In addition to true crime documentaries, true crime re-imaginings are a new way for streaming platforms and television networks to take ripped-from-headlines stories and turn them into entertainment. HBO’s newest addition to the genre is Reality. The film stars Sydney Sweeney (from Euphoria) as Reality Winner, who leaked documents from the National Security Agency. The film is actually based on a play Is This A Room (created by the film’s director Tina Satter).
In an interesting creative direction, the play and the film’s dialogue are pulled entirely from a transcript of the FBI’s interrogation of Winner. The film has already premiered and received positive reviews at the Berlin International Film Festival, and HBO’s reputation for quality television and movies speaks for itself. Reality is bound to be up to the premium network’s high bar, and a worthwhile watch for anyone interested.
While the film likely sticks to the facts due to the nature of its creative angle, the FBI transcript may not provide the full context of the story. Plus, there’s of course the aftermath of the saga, which saw Winner sentenced to prison. So before you see the film, it may help to get a primer on what actually happened in real life to help compare reality to the film. And if you want to know where Reality Winner is now, we’ve got the most up to date news of what she’s up to now.
Here’s the true story behind Reality.
What’s the true story behind Reality?
Originally from Kingsville, Texas, the now 31-year-old Reality Winner served in the U.S. Air Force from 2010 to 2016. As NBC News reports, she worked as a cryptologic language analyst, listening in on intercepted conversations in multiple languages, including Farsi and Pashto, to provide the U.S. with foreign intelligence. Due to her work, she received an Air Force Commendation Medal. After her honorable discharge in November 2016, she moved to Augusta, Georgia, where she taught at a CrossFit gym. She then used her coveted top security clearance from her time in the army to land a job at Pluribus International Corporation, a firm which provides contracted services to the NSA.
Around the same time as her job search, Winner broke up her boyfriend in the fall of 2016, and days before Christmas, her father died. Intelligencer says Winner wrote in a letter she’d lost her “confidant.” The holidays were hard on her. “It was Christmastime and I had to go running to cry to hide it from the family. 2016 was the year I got really good at crying and running.”
In mid-February 2017, Pluribus assigned Winner to Fort Gordon, a U.S. Army post. While at Fort Gordon, Winner translated various documents related to the Iranian Aerospace program. According to Intelligencer, Winner found the work boring. Due to her top security clearance, she had easy access to other, more interesting documents, like information about a Russian attempt to interfere in the 2016 election, which she ultimately leaked.
The report itself details how Russian intelligence sent phishing emails to various employees at a company which provides election support in eight states. When they acquired log-in credentials, Russian intelligence sent malware to over 100 election officials mere days before the election.
Winner often listened to the non-profit new organization The Intercept‘s political podcast Intercepted. On the show, hosts Jeremy Scahill, and Glenn Greenwald (who Edward Snowden famously shared his classified NSA documents with). Scahill and Greenwald discussed Russian election interference on the podcast, and voiced their skepticism. Without evidence, the idea that Russian intelligence meddled in the election was nothing but a theory.
Frustrated that the government kept the knowledge hidden from the public, The Cut says Winner one day decided to make a copy of the documents, stuff them in her pantyhose, and walk out of the office. She then sent the papers to The Intercept.
While journalists have a standard practice to keep the identity of major sources like Winner concealed, various journalists at The Intercept reportedly erred in their handling of the documents. Court filings revealed an unnamed reporter on May 30 sent pictures of the document to a contractor for the U.S. government and asked if they were real. After speaking with someone at the NSA, the contractor confirmed the papers’ veracity. The NSA then alerted the FBI of a security leak. On June 3, The New York Times reports the FBI found Winner at her home, where she confessed to leaking the documents.
The Intercept published the documents on June 5, 2017, headlined “Top Secret NSA Report Details Russian Hacking Effort Days Before 2016 Election.” Lightly redacted, the papers showed creases as if someone had folded up the paper, and featured watermarks including the date and time the document was printed, which was May 9, 2017 at 6:20am, along with the printer’s serial number.
After a lengthy trial, Winner was sentenced to five years and three months in prison. According to NBC News, Winner’s sentence was the longest ever for the federal crime involving leaks to the media.
Where Is Reality Winner Now?
Reality Winner on 60 Minutes.
On June 4, 2021, Reality Winner was released from prison early on good behavior. NBC News reports she currently lives near Corpus Christi, Texas and is prohibited from leaving the state of Texas, as she’s on probation until November 2024. Winner has a nightly curfew, and has to report any interactions she has with the media.
While there’s not much more information of what she’s up to, her lawyer Alison Grinter Allen told The New York Times, “It would surprise me if advocacy and activism was not a part of her life going forward.”
Milan Polk is an Editorial Assistant for Men’s Health who specializes in entertainment and lifestyle reporting, and has worked for New York Magazine’s Vulture and Chicago Tribune.
