Criminal Adaptations
Criminal Adaptations is a True Crime/Movie Review Podcast discussing some of your favorite films, and the true crime stories that inspired them. With hosts Remi, who spent over a decade working in the film and television industry, and Ashley, a clinical psychologist and forensic evaluator. They discuss a new movie each week and compare the film to the real life events that the film is based on.
Criminal Adaptations
Reality / Winner
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Two films, one real-life National Security Agency (NSA) whistleblower, and a story that blurs the line between truth and fiction. In part two of our season finale, we dive into two very different films: Reality (2023), the HBO American crime drama directed by Tina Sater and staring Sydney Sweeney, and Winner (2024), the black comedy directed by Susanna Fogel, staring Emilia Jones, Connie Britton, and Zach Galifianakis. The films offer two very different cinematic interpretations of the life and arrest of Reality Winner, a former US Air Force linguist turned NSA contractor who leaked top-secret documents about Russian interference in the 2016 presidential election.
We unpack how each film portrays Winner’s character, choices, and the forces that brought her from military service to a leak that made national headlines. Next, we contrast those portrayals with the real events – from the NSA leak and Federal Bureau of Intelligence (FBI) investigation to her 2018 guilty plea and five-year sentence under the Espionage Act, the longest such punishment for unauthorized media disclosure in recent history. Whether you’ve seen the movies, followed the headlines, or are just curious about the real woman behind both scripts, this episode peels back Hollywood’s layers to reveal the truth beneath.
Primary Sources:
- Howley, Kerry. Bottoms Up and the Devil Laughs: A Journey Through the Deep State. Knopf (2023).
- Winner, Reality. I Am Not Your Enemy: A Memoir. Spiegel & Grau (2025).
- NSA Document
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Theme: DARKNESS (feat. EdKara) by Ghost148
Welcome to Criminal Adaptations, the show where we take a look at some of your favorite movies and the true crime stories that inspired them. I'm Remy. I spent over a decade working in the film and television industry in Los Angeles, California.
AshleyAnd I'm Ashley. I'm a clinical psychologist and forensic evaluator in the state of Oregon.
RemiHello, everybody. Court is back in session. Welcome to our second of two whistleblower season finale episodes. How are you doing today, Ashley?
AshleyI am doing fantastic. How about you?
RemiI am doing a-okay. I think some of our viewers know that we record these episodes in advance. So you and I have been ramping up for our wedding, which will be happening in just a few short months. So that is something we are looking forward to. But as far as today's episode, when I say the name reality winner, what is the first thing that comes to mind?
AshleyWell, because I know the story, it's probably election.
Who Is Reality Winner?
RemiHonestly, the first thing that I think of is probably somebody who won a reality TV show. But that is not what we are discussing today. We are discussing a person named Reality Winner, who is a former NSA contractor who leaked a classified intelligence report on Russian election interference to the press in 2017. So today we will be covering two films: Reality, directed by Tina Satter, and Winner, directed by Susanna Fogle. I honestly had absolutely no idea that these two very different movies were both true stories about the same person at first until actually looking into it. Which is probably because I had never heard the name Reality Winner before. Had you, Ashley?
AshleyNo, I knew nothing about this girl until we saw the trailer for the second movie, Winner, which I swear we watched it. Did anything seem familiar when you watched it this time around?
RemiIt didn't actually. I don't think we watched this one. I think you might be mistaken here because nothing that I saw really rang a bell to me.
AshleyAnd for the first movie, Reality, I saw a trailer for it on HBO. It's starring Sidney Sweeney, and I remember the trailer, but it wasn't until after we watched Winner, I'm still sticking to that, that I looked up this movie, or I think I looked her up on Wikipedia and I saw the name of this movie, and I was shocked. I had no clue what the movie was about.
Two Films, Two Tones
RemiMe neither. I think that I realized that the films were about the same person after just reading the descriptions, which is pretty basic. However, one thing that really intrigued me was how different these two films seemed from each other. One is basically a box drama built from the actual interrogation script, while the other basically tells her entire life story only as a comedy. So I found that juxtaposition to be very intriguing, and these films are done very differently. And both films also feature very different actresses portraying the same real person into entirely different performances. Sidney Sweeney is showcasing her dramatic chops in reality, while Amelia Jones is delivering a much more cynical comedic performance in the film Winner. Now, I don't know a ton about Amelia Jones, except that she was in the film Coda, and is yet another actor I had absolutely no idea was British until hearing them interviewed.
AshleyCoda was so great. She was the daughter?
RemiYes, she was the daughter in Coda, and beyond that, I really have not seen very much of her work, but after seeing her performance in this film and watching interviews with her, she is a very good actress. I had absolutely no idea that she was a British-born citizen while watching the film. So bravo! Good accent work, Miss Jones.
AshleyAnd Sidney Sweeney, that's someone we are much more familiar with.
RemiYes, she seems to be everywhere these days, and not always in the most positive light. But she just keeps on trucking. I think we both saw her first in the HBO sex drama Euphoria, along with Zendaya and Jacob Alordi, who have gone on to their own levels of fame. And I was pleasantly surprised by her and Glenn Powell's romantic comedy, Anyone But You. And she was amazing in the last scene of that random horror movie Immaculate, where she plays a nun who gives birth to the Antichrist.
AshleyI remember when we put on Anyone But You, we just assumed it was gonna be like a nothing burger of a movie we were gonna watch because nothing else was on, and we both loved it.
RemiAnd I'm not a huge fan of romantic comedies in general, but this one just hit all the right marks, and I found it very charming and a very entertaining film. But then old Sweeney kinda hit a slump for a little bit, until her most recent film, The Housemaid, somehow grossed $300 million at the box office.
AshleyAnd it's already been greenlit for a sequel.
RemiThat is utter insanity. This is not a story that needs a sequel, A. And B, you and I saw this film and were highly entertained by it, but I don't think I even realized it was a theater release until reading the box office numbers later on. And this thing was a massive hit. Now, initially I went into her film Reality with super low expectations after we recently saw her in the true crime boxing film, which we will also be covering someday, Christy. And I thought she was absolutely terrible in that film. Like, really, really bad. But spoiler alert, Sydney Sweeney fucking kills it in this role. She totally blew me away, and it's seriously the best acting I've ever seen from her in anything. She really, really impressed me.
AshleyI had told you that I was listening to a podcast and one of the hosts mentioned um Sydney Sweeney, he really likes her just because of her physical appearance, but he mentioned the movie reality, and everyone was like, wait, what? You watched that? And he's like, Yeah, Sydney Sweeney was awesome in it. So I'm glad his review was accurate.
Sidney Sweeney’s Performance And Career
RemiThis film would unfortunately be classified in one of Sweeney's bombs over the past two years, This and Christy. I know neither film did very well at the box office at all. However, I think reality deserves a second glance from people. That was a pretty well-made film, and we'll get into it more in a bit, but it had a lot of the feeling that I was craving from the movie Snowden, and did a very good job of building tension and developing characters with very little to work with.
AshleyWell, let's dig a little into these movies, shall we?
RemiAbsolutely. Are you ready to get real about how reality and winner actually got made?
Reality Winner - Sydney Sweeney125 pounds, you guys. Flatter me.
FBIThat was on your driver's license. That's right.
Reality Winner - Sydney SweeneyOkay, well, I lied. Don't we all?
RemiReality is a 2023 American film directed by Tina Satter, who co-wrote the screenplay with James Paul Dallas, rescripted almost entirely word for word from the original FBI transcript taken during Reality Winner's initial interrogation. The film stars Sidney Sweeney as Reality Winner, with Josh Hamilton and Merchant Davis co-starring. Reality centers on the FBI interrogation and arrest of Winner that took place on June 3, 2017, at her home in Augusta, Georgia, where she was questioned for roughly an hour by FBI agents R. Wallace Taylor and Justin C. Garrick. Before the film adaptation, director Tina Satter actually turned the interrogation transcript into a verbatim stage play called Is This a Room? named after a line spoken during the interrogation.
AshleyAnd fun fact, that play, it's not only every word that's verbatim, it's every audible breath and cough.
RemiWow, that is a crazy amount of attention to detail. The play first premiered at The Kitchen in New York City in 2019, then ran off Broadway at the Vineyard Theater before eventually making its way to Broadway at the Lyceum Theater, opening on October 10th, 2021, and closing on November 27th of that same year. Because Reality Winner was incarcerated during the early runs and later under supervised release, she was never able to attend the productions in person, but did stay in contact with the creative team and even joined the Broadway Curtain Call remotely on opening night.
AshleyShe was actually on house arrest when it was playing in 2021, and it ended like right around the same time that the show did. So it's pretty unfortunate timing.
RemiI would be so bummed if someone made a stage play about me and I never got to see it.
AshleyI feel like it's also rare, too, that the writer and director of the play would go on to also write and direct a movie. I feel like they usually switch those out.
RemiUsually they do, but we talked about one not too long ago that did something similar with a few good men and Aaron Sorkin. He had written the play and went on to write the film adaptation as well. But it is much more rare for someone who wrote and directed the play to also come back to write and direct the film adaptation. It's just a very different medium, stage plays and film, so a lot of the time they want to hire someone more familiar with that medium. Is This a Room helped draw broader industry attention to Winner's story and eventually led to plans for a screen version. As the adaptation moved into development, Satter remained attached to Direct, and in June 2022, it was officially announced that Sidney Sweeney would take on the lead role of Reality Winner, starring alongside Josh Hamilton and Merchant Davis in what would become Satur's feature film directorial debut. And I think Satter did a very good job with this film. I look forward to her next project. If she gets one, I know this one didn't do that well. Once cast, Sweeney prepared for the role by studying interviews and communicating directly with Reality Winner through Zoom calls and text messages, allowing her to better understand Winner's speech patterns, mannerisms, and overall personality. Sweeney also incorporated some of Winner's publicly shared workouts into her own training as part of her preparation. Winner additionally stayed involved throughout the production as well, often consulting with different departments throughout filming to help maintain accuracy. Did you check out any of Reality Winner's workouts online for this episode, Ashley?
How “Reality” Was Made From A Transcript
AshleyI did not. I should have. She is definitely a workout buff.
RemiYeah, she's like one of those crossfitters from what I've seen, and seems like she could probably kick my ass and outrun basically everyone I know. Filming began in May 2022 and was completed in just 16 days. They started by shooting the exterior scenes first, then moved inside to film the interrogation sequences, which were shot mostly in chronological order, which is pretty unusual since most movies are filmed out of sequence.
AshleyI get why you would want to film those in order though, because the mood and tension of what's happening in the scene is going to build based on the questions asked and the dynamics between interrogators and reality winner. It would be harder, I imagine, to film that out of order.
RemiI totally agree, and one advantage this film had going in was that it is a box movie, and for those of you who are not familiar with that term, it is a movie or TV episode that takes place primarily in just one location. So the film reality takes place entirely at reality's home and her front yard, allowing for filming chronologically to be a lot more plausible. Because in normal productions, they have several different locations that they may have only for a limited time, so they will have to film all of the sequences that are at that location in a single day or a couple of days, just so they don't have to pay to return to that location later on. In a film like this, that's not really an issue. Our second film, Winner, takes a very different approach to the same story. The film was released in 2024 and directed by Susanna Fogle and written by Fogel and journalist Carrie Howley.
AshleyOh, Carrie Howley, that's funny. One of the books I read for this is actually written by her. It didn't have as much information about Reality Winner as I wanted, so I had also supplemented it with Reality Winner's autobiography, which she just released in September.
RemiThe film stars Amelia Jones as Reality Winner, alongside Connie Britton, Danny Ramirez, Catherine Newton, and Zack Galifanakis in supporting roles. I never thought we would talk about Zack Galifanakis in two separate episodes in this podcast. He was also the star of the film Masterminds, which we covered a few seasons back. We don't get a lot of comedies on this show, believe it or not. While the film Reality focuses almost entirely on the interrogation itself, Winner expands outward, telling a broader biographical story that explores her upbringing, Air Force service, and the events that ultimately led to the intelligence leak. Fogle has described the film as a coming-of-age story about a regular young woman trying to figure out what the right thing to do is, even when that choice could turn her life completely upside down.
