As the FBI’s Q&A session with Winner unfolds, there is some collegial banter between the ex-Air Force recruit and agents (including veteran actor Josh Hamilton—who, interestingly, previously co-starred in Clint Eastwood’s 2011 Hoover biopic J. Edgar—as Justin Garrick) and shares her interest in firearms (she possesses no less than three), bodybuilding and even pets.
But it just so happens that this is much more than a mere social call or friendly questioning of the skilled linguist, who understands Farsi, Pashto and Dari, tongues spoken in Iran and Afghanistan.
Her tête-à-tête with the FBI agents arguably progresses from interview to interrogation to, ultimately, inquisition. During the “voluntary” interview, wherein Winner is never read her Miranda Right against self-incrimination, more and more vehicles filled with feds arrive at and search her house. At one point, agents place yellow crime scene tape around her property. It turns out the FBI suspects that Winner has illegally accessed, printed out and leaked a classified document and arrest the 25-year-old.
Most of the film has a documentarian, at times cinema verité style, as if it was shot by a fly on the wall. The acting by Sweeney is extremely realistic, and the rest of the cast is likewise naturalistic—sometimes it seems as if they’re not even acting at all.
However, there are some filmic flourishes, including quick flashbacks (such as Sweeney folding the top secret report and hiding it in her pantyhose, in order to smuggle the classified document out of her office and mail it to The Intercept) and cuts to a soundtrack as Winner is recorded. When words or images might reveal classified info, they are blipped off or out of the screen, which cleverly, cinematically denotes the redaction of top secret material (and might legally possibly protect the filmmakers by doing so). There also seem to be a few images of the actual Reality Winner. Sweeney’s performance is nuanced and sometimes very interior, and the well-directed film skillfully divulges Winner’s inner state of mind.
Reality narrowly focuses on her questioning by the FBI (wherein she naively or stupidly never asked for an attorney) and doesn’t dwell upon the consequences Winner suffered. She was charged with violating the Espionage Act and sentenced to serve five years and three months in prison. This was the longest prison term ever imposed by a federal court for leaking classified information to a news outlet.
Reality is an impressive directorial debut for Satter. But at 83-minutes-long, it’s quite short for a feature film. Basic information pertaining to Winner’s case is only mentioned briefly, often in passing—if at all. A more experienced filmmaker might have included additional exposition clarifying Winner’s background, what she did and what befell her as a result.
Most of all, Reality arguably perpetrates a crime of omission by not making it perfectly clear what the document Winner stuck her neck out by releasing it to The Intercept was all about. In one of the news clips glimpsed onscreen from time to time, a female pundit criticizes Tucker Carlson and the media for being “more concerned with what Reality Winner did” than with what she revealed. Reality is also arguably guilty of doing the exact same thing.
As I recall, at the beginning of the movie, Winner watches, in disgust, then-President Trump’s dismissal of Russian electoral interference in the 2016 presidential election and she proceeds to break protocol by printing out a report from a secure site regarding “Russian cyberattacks on American voting software” according to The New York Times.
The Guardian contended that the document “detailed how Russian military officials hacked into at least one supplier of voting software and attempted to breach at least 100 local election systems during the 2016 election”
Winner fatefully went on to illegally mail a printout of it to The Intercept in an envelope without a return address (although it is, tellingly, postmarked “Augusta,” which it turns out an Intercept brainstorm negligently disclosed to a NSA source, purportedly empowering the FBI to pinpoint her location, turning Winner into a loser).
After Donald Trump—who was president when Winner was persecuted over a single document—faced a 37-count (now up to 40, as of this writing) in federal court for retention of 300-plus classified documents, including some marked top secret and 32-counts for violating the Espionage Act—the whistleblower told The Guardian his arrest and charges were “incredibly ironic.”
