She Tried to Resist and Found Herself Alone

It was a big deal that Reality Winner’s probation officer let her travel from Texas to her sister’s house in North Carolina over Thanksgiving. She is, after all, a traitor, in the eyes of the law.

Ms. Winner was arrested in 2017 for leaking to journalists a classified intelligence report on Russian hacks into U.S. election infrastructure and has been confined ever since — in a Georgia county jail, a federal prison, a halfway house and, most recently, in a probation so strict that she often feels strangled.

Still, Ms. Winner viewed the trip with the wariness of an underdog conditioned to expect any small kindnesses to turn back against her.

“It wasn’t my idea,” she said flatly by phone. “I preferred not to go.”

Oh, and another thing, she said pointedly: She went during Thanksgiving but for her niece’s birthday.

“I hate Thanksgiving,” she said. “I hate the food. I hate the vibe.”

This side of Ms. Winner becomes familiar after a while: the cranky prison yard impulse to let everyone know just how much she doesn’t care and can’t be hurt. It poorly camouflages the battered idealist who, despite disillusionment and harsh punishment, appears bent on finding some way to make herself useful on a grand scale. She never had much money, education or connections, but in her own way, she has repeatedly tried to save the country — first as a military linguist guiding foreign drone attacks and later by warning the public that Donald Trump was lying to them about Russia.

Both efforts went bad, though, which is why I think of Ms. Winner as a sorrowful casualty — not only of our poisoned political culture but also of a contemporary America replete with corruption and amoral bureaucracy. The harder she tried, it seems, the more her ideals soured into disgust.

When I first spoke to Ms. Winner, in the summer of 2021, she was still fighting the drug habit she’d picked up behind bars and trying to tamp down the explosive aggression she’d used on the guards. On home confinement at her mother and stepfather’s ranch outside Corpus Christi, Texas, she held forth in meandering, disarmingly frank phone calls about the degradations of prison, the power of linguistics, a surreal childhood crossing back and forth into Mexico on pharmacy runs with her opioid-addicted father.

All these months later, Ms. Winner is still on probation, but she’s grown more focused and stable. Most of her energies now are fixed on attracting clients to her CrossFit coaching practice. At 31, she is already a living relic of one of our nation’s most surreal political crises.

She still isn’t allowed to talk about her military service or the contents of her leak, leaving me to puzzle over why a young woman who still guards the secrets of the terrorism wars would risk everything to expose a five-page National Security Agency file on efforts to hack voter registration systems.

Ms. Winner mailed the report anonymously to The Intercept, where a reporter took the ill-advised step of giving a copy to the N.S.A. for verification. The authorities almost immediately zeroed in on her. She was charged under the Espionage Act, the same laws used to prosecute the Rosenbergs, Aldrich Ames and pretty much any other 20th-century spy you can name. The act has long been criticized for lumping together leaks motivated by public interest and, say, peddling nuclear secrets to a foreign government. Ms. Winner is considered a prime example of its downside.

She pleaded guilty and was given 63 months in prison, the longest federal sentence ever for the unauthorized release of materials to the media. (The former C.I.A. director David Petraeus got off with probation and a fine for sharing eight notebooks full of highly classified information with his biographer, who was also his mistress.)

Deemed a flight risk and denied bail, Ms. Winner languished for 16 months in a crammed Georgia county jail cell. While negotiating her plea deal with prosecutors, she said, she plotted suicide and fantasized about federal prison “like I was going away to an elite university — ‘Oh, look, they have a rec center, they have a track, they have a commissary, they sell makeup.’”

All of that for nothing or, at least, for very little. Ms. Winner’s intervention hardly registered. She wanted to prove that the White House was lying: U.S. officials knew that Russia had attacked U.S. voting infrastructure just days before the 2016 election. But the revelation hardly scratched public awareness.

“Reality Winner is a whistleblower because?” said Ben Wizner, the director of the American Civil Liberties Union’s Speech, Privacy and Technology Project. “How many people would give the same answer to that?”

“You can’t imagine a more unlikely person to serve the longest-ever sentence under the Espionage Act” for leaking to the media, he added. “It’s perverse.”

The hardest part, Ms. Winner said once, is not the punishment but “just knowing that you really didn’t change anything. Nobody cares.”

“The people on the left who pretend to champion you. They really didn’t do anything for you,” she said. “The people in the center won’t say your name. And the people on the right still think you’re a terrorist.”

Why did she do it? Ms. Winner bristled at this question. “Come on, you were there, too. You remember how it was. It was such a weird time,” she said.

She’s right. I remember.

It was Mr. Trump’s first year in the White House, and America was having a nervous breakdown all over the internet — MAGA fanatics in rapturous dreams of banning Muslims and building shark-infested moats along the border and, from others, fevered warnings of impending fascist takeover and Vladimir Putin as Mr. Trump’s puppet master. The thick suspicion that we were drifting toward something intolerable. The hyperbole of it all.