AshleyReality Winner was a crypto-linguist for the Air Force and NSA. She also knows several Middle Eastern languages. I would not call her a regular young woman.
RemiYou know what, you make a very good point there. Fogel said that at first, Reality Winner was just another name she had seen in the news, but years later she read journalist Carrie Howley's long-form New York magazine profile, Who is Reality Winner? Which eventually became the basis for the screenplay that Howley later co-wrote. For the film, Fogel reunited with actor Amelia Jones, whom she had previously directed in the 2017 psychological thriller Cat Person. After being cast, Jones spent time preparing for the role through extensive research, including traveling to meet Winner in person so she could better understand her life, personality, and experiences.
Box Movie Filming And Chronology
Emilia JonesAnd then when I read the script, the script was quite funny, and I was a bit shocked. And then when I was able to go fly to Kingsville to meet her, I understood why the script was funny because she's a hilarious person. And um yeah, I uh I had a really good time getting to know her on a personal level. I got to meet all her animals that she rescued, and I got to do her CrossFit class and her yoga class, and I had loads of questions to ask her, but I also got to know her and I think it was perfect, really, because that's what we're trying to do with this film. We're trying to humanize reality and show people that she's so much more than just a name and a headline.
AshleyIt must have been so weird for a reality winner meeting and working closely with these two actresses that are going to play her in two different movies that came out right around the same time.
RemiThe timing of this is pretty crazy. She most likely got a call from Sidney Sweeney and just a few months later was talking to Amelia Jones. Two films about your life coming out so close together like this must have been a very strange, surreal experience for reality.
AshleyAnd so close to getting out of prison, too. Like that's a really tough time when you're trying to readjust to normal life, and now her life isn't normal because Hollywood is breaking down her door.
RemiOther cast members also did their own preparation by connecting with the real people they were portraying in the story. Connie Britton and Catherine Newton both spoke with their real-life counterparts and apparently would call them before specific filming days to understand exactly what they were feeling when the events had happened. Winner herself also spoke with the filmmakers and shared details from her experiences, though she has said that she does not plan on ever watching any movies about her own story, and would rather people focus on the bigger issues behind the case instead. So she most likely didn't even see these movies after all of that. Filming for Winter took place in Winnipeg, Canada, and other locations across Manitoba, and production wrapped on November 21st, 2022. Alright, Ashley, should we open the last file of season 5 and see how reality and winner present the evidence on screen?
AshleyYep, I have my magnifying glass ready.
RemiWinner opens with Reality Winner, played by Amelia Jones, being escorted away and handcuffed by federal agents, as she introduces herself through a voiceover, admitting that most people have probably never heard of her. The film then flashes back to Kingsville, Texas in 2001, when Reality was only nine years old. Little Reality is in the midst of helping pick out a puppy for her older sister Brittany's birthday, along with her mother Billy, played by Connie Britton, and her father Ron, played by Zack Galifanakis. Despite his children's rousing glee at the prospect of owning one of the lovable furballs, Ron still has ethical objections to buying a puppy from a pet store and proceeds to explain exactly what a puppy mill is to his two young daughters.
AshleyThey gotta learn sometime, I guess.
RemiUtterly distraught by the thought of the remaining dogs being left behind to potentially be euthanized, reality impulsively opens up all of the cages, releasing a playful pack of pint-sized puppies into the mall as her father looks on approvingly from the sidelines.
AshleyIf I was at that mall and I saw that, I would scoop up one of those pups and leave the store.
RemiIt was very adorable chaos that she started, I will say that. However, I don't think you would have grabbed one of these dogs because they were all huskies. And huskies can be a handful, and you have talked me out of purchasing one before. Unfortunately, reality's rebellious rescue results in her family being unable to purchase a dog that day, causing tensions between the family later that evening during Britney's birthday celebration.
AshleyI mean, yeah, she now has zero presence because the dog was supposed to be their present.
RemiThis is a recurring theme between reality and Britney. Reality seems to ruin a lot of things for her older sister. Over cake, we learn that Billy works as a social worker, while Ron is a self-proclaimed unemployed writer, still dealing with the lingering effects from an injury he sustained years earlier by regularly consuming prescription pain medication like Tic-Tacks to help manage his discomfort.
AshleyAnd clarifying question: Billy and Ron are married at this point?
RemiYes, they are married at this point. It's not outright stated, but it is implied, I guess.
AshleyBecause they live together.
RemiYes, they are all living under the same roof at this time. The next morning, as reality and her sister are watching cartoons, their program is suddenly interrupted by breaking news coverage of the September 11th attacks. The entire family soon gathers together watching the events unfold in stunned silence. The following day, while target shooting with her father, reality asks why the United States can't just talk to the terrorists to find a resolution. Ron tries to explain that when people don't speak the same language, they often can't understand each other, an idea that sticks with reality, prompting an early interest in learning other languages so that she can one day understand both sides of global conflicts. The story then jumps ahead to H. M. King High School in 2008, where a staunch Air Force recruiter is speaking to a shop class full of slack jawed teenagers, along with reality. During the recruiter's spiel, he incorrectly states that Iraq was. Responsible for the September 11th attacks. So reality quickly chimes in to challenge the claim and speak a little pashtu, showcasing both her knowledge and research into Afghanistan as well as her fluency in Iranian languages. After class, the recruiter expresses interest in harnessing reality skills into a career in the Air Force, but reality shows little interest in military recruitment at first, being far more interested in focusing on her volunteer work while getting ready to attend Texas AM in the fall. Later on, reality gets a call from a female Air Force recruiter who speaks to her on a more personal level by explaining exactly how reality's language skills could make a real difference helping civilians in conflict zones. The recruiter's words seem to resonate with reality, and over the next few days, she becomes increasingly frustrated by the rampantly casual racism she keeps noticing throughout her community.
AshleyDid you ever have military recruiters come to your school?
RemiI don't think they ever came to my school. I remember seeing them at malls and things like that, but no, I don't think we ever had a recruiter come into class and like pitch the idea of joining the military to us, did you?
AshleyWe didn't have them come into class, but a few times I uh vaguely remember them having like a table set up in the cafeteria for lunch. And I don't really like the idea of that.
RemiNow that you mention it, I think my school did have something like that. Like they didn't come in and speak to people, but I'm pretty sure they did have a table outside of the cafeteria with pamphlets and a recruiter there to speak to anyone interested. And yeah, I totally agree. The army should not be out here trying to recruit kids in high school.
AshleyThe argument for it, I guess, could be that it can open doors and give people a career that might need to take a more unconventional career route for whatever reason. But I also feel like 16, 17, 18, even 20-year-old people, you don't fully understand what you're signing up for.
RemiI totally agree. This seems like something that teenagers would join while not fully understanding all that it would entail.
AshleyEspecially in situations where they offer like a huge signing bonus.
“Winner” Plot: Childhood To Air Force
RemiWhen I was a teenager, my decision-making skills were pretty impulsive and not very researched, so I think a lot of people get recruited in similar circumstances where they don't fully grasp what they are getting themselves into. However, I could be wrong. I know a lot of people out there are in the military, and if you have a different point of view, we'd welcome to hear it. Back at home, Brittany is preparing to announce her engagement during a family dinner that evening. But just as the family is settling down into some casual conversation around the table, reality suddenly cuts in to announce her own impulsively life-changing decision. Brittany, how is your job at the lab?
Brittany - Kathryn NewtonOh, it's good. It's part-time, so I still have time to study. And I really can't drop below an A-. Um want to get that internship with the microbiologist that Taylor already has that he got freshman year.
Brittany's boyfriendThere is actually only one problem that you might think that she's too cute to be a scientist. I mean, maybe he just likes hot interns, right? He chose me.
Reality Winner - Emilia JonesOh my god. So I joined the Air Force. Boot camp starts the day after I graduate. Really? You can say that right now.
Ron Winner - Zach GalifianakisShe's joking. It's a joke, right? The military has no humanities. You you realize that, right? No literature, no, no philosophy.
Reality Winner - Emilia JonesI can read all that stuff on my own.
Ron Winner - Zach GalifianakisI don't think you understand the full context of what you're doing.
Reality Winner - Emilia JonesThe full context is I'm not spending another four years in a hick term full of racists who don't care about humanity. And I already signed the contract. Basic training, language school, Afghanistan. It's done.
Brittany - Kathryn NewtonSpeaking of contracts, we're getting married. Oh two comments.
AshleyI love how they're both trying to one-up each other. That really seems like what the sisters are doing here. And man, great call on the casting. They look like they actually could be related.
RemiSeriously, Catherine Newton and Amelia Jones in this film, they have very similar hair colors, and their facial features even are remarkably similar as well. It was a very good casting choice for these two to play sisters. After completing basic training, Reality spends the next two years in language school, studying Farsi and Dari, before later being assigned to Fort Meade, Maryland in 2011. There, she begins working in a large open office lined with cubicles similar to a call center, where she is tasked with monitoring and translating intercepted Taliban communications from Afghanistan. Though the work is tedious and repetitive, reality nevertheless quickly excels in her new position.
AshleyEven though it is not what she hoped for or expected, she really, really, really wanted to be deployed overseas, and unfortunately, the recruiters neglected to tell her that linguists typically do not have that career trajectory.
RemiSnowden also wanted to be sent overseas, but did not get to go to where he wanted. And I think people need to realize if you join the military, you don't have any control over where they are going to be sending you.
AshleyOne thing that Snowden and Reality Winner have in common is that they both got into this career because of 9-11. They were deeply impacted by that, and a desire to help people that they viewed as vulnerable and needing of aid.
RemiBut beyond that, those two do not have very much in common. I know you and I have discussed reality off-mic quite a few times, and she's a little firecracker, and Snowden has a much more, let's call it, monotone personality. So beyond their NSA work and leaking confidential information, I don't think these two have a tremendous amount in common.
AshleyNo, they don't. We'll get into this a little bit later, but even how they leak the documents is starkly different.
RemiOne night, while working the graveyard shift, reality intercepts a live transmission indicating an imminent attack, which she then relays to her superiors, leading to a counter-strike, resulting in multiple civilian casualties. Though situations such as this are considered part of the job, reality is still unsettled by the thought of her actions directly contributing to the loss of innocent lives. As a coping mechanism, reality begins channeling her emotions into intense CrossFit workouts, along with extra volunteer work at the Henley Hills Assisted Living Facility. One afternoon, while walking home, Reality impulsively drops in for a drink at a local watering hole, where she meets a handsome bartender named Andre, played by Danny Ramirez. As it turns out, Andre regularly attends the same CrossFit classes as Reality, but she has always been so focused on her own workouts that she never even noticed him. The two soon begin chit-chatting for a bit as Andre shares his ambitions of returning to school someday to become a veterinarian, which reality finds exceptionally appealing.
AshleyShe is an animal lover.
RemiShe sure is. She does a lot of volunteer work. She works with the elderly, she works at animal shelters.
AshleyAt one point, she even signed up to help push kids in wheelchairs during marathons.
RemiShe honestly seems like a generally good person who just wanted to help others. That week, after another CrossFit session together, Andre asks Reality Out for an impromptu hang sesh, leading to an evening of burgers and bonding in Andre's Chevy and Paula.
Reality Winner - Emilia JonesHave you volunteered at an animal shelter? Because vet schools want that.
Andre - Danny RamirezNo, but I do watch a lot of like vet TV shows. I watched this one called um Dr. Chris Petbet. You know, it's this guy that's uh a vet in Australia. Uh-huh. You've seen it?
Emilia JonesYeah, yeah, I've seen it.
Andre - Danny RamirezDo you watch it? Like people walk in with like animals like Katie in the second, and they're like, Mike, do you know anything about mall soupils? My pit wombat's been bit by Fawn Stiles.
Reality Winner - Emilia JonesYeah, hoy might. Can you can you get this poison dot shooting shrimp out of me, Garrett?
Andre - Danny RamirezYou sound like a pirate.