MAGA supporters complain that the legal system has a double standard when it comes to prosecuting Trump. But in comparison to Winner, who was denied bail, Trump has received extremely favorable treatment, not having to have a mug shot taken for the classified documents case or relinquish his passport, as he gallivants about the country a free man, despite threatening judges and prosecutors plus four other criminal indictments coupled with 91 felony charges.
This is in stark contrast to Winner’s severe mistreatment by the judicial system because of only one classified document. While behind bars Winner caught coronavirus and after leaving prison in 2021, she’s still subject to supervised release. But the all-too-short Reality never goes into any of these glaring discrepancies. Although it’s true that Trump was indicted in the classified documents case on June 8, 2023 about a week after Reality was released, the Mar-a-Lago searches took place about a year earlier. A quick title could have been added at the end of the film.
(It seems true, as far as we know, that Trump did not leak any classified documents directly to the press per se, like Winner did, but the latest accusation buzzing about Trump is that he disclosed top secret nuclear information to an Australian billionaire, who purportedly revealed the info to many others, including members of the press. Trump, however, has not been explicitly charged with leaking classified material to the media.)
In Reality Sweeney’s Winner comes across as a conflicted individual who leaks classified information on the one hand, but also volunteers to serve in the U.S. military. After being honorably discharged, she still hopes to be deployed overseas with what Sweeney’s character calls “special forces,” where presumably she can make full use of the language skills she learned while in the Air Force.
Her lack of a formal university education may have been a determining, detrimental factor for Winner. But one thing comes across loud and clear: She is an individual of conscience willing to put herself in harm’s way by taking a bold stand. The film ends with the onscreen words of her heroic statement about that fateful top secret document she courageously disclosed: “I knew it was secret but I also knew I had also pledged service to the American people. And at that point in time, it felt like they were being led astray.”
Did The Intercept “Intercourse” Reality Winner?
Reality briefly alludes to the role The Intercept may have played in the Reality Winner debacle. eBay founder and philanthropist Pierre Omidyar funded the launch of The Intercept in 2014 as a reportorial vehicle dedicated to transparency and accountability, among other things. When The New York Times investigated what it called “the highest-profile journalistic disasters in recent memory” in order to “provide broader insights into the limits of a news organization dependent on an inattentive billionaire’s noblesse oblige,” Omidyar, the professed avatar of openness, declined the Times’ interview request.
Either The Intercept blundered badly and in effect betrayed its source by providing key information that led to the unmasking of Winner, or the intelligence community is using the Winner case to discredit a media entity that had been one of its leading critics. Two top MSM outlets looked into the strange case of Reality Winner vs. The Intercept.
According to Ben Smith in the September 13, 2020 New York Times article “The Intercept Promised to Reveal Everything. Then Its Own Scandal Hit. Internal documents show how a source ended up in jail—and the fallout in the newsroom”
“Ms. Winner, then 25, had been listening to the [Intercept] site’s podcast. She printed out a secret report on Russian cyberattacks on American voting software that seemed to address some of Mr. [Intercept co-founder Glenn] Greenwald’s doubts about Russian interference in the 2016 campaign and mailed it to The Intercept’s Washington, D.C., post office box in early May.
“The Intercept scrambled to publish a story on the report, ignoring the most basic security precautions. The lead reporter on the story sent a copy of the document, which contained a crease showing it had been printed out, to the NSA media affairs office, all but identifying Ms. Winner as the leaker.”
“…‘They sold her out, and they messed it up so that she would get caught, and they didn’t protect their source,’ her mother, Billie Winner-Davis, said in a telephone interview last week. ‘The best years of her life are being spent in a system where she doesn’t belong.’”
The Times went on to allege: “Failing to protect an anonymous leaker is a cardinal sin in journalism, though the remarkable thing in this instance is that The Intercept didn’t seem to try to protect its source. The outlet immediately opened an investigation into its blunder, which confirmed the details that the Justice Department had gleefully announced after it arrested Ms. Winner. They included the fact that The Intercept led the authorities to Ms. Winner when it circulated the document in an effort to verify it, and then published the document, complete with the identifying markings, on the internet.”
