Reality Winner, the decorated U.S. Air Force veteran who spent three years in federal prison for leaking a classified document on Russian hacking in the 2016 election, is prohibited by her criminal sentencing from profiting from movies about her story. That’s too bad for Winner and her family, because in the past three years, three feature films have been made about the unusually named South Texas native—the most recent two with serious star power.
First came the documentary United States vs. Reality Winner, in 2021. Then, in 2023, the play Is This a Room, a staged reading of the transcript of her interrogation by the FBI, was adapted into the claustrophobic drama Reality, starring Sydney Sweeney. This Friday the coming-of-age biopic Winner, which stars Emilia Jones (CODA) in the title role and Connie Britton and Zach Galifianakis as Winner’s parents, puts the life of the 32-year-old ex-con and current Kingsville CrossFit instructor on screen for a third time. This one’s the charmer.
Director Susanna Fogel (The Spy Who Dumped Me) says she felt there was more to Winner’s story than what can be seen in the previous two film portraits, which focus mostly on the events that made her famous. After forming a friendship with Winner on visits to Kingsville after her release from prison, Fogel says she came to regard her as a young woman like many she knows—sarcastic yet idealistic, wanting to make a difference but not knowing how, feeling disenfranchised by impenetrable systems of authority, and not always acting with her best judgment.
“I was really fascinated by how fun she seemed,” Fogel says. “Characters who do big things in movies about important ideas are usually so self-serious, and they’re usually men, and they’re usually idealistic—at least in the movies they are. They’re not fun, relatable people. I wanted to ground that for the audience, so they’re just watching a movie about a person like them who made a choice that they could make.”
Fogel, who earned a writing credit on Booksmart, says she and her collaborators aimed for a tone that was a mix of Lady Bird and Little Miss Sunshine, with an ensemble cast portraying an exceptional but unpretentious family from an unglamorous part of the country.
Britton, making her return to playing a Texan for the first time since Friday Night Lights went off the air in 2011, is a crucial part of that ensemble as Billie Winner-Davis, who became her daughter’s staunchest advocate as Reality was confined and at times unreachable inside the criminal justice system. Britton was drawn to the project by the salience of the subject matter. “Reality’s story, to me, feels like a representation of that very specific period in our history,” she says.
That story is bookended in the film by the national upheavals of September 11, 2001, and November 8, 2016. Watching the 9/11 attacks on TV at nine years old, Reality asks her father, played by Galifianakis as a loving and lovable underemployed freethinker, why the terrorists didn’t just ask the U.S. to meet their demands. “First of all,” he replies, “we don’t speak the same language.” Cut to Reality studying Arabic and Pashto. By the end of high school, her skills draw the attention of military recruiters, who entice her away from Texas A&M–Kingsville with the promise that she can help people as a linguist in war zones. Instead, from a desk at Fort Meade in Maryland, Winner eavesdrops on enough conversations to be credited with aiding in 600 enemy captures and 650 enemies killed in action.
Eventually, like many ex-military translators, Winner takes a lucrative job with a contractor to the National Security Agency. From here, much of the film takes place outside of Texas, including in her employer’s high-gloss office that is an effective and moving contrast with Reality’s visits home to scrubby Kingsville as her dad descends into painkiller addiction and ill health. She is working for the firm when Donald Trump is elected in 2016. As the debate over Russian interference plays out on overhead TVs via archival cable news clips, Winner sneaks a peek at a classified document that directly contradicts something that the president and some talking heads are claiming. She prints it out and sends it to The Intercept, an online publication then widely seen as committed to nonpartisan truth-telling about national security and surveillance issues. She’s quickly caught and arrested in a scene that highlights just how long she naively believes she can outsmart or appeal to the better angels of her fellow security operatives.
Fogel says one aim of the film was to subvert what she calls a “misunderstanding” that Winner leaked the document out of left-wing hyperpartisanship. “What she did came from such a simple desire to just be transparent about a thing that people were hiding,” she says. “It wasn’t some liberal, socialist agenda, by any stretch.”