NSA Work, CrossFit, And Moral Strain
AshleyA hoymite. So Danny Ramirez is kind of having a little moment. He was in the last season of The Last of Us. I cannot recall who he was. He's not Pedro Pascal's brother, and he was only in four episodes. So I'm not sure if he was someone at the camp they were at or if he's on the bad side. But he is also reuniting with Pedro Pascal for a movie called De Noche. And it is the movie, Remy, that has had a bit of a sordid production. Walking Phoenix was initially attached and apparently demanded to have the script rewritten. So it was very graphic. It's about two men that fall in love and flee to Mexico. And apparently, Walking Phoenix just wrote these crazy scenes in it that ended up being too much for him, and he just suddenly dropped out, and the movie was in limbo for a while until Pedro Pascal signed on recently and has saved it.
RemiI knew I recognized this actor from something. I thought he was the blue beetle in that movie at first, but that is not who this actor is at all. However, I do remember him from The Last of Us, and he was good in that show. And I'm actually looking forward to that film he is making with Pedro Pascal. I know there was a lot of controversy surrounding it. However, him and Pedro, I think, will do a remarkable job, and I'm very interested in seeing the finished product, especially after Joaquin Phoenix was so bashful about partaking in the production. Later that night, Reality convinces Andre to help liberate a neglected dog that has been left outside in the freezing cold and snow for the past several days. Once freed, reality decides to keep the canine and is extremely turned on by Andre's humane heroics, leading to both reality and the dog staying overnight at his place. The following morning, Andre learns that reality isn't just a nickname like he had originally assumed, but rather her actual given name, chosen by her father before she was born. I honestly was expecting a bit more of a story during this scene, but that's literally all she says is that it's her real name and her dad picked it out for her.
AshleyI have the story. Do you want it now or later?
RemiLet's go with now. I'm curious.
AshleySo, Ron and Billy have two daughters. Billy got to choose the name for their first daughter, Brittany. And part of the deal was that Ron got to choose the name of their second child. And Ron really wanted his children to succeed and lead a successful life that he hadn't. And one day in Lama's class, he saw a woman wearing a shirt saying, You coached a real winner. And he thought the name Reality Winner would help emulate the success that he wanted for her.
RemiSo her dad literally just saw it on a t-shirt one day and said, Yep, that's my daughter's name.
AshleyFrom what I could tell, yeah, that's it.
RemiWell, when inspiration strikes, who are we to deny it? On the day of her sister Brittany's wedding, their father Ron misses the rehearsal dinner and arrives late to the ceremony, visibly loopy and overly medicated.
AshleyGod, my mom would kill my dad if he did that.
RemiYeah, it's pretty tragic seeing him come in, and he still desperately wants to be a part of the wedding, but he's in no condition to do so, so they just kind of have to keep him in the back room for the most part, away from everyone. And you can tell he's very saddened by this, like he wanted to be a part of it, but his demons and his addiction are getting the better of him. During the reception, reality also learns that her parents have decided to separate, adding another layer of emotion to what was already a tense family gathering. Two years later, Reality and Andre are living together, and her life has settled into a steady routine of intelligence work, intense workouts, occasional intermingling, and often attempting to subdue her own conscience from the mounting moral compromises tied to her current occupation. One evening, while watching television together, a breaking news report interrupts the broadcast, announcing that Edward Snowden has been identified as the person behind the NSA Leak of Classified Documents, exposing America's Global Surveillance Program.
AshleyThis is really all reality winner knew about Snowden? I didn't know this, but apparently, if you have security clearance, you are not allowed to go on the internet and look up information that is related to security breaches. If it's discovered that you have done that, you can get your security clearance taken away. So how this played out later at her trial is her lawyers that had security clearance, only one of them did, the other ones were trying to get it, and I think eventually did or were still waiting by the time she pled. Spoiler alert. But they couldn't even Google the document that she was accused of leaking.
RemiBut I just couldn't imagine working at a job with such strange, strict guidelines.
AshleyI don't even think it does make sense. If it's on the news and all over the internet, it's not like you're violating anything or risking national security by seeking more information about what's already out there.
RemiThat is true, but I'm assuming that they want people to only be looking into the information that they are supposed to be looking into and not anything else. Like, stay focused on your task, and that is it. As time passes, reality begins to consider alternative career options once her military service has been completed, and is flabbergasted to learn of the exceedingly high starting salary for an NSA contractor, somewhere in the realm of $150,000 a year. Even so, Reality chooses to spend the majority of her efforts on applying to various humanitarian organizations, preferring to pursue work that would allow her to help more people directly. Eventually, Reality receives an invitation to interview with the nonprofit organization Friends Across the World for a potential position in Pakistan. Overcome with joy at the prospect of finally working in the Middle East like she had always dreamed, Reality impulsively quits her surveillance job, causing a severe rift in her and Andre's relationship, ultimately ending in the couple's breakup.
AshleyWait, isn't she still with the Air Force? How could she just quit?
RemiIt's a little murky the way the film presents it. It seems like she is applying to these jobs, and her service is basically almost up by the time she's applying to this job. So when they call her in for the interview, I just assumed her service had been completed at that point and she was just staying around for the paycheck. But it is a little unclear. Now, more ready than ever to leave her old life behind, Reality travels to Seattle for the nonprofit organization's initial interview, which unfortunately does not go as she had planned.
InterviewerYou have a fascinating resume. The volunteer section goes on for pages. Well, it's recycle paper, so thought I'd be thorough. Well, um, there's just one thing I need to clear up, just to check that box before I send your paperwork through. There's just a small mistake on the application.
Reality Winner - Emilia JonesOh, sorry about that. What is it?
InterviewerWell, in the space for college degree, you wrote Air Force. So I'll just have to correct that and put your undergraduate information here.
Reality Winner - Emilia JonesWell, actually, I went straight to basic training out of high school.
unknownMs.
InterviewerWinner, you are aware that this job requires a four-year degree?
Reality Winner - Emilia JonesYeah, I did see that, but I figured since I spent those years in the Air Force learning languages, they don't even teach a Texas AM.
The Leak: Printing, Mailing, And Motive
InterviewerBut the military isn't college. You're really telling me I need a degree to hand out blankets? Well. We do much more than hand out blankets, of course. We think through problems. Just like we do in the military. Life or death problems. I'm just saying we have a protocol.
Reality Winner - Emilia JonesThey they they told me I could do my time in the military and then work in a refugee camp.
InterviewerWho told you? The recruiter. Which recruiter? Someone from here? No, the Air Force. I understand you're disappointed, and I please take all the time you need.
AshleyAnd this is a real problem she encountered. She didn't go to college, but she spent two years in intensive training, learning very unique languages, and got a whole slew of real-world hands-on experience that no other applicant will have. But because she doesn't have a BA or BS by her name, she was just shut out from all these positions that she was well qualified for.
RemiAnd I do think that this is another aspect that many teenagers might not realize, thinking going into basic training and a career in the military could count as a college degree later on when it is considered something separate.
AshleyI wonder why she could have qualified for the GI bill. Maybe her prison sentence disqualifies her from that now, but I know several people who have done time in the military and then use funds from the GI bill to later complete a college degree, and it pays for a good chunk of it.
RemiIt still has to be a bit of a bummer to go through everything and then realize you need to start college after going through the military. Now, with no job and nowhere else to go, Reality must move back in with her mother until she can get back on her feet again. While spending some time target shooting with her father one day, reality learns that Ron has been avoiding treatment for his recurring heart condition due to lack of health insurance coverage. Because of this, Reality reluctantly decides to pursue a position as an NSA contractor in order to help pay for her father's medical bills. The story then flashes forward to Georgia in 2017, where Reality is about to begin her first day on the job at the NSA. Though the job is mentally stimulating and pays very well, Reality must endure hours upon hours of 24-hour news stations playing as a constant backdrop whenever she is in the office. This would drive me absolutely fucking crazy.
AshleySo I left this out of my part. It's not the news coverage that upset her. It was the NSA was playing Fox News. And reality winner, spoiler alert, did not vote for Donald Trump and disagreed with much of his politics and policies. And in the human resources rules, the NSA was supposed to be like politically neutral. And so she complained that her facility was violating that policy by putting on news shows that were right wing instead of more in the middle like they should have been. And I would lose my mind if I had to listen to Fox News for 10 plus hours a day.
RemiYeah, my apology to any Fox News fans out there, but I primarily consider that sort of thing to just be propaganda to get people worked up about certain issues while having them ignore other issues. It's just my personal belief. I do not watch any 24-hour news stations. In fact, I primarily avoid the news because it's very bad on my mental health. But Fox News is definitely the worst channel you could have playing at your job all day, every day.
AshleyWell, especially during that time, right after the 2016 election, like the whole country was so divided.
RemiSeriously, I quit Facebook around this time because the content that was showing up on my newsfeed was just getting me angry. And it really does seem like this was a period of time when there was a lot of anger and a lot of conflict in the country between the left and the right. Not that much has changed, but it seems to really have kicked off around this time. Despite the annoyance, reality does her best to just stay focused and do her job day after day. This strategy seemingly works, at least for a while, until one day when reality can't help but catch a news clip from an interview with Donald Trump dismissing rampant allegations of Russian. Interference in the 2016 presidential election. Letting her curiosity get the better of her, Reality decides to dig a little deeper by using her own authorized access to personally investigate the issue. Much to her surprise, Reality soon stumbles upon a virtual smorgasborg of classified files, extensively detailing numerous Russian cyber attacks, targeting U.S. companies, voter registration systems, and local election infrastructure. That night, during her evening run, Reality receives a phone call informing her that her father has been hospitalized. Reality rushes to be by his side, staying with him overnight in the hospital as he peacefully passes away in his sleep. Though she is emotionally devastated, reality returns to work the following day as a means of distraction, but is still unable to avoid the incessant talking heads relentlessly playing on multiple TV screens in every office. Throughout the day, reality becomes increasingly unsettled by the public narrative, claiming that there was no proof of Russian election interference, which directly conflicted with what she had personally uncovered the previous day. Though she may have felt powerless in the face of her own father's mortality, telling the truth is one thing she still feels she has control over. Acting on impulse, reality covertly prints out several classified documents and hides them in her pantyhose to pass through security undetected.
AshleySo it wasn't several documents. It was actually one document that was five pages. That is all she printed out and all she sent.
RemiI guess I just had assumed it was multiple documents because I saw her stuffing five pages into her underwear before leaving work. After work, reality stops by a mailbox on her way home and anonymously sends the documents to an independent investigative news organization called The Intercept.
AshleySo here is another connection to Snowden. The Intercept is actually a publication that was founded in 2014 by Laura Potrius, Glenn Greenwald, and Jeremy Shaw. Remy, do you recognize those first two names?
RemiI absolutely do. They were involved in the release of the Snowden story.
AshleyExactly. So after that, they founded the Intercept in 2014 and really prided itself on the security and protection it typically provided whistleblowers.
RemiAh, alright. I was not familiar with the Intercept, but knowing that now, it makes perfect sense that that is where she decided to send the document.
AshleyAnd unlike Snowden, this is the only place reality sent the document. She had no plans on releasing it elsewhere. Snowden was talking to people initially from two different news organizations, and then when he was in Hong Kong, a third became involved.
RemiYeah, it really seems like this whole thing was done almost spur of the moment. Like she prints it out, she smuggles it out of the building pretty easily, and then literally just mails it out on her way home. It does not seem like this was a really planned out thing at all. While Snowden was reaching out to reporters, he was planning his escape, reality just kind of did it.
AshleyIn her book, she actually does say that she doesn't know why she chose to print it that day. But then there's several reasons that are provided or explained. So I think she does know, but she does say that it was just a very impulsive act.
The FBI Knock: “Reality” Interrogation
RemiOn June 3rd, 2017, Reality goes to work at the NSA as usual, still waiting anxiously for the story to hit the media. After finishing her shift, she returns home, parks in her driveway, and begins casually scrolling through Tinder profiles on her phone. From here, our story shifts over to the events depicted in the film Reality, which opens with two FBI agents arriving outside of her car and tapping on the window. Much to her surprise, reality looks up to see two FBI agents standing outside of her vehicle. Agent Garrick, played by Josh Hamilton, and Agent Taylor, played by Merchant Davis.
FBIHow's your day today?
Reality Winner - Sydney SweeneyPretty good. Just got some groceries.
FBIAlright. Okay, well, the reason we're here today is that we have a search warrant for your house.
Reality Winner - Sydney SweeneyOkay.
FBIAll right. Uh, do you know what this might be about?
Reality Winner - Sydney SweeneyI have no idea.
unknownOkay.
