Reality Winner’s mother and stalwart advocate, Billie Winner-Davis, talks about her daughter’s ongoing imprisonment, the Espionage Act, a Presidential tweet, and the disturbing lack of Press attention
By Gretchen A. Peck
Billie Winner-Davis’ Twitter followers know her to be a near-tireless digital advocate for her daughter, Reality. With only hashtags – #FreeRealityWinner, #CompassionateRelease4Reality, #ProtectWhistleblowers – in her quiver, she’s on a quest to see that her daughter is released from the Federal Bureau of Prisons’ Medical Center in Carswell, Texas – and that Reality’s incarceration hasn’t been in vain.
With a memorable name like Reality Winner, you’d think it would be “household,” part of the pop vernacular. Yet, many Americans still don’t know her name, nor the action she took – she contends, on their behalf.

At 18, Winner enlisted in the United States Air Force (USAF), and her natural aptitude for languages carved her path the military. She served as a cryptologic linguist, a marketable skill beyond her six years of service.
Winner was in her mid-twenties and fresh out of the service when National Security Agency (NSA) contractor Pluribus International hired her to be a translator. It was during the course of her work there that she obtained a classified document that outlined Russia’s sustained campaign to undermine the 2016 U.S. election that pitted Hillary Clinton against Donald J. Trump for the Presidency.
The classified report detailed Russian hackers’ objective to compromise local election and voter registration systems across the country. Winner copied the report, hiding it in her pantyhose to get it off site, she later told investigators. She sent the document to Glenn Greenwald’s former outlet, The Intercept.
Winner was arrested in June 2017, two days before The Intercept published its story.
Now, three years and another Presidential election later, the information Winner disclosed seems somehow quaint. Volumes have been written on Russia’s meddling, including the thick tome Special Counsel Robert Mueller’s team produced, but few read.
The United States of America charged Winner under the Espionage Act, law intended to prosecute the nation’s most insidious traitors. Prosecuting counsel portrayed Winner as an existential threat to the nation, suggesting she’d caused “grave damage” and compromised national security.
For any objective observer, it’s hard to quantify those damages; certainly, the Federal Government was embarrassed by the disclosure – caught on its heels, slow to mount a defense against Russian aggression, and intent on keeping that failure hidden from the American people.
In June 2018 – after a year in prison – Winner pleaded guilty to a single felony count of unauthorized transmission of classified information. She was sentenced to five years and three months and has been incarcerated since.

Reality’s mother hasn’t seen her daughter, in person, since February 2020. On March 13th, the Federal facility halted all in-person visitation to mitigate the COVID-19 virus.
“She calls when she can. It’s a little hard with my work schedule, but she tries before I go to work. She also has to fight for the phone, because she’s in a large unit, and there are only so many phones. That means standing in line and waiting,” Winner-Davis said. Some weekends, she has the good fortune to connect with Reality through video chat. “It’s good to lay eyes on her, to know she’s okay.”
Despite the prison’s attempts to keep the virus at bay, Winner tested positive in July. She reported to her mother that she had telltale symptoms – body aches, severe headache and muscle cramps. Several months later, her mother was comforted to know that she was doing well and seemingly “over it.”
Winner is scheduled for release on November 24, 2021. In May 2021, she’ll be eligible for a supervised early-release program. Naturally, Winner’s legal team sought clemency for their client, a pardon that can only come from one person in all of the land – the President of the United States.
“It could be this President. It could be the next President,” Winner-Davis said. “She really doesn’t have very high hopes of getting out. She feels like she’s going to be there until her release date.”
President Trump appeared to take a passing interest in Winner’s conviction when he tweeted about her on August 24, 2018:

“I always look back at the tweet, and I use it out there on Twitter, to remind [President Trump] that it’s still very unfair. It was really cool to see that tweet, and it was good, because during her pre-trial phase, her attorneys told us not to use the word ‘unfair,’ because it might upset the Courts; and so, for Trump to use that word was amazing for us. This process has been unfair from the beginning.
“But when you look at the tweet, you see that his intent was to get back at Jeff Sessions, who he was angry with at the time. And he was trying to say something disparaging about Hillary Clinton. He was using Reality to get at them,” she said.
As Reality’s chief champion, her mother spends untold afterwork hours writing letters, emails, and making calls to the White House and members of Congress. At best, she receives boilerplate letters in response. Worse yet, she says, is the silence.
“That’s one of the things that has been difficult for me — feeling like Reality doesn’t have support, even from my officials here in Texas,” she said. “I write to them, and I get form letters back saying that they don’t have the authority to intervene. I’m not asking them to intervene. I’m asking them to support her. When we were going to Washington, DC for the second-year anniversary of her arrest, I wrote to a number of Senators, asking if I could have a meeting with them while I was there – and to Nancy Pelosi, as well — but I never heard from anyone.”
She is heartened, however, by the number of people who have expressed support and empathy for her daughter, including some of those famous whistleblowers – Thomas A. Drake, Lisa Ling, Edward Snowden, and others.
Former Trump attorney Michael Cohen reached out with interest in advocating for Winner’s compassionate early release – a privilege he was afforded while serving time for his own 2018 conviction.
Hollywood came calling, too. Winner’s mother said that a documentary is planned for early 2021. There’s also a greenlit feature film in the works.
Reality Winner appealed for compassionate release on November 16, 2020 hearing. Chief U.S. District Judge Randal Hall said that Winner had not provided the prison warden 30 days to consider a compassionate release appeal, and that her attorneys failed to present a compelling case.
Beyond a handful of legal publishers, few news organizations covered the hearing.
“The media just isn’t there,” Winner-Davis said.
When Reality and her mother have the opportunity to speak, they talk about lots of things – about her daughter’s health, her perspective on prison and the law, and what the future might hold. Winner is working on a degree in sociology. She’s become a certified instructor in yoga and spin-cycling.
Her mother expects that she’ll leverage this experience and become an advocate for criminal justice and social justice reform. She’s expressed interest in working with at-risk youths.
What the pair haven’t spoken about is the former government contractor’s decision to disclose the information – the risk-benefit analysis she considered before she sent the classified report to The Intercept.
“She and I have never been able to have a real conversation about this. All of our conversations are monitored,” Winner-Davis said. “There have been times when she’s mentioned that she hopes that what she did paid off in some way, you know – that it made a difference, that it made some sort of a difference.”
Winner-Davis expressed frustration that the very information Reality disclosed is still being used as political fodder, and that its veracity is being undermined by members of the United States Congress.
“We seem to have come full circle,” she said, exasperated. “Now, they’re trying to disprove it again, trying to say that there was something malicious about the investigation itself. And I sit here, and I want to scream, ‘But the Russians did it!’ It warranted an investigation, but now they’re trying to say that the investigation itself was wrong.”
In the meantime, her daughter serves time.
“The only thing I’ve been fighting for this whole time is to keep her name out there, and for people to learn who she is. She really is a remarkable young woman. Her service in the Air Force, her volunteerism? You’re not going to find someone that young who has given so much. I just want people to see her for who she is,” Winner-Davis said.
“I also want people to recognize that she didn’t do any harm to her country, and to press our nation into reforming the Espionage Act. It should only be used for people who actually damage us, who trade secrets, sell secrets, and work against our country. It should not be used on people like Reality, like Edward Snowden, like Chelsea Manning. There has got to be a line where we say, ‘No, this doesn’t fit.’ Reality did not conspire against the United States of America.”