day in October, after weeks of planning and practicing my death, the only thing I knew to do was I randomly called one of my attorneys on the jail phone and I told him that I wasn’t OK and that I had bulimia. I didn’t even know that attorney very well and I don’t know why I called that member of my legal team, but it was a blessing because he immediately understood that it wasn’t OK. Within two weeks I was medicated, and I wasn’t in any less pain, but it saved me enough to get me out of that place where I was suicidal. Through all of that, my mother never left Georgia. And nobody knows why.

According to Sonia Kennebeck, the director of Reality Winner who spent extensive time with Winner’s family during her pre-trial detention and prison sentence, Winner’s mother kept saying she’d stay in Georgia for another week — and Kennebeck believes her mom could sense just how much her daughter needed her there.

How is your mental health now and what sort of steps are you taking to help it?
Everything with me winds up being humorous, to a degree. Right now, so much of the incarceration and trauma winds up being vicarious through my puppy. One of the healthiest things you can do with your dog is crate train them. I can’t put her in her crate. I count the hours when she’s contained and ask myself, “How can I get her outside?!” We’re building her a doghouse and it can’t be small. It must be brightly-colored, brightly-lit, air-conditioned, with a giant front porch on it and a fenced-in yard space around it that she has free access to. I’m emotionally not able to contain another living being like that. Every time I’m anxious about something that I’ve gone through I see it by how much I’m feeding my dog or if she’s outside. All of those decisions were made for me for four years. I know what it’s like to be treated like an animal. I carry that trauma with me.

There’s the distinct possibility that the FBI was trying to compose some kind of a setup that day… I was not completely unaware of what law enforcement does to suspects, and that if anything were to ever happen to me, I would still be put on trial in the court of public opinion as a dead person.

What do you do to unwind? I watch dumb reality TV or rewatch comfort shows.
I need things that are funny, so we’re always looking at the top comedy specials to watch on Netflix or look at who Joe Rogan is interviewing to see if they have a new special out. We loved Jerrod Carmichael’s Rothaniel. Curb Your Enthusiasm — that type of humor. I need shocking humor because of what I’ve been through, but never horror because I have a photographic memory. I’m terrified of the dark now. I sleep with the light on, and because my dog sleeps with me, I’m worried that I’m throwing off her circadian rhythm. I was in solitary for seven straight days once and the light never turned off. It was one of the most unsettling experiences you can ever have. We’re living for One Piece. Never true crime. I think there’s something cruel about watching true crime. People don’t want to accept that it’s real or get off on the fact that these are real things that happened. Every episode ends with someone doing life in prison and people think they’ll never meet these people, but then you meet them and they’re wonderful. We’ve turned the darkest parts of our society into a circus.

When you say “we” are you referring to you and your partner? Because not only did the FBI entrap and harass you but they also cockblocked you. You were about to go out on a date.
Cockblocked by the FBI! There’s your headline. [Laughs] I’ve been living with my boyfriend for over a year now. We had known each other in high school and had gone our separate ways, and then in 2013 or 2014 he reached back out and said he was in the Marines since I’d been in the Air Force. We always had the military in common. When I was arrested, he was harassed on social media and almost had to get off Facebook entirely since it shows who you’re friends with. They would say he was “with a traitor” and create fake accounts to try to get him to talk about me. I tried to find him in prison because he never wrote. I was out for eight, nine months, going through Instagram, and saw Eddie’s handle as an account that liked one of my new photos. Within a month he was visiting for the first time and I made him do CrossFit immediately. Now, it’s to the point where if anything were to happen my parents would pick him over me because he’s very handy around the house.

A number of politicians and pundits have called you a “traitor” and said that what you did “endangered national security.” What does it feel like to be called that?
Even with all these public campaigns, the movies, and my upcoming memoir, it still makes my blood boil when I read the word “traitor.” And I have to remind myself that so many people are completely media-illiterate, so they’re either one hundred percent trolling, and the word “traitor” could be replaced by any other word that they felt would get under my skin, or that they truly don’t understand what happened. When I hear that word it’s just a reminder to me that that’s an unchangeable situation. That person isn’t slinging that word because they want their mind changed or they’re capable of understanding more. It’s a complete no-go zone and I don’t let myself engage with that. I will spend the rest of my life reclaiming my military service, reclaiming the way I view the world, and thinking about how to resolve conflicts around the world — and will forever be telling my own country who I actually am, thanks to the U.S. government and thanks to that prosecutor. I have this bigger mission of reclaiming my identity publicly, and the truth about me is only being realized and known by more and more people. There are people who believe in me.