FBIThis is about uh possible mishandling of classified information.
Reality Winner - Sydney SweeneyOh my goodness. Okay.
AshleySo the second they said that, reality says in her book that in her mind, she's just like, I am so screwed here. I would be peeing myself if this happened to me. Two FBI agents just knock on my door, and the silence between them, which we have cut out of the clip we just played just for time's sake, is deafening.
RemiYes, the audience couldn't see in the clip that I just played you that the agents both flash their FBI badges to reality before jumping into the fact that they have a warrant and what they are there for. And I would absolutely be freaking out. I don't know if I could stay as calm as she appears on the outside in this scene, but I love how you can still see a bit of nervousness in Sweeney's performance. Like she's trying to play it off, but you can tell she's like, oh no, this could be something bad.
AshleyWell, and after they show her the badge, there's a good 15 seconds where they're not saying anything and they're just staring at her. And that's an interrogation tactic. People feel uncomfortable when there is silence. So a lot of times, detectives will purposefully be quiet for a long time, hoping that the person they're talking to will fill the silence.
RemiIt makes the other person feel awkward, so they are compelled to just talk in order to fill the space. And the entire film is full of interrogation tactics. And I found it very interesting to watch it all play out, as it actually did in the real FBI transcript. After stepping out of the car, Reality, played by Sidney Sweeney, is informed that the agents have a federal warrant allowing them to search her residence, vehicle, electronic devices, and person for evidence related to the mishandling of classified information. And I didn't mention this in my summary, but they take her cell phone and ask for the password to unlock it, and she just says, Oh, there's no password. And they look at her like, What? You don't have a password on your phone and you work for the NSA? During the encounter, the agents repeatedly remind Reality that speaking with them is voluntary, but she agrees to cooperate and answer their questions without an attorney present.
AshleyThe whole nature of the voluntariness is something that her lawyers bring up before her case is resolved, because yes, they told her she was there voluntarily, but at this point, they have taken her phone. She is a 25-year-old girl surrounded, surrounded by federal agents that are tearing her home apart. And how voluntary would that actually feel?
RemiYeah, it would be a very intense situation to stand up for yourself in. And I think that's exactly what the FBI was hoping for in this situation. It's almost an intimidation tactic. Like you can say you're not gonna speak to us, but do you know what's gonna happen after you say that? Probably not.
AshleyAnd she also had two rescue animals, a dog and a cat, that both did not like men. So throughout this whole encounter, she's worried that her dog is gonna attack one of these guys. Her cat is gonna attack one of these guys, and they're gonna be shot and killed. So I could not imagine her being like, okay, I'm gonna leave, and I'm just gonna leave my beloved animals in here, having no clue what you're gonna do to them or what they're gonna do to you.
RemiAnd that is portrayed in the film. It shows the agents having a difficult time getting the animals wrangled into an outside area. And reality is really, really concerned for her animal safety. She seems more concerned about them than she does about her own well-being. As FBI agents begin swarming through reality's property, Agent Garrick tries making casual conversation about the neighborhood, her dog, and even CrossFit, offhandedly insinuating that he already knows a great deal about her. Permission to speak freely here. This movie is filmed exactly the way I wish Snowden had been filmed. The scenes are incredibly tense, and so much of the drama comes from what isn't being said, like you had mentioned earlier, Ashley, with those long pauses in the conversation. The agents clearly know that she understands why they're there, she knows that they know, and the unspoken tension makes the whole sequence incredibly riveting to watch.
AshleyAnd we had talked about that in our Snowden episode. We had mentioned several different points in the story that could have been translated exactly like this on screen, where the tension is, like you said, created by what we as the audience understand and what we know the people understand, but isn't being said. It is being shown to us, not told to us.
RemiWhile the other agents secure the house, Winner discloses that she owns several firearms, including a handgun and a pink AR-15.
AshleyI plan on never owning an AR-15 just because I don't think they're necessary, but if I did, I would want that one.
RemiI'm pretty sure one of my New York friends who has a lot of similarities to Reality Winner has a pink shotgun of sorts. The agents then carry out a full search of her home, seizing her cell phone, laptop, and other electronic devices as part of the warrant. She eventually agrees to sit down for an interview in a creepy back room of the house.
AshleyWhy it's creepy is because it's a room that she never used, so there was no furniture in it. It was basically just a storage space she was using. It's like the front living room sitting area, but she never went in there, and there was just nothing in there. So they just all sit on the ground.
RemiAnd this is the room that the play, Is This a Room, is named after, I assume. And I referred to the room as creepy because that is how reality referred to it. She thought it was a weird, creepy room as well.
AshleyI can't remember why she thought it was creepy. It was listed in the book, but I didn't write it down.
RemiIt's basically just an empty white room in the back of the house that looks like it hasn't been well maintained in a while. It's just weirdly eerie and empty. From there, Agent Garrick and Agent Taylor formally identify themselves on the record, explaining the warrant and beginning the official questioning while the search feverishly continues elsewhere in the home.
AshleyAnother point going back to the voluntariness of this confession, I believe at this point they had taken her keys.
Tactics, Voluntariness, And Confession
RemiI may have missed that part, but at this point they are already starting to photograph things, bag them up as evidence, and they are taking basically anything that they want to as potential evidence. During the interview, the agents begin documenting her personal background, employment history, and security clearance. She confirms her prior service in the U.S. Air Force, her TSSCI clearance, and her employment as a contract linguist for Plurberus at the NSA's White Law Building, including her assignment to the Iranian Aerospace Forces office and her proficiency in Farsi, Dari, and Pashtu.
AshleyWhat did you think about when you saw the name of that company?
RemiI thought of the show Plurberus, of course, one of the best shows on TV. I don't think I had ever heard that word before the show, and now I saw it here too.
AshleyThat's exactly what I thought about too. If you guys have not watched show Plurbus on Apple TV, watch it. It is phenomenal.
RemiYes, that is completely unrelated, but nevertheless, watch that show. It is probably the best thing on TV right now. When the agents explain that the investigation is tied to a report about mishandling classified information, she quickly brings up an earlier workplace incident from February 2017, saying that during onboarding, she accidentally printed a classified email and without realizing it, carried it past an internal security checkpoint before the mistake was caught and reported. Something she insists was simply an accident that had already been taken care of.
AshleyIt was actually so much more benign than that. It was her first day on the job, and the document she brought with her was a printout with her temporary email password that she had already changed, and she didn't even leave the building. She went into the cafeteria area, not knowing that that was technically outside of the quote unquote secure perimeter.
RemiAgents Garrick and Taylor acknowledged the earlier workplace incident, but continue to repeatedly circle back to the same core questions, such as asking whether she had ever taken classified documents out of the facility, emailed or downloaded sensitive material in ways she wasn't supposed to, or shared classified information with anyone who wasn't authorized to see it. Each time she says no, consistently denying any purposeful wrongdoing. She does acknowledge that she occasionally viewed internal drone feeds and mission-related material through authorized systems, but maintains that her access was within the scope of her clearance and not connected to any misuse of information. The agents keep probing for inconsistencies, asking detailed questions about her clearance history, how much system access she actually had, whether she ever printed materials that weren't related to her assignments, and whether she had ever taken reference material or NSA pulse articles out of the building. Agent Garrick then bluntly tells her that they have evidence she printed documents related to and that investigators know far more than they have let on so far. Reality responds by admitting that she sometimes printed internal pulse articles to use as scratch paper, but insists that they were always properly thrown away and never taken home.
AshleyA fun fact, most offices use shredders to get rid of documents. No, not the NSA. They have burn bags.
RemiSo they put it in a bag and it gets burned at the end of the day, or is there like an incinerator in the cellar?
AshleyIt gets burned somehow.
RemiProbably just a guy in the basement with a book of matches.
AshleyIt makes sense because technically with shredders, as we saw in Better Call Saul, if you are really committed to it, you can reconstruct that.
RemiOh, I learned that at a very young age from the film Batman Returns, in which the penguin glued together an entire pamphlet of documents that had been shredded. So yeah, burning is the way to go if you're trying to get rid of sensitive info. Throughout the interview, reality stays cooperative and conversational, though she clearly becomes increasingly nervous as the seriousness and scope of the investigation begin to sink in.
FBII don't think you're a, you know, a a big bad master spy or anything, okay? I don't. I don't think that. I think that I've looked at the evidence and it's compelling. No, I'm not sure why you did it. And I'm curious as to that. But I think you might have been angry over everything that's going on politics-wise. Because you can't turn on the You can't turn on the TV without getting pissed off. Or at least I can. I think you might have just made a mistake. Now, why I'm here and why I want to talk to you is to figure out the why behind this, okay? So I ask you again. Did you take it out and send it?
AshleyAnd unfortunately for reality, she believed him when he said he just wanted to understand why. The FBI did not want to understand why. They were there for one reason and one reason only, and that was to get information against her.
RemiAnd the tactics of trying to be like, I relate to you, I know the news is really stressful. Is this why you did it? Like trying to rope her into confessing. It's very, very fascinating to me watching these sort of procedures go down. Realizing the agents already know far more than she initially thought, reality eventually admits to printing out the documents in question, then smuggling them out of the building and mailing them to Why did you print that one out?
Reality Winner - Sydney SweeneyBecause I wanted to read it. Uh the way I I downloaded it, it was hard to read, so uh uh just it looked like a piece of history, you know, and I I I wanted it on my desk for like a day.
FBIDid you uh how did you find it?
Reality Winner - Sydney SweeneyUh so if you go on polls, there's uh uh at the top right they have a tab that says articles, and I I scroll through those. And I don't know if you guys saw the one about the miniature ponies, but uh yeah, no, no, that was uh that was number one for like a year, so obviously I go to check to see if there's any other gems, and then there was there was that one, and I saw it in the news, and I was just like, yeah, I uh I wanted to read it. So yeah.
RemiShe then walks them through exactly when, where, and how she sent the material, along with any reasoning behind her actions. Although the agents seem satisfied with her full confession, reality is still asked to wait as the process continues. Finally, at around 5 15 p.m., she is placed in handcuffs and taken into FBI custody.
AshleyAnd one of the reasons they had to wait is because they wanted to search her before, and when I say search her, I mean her body, before they took her into custody. But these ding bats, even though that was listed in the search warrant, they didn't even bring a female officer with them. So they had to wait for one to be sent, which took another like 20 minutes.
RemiThat's what they were waiting for. Okay, that was not clearly stated in the film, but it is a female officer who finally searches her and places her in handcuffs at the end.
AshleyYep, they had to wait for that person to get there.
Charges, Solitary, And Diesel Therapy
RemiThere is a scene in the film where they are waiting for the female officer, and reality goes to the restroom, and she has this brief moment by herself where she looks at her reflection, and you can tell just the weight and gravity and severity of this situation is really sinking in. And the fact that she has this time to let it sink in further and further and further, I would just be a mess by the time I actually got arrested. And I also want to mention, while she's being arrested in this scene, she is really concerned about her animals. She wants to be able to call someone to come and take care of her dogs and feed her cat, and she really does not seem that concerned about what's going to happen to her. She just wants to make sure that while she's gone, her pets will be taken care of. The film Reality closes with the following quote from Reality Lee Winner. I knew it was a secret, but I also knew I had pledged service to the American people.
AshleyAnd it's funny because the Russian interference in the election wasn't a secret. By the time she leaked this document, it was on the news 24-7. It was already out there. She just had this document that proved it.
RemiShifting back to the film Winner, we watched news footage from multiple networks announcing that a 25-year-old NSA contractor named Reality Winner has been arrested for leaking classified documents related to Russian interference in the 2016 election. Though there is some coverage focusing on the documents leaked, the majority of media attention seems to be primarily focused on her unusual name while ignoring most of the facts. Through narration, reality reflects on the fact that if people recognize her at all, It is often because of her name rather than her actions. Reality is indicted under the Espionage Act and charged with the willful retention of national defense information, entering a plea of not guilty. During the early court proceedings, the prosecution highlights elements of her background, including her interest in Middle Eastern languages and travel, while also introducing personal text messages as evidence. And the messages in question that they bring into evidence in the scene are mostly joking messages that she was sending to her sister. Like one message was reality claiming that she says, I hate America three times a day, which is obviously meant to be a joke, but it is taken out of context for the court proceedings. Reality is denied bond and held in solitary confinement while awaiting trial, spending 41 days in near total isolation before being subjected to a legal form of torture called diesel therapy, in which a prisoner is repeatedly transported between facilities, often for long stretches of time, on multiple flights or bus transfers, leaving the prisoner sleep-deprived and disoriented. And this sounds like my personal living hell. I can't stand being on airplanes, and the idea of being stuck on an airplane for days and days and days, I would totally lose my mind by the end of it. Had you heard of diesel therapy before, Ashley?