Winner is portrayed as someone who doesn’t fit neatly into typical political categories—a vegan and rescue-animal lover who also boasts a large collection of firearms, including a handgun under her pillow decorated with an “I voted” sticker. (“Who are you?” the guy she’s dating asks, baffled and smitten, when he discovers it.) She deeply resents elitist types who look down on her for never going to college. And she’s a CrossFit fanatic, in one scene punishing herself with an extreme workout to quiet the lingering moral doubts that come with her involvement in a targeted airstrike halfway around the world.
Winner’s real-life family is likewise difficult to pin down on the left-right continuum. She was raised religious, going to church every Sunday, as we learn in the film. Billie worked as a social worker, helping get kids out of abusive homes. The family is very much part of the tight-knit Kingsville community —Fogel calls it a fishbowl—with a reputation for volunteer work and altruistic values, of which Reality’s military service is just another example.
All this might remind one of another do-gooder family from the opposite side of Texas, also led by a full-hearted mom played by Britton. But the actor says her previous role as Tami Taylor on TV’s Friday Night Lights didn’t even occur to her as she was preparing to play Billie—who is, after all, in a much more difficult marriage and whose troublemaking kid has pulled something quite a bit more dramatic than banging up the new sedan.
“I never even thought of Tami—other than the Texas connection, which, of course, contributes so much to who this family is,” Britton says. “I love playing mom roles and finding the individuality in each one. Society has so many generalizations about moms and who moms are. For me, to play so many unique moms and show how completely individual they are feels like a great privilege.”
Britton points to Billie’s “eye-opening” experience of seeing her daughter suddenly stuck in a brutal prison system—Reality is depicted in solitary confinement for a long stretch, then shackled and transported around the country for weeks as a form of emotional torture, a practice known on the inside as “diesel therapy.” But Billie rises to the occasion, honing her presentational chops and going on national television to speak out for her daughter and others stuck in the system, eventually perhaps aiding in securing Reality’s early release.
“She’s a very regular gal who feels like she would be a great next-door neighbor, and she was thrust into this situation and dug so deep to discover her own power,” Britton says. “I’m fascinated with women’s power—not necessarily the women that we see in power positions out in front but everyday women, the women that we all know, and what we’re capable of finding in ourselves and accomplishing. Billie is an incredible real-life example of that. She’s such a kick-ass woman.”
That same phrase might be said to apply to Winner’s depiction of Reality herself, though the film never labors to make a case that her decision to leak the document was the correct one. She’s not a hero, just a fascinating character—a kid from a small town with few privileges who shaped herself into a person of extraordinary abilities, did something reckless and brave, and has become a twenty-first-century outlaw legend.
Fogel says she formed a real bond of trust with Reality, first sending humor books to cheer her up in prison, then meeting her for a “tour of the Hobby Lobby and the Marshalls in downtown Kingsville” on an excursion from house arrest, and eventually coming to Kingsville for longer and friendlier visits, culminating in a Passover holiday this spring. (Always full of surprises, Reality converted to Judaism while in prison.)
“You’ve never had a Passover seder until you sleep in a camper van on the Winner property and make a Jewish brisket in their Texas brisket cooker, with her parents helping you and shaking their heads with how little you know about cooking with it,” Fogel says.
Still, there’s one thing Reality will never do, and that’s watch Fogel’s movie. Reality has steadfastly avoided watching any of the movies made about her, the director says. It’s a tribute to the film that this feels like exactly how the Reality we meet on-screen would deal with postprison fame.
“She wants the story to get out there, and she wants to feel like what she did meant something and will inspire people to take action,” Fogel explains. “But in her own telling of it, she’s just like, ‘I don’t want to fixate on the fact that you put the wrong socks on my character and then hate the movie and then hate you. I’d rather just be friends with you and have everyone see the movie, and I’m fine.’ ”
Only Reality can judge her character’s socks, but Texas audiences are likely to feel that the film has a knack for our landscapes (some exteriors were shot here, even if much of the filming took place nearly two thousand miles away, in Manitoba), our ever-contentious variety of patriotic values, and our quirky characters. Whatever one thinks of Winner’s crime, she has done her time. It’s time we treated ourselves to her story.