You say in the doc that there was “one question mark holding the country back,” the question of Russian interference in the 2016 presidential election, and that’s why you did what you did. Can you explain to me what you did, why you did it, and what was in that document? Because your narrative has been twisted by people with agendas.
I think the distortion is coming from this inherent laziness — that people don’t want to do the work and learn for themselves. As far as explaining it, I’m forever bound by not only a plea deal, but I still do abide by my non-disclosure agreement with the government. I fully intend to honor the oath I gave to the United States government and its people. As far as why I did what I did, it’s pretty much to answer that. I thought that I could solve this issue where people could see through the partisan media and see through the one side of the story that their chosen news outlet was giving them and hold it up to the truth, which was in black and white on a piece of paper. The one thing I didn’t realize is that people don’t like to read more than a headline, so it was completely ineffective, and the illegal method I had chosen — to steal the document from the government and mail it to The Intercept — meant the entire focus was going to be on who I am as a person and what I did instead of the message I had for the American people. By breaking the law, I completely undermined what I was trying to do for my own country.

You describe the FBI’s interrogation of you in detail in the documentary, and you say that you had visions of the FBI agents shooting you in the back — and that the very last thing they did was secure your weapons, which seems beyond sketchy.
There’s the distinct possibility that the FBI was trying to compose some kind of a setup that day. I had asked to use the bathroom and had made it very clear that with the layout of the house, I would have to go through my bedroom to get to the bathroom, and that the agents had not yet cleared the area. I had immediately declared that I had weapons and told them where they were, and they still allowed me to go — unaccompanied — into my bathroom. I had even asked for an officer to go with me because I knew what was in that bedroom. But I also knew I really had to pee, so I was going to go in the yard or walk past my weapons in the bedroom to go in the bathroom, like a human would. There is this very nefarious side where it could have all been a setup. I was not completely unaware of what law enforcement does to suspects, and that if anything were to ever happen to me, I would still be put on trial in the court of public opinion as a dead person. I was walking on eggshells.

In the original cut of the film that premiered at SXSW in March 2021, voiceover narration was provided by Stranger Things star Natalia Dyer, who dictated Winner’s words. The Intercept’s sloppy reporting that helped lead to Winner getting apprehended was also emphasized more, as were Winner’s struggles behind bars. According to Kennebeck, both versions of the film took over a year to edit each, and they “felt the ethical responsibility to put it out at that time… to shine light on her situation in prison because it was so extremely harsh,” since the filmmaking team couldn’t get access to Winner. In the new version, they were able to capture Winner’s release from prison as well as conduct extensive interviews with her.

I have a pretty unique name too and I’m sure you get asked this a lot, but how do you feel about your name and how has that feeling evolved over time?
I still hate my name. [Laughs] It still is very hard, even in a non-serious context, to be taken seriously — or have someone look at your name on a piece of paper and pronounce it the same way they would pronounce any other name. It’s hard when it’s two everyday nouns we use all the time. When you see them together as someone’s first and last name, I feel like people all of a sudden mispronounce it horribly. I still wish it was “Sarah.” I always use my sister’s name [Brittany] when I’m at Starbucks.

I saw in the credits that Roger Waters of Pink Floyd is one of the film’s financial backers, and I’m curious how you both feel about the irony of that given how he’s one of the biggest celebrity Russia apologists?
So, this is something that I’m completely unaware of. I do not discuss a lot of the logistics of the film — of how it needs to be made or how it needs to be funded. I’m only here to get out the truth of my experiences, and as far as the distribution, the funding, the advertising, screenings, or who else Sonia chooses to speak with or include, my approval wasn’t required, and it wasn’t even a conversation. When you’re me and your life is made publicly accessible through court documents, people are going to make documentaries and movies about your name, your image, and your history no matter what. The only thing that I can control is the filmmakers or journalists that I can trust, and if I give my experience or my story to them or not.

“He’s a donor. I think we now have 540 individual donors, plus the foundations, and he has been a really great and valuable supporter of my work. It does show that we have editorial independence, and that’s always been very important to me,” explains Kennebeck. “This film was grant and donation-funded. The most substantial support came from the Reva and David Logan Foundation, which supports investigative journalism… I’m not an activist filmmaker who works for someone. I see my work as journalism.”