AshleyNot the term, but it's basically referred to, or as how she describes it in her book. It is not quite how you explained it. It's a way to transport prisoners in very uncomfortable ways. So she wasn't on a plane for eight days. They just really didn't tell her where she was going and transferred her to these places where she shouldn't have been for no reason at all, and she wasn't even told why she was being taken to these different places.
RemiWell, in the film, after eight grueling days of so-called diesel therapy, reality is eventually placed in a crowded detention setting. You know, one of those places where the prisoners are all in one room and there's a bunch of bunk beds all over the place, and there's like 15 prisoners in the room. And this results in reality being assaulted by one of her cellmates.
AshleyAnd the inmate that actually assaulted her, she was having a mental health crisis at the time. I think how she described it in her memoir is the jail had been withholding this woman's medications.
RemiSo she wasn't attacked because her name was in the news and the person recognized her or something like that. The person was mentally ill and took it out on reality.
AshleyAaron Powell Exactly. And they ended up making up and being fine afterwards.
RemiWell, reality struggles to adapt to her life of incarceration, and soon realizes how limited her ability will be to publicly tell her side of the story. Facing the possibility of a lengthy sentence, she ultimately agrees to accept a plea deal, coming to the conclusion that fighting the system on her own may be nearly impossible. The film then moves forward to her sentencing, where she receives a prison term of five years and three months. While incarcerated, Reality receives a letter from her former boyfriend, Andre, including a photograph showing him holding his veterinary certificate and wearing a wedding ring, signaling that he has moved on with his life and completed the goals he once dreamed of.
AshleyAw, good for Andre. Dreams are possible.
RemiI know, right? I was rooting for Andre throughout all of this, and he also has a new adopted dog that is very cute in the photo as well. The film ends with Reality acknowledging that meaningful change often requires risk, leaving open the question of whether the cost of her decision was truly worth it. Before the closing credits, we learn that Reality Winner was incarcerated for four years and was released on probation in 2021.
AshleyAnd it ended up being four years instead of the five years and three months that she was sentenced to, because the sentence did include credit for time served, which she ended up being in jail for about a year, and then she had a few months earned for good behavior.
RemiAnd we failed to mention this up until this point, but this is actually the longest sentence in modern history that a whistleblower has ever received. Reality currently works as a CrossFit coach in Texas. She plans to found a charity, research climate change solutions, study neuroscience, and lobby for prison reform. And that was Susanna Fogle's Winner and Tina Satter's Reality. Any initial reactions, Ashley?
AshleyYeah, I'm really curious. What movie did you like better?
Sentencing And Aftermath
RemiHands down, reality was the better film. Reality is taking the subject matter extremely seriously, extremely realistically, and it is clear that they are trying to portray these events as accurately and detailed as possible. And it shows. And Sydney Sweeney is a powerhouse in this role. She has so many emotions that she runs through so well and so convincingly. She starts off as nervous, she's trying to make casual conversation, and you can see the anxiousness and fear kind of rising in her throughout the film. You see her feeling relieved after she has finally confessed to everything. And there are brief moments where she's in the midst of being questioned and she's very, very nervous, but there'll be a moment where she brings up her dog or her cat or something, and her demeanor just changes for a few seconds to feeling very happy and comfortable when she's talking about her pets, then immediately reverts back to anxiety when she's finished talking about them. It's an amazing performance, and it's a very well-made film.
AshleyWas Winter even funny? It's listed as a dark comedy, and I guess there were a few scenes that you showed me that I was just like, huh. But it didn't strike me as something that would make people laugh.
RemiThere are comedic scenes, or scenes that are supposed to be comedic, but it's not like a clever comedy or anything like that. If anything, this is a serious story that Winner decided to film like a comedy. The few jokes that I can even think of off the top of my head have to do with her relationship with her sister and how she keeps ruining things for her sister. But beyond that, it's a serious story, but it is shot and acted like a comedy. It's a strange choice that I don't think does the story justice.
AshleyWell, let's get into post-production. I'm curious how these movies did.
RemiReality premiered at the 73rd Berlin International Film Festival on February 18, 2023. Prior to the premiere, MK2 Films acquired the film's international sales rights, and HBO Films later secured U.S. distribution. The film debuted on HBO on May 29, 2023, followed by theatrical releases in several international markets, including the United Kingdom and Ireland on June 2nd, Australia on June 29th, and France on August 16th.
AshleyOkay, so I was right. It wasn't released in theaters at all in the United States. It was just thrown on HBO.
RemiYeah, this film had an extremely limited release. In fact, I was surprised to find out that it was released in theaters at all. Reality currently holds a 93% approval rating on Rotten Tomatoes, with a critical consensus that reads Reality's narrow scope and gripping fact-based story add up to a riveting showcase for Sidney Sweeney in the title role. And here is just a brief clip of Miss Sweeney discussing what she hopes audiences take away from the film.
Sydney SweeneyAnd I hope that they see that we are humanizing a moment in someone's life.
RemiWell, in that regard, I think the film succeeded. I did think that reality was a person.
AshleyIt seemed like she was not expecting that question and tried to think real quickly on her feet.
RemiWell, nevertheless, Sidney Sweeney received a 2024 Critics' Choice Award nomination for Best Actress in a Movie or Miniseries for her portrayal of Reality Winner, while the film itself was nominated for Best Movie Made for Television. Reality also went on to win a Peabody Award, recognizing the film as a powerful dramatization of real-world events. The following year, Winner premiered at the 2024 Sundance Film Festival on January 20th, with Reality Winner herself in attendance.
AshleySo she had to have seen it if she was at the premiere.
RemiNot true. Many celebrities and guests will attend the red carpet portion of a premiere and then not stick around for the film itself. I know your man Leo does that with all of his films. He doesn't like watching himself on screen, so he'll attend the premiere and then leave for the film. Winner was released on September 13th, 2024, and currently has a 56% approval rating on Rotten Tomatoes, with a critical consensus that reads, Susanna Fogle's comprehensive take on this true story has some rooting interest thanks in part to Amelia Jones' engaging performance. But a discordantly jaunty tone keeps it from being a real winner.
AshleyAh, so it seems like critics agreed with you on which movie was better.
Box Office, Reviews, And Awards
RemiAlright, well that's how the movies tell the story. But now let's get into the actual reality of Reality Winner.
AshleyHer dad, Ronald, often said his chance at success was deliberately sabotaged by his own family. As the story went, he'd once been a baseball prospect invited to try out for the New York Yankees, but his father allegedly broke his ankle to stop him from playing.
RemiWhat the fuck? Why would he do that? He didn't want his son to play for the Yankees? He must have been a Boston fan.
AshleyLike many of his stories, it wasn't always easy for reality to separate fact from fiction. Ron was a compulsive storyteller, and over time, his claims became the cornerstone of his life. He said he studied theology and psychology, but rarely said where. After his undergraduate thesis was reportedly rejected, he dropped out and moved to a reservation in Canada for several years for reasons that were never explained. Reality suspected he fled the country to avoid being drafted into the Vietnam War and hid his true reasons out of shame. By the early 1970s, he'd returned to the United States and drifted into a life of petty crime. He briefly married and had a daughter named Nikki, but was not involved in her life after he spent two years in the Ohio State Penitentiary, possibly for stealing a vehicle from the cemetery where he worked. Reality's mother Billy also had a difficult childhood. Her parents were poor, abusive, and mentally ill. Determined to escape that cycle, she put herself through college and studied sociology at the University of Wisconsin, where she met the much older Ron.
RemiWhat was the age gap between the two?
Ashley21 years. They quickly married in 1990 when Billy became pregnant with her first daughter and moved to Texas, where she began working for child protective services. Only weeks after Britney was born, the family was T-boned by a drunk driver. Ron's lower spine was shattered, and Britney's umbilical cord stump ruptured. Within the year, the family bought 60 acres of land near Kingsville, Texas, about 100 miles north of the Mexican border. Reality, her mother, and her stepdad still live there to this day. Reality was born on December 4th, 1991. Within the year, he had over 10 surgeries to rebuild his spine and became addicted to oxycotton when it hit the market in 1995.
RemiOkay, that's what he was addicted to. The film is a bit unclear as to exactly what pills he is taking throughout.
AshleyThere's been several movies and TV shows about all the lawsuits that came following the introduction of this drug. One of them we do have on the list.
RemiAnd it is criminal how frequently and carelessly this stuff was being prescribed.
AshleyWell, unlike many Americans, Ron's addiction to Oxy lasted the rest of his life and had grave impacts on his functioning. He was sick and bedridden for most of reality's childhood and never could hold down a job. As his illness worsened, he grew paranoid, delusional, and suicidal. After their parents divorced when reality was six, the girls saw their father every other weekend. At first, they enjoyed these visits since they ended with extravagant shopping sprees. But the appeal dimmed as the girls grew older and started to realize that their dad wasn't a functional parent. When he wasn't laying in bed in his trailer, he took the girls with him to bars, trips to Mexico, and drug runs involving the pharmaceuticals he was now using and peddling.
RemiThis was all excluded from the film.
The Real Backstory: Family And Formation
AshleyBilly, on the other hand, worked constantly. As a CPS supervisor, she spent long hours away from home, but made sure her daughters were never late to school or activities. She poured herself into holidays and birthdays, determined to give her children stability and joy. Because of her work ethic, the family lived just above the poverty line and owned their mobile home and land. It wasn't until Billy married reality's stepfather Greg in 2000 that she finally got a stable conventional father figure.
RemiGreg is in the film winner, but much later in reality's life.
AshleyDespite everything, Reality loved her dad deeply. He was intelligent and curious, but just not motivated, willing, or able to really achieve anything. He loved testing her with IQ questions, trivia, and word games. They bonded over history documentaries, politics, religion, and guns. After 9-11, Ron was the only adult who spoke to 10-year-old reality directly and seriously about what happened and encouraged her growing interest in politics and global affairs.
RemiI got the impression that reality was much closer with Ron while Brittany was much closer with her mother Billy.
AshleyIn high school, reality worked hard to earn her father's attention. She began studying Arabic and Islam largely because it was what he wanted to talk about.
RemiCould he speak those languages?
AshleyNo, he was just interested in global politics.
RemiSo she was taking up hobbies that interested him.
AshleySo she could talk to him about them.
RemiThat is very sweet.
AshleyDrawn to Judaism and its history, she also learned Hebrew.
RemiThat is impressive.
AshleyShe studied Latin and was so committed to Arabic that a Turkish art teacher connected her with a tutor. Despite her academic and athletic successes, reality struggled behind closed doors. As a teenager, she developed bulimia and hid it from everyone until she was arrested. As the stress grew, binging and purging became the only thing she felt like she could control. By her senior year of high school, she realized her parents couldn't afford to send her to college. Her love of languages, interest in global affairs, and desire to make a difference pushed her towards the military.
RemiThat is something that I wish was highlighted more in the film. It seems like it was a conscious decision of reality in the film winner to pursue the military instead of college, while I think a circumstance where someone may not have the financial means to go to college and joins the military instead is much more relatable and realistic.
AshleyWell, interestingly, she did apply to Texas AM and was later accepted into the engineering program with a full scholarship, but by that point, she was already intent on enlisting.
RemiSo she had already made up her mind at that point, but could have gone to Texas AM.