Commentators suggested that the president could be a Russian asset; retired government servants openly urged their successors to insubordination; Mr. Trump described a “deep state” within the government working to undermine him. What does it mean, in such times, to be a traitor?

Ms. Winner left the Air Force and started a desk job with an N.S.A. contractor in Augusta, Ga. She’d found her house online for just $500 a month and rented it sight unseen because it was close to her gym. The neighborhood proved rough; her dog cowered at gunfire outside. But she didn’t mind. She had her dog and a few guns, including a Glock and a pink AR-15. ( “Georgia has castle laws, so as long as you don’t shoot ’em in the back, you get off. So, duh.”)

She practiced yoga and CrossFit and spent her days off wandering downtown, daydreaming about buying a derelict Woolworths and turning it into an ashram where people down on their luck could get a free meal. She had a Sunday morning ritual: chop vegetables to prepare her dinners for the week while talking on the phone with her mother.

“It was getting more and more political because, like, we can’t help it,” Ms. Winner recalled.

Mr. Trump was a constant theme. According to Ms. Winner’s mother, Billie Winner-Davis, her daughter was convinced that he would destroy the country. Ms. Winner told her mother she was glad she’d left the Air Force, because there was no way she could serve under him. When the United States bombed an air base in Syria, Ms. Winner told her mother it was “smoke and mirrors,” Ms. Winner-Davis recalled — Russia was given warning to evacuate the base, her daughter said.

Ms. Winner watched Mr. Trump on TV scoffing at suggestions of Russian interference. “He’s lying,” she thought; she’d seen the proof. She recalled that the whole enterprise of government and war had started to seem rotten; she’d thought that she could make a difference working quietly within national security and, eventually, gaining enough authority to make better decisions. Now it felt pointless.

“If there’s this jackass in the White House, apparently none of this matters,” she said recently, trying to describe her mind-set when she printed the report and dropped it in the mail. “It was the repeated lies.”

For years, Ms. Winner had dreamed of distinguishing herself in a moment of heroism. “I always wanted to be a badass like Carrie from ‘Homeland,’” she said. “Somebody who got something done in counterintelligence or counterterrorism and I think — I don’t know — just kind of being that stand-alone figure.”

There was a lot of talk about insurgency that year. Twitter was full of grandstanding and “I am Spartacus” declamations. But Ms. Winner slammed into a hard realization: Despite all the grumbling and proclaiming, the resistance, if it existed, did not rush to defend her.

Ms. Winner talks a lot about social media, about its capacity to warp political life and set traps for people — including herself. She is haunted by the experience of watching news stories about politicians’ tweets from inside prison, where she had zero access to social media.

Twitter didn’t give the prisoners protective gear during the pandemic. Facebook didn’t prevent inmates from losing family members to street violence. Nothing came of it, she realized, but cluttered minds and wasted time.

“When you’re pulled away from it and you see all the energy put into it, it’ll break your heart,” Ms. Winner said. “Nobody is coming to save you, because they’re so busy with a tweet.”

It is hard to understand how Ms. Winner evolved into an ideological insurgent, because she can’t talk freely about the days when she was a loyal service member. The state-imposed silence about the years she spent identifying drone targets and helping to assassinate people casts a fog of ambiguity over a complicated and perhaps even morally compromising part of her story.

Everything we know about Ms. Winner’s war contributions comes from an Air Force Commendation Medal praising her for “enemy intelligence exploitation” and geolocating combatants. According to the medal, she aided in 650 captures and 600 kills.

That’s a sobering body count for a young woman who, just a few years earlier, was teaching herself Arabic at the public library to better understand the faraway land that her country had invaded. As a teenager, Ms. Winner joined the military to learn more languages and because college looked like “somebody else’s moneymaking machine.” In the Air Force she learned Pashto, Dari and Farsi but ended up sequestered in a Maryland base eavesdropping on the other side of the planet.

At times she expressed empathy for the people on the receiving end of the U.S. wars, fantasized about burning the White House down and even told her sister that she hated America. Those expressions of disgust, captured in online messages and private notes seized from Ms. Winner’s home, were eventually resurrected and patched together by prosecutors who seemed, Ms. Winner thought, to imply that she was a terrorist.

Ms. Winner-Davis believes her daughter ended up leaking, at least in part, because she had been disillusioned by her military service. She recalled her daughter fretting over the reliability of the intelligence, telling her mother, “When you see somebody go poof on the screen, you’ve got to make sure it’s right.”

“Through her work, she saw a lot of lies,” Ms. Winner-Davis said. “Reality saw another side of our country.”

In the military and as an N.S.A. contractor, Ms. Winner vanished into the secrecy of federal institutions. It happened again when she went to prison. Each time, it seems, she emerged traumatized and depleted.

Ms. Winner lived through both the pandemic and the racial tensions of 2020 in prison, where the social upheaval manifested in flares of violence and harsh recriminations. Covid meant draconian, monthslong quarantines and lockdowns in cells so tightly packed, she said, that inmates had to take turns standing up. As nerves frayed, guards began to randomly engage in collective punishment like tossing the cells and destroying people’s belongings.