I wanted to ask you about the two movie projects based on your life — first came Reality, starring Sydney Sweeney as you, which came out this past year, and was adapted from Tina Satter’s play Is This a Room that was based on your FBI interrogation. I understand you haven’t seen it.
I’ve heard really excellent reviews of Reality and Sydney’s performance, and I’m really proud of her for taking a role where she’s not fabulous or sexy. We had spoken a couple of times via Zoom, and my favorite thing about her is that her natural speaking voice is like mine — kind of a lower pitch. She doesn’t speak softly and is not overly feminine in how she speaks, and that immediately allowed me to become comfortable talking with her. The biggest things she wanted to get were voice pitch, accent, and general demeanor. She really does care about acting, and those couple Zoom meetings were things that she was studying. I’m glad she took that role and became someone like me at a tense and vulnerable moment.

Not that I wanted a theatrical production of one of the most intense moments in my life, but I’m so proud of that director, Tina Satter. When my interview with the FBI was made public as evidence in a court hearing, the prosecution had done that on purpose to humiliate me. Someone like Tina Satter was able to read between the lines and say, “This wasn’t a stupid girl. This was a scared woman, but she’s also fantastic and clever.” And by the end of the year, it was an Off-Broadway play. That Off-Broadway play not only went to several theaters around the United States, but it went around the world. Then Covid happened and it had to stop. Then, they were one of the first theatrical productions when Broadway reopened in 2021. It had sold-out performances and rave reviews, and out of nowhere Broadway producers called Tina and said they weren’t going to go on with it because it was too political. Tina Satter said, “Thank you,” and then made a movie about a play that Broadway rejected for no reason. I couldn’t be more proud of her tenacity.

There’s zero money. This is simply my way of reclaiming my future, my integrity, and it’s my explanation to my country of what I did.

And then there’s next year’s Winner, with Emilia Jones playing you and Zach Galifianakis and Connie Britton playing your parents. It’s being described as a “black comedy,” which kind of… worries me a bit. Are you being compensated for these movies?
[Laughs] I can answer the second part. If you refer to my plea deal, the United States government lovingly included an entire section that is broad yet vague— and very menacing — saying that I cannot make any money off my felony (the action that I committed), the process of being prosecuted by the United States government, my conviction, my incarceration, or even my time in the military. And that anyone associated with me or my family, and “future family members,” cannot even make money off my story or life rights. It’s a gray area because I signed that document but my mother, who might want to write a memoir about what it’s like to have a daughter incarcerated, did not sign that document. If she makes money off her memoir about her life as my mother, I go back to prison. So, there’s zero money. This is simply my way of reclaiming my future, my integrity, and it’s my explanation to my country of what I did.

As far as the upcoming film Winner, it has a special place in my heart because, like Sonia and Tina, Kerry Howley visited me while I was in jail — and was immediately kicked out of the jail visitation room for taking notes. She was one of the first people to write in New York Magazine one of the most in-depth pieces about who I am as a person. That was immediately bought to be turned into a film. The director, Susanna Fogel, sent me her books. Her book Nuclear Family is so funny. She and the film’s producer, Amanda Phillips, visited me while I was still with an ankle monitor and witnessed firsthand what it was like for me to go on a BOP-sanctioned outing to a nearby store. They have always checked in and we’ve just become lifelong friends. I am incredibly relieved that this upcoming film is fictionalized because it’s not something I have to respond to or fact-check. They made it very clear that this is Hollywood and they’re gonna do what’s right for the film. The star actress, Emilia Jones, came down for a weekend and took my yoga and CrossFit classes. It’s become a thing now where if someone wants to talk to me in person, they have to take my yoga and CrossFit classes first. She did so well. A huge part of the film is my transformation from someone who wasn’t into fitness to getting into CrossFit as a form of healing. She was showing me her progress photos all along the way right up until filming and she put on some serious muscle.