Smith added that “two internal reports on the Reality Winner incident that have not been made public, were given to me by people who were senior employees in 2017 and contend that the organization failed to hold itself accountable for its mistakes and for what happened to Ms. Winner as a result.”
He went on to write: “Ms. [Laura] Poitras [another Intercept co-founder and the Oscar winning director of the 2014 Edward Snowden documentary Citizenfour] said The Intercept should have held itself to a higher standard.
“‘We founded this organization on the principle of holding the powerful accountable and protecting whistle-blowers,’ Ms. Poitras said in an interview. ‘Not only was this a cover-up and betrayal of core values, but the lack of any meaningful accountability promoted a culture of impunity and puts future sources at risk.’”
According to the New York Times, one of the two journalists originally assigned to work on the story regarding the document Winner mailed to The Intercept was broadcast news veteran “[Richard] Esposito, [who] was brought in from outside and is now the top spokesman for the New York Police Department.” (Emphasis added.)
Smith’s article also stated: “The startling carelessness about protecting Ms. Winner was particularly mystifying at an organization that had been founded on security.”
“On July 11, 2017, Ms. [Betsy] Reed published a post on The Intercept announcing that First Look would pay for Ms. Winner’s legal defense. Ms. Reed also announced that an ‘internal review of the reporting of this story has now been completed.’
“‘We should have taken greater precautions to protect the identity of a source who was anonymous even to us,’ she wrote. ‘As the editor in chief, I take responsibility for this failure, and for making sure that the internal newsroom issues that contributed to it are resolved.’
“Ms. Winner was sentenced to five years and three months in federal prison in 2018, and The Intercept has covered her case regularly, always noting its own role—‘an important part of accountability,’ Ms. Reed said.
“But there hasn’t been any further accounting. Neither internal report was shared with the public. Nobody at The Intercept was fired, demoted or even reassigned.”
Shortly after the Times piece was published, Greenwald resigned from The Intercept and became a habitue of Tucker Carlson’s Fox News show.
New York Magazine also covered the brouhaha as early as Jake Swearingen’s June 6, 2017 article headlined “Did The Intercept Betray Its NSA Source?”
“[O]n May 24, a reporter from The Intercept reached out to an unnamed government contractor, trying to determine the validity of the leak. During the exchange, The Intercept revealed that the leak had been mailed with a postmark of Augusta, Georgia, where Winner lives… The contractor told The Intercept that they believed the leak to be fake; when The Intercept returned on June 1, saying that the leak’s authenticity had been confirmed, the original anonymous government contractor turned around and alerted the NSA to the matter—including the key detail that the document had been mailed from Augusta… The Intercept provided a copy of the report itself to the NSA on May 30 [which] the NSA then turned the report over to the FBI for further investigation… the decision to publish the PDF with the tracker dots unobscured—especially considering The Intercept likely had no knowledge that Winner was the leaker, and she was already in custody—is a baffling unforced error from a site that hinges on being a secure place to send documents.
“…It’s worth reiterating that the FBI has a strong incentive to cast The Intercept as incompetent handlers of sources. There’s a decent chance that the case was built against Winner in a completely different way—one that didn’t rely on mistakes by the journalists at all—and this particular parallel construction of the case is being put forward to cast aspersions on one of the most notorious investigative outfits online. But there’s no escaping that the mistakes made by The Intercept and Winner—small as they may have been—were enough to get a search warrant and indictment signed.”
Reality is a classic David versus Goliath story (with, possibly, some Judas tossed in) for the era of the high-tech national security surveillance state.
Reality can be streamed on Max.
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About the Author
Ed Rampell is an L.A.-based film historian and critic who also reviews culture, foreign affairs and current events.
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Why the quippy jibe about Glenn going on Tucker’s show thrown in here? Seems unnecessary.