But it was the death of George Floyd that, to Ms. Winner, made prison life unbearable. Just hours after his murder hit the national consciousness, she said, she watched a white guard assault a Black inmate who’d made a rude comment.

It was in those supercharged early days, stressed by increased hostility from prison staff members, Winner said, that she started getting high. Everyone, she said, had stores of psychiatric medications and other pills; you could combine them in different ways and crush and snort them to produce a buzz.

“I was very, very aggressive” toward the guards, Ms. Winner said. “I’d just sit at the door punching the glass every time they walked by.”

And so it was: a gradual disintegration in situation and morale until, at last, anticlimactically, Ms. Winner was released.

Ms. Winner landed back where she started — at her mother’s place, saddled with an ankle monitor, dreaming of escape. She couldn’t bear to tell her mother how bad things had been in prison, but she couldn’t act normal, either. Her mother sensed that Ms. Winner had regressed to adolescence.

“It definitely feels like there’s been some permanent damage,” Ms. Winner told me around that time. “Coming home and being in a stable environment and trying to have that control day to day — it hasn’t really fixed anything.”

In those early weeks, Ms. Winner sought solace with a high school friend who, like her, had struggled with substance abuse and the law.

“The scars were still healing from where I cut myself in quarantine,” she said. “He was the only person I could show those to and say, ‘Look, all I want to do is get high.’”

In the confusion of those early weeks, she married her friend in secret — a decision that scandalized her disapproving mother and unraveled when the pair split up after just 44 days of marriage. Describing all of this, Ms. Winner suddenly laughed.

“I’m obviously a 130 percent person,” she said. “Obviously.”

She spent time with her family’s menagerie of four rescue dogs, three cats and a young horse. The Winner-Davis place has long operated as an informal refuge for rejected animals, giving Ms. Winner early lessons in the unforeseen complications of benevolence. She was a teenager when her pet kitten was killed by a pack of 15 dogs. Realizing their good intentions had mushroomed beyond control — and getting no help from the local animal shelter — the family ended up shooting some of the dogs they’d tried to save.

Her childhood memories unfolded like tales from the forgotten margins of America, especially when it comes to her father, who bestowed on Ms. Winner her unforgettable name and lectured her at length about the importance of the traitor Judas to Christian theology. She called her father a “forever student”; she also described him as a junkie, gambler, possible draft dodger and would-be minister. His spine was shattered in a car accident before she was born, leading to years of excruciating surgeries and an unshakable dependence on painkillers.

“OxyContin became his best friend, and of course nobody saw it as a vice,” Ms. Winner said. “But after that, he was never a competent person.” Eventually he split up with her mother and moved to Harlingen, Texas, near the U.S.-Mexico border.

Still, he kept turning up to collect her and her older sister for allotted custody weekends. As they drove south along the coast, he’d hold forth on mystical and pseudoscientific topics. “Ninety minutes of ancient aliens, the Maya, the enigma of cultures, people coming from the sky,” Ms. Winner recalled.

When their father won at cards, they’d take his winnings over the Rio Grande into Nuevo Progreso, Mexico, where he’d drop the girls at the orthodontist to have their braces checked while he sauntered from pharmacy to pharmacy, telling the clerks to keep the change so they’d leave his prescription unmarked. He’d redeem the same prescription at eight or nine shops.

“He was a trafficker,” Ms. Winner said. “We learned everything. All the different checkpoints all the way up into Texas.”

At first she loved the adventure of these trips, but as she got older, the shine began to wear off. Their father was getting sicker, surviving a few overdoses. Today these trips are the stuff of bad dreams.

“I have nightmares about trying to get out of Harlingen, just the anxiety of needing to go home,” she said. “And realizing how many times he was probably high on pain pills and driving us.”

Ms. Winner’s father didn’t live long enough to witness her moment of disastrous fame. Incapacitated from a series of heart attacks, he died in 2016. Like his daughter, he’d been radicalized by the Trump era — but in the opposite direction. He had become an ardent MAGA supporter, a development she attributes to incessant exposure to Fox News broadcasts in his nursing home.

Relations between the unreliable father and the rest of the family had been strained for years. And yet at the end, Ms. Winner drew close to him.

Watching him slip deeper into dementia, she realized that he could offer her a unique gift: He wasn’t lucid enough to repeat her secrets about the Air Force and the wars. So she unburdened herself into the closing door of a fading mind, this unfathomable father figure collapsed into moribund confessor.

Back in Texas, Ms. Winner has narrowed her ambitions down to her local community. She said that she wants to do good things there, at home, where she can see them. She wants to coach, to use physical activity to fight addiction and give young people a chance to work through their stress.

She’s got her scars — and maybe we do, too — but she’s ready to try, yet again, to turn all this into something good.

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