AshleyOn a full ride scholarship. She began speaking with recruiters about being a linguist specializing in Middle Eastern and African languages. She even excelled on the language aptitude test. But at the urging of her mother, she changed gears and instead joined the Air Force. One of Gary's kids was in the Air Force for like eight years. So she talked to him, and after that conversation, she decided to enlist in the Air Force instead of the Army. Six months after graduation, Reality left for eight weeks of basic training in Corpus Christi, Texas. From there, she was sent to the Defense Language Institute on a military base near San Francisco. She really wanted to learn Arabic or Pashtu, the primary languages spoken in Afghanistan. Instead, she was assigned Farsi, a language spoken almost exclusively in Iran. This was a huge disappointment since Iran was a middle-income country with a highly educated population and a large military presence. She imagined herself helping the world's most vulnerable people and assisting middle-class Iranians didn't fit the bill. Language school was one of the most stressful times of reality's life. She started having panic attacks, returned to binging and purging almost daily, and became fixated on exercise, running so much that she fractured her feet.
RemiIn the film Winter, it does show her running pretty consistently as an outlet for her emotions, but it does not depict her fracturing her feet while doing so, though she does pass out at one point.
AshleyWell, the gym became really the only place where her mind felt quiet. After language training, she moved on to military intelligence school at an Air Force base in San Angola, Texas. She was given her first assignment before leaving San Francisco. The Farsi team would be working under the NSA. What she hadn't known before enlisting is that cryptologic linguists were typically stationed at only two places Fort Meade in Maryland or Fort Gordon in Augusta, Georgia. She asked her superiors what she had to do to be stationed abroad. She was told that if linguists were deployed, it was typically alongside the army to Iraq or Afghanistan to help with interrogations or debriefings. This future was possible for her, but she had to finish her Air Force enlistment first before transferring branches.
RemiIn the film Winner, the Air Force recruiter pitches her by telling her a story about basically being able to open the line of communication between soldiers and the civilians there and how beneficial that could be, and really frames it like you would be there in person helping these people communicate. But it seems like that was not the case at all.
AshleyAnd that is really what she wanted to do. After nearly a year and a half of training, Reality was stationed in Maryland and got her security clearance in early 2013. She was ready to put her language skills to use. The classified surveillance operation run by the NSA involved recording and archiving the content of virtually every cell phone call in Afghanistan. The scope of the program in Pakistan remains unknown. Conversation deemed concerning were routed to linguists like reality who transcribed them for intelligence databases. But the people reality listened to were not what she expected. Most of them weren't al-Qaeda or professional terrorists speaking in code. A lot of the conversations were painfully ordinary, people talking about their families, meals, weather, or daily frustrations. She started pulling up the real time greeny aerial videos of the people she was listening to in an effort to get more context. She wanted to learn the customs, politics, and rhythms of life in the country whose language she was translating. If a conversation seemed relevant, she typed a summary. Into a computer forum, and sometimes someone far, far away would act on it by ordering airstrikes. Over time, reality became horrified by how many people were being killed. Despite excelling at her job, she wasn't proud of being good at identifying who would die. What haunted her most were the civilian deaths, or as the military called them, collateral damage. To supplement her work, she watched Afghan news broadcasts and followed Taliban's social media accounts. Because yes, the Taliban has social media. Isn't that crazy?
RemiYes, that is insane.
AshleyWell, she began to notice movement patterns that troubled her. The NSA was routinely scheduling airstrikes when targets were traveling to and from conflict zones, often with their families. In some regions, the Taliban was actually actively fighting ISIS. It seemed that the US was inadvertently strengthening ISIS by their attacks on the Taliban.
RemiThat's very interesting. It never even occurred to me that that could be the result of this.
AshleyAnd it makes sense, right? If you have two enemies and your two enemies are also fighting each other, if you're targeting one of those, the other one is gonna get stronger. Meanwhile, political leaders on both sides claimed that the war was being won. But from reality's vantage point, that narrative felt like a lie.
RemiOh, like how George Bush did that public announcement on an aircraft carrier saying mission accomplished when the Iraq war first started.
AshleyNo president is gonna go out there and say, well, we're involved in this really lengthy, costly war and we're losing.
RemiI don't know. I would kind of respect a president if he just came out and said, you know, folks, we're not doing too great, and just was honest for once.
Language School, NSA Reality, And Remorse
AshleyGiven the top secret nature of her work, reality was prohibited from talking to anyone about anything she saw, heard, or translated. She had no choice but to suffer in silence. Here's a clip of her mom remembering the only time her daughter mentioned how deeply her work was impacting her.
Billie WinnerOnly one conversation that I had with her did she ever let on how heavy her work was. I'll never forget because she said, you know, when you're watching somebody on your screen and that person goes, poof, you've got to make sure that you've got everything right.
RemiThis is a lot for a person to keep inside of them. I cannot imagine not being able to talk about anything having to do with what you're doing eight hours a day, five days a week.
AshleyReality sought therapy in the summer of 2015 and was reassigned to another NSA posting in Augusta, Georgia. She loved it there. She developed a routine and worked fewer hours. By the time she received her reenlistment offer in September 2016, she had spent six years working as an Air Force cryptologic linguist, four of those with the NSA. The hope she had of getting to the Middle East collapsed when it started to look like Trump would win the 2016 election. She also spoke to a supervisor who bluntly told her that her military career would involve her sitting in a basement until she retired. There was no desirable path forward for her as a linguist in the military. The classified nature of her work posed another problem. Any resume she submitted had to be approved by the Air Force. And they wouldn't let her mention anything about missions, intelligence work, or regional specialization.
RemiSo it's like having something on your resume that you can't say anything about.
AshleyIt has to be like really, really, really watered down. And I think that's why in the clip from Winter, where it shows the person she's interviewing with for the job, and that lady says, Oh, you have a really impressive volunteer section, because that's the one thing she could actually expand on. Reality also lacked a traditional college degree, having spent her formative years in military training schools rather than universities. On paper, she wasn't competitive enough for the overseas humanitarian or policy work she wanted.
RemiWhich is absolutely crazy. This woman was built for humanitarian work. It's all she wants to do, and they're not letting her do it for ridiculous reasons.
AshleyIn October 2016, Reality received an Air Force Commodation Medal. She was praised for assisting in the geolocation of 120 enemy combatants during 734 airstrikes, facilitating more than 800 intelligence missions, producing thousands of reports, aiding in hundreds of captures, and contributing to the deaths of more than 600 people. In other words, she was good at killing people.
RemiYeah, I'm sure she would have preferred to get a medal in how many people she had saved as opposed to how many people she played a role in their deaths.
AshleyReality elected not to reenlist and was honorably discharged in November 2016. She started looking for contracting jobs to strengthen her resume. In December, Reality was visiting her family in Texas and planned to make a trip out to see her dad. By that time, he was in hospice at her half-sister Nikki's home. His health had been deteriorating for years, with dementia taking his memory and ability to speak. She never got to make that final visit. Just four days before Christmas, he fell out of his bed and died. While processing the loss of her father, Reality got a call from Pluribus International Corporation, a Defense Department contracting company. She signed a one-year contract and started orientation in Augusta, Georgia on February 9th, 2017. Her job involved translating Farsi documents related to Iran's aerospace program. On her first day, she took a slip of paper with her already changed temporary email password to the Starbucks in the downstairs cafeteria because she didn't even have a desk yet. So there's nowhere she could have even left the piece of paper.
RemiYeah, that's completely understandable. It was her first day, she needed her password, and she went to get a coffee.
AshleyAnd she didn't even leave the building. But because the cafeteria was downstairs, no one had told her that that area was out of the secure perimeter.
RemiThen that was a complete accident.
AshleyAnd she was written up for this, but she only had to watch a PowerPoint presentation. Nonetheless, it reinforced how rigid the environment would be. The job itself was mind-numbingly slow. Like Edward Snowden, reality had hours to kill every day and started perusing the NSA's internal internet. She also started listening to a podcast from the Intercept called Intercepted.
RemiClever.
AshleyIt was hosted by journalists specializing in foreign affairs and national security. For reality, it became a lifeline, a welcome distraction from the growing political climate she disagreed with to her core. At one point, she even emailed the publication for a transcript of an episode about climate change. On May 9, 2017, Reality came across a five-page classified intelligence report detailing Russian-directed cyber attacks on VR Systems, a U.S. company that sold voter registration software. The document described two cyberattacks carried out by Russians' military intelligence agency during the 2016 election. Essentially, Russian operatives first sent phishing emails to employees at VR Systems and successfully obtained login credentials from at least one staff member. Using that access, they sent malware-infected emails to more than 100 election officials, disguising the messages to appear as if they came from the legitimate vendor. For months, reality had watched the public debate swirl around whether Russia had attempted to undermine American democracy. And now, she and thousands upon thousands of other federal employees now had concrete proof. To her, this seemed like something the public deserved to know. A document that could shut down this pesky debate once and for all. There was also the fact that everyone at her office was openly talking about it. It was the most read item on NSA Pulse, an internal platform similar to Twitter that showed which reports were trending among intelligence staff.
RemiIn the movie Winner, this is kind of streamlined to her just opening files on her desktop.
AshleyYeah, she didn't set out searching for this document. This was an internal feed that everyone at the NSA had access to, and this document just showed up as number one, as the most read document. During this time, the Trump administration was also seeing unprecedented levels of leaked information, more than the past three years combined. Reality assumed it was only a matter of time before someone would bring this document to light, if it hadn't been done already. Later that same day, the same day she saw this document, Trump fired FBI director James Comey, who was leading the investigation into Russian election interference. Reality imagined the possibility that reports like this one would be buried or destroyed. So she decided to print a copy. That way, at least one would exist outside a classified server. Isn't that crazy? The day this document starts trending is the same day that the FBI director looking into the same topic that this document is about is fired.
RemiIt does not surprise me in the least that this man was fired for trying to do his job in this situation.
AshleyI know, but Trump didn't know that this was showing up on NSA servers as the number one document. It's just such a weird coincidence that these two things happened the same day. Well, when there was no news of a document leak the next morning, reality printed it, folded it in half, stuck it in her pantyhose, and smuggled it out of the facility. After teaching yoga class, she slipped it into a parking lot mailbox without leaving a return address or any identifying information. The document was on its way to the Intercept.
RemiI forgot to mention in my part that she sent the document out anonymously.
The Document, The Intercept, And The Trace
AshleyAnd the reason why she chose the Intercept is they were known for their standout security protocols. For example, for the Snowden documents, they kept all those files in a locked room that was being video recorded at all times, and you couldn't go in there alone.
RemiI mean, this seems like the logical place to send out these documents to. You mentioned this to me off mic a little while ago, that reality is incredibly naive throughout this situation. And this is a pretty prime example, thinking that you're just gonna get a slap on the wrist for this sort of thing.
AshleyIt really is. That and her not realizing why the FBI was at her house that day and what their true intentions and motivations were.
RemiYeah, she didn't seem to really grasp the severity of doing this sort of thing.
AshleyThe political climate no doubt contributed to her decision. She strongly agreed with much of the policies being enacted, including military actions overseas. She also believed this document shouldn't have been classified in the first place, since Russian election interference was everywhere on the news and any potential damage had already been done. There really wasn't anything in there that she thought pose a national security risk.
Reality WinnerBecause in 2017, that was there was one question that was being asked every single day, and it was not something that we had as a nation really um had faced before. Like people, it was just one debate that was going on, and I honestly felt like it was the NSA's job, or at least it was someone in the government's job, to lay bare the actual facts for everybody. I get just felt like that was their responsibility instead of letting it foment to such a toxic level that things weren't getting done.
RemiSo it sounds like she was just sick and tired of hearing everybody argue about it. And she was just like, here it is, here's the proof. Can we just shut up about it and move on?
AshleyYeah, here's the answer. The NSA and so many other people had access to put this debate to rest and no one was doing it. And she's like, What is going to hurt national security by showing, yes, this did happen? Trump wasn't involved per the document. It was just this phishing scam.
RemiAnd we do need to clarify that the documents did not prove that Russia interfered in the elections. It just proved that they attempted to interfere in the elections.
AshleyAfter mailing the document, days passed with nothing about it on the news. Reality continued to go to work as normal, frustrated that she risked losing her job for nothing. One day, she got an email from a small airline advertising heavily discounted flights to Tel Aviv. She clicked the link and perused other flights to some of the places she had always wanted to visit. Needing a change of scenery, she settled on a trip to Belize for Memorial Day weekend. It was closer, cheaper, and a place of personal significance. Her dad had always been fascinated by the disappearance of the ancient Mayan civilization in the country, but he never got to go visit himself. The trip was a chance to get away and to honor him. While reality was in or planning her trip to Belize, the Intercepts office in Washington, D.C. was looking into the five-page document that landed in their rarely checked P.O. box.
