Reality Winner on Sydney Sweeney and leaking government secrets

Arrested aged 25, whistleblower Reality Winner received the longest ever sentence for releasing intelligence to the media. Euphoria star Sydney Sweeney plays her in a stunning new film. Here, in her own words, is Winner’s story.

It’s 3rd June 2017, a sweltering hot day in Augusta, Georgia.

A 25-year-old woman, little more than five-foot-three, stands in her small kitchen.

Also crowded in there: six FBI agents, ranging from lanky to muscly to tubby, most of them armed, all certainly wearing ankle-holsters. Another five are in the front yard or rifling through her possessions. That’s a lot of chinos and testosterone.

As the agents make excruciating, distracting smalltalk, she enquires about when they’ll return the phone they’ve just confiscated. A keep-fit aficionado who does CrossFit and competitive power-lifting, she’s teaching yoga tomorrow and her music for the class is on that phone. Also worrying this animal-lover: the safety of her dog (who doesn’t like men and is in a cage in the yard) and her cat (currently hiding under the bed). The agents fret as much about leashing the cat as they do locating the three weapons the woman legally holds: a pink AR-15 rifle, a 15 gauge” and a Glock 9 pistol under the bed.

Then two of them take her into a back room of her rented property – all-white, devoid of furniture, grotty, unfortunately cell-like – and start interrogating her.

This is the setting of Reality, a brilliant new film starring Euphoria and The White Lotus star Sydney Sweeney. And this was the, well, reality six years ago when Reality Winner (a real person, her real name), a National Security Agency contractor and linguist, was arrested on charges of mishandling classified information. At her trial 14 months later, Winner would be sentenced to five years and three months in prison, the longest sentence ever handed down for the unauthorised leaking of US government information to the media.

The script for Reality – directed by Tina Satter and adapted from her off-Broadway play Is This A Room?, which opened in January 2019 – is drawn verbatim from the FBI transcripts of Winner’s apprehension and questioning. Within a little more than an hour, the former US Air Force senior airman [sic] had admitted leaking to news website The Intercept a secret file documenting Russian attempts to hack the previous autumn’s Presidential election – the one that brought Donald Trump to power.

I don’t think you’re a big, bad master spy,” says Agent Garrick, played by Josh Hamilton (The Walking Dead), trying to inveigle himself into Winner’s confidence. He suggests that she was just angry about American politics. Which, it seems, she was.

I wasn’t trying to be a Snowden or anything,” says an increasingly agitated Sweeney-as-Winner, referencing arch-whistleblower Edward Snowden (who’s hiding in Russia to this day, 10 years after his mass leak of NSA files) as the heaviness of her situation dawns on her. It was just the one document because, like you said, I’ve had a really hard time at work. I’ve filed formal complaints about them having Fox News on all the time….”

Sweeney is sensational in a film that currently enjoys a 100 per cent fresh rating on Rotten Tomatoes. The drama is a tight, brow-furrowing, almost-real-time 83 minutes posing wide, far-ranging questions. Was the manner of Winner’s apprehension legal? Why so many blokes? Was this specialist linguist – who joined up at 18; can speak Farsi, Dari and Pashto; and was trusted with translating Iranian Aerospace Forces Office documents – breathtakingly naïve? Was she fairly treated by the American justice system?

And also: what would you have done in her position, at a time when President Trump was busy firing FBI director James Comey and there was furious back and forth in the American media as to whether Russia had been directly involved in the election of a Putin lickspittle?

Winner was released from prison in June 2021. Now 31 years old, she’s not been able to watch Sweeney’s reenactment of her arrest yet. I can’t relive that trauma. I can’t even watch the full trailer,” she says, Zooming in from what looks like the living room of her childhood home in the small town of Kingsville, South Texas. I actually get queasy reading the interrogation document.”

But Winner was able to speak calmly, thoughtfully, reflectively and insightfully to THE FACE, and didn’t duck any question. Here’s what she had to say.


Thank you so much for your time, Reality. What’s been your involvement with the film?

Not much. Throughout my time when I was incarcerated, the director, Tina, actually became a major form of emotional support for my mother. And that is why, once I was released from prison, and actually had a first conversation with her, I felt an immediate trust and connection and appreciation for her.

So I tried to just answer basic questions. What did your dog look like? What were you wearing? How did you feel? How was your car parked?” Other than that, they really took this project on and made it their own.

What interactions did you have with Sydney Sweeney?

We did get to have a video chat, and get to know each other. People always use the [phrase] down to earth”, but she was just so personable and relatable. I had seen her on her other shows, and I was starstruck. But three minutes into the conversation I felt like I was talking to someone I’ve always known.

Did you get a sense from her why she wanted to portray you in a movie?

We talked about how I was feeling that day, and we talked about vulnerability, and that fine line between being too stoic and too strong. Obviously, I didn’t fall apart. I wasn’t hysterical. And it’s very hard as a woman to tread that line where you’re calm, and you’re scared, without people giving you other attributes.