In the documentary, you call The Intercept reporters who worked on your story “well-intentioned but misunderstood journalists.” How do you feel about The Intercept’s role in your story and your arrest? There’s a scene in the doc where former Intercept editor-in-chief Betsy Reed says that you would have been caught anyway and doesn’t really acknowledge their reporting mishaps. Plus, now Betsy Reed is running The Guardian, the very outlet that helped break the Snowden story.
I think Betsy is completely misunderstanding where a lot of my frustration has come from. I did little to cover my tracks, so I wasn’t surprised that I was caught. I was surprised by the context in which I was caught. The Intercept did not think that the document was worth publishing until they had gotten word that I was arrested and going to be arraigned that Monday morning, and then all of a sudden, they published it that day — even though they had the document for three weeks. The Intercept now has a serious reputation of outing sources and then pretending to champion them because they felt the outed source, and the clout behind supporting a martyr, was a stronger story than what they could have done with the information that a source had trusted them with in the first place. They had been sloppy for years even before my leak and my arrest, with Daniel Hale. A year into my incarceration, Terry Albury was also caught. A lot of that has to do with how The Intercept works with their sources in the NSA to verify information. They want to use the NSA to verify the information, but also to alert the FBI because they don’t know who their anonymous sources are, and they want to find out too. It’s not even a flaw anymore — it’s a feature of their reporting.

I’m not a criminal mastermind. I definitely deserve to be on World’s Dumbest Criminals for what I did. I committed a felony and had zero awareness of the giant footprints that I left in my wake. Betsy is completely misguided if she thinks I’m mad at The Intercept because I got caught. It was the fact that I trusted their journalists with information that I thought was important for the American people that they never intended to publish, but they fully intended to use law enforcement to figure my identity out. The Intercept gave this air of wanting to be the light in the dark, and it was a trap all along. There are three people still under some sort of federal supervision today — me, Daniel Hale, and Terry Arbury — since they started their “If you see something, leak something” campaign online.

A spokesman for The Intercept gave the following statement to Rolling Stone: “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 we 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 U.S. surveillance state in all cases.”

I have to ask about Trump. The man under whose administration you were indicted, and who said very negative things about you publicly, has now been busted for, among other things, mishandling classified documents and has been charged under the Espionage Act — the same arcane law you were charged under.
I think this is actually the true definition of irony. I have completely separated my emotions toward Trump the person in this case because I am very interested in seeing what it looks like when many counts of the Espionage Act are carried out in a court of law against a defendant with a very different power differential from my own. He’s not being held on any pre-trial restrictions, and it will be interesting to see what he is able to do as far as a legal defense as to why those documents were at Mar-a-Lago, and whether or not those documents listed in the indictment were actually national defense information or not. Previous defendants under § 793 were actually not even allowed to make that argument. Once the government has deemed information in a document to be national defense information, defendants who are accused of willfully retaining and/or disseminating it are not even allowed to question in a court of law if this is national security information or not. I’m curious to see how someone who will have all the favor and all the privilege of wealth, influence, and being a former president in a court of law can actually legally question this law and its use in court, and maybe set some legal precedents that will favor a future whistleblower. But I’m absolutely not surprised that he’s not detained and has been given the utmost respect and deference by the court. I never expect anybody to be treated as poorly as I was. My vision for the United States Department of Justice is a system under which every defendant, no matter how poor or how small of a person they are, can receive the same respect that a former president is receiving.

What’s the status of your memoir?
The manuscript is complete for the memoir and we’re in the editing process, which could take forever. We hope to present it to my pre-publication review at the NSA, and it’s very likely that they will sit on it for a long time. But if everything goes right, and even if they were to take a year with it, we are hoping to have it out by the end of 2025. So, I’m very excited to bring some of the more intimate details of my early life, my time in the military, and that kick in the teeth of what it’s like to be silent while a prosecutor dissects your personality for the world to see. I’m hoping that it can hold a mirror to America in general.

How do you feel about America now given the way it’s treated you?
One of the lessons I was learning before I leaked that document and committed that felony — I just didn’t learn it quickly enough — is that it really doesn’t matter where you are in the world, the most meaningful form of activism is what you can do for the person next to you. My whole life I had looked outside of America’s borders to global conflicts and thought I would have to pass out blankets at a camp for Afghan refugees to be good enough. I didn’t realize that you can go into your own city and change people’s perspectives on homelessness, or to offer youth programs to kids who are in trouble or register people to vote. Activism can be done within your own city. One of the greatest things about America is that we’re not so far gone into corruption at the city level to where people are one hundred percent powerless. What we’ve seen over the past ten years coming out of real activism and real investigative journalism is that if you uncover something that’s wrong, you’re telling thousands of people how to fix it. That is a uniquely American approach and things have been fixed. America is not broken, and I am here for it.