RemiThey don't check the mail often? Hire a mail clerk.
AshleyYeah, it was thought that it had been in there for a couple weeks before they even found it. The document was labeled Top Secret and marked SI for Special Intelligence. Instead of going through the top-notch security team, who didn't even learn about the report until after it was released, it was handed over to two relatively new reporters, Matthew Cole and Richard Espesotto. Both came from television news and had no experience in digital security protocols or the handling of classified documents. For days, Cole questioned whether the document might be a hoax, since it wasn't from a cultivated source and no one had reached out to them about it through the secure online platform. In an attempt to authenticate the document, Cole contacted the NSA's head of public affairs on May 30th, 2017.
RemiWait, so he just called the NSA and was like, hey, did you guys send a document to us?
AshleyNo, so he wasn't asking if they sent it. He was trying to see if this document was real, which actually isn't unheard of or uncommon. What is uncommon is the steps he took next to authenticate it. So he said the Intercept had a classified report concerning Russian election interference. That's fine. When the NSA spokesperson asked to see it, he sent photographs of the printed pages. What he should have done is retype the text or paraphrase it, which is the standard protocol for verifying sensitive material while protecting the source. Instead, because he sent pictures of the actual pages, the NSA could see the crease down the middle from where reality folded it, which alerted them to the fact that it was printed. Also, most modern-day printers use identification marks that can't be seen with the naked eye, but include the serial number of the printer that was used and the date and time that it was printed.
RemiI knew it was gonna be something like a code of numbers that revealed where and when it was printed. But that is crazy. I had no idea they could basically have it made with invisible ink.
AshleyI had no idea either.
RemiAnd they got all this from a crease. That's incredible.
AshleyThe NSA then contacted the FBI on June 1st, 2017. And it did not take long for them to pinpoint the source of the leak. Only six people in Augusta had printed that report. Among those six, only one had communicated with the Intercept using a government computer because she emailed them asking for that podcast transcript.
RemiWow, that really came back to bite her in the ass.
AshleyJune 3, 2017, just a few days after she came back from Belize, began as an ordinary Saturday for Reality Winner. She was at the gym by 6:30, had lunch with the guy she was crushing on, went grocery shopping, and got home around 2 o'clock. Immediately after, FBI special agents Wally Taylor and Justin Garrick pulled in. They told her they needed to talk to her about an investigation involving mishandling of classified information. Reality thought they probably knew something, but perhaps not everything. Maybe she could stall, figure out what they knew, talk to a lawyer, and figure out how to professionally survive this.
RemiThat ain't gonna work with the FBI.
Bail Fight, Media Frenzy, And Strategy
AshleyReality and the agents waited outside while countless others cleared her house and seized all of her electronics and personal diaries. For the next three hours, they sat on the living room floor while they questioned her. At first, the conversation didn't seem that scary. She was told her participation was voluntary, and the agents built rapport by talking about their careers, workouts, and pets.
RemiRelating to her.
AshleyShe acknowledged accessing information that she didn't technically need to know by sometimes watching drone footage of missions that her friends were working on. She occasionally printed out documents, another no-no, because she found it easier to transcribe them by hand. She also mentioned that she downloaded the secure server tour, but only accessed it once because she was curious about WikiLeaks. She also gave them the passwords to her computers. Through it all, she adamantly denied ever taking anything classified out of an NSA facility. At this point, the agents told her they knew she leaked the report and just wanted to understand why. And she believed them, thinking they would understand that she did it for benign reasons. After she told them everything, she was allowed to call her parents and someone to take care of her pets before being carted off to the Lincoln County Detention Center in federal custody.
RemiShe was not allowed to do that in the film Reality.
AshleyReality was indicted at her arraignment two days later. Her attorney, Titus Nichols, was assigned to the case just minutes before, since he was the only federal public defender in all of Georgia who had the security clearance to even review the classified material connected to the case.
RemiSo is he just in the lobby and someone's like, get in there! You got a trial.
AshleyA lot of times offices are in the courthouse. So yeah, they gave him the case and was like, She's gonna get charged with this crime in five minutes. Go down there and meet her.
RemiTalk about feeling overwhelmed in a hurry. This is quite the case to get slapped in your lap.
AshleyDuring the brief hearing, the judge read from transcripts of jailhouse phone calls to her mom that reality didn't realize were being recorded.
RemiShe didn't realize that her jailhouse phone calls were being recorded?
AshleySo another person in jail let her call her mom using her pin, so she might have missed the this message is being recorded, blah, blah, blah, blah, blah. Based on a conversation about her finances, she was told that the government would not be paying for her. Legal representation. Luckily, Nichols said he would stay on the case with the help of another attorney named John Bell. He initially decided to do so pro bono. I'm not sure if he got paid or how much he got paid, but as I mentioned in a few minutes, she did get financial legal help. About an hour after the hearing, the Intercept published their article about the classified report.
RemiWhat timing?
AshleyAgain, it was done by just including a scan copy of the printed pages, even though the NSIA warned them that they were searching for the source of the leak.
RemiHow lazy are the people down at the Intercept that they're not willing to just type up an article? Okay, we scanned it in, let's print it.
AshleyAnd if the security team would have been consulted at any point, they probably would have recommended doing that.
RemiThat seems like common sense, yeah.
AshleyAround the same time, the Attorney General released its own statement describing the leak as a threat to national security. Historically, defendants charged under the Espionage Act had been granted bail, since the crime is classified as a nonviolent white-collar offense. But reality's release hearing went differently. Her defense team came in at a disadvantage. They still needed security clearances to even review the classified evidence and didn't know the scope of what the government had against her.
RemiHow were they allowed to proceed then? That's crazy. They couldn't even review the evidence?
AshleyIt's just a release hearing, and it had been five days since she'd been arrested, so they're not really arguing anything having to do about the report. It's just whether she poses a danger and should or shouldn't be released. It still sucks for them. They should know a little bit more. I guess you could argue it's not necessary at this point.
RemiYeah, but at what point are they allowed to know the details of what their client is being accused of? I mean, this is crazy.
AshleyOnce those security clearances come through. So the defense was essentially going into this release hearing blind. But the prosecution, they were well prepared for battle. They painted reality as a highly dangerous national security threat. In their words, what they found in or her house was, quote, downright frightening. They referenced the tour browser, noting how it was often used to access the dark web. Social media posts criticizing Trump and sarcastic texts to her sister were spun as proof of her deep hatred of the United States. They cited entries from her personal journals. In one, she had written, I want to burn the White House down, find somewhere in Kurdistan to live or Nepal. Ha ha, maybe. Her browser history was submitted, showing that she Googled flights to Iraq and Jordan, looked up job postings in the Middle East, and visited Taliban news sites and Afghan papers, omitting that the later searches were done while she was working with the NSA to supplement her work.
RemiSo they're trying to frame her as a possible terrorist sympathizer.
AshleyEven her early interest in learning Middle Eastern languages was used against her. To the prosecution, this all proved that reality wanted to be anywhere but the United States. Lastly, her travel interest, childhood trips to Mexico, and recent trip to Belize was introduced as proof she might flee.
RemiBecause she took vacations before she was accused of anything.
AshleyAnd because she wanted to travel, which I think most people want to travel.
RemiYeah, I don't think I'd be granted bail under those circumstances.
AshleyHer defense team tried to push back. They called her parents as character witnesses, and they offered to post her bond by using their house and land as collateral. They promised to take responsibility for her and make sure she didn't miss a single court appearance. On cross-examination, the prosecutions implied that Billy and Greg didn't know reality at all. Her career and secretive nature of it was spun as proof of her quote, fractured personality, unquote, and sympathy with extremists. In closing arguments, assistant U.S. Attorney Jennifer Solari even argued that if reality was released, she might try to burn down the White House, move to Afghanistan, and join the Taliban.
RemiThat seems pretty extreme.
AshleyIt's insane.
RemiSo they're just using scare tactics, basically.
AshleyAnd it worked. Twenty-five-year-old reality winner was the first civilian defendant accused of leaking information to the media under the Espionage Act to ever be denied pretrial release.
RemiAnd she was not a flight risk. This woman did not have all the resources in the world to just escape to another country and disappear.
AshleyNor did she have the personality or desire to do so. In the days and weeks that followed, reality was a media sensation. Mainstream outlets scored through her social media history, she was mocked for her name and appearance, dismissed as a joke, or slammed as a traitor. To get a taste of what was out there, here's some clips from the late show with Stephen Colbert and the Daily Show with Trevor Noah.
Stephen ColbertThe leaker's name, and this is true, Reality Winner. So it's official. So a young female spy named Reality Winner stole intelligence from the Plurbus Corporation. That sounds like a James Bond movie, which of course makes Donald Trump small finger.
Trevor NoahOh, okay. Look, if you're confused right now, it's because you're paying attention. Let me try to explain. What happened was someone leaked top secret information about Russia to the press. And that person's name is Reality Winner. Their real name is Reality Winner. And I mean, how is this real life? You know what it feels like right now? It feels like God had a midlife crisis and he quit his day job to make a web series. That's what this feels like.
RemiThese are prime examples of why I do not watch late-night talk shows.
AshleyAnd I hope they feel pretty bad for making these jokes about her name. Like, come on, guys. Although her parents were discouraged from talking to the media, they quickly realized they had to if they wanted people to know who their daughter really was.
Billie WinnerShe's a good girl. She's a good person. She's never been in trouble with anyone or the law or anything. She always does what's right. She serves her country. She was in the Air Force for six years. Um, she she is a good person. She volunteers, she does whatever she can to make the community and the world better.
RemiThis is depicted in the film Winner as the mom basically going a bat for reality because her daughter can't tell her side of the events, and she does a lot of appearances and really, really tries to advocate for reality.
AshleyWell, because all she was seeing are people that are making fun of her daughter because of her name or how she looks or being slammed as a traitor. And she's like, that's not the full story. This is who my daughter is.
RemiYeah, it's pretty stupid that everyone just focused on the name and not actually what the person did.
AshleyAt the same time, the Intercept was handling their own fallout. Reports surface that the head of operational security wasn't consulted at all. Outside organizations slammed the publication for not following the necessary precautions the publication so prided itself for.
RemiYeah, this looks really bad for their reputation.
AshleyThe Intercept released a statement saying the allegations against Reality Winner had not been proven and that it wouldn't make any further comment. Soon after, editor-in-chief Betsy Reed issued another statement taking responsibility for, quote, this failure, and acknowledged that the organization's practices had fallen short of their standards. The publication conducted an internal review, but employees were instructed to not talk to the press. Co-founder Laura Portress did not heed this advice and was fired after expressing her dissatisfaction with how the report was handled.
RemiThey fired her?
AshleyThey fired her. And they did fuck up. The whole reason she was caught was because the security team didn't consult security at all and just sent photos of this document everywhere.
RemiProper procedures were not followed at all in this situation, and Laura should not be punished for simply telling the truth in this circumstance.
AshleyEspecially when she essentially just said the same thing the editor-in-chief did. Within a week of the release hearing, the government offered a plea bargain of five years in federal prison. To reality and her supporters, this was beyond harsh. Other public officials who mishandled classified information typically got off with probation or minimal sentences. For example, in 2016, retired Marine General James Cartwright pled guilty to giving the New York Times information about a cyber operation targeting Iran's nuclear program. He was sentenced to six months in jail, but almost immediately he was pardoned by President Obama, who also restored his security clearance. Although reality was facing up to 10 years in prison and a $250,000 fine, she decided to not take the deal. Public support was growing. A GoFundMe had raised over $12,000, and the freedom of the Press Foundation, whose board of directors included Edward Snowden and oddly nowadays John Cusack offered to help fund her defense along with the Intercept's parent company, First Look Media.
RemiWe just discussed him a few episodes back in Midnight in the Garden of Good and Evil. I would not have expected any connection between him and Edward Snowden.
AshleyYeah, so now he's kind of rivaling Bill Camp with how many podcast episodes he's been mentioned in.
RemiI look forward to John Cusack's biography one day. He seems like he has had a pretty interesting life.