That idea of vulnerability” did strike me – your small home is filled with these FBI agents, all big guys, all towering over you. How overwhelmed did you feel by this physical male presence, in your home, in your face?

I absolutely noticed it. I could see the concealed weapons. I was later corrected in court: out of the 11 men walking around my house that day, only nine were armed. I said they were all armed. I mean, I could see ankle holsters on everybody.

I live in America: not everybody gets to survive their own arrest. That was in my mind – any sudden movements… I had a foster dog who did not like men. I had broken up with a guy the week before, because the dog attacked him. And I thought that the dog would attack one of the agents and they would shoot her. And [in that scenario] I would lunge forward to protect my dog, shield her, and they would shoot me.

I remember begging for them just to keep the door shut so my cat wouldn’t get out. Because if I chased her down the street, they would shoot me.

Why did you want the movie of your story to be made?

I don’t know if I actually do [want my story told]. It’s terribly embarrassing. People at my job found out about it, and I’m just trying to hide it! It’s very, very embarrassing to have a movie made out of your arrest.

But we did have some very contentious court hearings about that particular interrogation. They used my gender. They said: For a woman to be that calm, that means she must be some kind of criminal mastermind. She wasn’t scared.” They painted me to be someone who was incredibly calculating and dangerous.

Tina saw the same exact words on the [interrogation document] and said: That’s a scared woman.” This is a story of what women do when they fear for their lives, and how we constantly, as a society, critique them for it, after the fact.

Did you want the political point that you made with the leak to also be foregrounded?

Not so much the political point. But rather just for people to understand that there is nuance here. That this is somebody who did not intend great harm, somebody who didn’t hate the United States, somebody who really intended to save their country and wasn’t afraid to tell the FBI that.

You joined up when you were 18. Why were you so keen to serve your country straight out of high school?

[Pause]. Because a pivotal moment of my childhood was 9/​11. And [it became] one of the only ways I had to talk to my father and to catch his attention – he was a theologist and a psychologist. So you can imagine when that happened, that really caught his attention for the rest of his life.

I wanted to be somebody that he would be proud of. Somebody who could, in a sense, figure it out”. I knew that there was only one school in the entire world that I could go to that would (a) teach me these languages, and then (b) help me understand the motivations behind such an attack. And that is the Defence Language Institute. So I had to enlist in the military to go there.

I wanted to figure it out for my dad.

I was young, and I saw one question mark on the brink of tearing my country in half. And if your superpower is having the answer, you would act on it”

In the film, we hear you talking about your keenness to redeploy. So that was a genuine desire, to be back in the field with US armed forces?

Yes, yes. My goal at the time was to build a resumé of overseas work experience, so that I could present myself as somebody who could then work in Afghanistan for the UN, for the Human Refugees Committee, for USAID, somebody who could pass out blankets at a refugee camp. But I didn’t have the college education to do it. So I sought to create that resumé through defence contracts.

Given that passion, that career ambition, that desire to do good in the world, there’s the fundamental question which I’m sure you’ve been asked 1000 times: why did you leak that document?

The one time I did go back to that interrogation [transcript], I was hoping I could read my words of what I told the FBI and it would jog my memory.

The day that I released the document, I don’t remember why I did it. It’s been so buried. When it was hashed out so many times in court, and when the government says who you are, and that becomes the fact in a court, you start to believe it. So it took me a really long time to find myself again. And in all of that, I don’t even remember the thought that started all of this.

You do talk in the transcripts about seeing that information [about Russian interference] being contested back and forth, back and forth, in the public domain, with everything else that keeps just getting released, and everything that keeps getting leaked, why can’t this get out there, why can’t this be public?” So it seems you had a desire to provide evidence and maybe end that debate.

Yeah. I think in some ways, I was young, and I saw one question mark on the brink of tearing my country in half. And if your superpower is having the answer, you would act on it.

What thoughts did you give to the possible repercussions of your action?

Zero. I was young, I was impulsive. Of course, the FBI didn’t tell me at the time of my arrest, but I didn’t even know what law it was that I had broken.

So were you naive on some level?

Oh, incredibly naive.

The film ends with you being led towards a car in handcuffs. What happened next?

At that point, the only other reference I had was Chelsea Manning, who disappeared for seven months in solitary confinement. I thought that that would be it. [The FBI] realised that they needed to search my person, to frisk me. And they needed a female to do it. So they called the nearest police officer.

I wasn’t wearing much – obviously, you’ve seen the film! – and she had a word with them. I believe she told them that they were not taking me to jail. That a police officer was taking me to jail. It might not be in the film, but a second female police officer came. She walked me to her car and she said: Oh, I’m gonna have to cuff you, would you turn around?”

The word relief” shouldn’t happen. But I was so relieved because there was somebody in a marked vehicle. They had a badge, they had a uniform, and I was going to a jail. So I knew that no matter what happened at the end of tonight, my family would be able to find me. That my locations would be documented. And I would not be in an unmarked vehicle with agents in civilian clothing.