AshleyDespite this public support, defending a national security case poses unique challenges. All the attorneys needed to have security clearances and couldn't talk about the case outside of secure phone lines and emails.
RemiThis seems like a red tape nightmare.
AshleyIt gets worse. Meetings had to be done in sealed rooms called sensitive compartmented information facilities, and so I don't have to say that phrase again. I'm going to call these SCIFs. Since reality's legal team was scattered across the mid and eastern United States, arranging meetings was difficult. Even more so if they wanted reality to attend. She couldn't just call in from jail or meet with her attorneys in jail, as normal defendants can do. Most of the time, reality met with people from her legal team in a converted supply closet inside the courthouse that was made into one of these CSIFs.
RemiWait, so a CSIF can just be a supply closet when it comes down to it?
AshleyThey had to convert it into one. I don't know what that means really, but they did that because otherwise, the only places these CSIFs are are inside secure NSA facilities. You need security clearance to get inside those.
RemiI'm just picturing her talking to her lawyer in a room that has like a bucket and a mop next to her.
AshleyThat and insulated walls is what I'm assuming.
RemiAnd one dangling overhead light with a pull string.
AshleyEven though security clearances were taking longer than expected, the judge refused to delay trial dates beyond the delay he granted after the defense's appeal of the bail decision was denied. By the spring of 2018, Reality's legal team advised her to take the new plea deal, which had increased by three more months than the last one, with credit for time served and three years of probation. As we talked about in our last episode, to be convicted under the Espionage Act, the government only has to prove that classified information was disclosed. Motive doesn't matter, and the evidence against reality was indisputable. She signed a plea deal in August 2018. Despite being promised to serve her time at the facility of her choosing, the Federal Medical Center in Carswell, Texas, Reality First had to undergo diesel therapy, which we already talked about. She was first sent to the Baker County Detention Center in Florida. She was put in solitary confinement, reportedly for her protection, since she was a high-profile inmate. After eight days, she demanded to speak to the warden and pled her case about why she should be in general population. Essentially, what she said is, This is an ice facility. That's right. Reality Winner was moved to an ICE detainment facility. So she's like, most of the people in here don't speak English. Why would they know who I was? She was moved to Genpop, but immediately transferred to a jail in Oklahoma before finally arriving at Carswell in November 2018. For the first time in months, her parents finally could visit and knew where she was.
RemiThis is depicted in the film Winner. Her mother is calling prisons all over the place trying to locate where her daughter is so she can see her and speak to her.
AshleyReality settled into a routine in prison. She got a job as a fitness instructor and incorporated nutrition into her classes.
RemiWhat did she talk about as far as nutrition? I mean, they were incarcerated. I figured nutrition was not the easiest thing to maintain in a situation like that.
Release, House Arrest, And Reflection
AshleySo it's not. And remember, reality struggles with bulimia. So nutrition is something that's very important to her. Her relationship with food is distorted. So what she was including in her classes is how to eat healthy in prison, and also importantly, how to eat healthy on a budget once you're released.
RemiThat's very admirable.
AshleyShe was doing pretty well until she awoke to a female correctional officer touching her while she was sleeping in early 2020. She filed a complaint under the Prison Rape Elimination Act, but it wasn't even investigated until a few months before her release. And then COVID hit. As you can imagine, the disease was rampant in closed quarters like jails and prisons. Extended lockdowns left inmates isolated, stagnant, and desperate for stimulation. Reality started binging and purging again after a year of not doing it and began taking benzos and K2.
RemiI think a lot of people reverted to some bad habits when they were stuck indoors for two years during that time.
AshleyWell, and it's even worse for people in prison. They were not only stuck indoors, they were stuck in their cells. They couldn't be let out for showers, they couldn't be let out for exercise time, they couldn't be let out for meals. They were essentially given sack lunches to eat in their cells for months.
RemiI was going nuts and I had a whole apartment and the outdoors.
AshleyOn April 24th, 2020, a federal judge rejected her request to commute the remaining 19 months of her sentence to home confinement due to COVID-19 risks. Her attorneys argue that her history of respiratory illness combined with immune complications linked to bulimia made her especially vulnerable to the virus. And she did, while she was in there, get it twice. On June 2nd, 2021, one day before the fourth anniversary of her arrest, Reality was released and transferred to the Residential Reentry Management Center in San Antonio, Texas. After six months, she was given an ankle monitor and released her parents on house arrest. Whenever she wanted to leave, she had to give the exact address and phone number of where she was going, the exact three-hour window that she wanted to be gone from her house for, and call whenever she left or arrived at either location.
RemiThis is a lot of overkill right here.
AshleyCan you imagine if she wanted to go to Walmart? She had to say when she was going, and then call before she left the house, when she got to Walmart, when she left Walmart, and when she got home. And that is the true story of Reality Winner. What do you think, Remy?
Objections And Final Verdicts
RemiI think Reality is a genuinely good person who did something sort of impulsively without thinking about the scale of the repercussions she would be facing. I do not think that Reality Winner is another Edward Snowden at all after hearing the story. I have met women like Reality Winner who do Crossfit and volunteer and love animals and are genuinely just good people. It seems like reality did something without considering at all how serious that action would be taken.
AshleyAnd it's really interesting because unlike Edward Snowden, she has straight up said, yes, I regret doing this. It ruined my life. It really seems that the government wanted to make an example out of her. People had been disclosing documents left and right. People way far higher up the totem pole had gotten caught for mishandling documents. Biden, Hillary Clinton, Donald Trump were all found to be in possession of classified documents in their home. All of these people get a slap on the wrist, if anything. But because she's just an ordinary person, she gets five years in prison for five pages of paper. That's wild. Five pages of paper that didn't include anything that would pose a security risk to the United States. If anything, it's good that this document was released because don't click phishing links.
RemiI don't know if she said this in any of her real life interviews, but at least in the film, she mentioned that part of why she regretted releasing it was the fact that the information she released didn't really prove anything. It proved that Russia had made attempts, but it didn't prove that they had succeeded in anything. And in the grand scheme of things, her life was destroyed for this not groundbreaking leak.
AshleyHer life was destroyed for leaking five pages of what the country already knew. They already knew Russia had attempted to interfere, they just didn't know how. And all this document showed was that they sent dumb phishing emails that at least one person fell for.
RemiI almost find it weird to compare her to Edward Snowden because they are not on the same level in what they were trying to do or any of it.
AshleyNo, he planned the leak of who knows how many documents. It ranged from what 50k to 2 million pages of documents that, as we discussed in our last episode, did have global ramifications. This didn't.
RemiPersonally speaking, I can relate a lot more to reality winner than I can to Edward Snowden. Reality does CrossFit, reality does volunteer work, she loves animals. She seems like someone that I could have ran into during the course of my life, and Snowden was far less relatable in that aspect. I can understand how someone would be watching the news with all of these people arguing back and forth, saying there isn't proof, there is proof, there isn't proof, there is proof, and being like, just shut up. I'm gonna send this out, and maybe that'll end this. Here's some proof. Let's move on, alright. It seems like it was almost an act of frustration rather than trying to like bring down the government or anything like that. She was just, here's the proof, stop fighting about it.
AshleyI totally agree with you. She didn't hate the United States. She disagreed with a lot of the current administration's stances, which a lot of people do. She wasn't trying to bring any sort of danger or ill will to the government. She was just like, this debate is going on and on and on. Here's this document that's probably gonna be released soon anyway, because there's been more classified documents leaked in the past six months compared to the past three years. I'm impulsively printing this out and sending it out there. Stop talking about it. It happened.
RemiWell, with that, let's get into our season finale's objection of the week.
Objection of the WeekYour Honor, I object! And why is that, Mr. Eed? Because it's devastating to my case! Overrule. Good call!
RemiAnd in case this is your first time listening in, first off, welcome. And our objection of the week is the most superfluous difference between the film version and the real story. I will kick things off this week. My objection is that in the film Winner, Reality spoke Pashtu in high school. While you had specifically mentioned that she couldn't speak Pashtu in high school. So that is my objection of the week.
AshleyThat's a pretty good one. She did learn languages in high school, but the Pashtu came while she was with the Air Force.
RemiAnd in Winter, there's an entire scene where she speaks Pashtu to the recruiter in class, and that's one of the big reasons why he wants to recruit her to begin with.
AshleyIt was Arabic that she was learning in high school.
RemiIt is definitely Pashtu in the film Winter.
AshleyThat's a really good one. This is gonna be tough because mine is also pretty good. Mine is actually from the movie Reality.
RemiI didn't have any for reality, so I'm eagerly anticipating this one.
AshleyIn one of the initial clips you showed of the FBI agents arriving at her home after she pulled in, the timestamp was listed as 3.30 p.m. It was actually 2.30 p.m. I don't know why that happened. I don't know if that was an oversight. Very weird. But in both of the books I read and the Wikipedia, which I know take Wikipedia with a grain of salt, but in everything that I reviewed for this case, it was 2.30 that happened. And the interrogation was three hours. It showed her in the movie being taken into custody at 4:15, 5:30. Three hours puts that time at 2.30, not 3:30.
RemiWow, I'm gonna just give you this one. That's pretty impressive. I had one more objection, but that will be much more appropriate for our verdict.
Objection of the WeekAt the conclusion of each episode, our hosts will deliver a verdict based on the film's accuracy. If the film is an honest portrayal of the events, then it will earn a not guilty verdict. If the adaptation is mostly factual, but creative liberties were taken for the sake of entertainment, the film will be declared a mistrial. But if the film ultimately strays too far from the truth, then it will be condemned as guilty and sentenced to a life behind bars.
AshleyI'll kick us off for this one. We're gonna be giving verdicts to each of the two movies separately because they are two separate movies. I'm gonna start with reality. Obviously, this is gonna get a not guilty verdict. It's based on the transcripts from the FBI. There's nothing to argue there of why this would not be a not guilty. Moving on to winter. This one is kind of tough. There was a lot of big changes that they made. For example, in the movie, her parents divorce when she's already in the Air Force instead of when she was six.
RemiThey announced that they're getting divorced at Britney's wedding.
AshleyThey also framed it as her decision to apply for contract jobs with the NSA, was because she wanted to help pay for her dad's health, which is not the case at all. Her dad was already dying in hospice care at that point. She also didn't go searching for information about Russian interference, she just stumbled upon it. So this one is really tough for me. I'm still, despite those changes, wavering between not guilty and mistrial. And I don't even have my mind made up right now, but I'm going to be forced to do so. The judge is not allowing me to leave. So I am going to go with mistrial. I think, especially when you compare it to the movie reality, they just kind of made these big decisions to change things that were rather large. So I'm being forced to make a verdict. I'm gonna go with mistrial.
Season Six Tease And Sign-Off
RemiAnd I agree with you 100%. The film reality is literally taken from the transcript, so it's kind of hard to argue with that. And the attention to detail and the performances and the directing of the film is all extremely grounded and makes it feel like you are a fly in the room while all of this stuff is going down, and it's done very well and extremely realistically. Winner, on the other hand, takes a few liberties. I am not a fan of framing this story as a comedy. I think that lessened a lot of the dramatic scenes that were depicted. And I don't really think that this story is a comedy. It's about a young woman who got in way over her head and didn't even realize it, in my opinion. And the film does a lot of movie things, like this happened at this time to make this be more dramatic. So let's move this here, let's move this location here. A lot of shuffling events and times and locations just for streamlining purposes or dramatic purposes. And that's just not how it really was. So I give winner a mistrial as well. So not guilty for reality, but mistrial for winner.
AshleyAnd with that, we are going to be closing our courthouse doors for a little bit to help us prepare for season six. Season six! That's nuts.
RemiYeah, I can't believe we've made it this far. Six seasons already, in the words of the show community, six seasons in a movie. So I guess we're gonna make a feature film for season seven. But we will be back after a few weeks. Like I mentioned earlier, we are planning a wedding, so that is a little time consuming, but we are still going to come back with another season that will have more cases, more films, and will be even more interesting and entertaining than anything you've heard before.
AshleyAnd don't worry, we will be dropping a little trailer about a week before. Listen to that because it'll give you a nice little overview of some of the movies and stories we will be covering.
RemiSo mark it on your calendars. April 20th is the date that season six will be premiering. And until then, court is adjourned.