Moving ahead: how shocked were you at the length of your sentence?

Um… I wasn’t. When you’re in jail, you don’t have any access to historical precedents. You don’t know what other people received. And I wasn’t asking about that. I was fighting for my life with an eating disorder in jail conditions that were not allowing me to survive it. When it became apparent that I couldn’t do it anymore, when I reached that breaking point, I decided to go to prison, because I needed to survive my eating disorder.

I was ready to take responsibility [and] the five years didn’t seem like anything. I was just so excited to go to a prison where I could go outside every day. Where I could exercise. Where I might have access to real food.

How did your close friends react to, first of all, the news of what you’ve done? And then secondly, of what was going to happen to you?

It’s interesting: I don’t even know if I asked them about that. I’m just so incredibly embarrassed about the whole situation. Obviously there’s very, very few friends from before this that are still in my life. I mean, I can count on one hand. So many of them still work in intelligence, so they’re afraid. I don’t blame them.

You mentioned Chelsea Manning: have you had any contact?

I actually spoke to her briefly by a jail email system, when I was in transit [between facilities]. I was transferred to probably the worst jail that I had ever been in. But it was such a bad jail, they didn’t monitor my communications. Anybody could email me as long as they bought credit. And so I was like: well, let’s do it – let’s talk to Chelsea. And I was asking her about prison. Coincidentally enough, the very next day, I was transferred out to prison. So, you know…

How did the other prisoners treat you? Was it evenly split between people seeing you as a traitor or as a hero? Or was it greyer than that?

It was very grey. That is one of the most interesting things about women’s prison: the nuance in the relationships between everybody. There were people who were kind of misguided who were like: Oh, she’s the girl that faced off against Trump!” And I’m like: No, not really…” Then there were the wackos who were like: She was in the Russian special forces, don’t mess with her!” And I would just start doing handstand push-ups, because I’ve gotta keep myself safe [and], you know, intimidate people.

So there was this huge spectrum. But eventually, most people found out that I was this goofy person who just wanted to work out and be outside [in the yard] as much as possible.

What does your life look like now?

Oh, it’s crazy busy! I gave birth” to a [four-legged] puppy. She keeps me busy from morning to night, and almost every night in the middle of the night. I coach about five CrossFit classes per day. I train for competitions. When I’m not doing that, we have chickens and a horse. I’m writing a book. And I’m doing press for this movie. So I am busy from four in the morning till nine, 10 o’clock at night, always working on a different hustle.

Do you regret the leak?

Absolutely. Most importantly, first and foremost, I caused so much pain to my family. I’m gonna spend the rest of my life making this up to my mom. And second most: I love being a CrossFit coach, and I love that I found a way to incorporate the cure for my most pressing health complication, my eating disorder. CrossFit is the only cure I’ve ever found. And that is now my job. It’s now my entire life. I love having that authenticity.

But: I set about to be a national security expert. I set out to protect my country and serve my country, till the day I die. Now that’s forever off the table for me. I’ll never, ever not regret throwing away my potential career in national security.

You were sent to prison at a pivotal age, 26. So many things would have been disrupted for you: career, socialising, meeting someone… How difficult has it been getting the different elements of your life back on track?

It really has been [difficult]. I don’t know how to juggle relationships, or friendships. I don’t know if I could before, but at least being in the military and being so busy was a shield against that. But I never learned how to be around people unless you’re locked in a room with them.

So you’ve been de-socialised?

Absolutely. The first year I was home, I was a different person. I didn’t come out of prison a pleasant person at all. I was extremely disruptive, outspoken, loud, belligerent. It took a year for me to finally calm down off of that.

If you’re not that person in prison, you don’t have rights. If you try to be nice, if you try to help people, the officers will crush you. The only way to get any room to breathe is if – pardon my French – you become such an annoying person to fuck with and make sure that every officer knows there’s an opportunity cost of trying to mess with you. That is the only way you can find any space.

And that’s exactly the opposite of what you want to do when not in prison! So I had to relearn how to socialise.

I know you haven’t seen the finished movie, but what would you like people to take from the experience of watching your story as told in this film by Sydney Sweeney?

My favourite thing that I’ve heard about the film is that it doesn’t tell you how to feel about me. And that it’s really close to the final transcript of that interrogation. I want, especially Americans – because we have such a difficult relationship with law enforcement – to understand: what would you do in that situation? How would you survive?

And also really ask themselves: how much power do we give law enforcement [so] that the experience that you’re seeing on the film was a perfectly legal encounter? That that confession counted in court. And that later on in court, those very same agents would say, with a straight face, that I was free to leave the scene at any moment. And that is their legal answer.

What would it take for you to sit down and watch Reality?

I mean [smiles]… maybe when they turn it into a musical?

Reality is in cinemas from 2nd June

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