“United States v. Reality Winner” is a principled, soulful documentary about the National Security Agency contractor who sent a document outlining Russian election hacking and influence efforts to The Intercept, only to be imprisoned for her efforts. Directed by Sonia Kennebeck, who previously made a film about drone-program whistleblowers, the 2021 movie provides a welcome introduction to the case, as well as an investigation into the nature of whistleblowing itself, its effects on one’s psyche and family, and whether our vast secrecy apparatus is compatible with democratic self-rule when it so routinely deprives the public, and even government officials, of information they have the right to know. But Kennebeck is still seeking distribution for her movie. Unless you happen to catch it at a festival (or via a reviewer’s copy, as I did), it’s nearly impossible to watch it. Is there a better metaphor for the public’s indifference to the excesses of the national security state?
On July 30, Kennebeck will premiere another new film, Enemies of the State (this one will be available in theaters and on demand). It tells the tangled, paranoid tale of Matt DeHart, a former participant in the Anonymous hacktivist collective, a Wikileaks associate, and an Air National Guard intelligence analyst who, after a disturbing and murky legal ordeal, including a failed asylum bid in Canada, was imprisoned on child pornography charges. That is only part of the story: DeHart’s parents cooperated extensively with Kennebeck’s film; DeHart himself failed to show up for his scheduled interview. The result is an extraordinary, unsettling documentary that’s just as much about DeHart’s devoted parents—former Army linguists who became convinced of their son’s persecution by the FBI—as it is about a young hacker and information activist facing legal jeopardy.
Taken together, these documentaries confirm Kennebeck’s emergence as one of America’s foremost cinematic chroniclers of the post-9/11 security state. Like Laura Poitras, who won an Oscar for Citizen Four, her film on Edward Snowden, Kennebeck is an acute observer of the complicated psychology of whistleblowing and its inevitable, uncontrollable fallout (whether DeHart, who ran a server for Wikileaks, was ever truly a whistleblower is one of the film’s animating questions). In methodically exploring the lives of her subjects and their families as they come under the unforgiving microscope of the authoritarian surveillance state, she has offered thoughtful, at times enraging, accounts of a national-security apparatus that may be beyond reform. Rather than providing a legal framework for safeguarding collective security, Kennebeck seems to argue, our elaborate structures of official secrecy and classification have made criminals of everyday people seeking to do what’s right. They also have created an unbridgeable gulf between an uninformed populace and the anointed class of securocrats that’s supposed to watch over them.
Whereas Winner’s case—in which she received a 63-month sentence, longer than any previously handed down to a press leaker, before being released on good behavior in June—projects a certain moral and narrative clarity, DeHart’s is far more complicated, resisting easy summary. In short, DeHart claimed that he was imprisoned, drugged, and tortured, and extensively interrogated by the FBI in a dubious but wide-ranging espionage investigation that cast DeHart as a traitor looking to sell information to foreign powers. DeHart also claimed that he had information—bound for Wikileaks but never delivered or otherwise published—that showed that the CIA was responsible for the 2001 anthrax attacks, which were never solved. (It remains unclear why DeHart never released this information publicly.) No charges were filed against DeHart as a result of the FBI investigation, which turned his parents’ lives upside down. He eventually pleaded guilty to lesser charges in a child pornography case, claiming, like others in similar situations before him, that it was the simplest way to settle his legal ordeal. Having served his sentence, he now lives with his parents in Indiana.
The secrecy and intrigue surrounding DeHart’s case, the difficulty in reconciling his possible guilt as a child pornographer with his apparent suffering at the hands of an unaccountable security state, makes Kennebeck’s disturbing, occasionally mind-bending film an altogether more impressive achievement. Without falling into false equivalences, Enemies of the State suggests DeHart is neither purely victim nor villain, worthy of sympathy but also, perhaps, an abuser who is deluded as to his place in history. The film opens by aptly quoting Oscar Wilde, who wrote, “The truth is rarely pure and never simple.” In Enemies of the State, truth is irreparably complicated; it’s also fungible in the service of state power.
Beyond questioning the strictures of governmental secrecy, both films point to the corruption and authoritarianism that may be inherent parts of a state that engages in mass domestic surveillance and unbridled, permanent warfare on multiple continents. In such an imperial system, the law is sacrosanct, unquestionable, with no room for mercy or consideration of motive. As United States v. Reality Winner chronicles, the Espionage Act, which has been used to target numerous leakers and journalists since 9/11, does not care about intent. A World War I–era law that predates our current classification system, the Espionage Act considers only whether classified information was disclosed to someone not authorized to receive it.
Consequently it didn’t matter that the single document Winner shared provided useful public information—without revealing clandestine sources or intelligence-gathering methods—about Russian attempts to hack election-related infrastructure. She broke the law and was punished forcefully for it, in what U.S. attorney Bobby Christine admitted was an effort to discourage future leakers. Calling her an “insider threat,” guilty of “treachery and betrayal,” who hated America and endangered national security, Christine promised that there was “very real damage done”—a claim belied by a lack of subsequent fallout, along with the fact that some state election officials thanked Winner for what she did. As Edward Snowden remarks in the film, in handing down a stiff sentence, the government exhibited “this weird kind of celebration” over what should have been a somber case, prosecuted “with some level of regret.”
While the stakes of Winner’s case are clear, there are some lingering questions. Interviewing other government whistleblowers like Thomas Drake, who disclosed information about NSA surveillance programs, and John Kiriakou, who was jailed for speaking out about CIA torture, the film asks how The Intercept could have been so sloppy in handling Winner’s material, which arrived anonymously in the form of a printed document. That document contained tiny microdots that could be used to identify who printed it, where, and when. Perhaps unaware of this fact, Intercept reporters sent the document to the NSA, asking them to authenticate it. While, as Intercept Editor-in-Chief Betsy Reed argues, Winner might have been arrested anyway—it’s hard to avoid the all-seeing eyes of billion-dollar intelligence agencies—this step contributed to her unmasking as the article’s source.
“It begs some really uncomfortable questions about what was the intent of The Intercept reporters of record,” Drake says in the film. “What did they actually share? Or what did they protect?”
Kiriakou is less forgiving, invoking his own experiences with investigative journalists at NBC, The New York Times, and The Intercept: “Because of their carelessness—subterfuge might be a better word—I spent two years in prison.” About Winner’s document, he suggests, “they either didn’t know that or didn’t care” about the security features.
Although the reporting of Winner’s story has been investigated by other journalists, a haze of uncertainty persists. Kennebeck’s film states that Matthew Cole and Richard Esposito, the first two of four journalists bylined on the story, didn’t respond to requests for comment. The other two reporters credited on the story—Sam Biddle and Ryan Grim—go unnamed in the film, which also blurs their photos in a shot of the article itself. While the Intercept’s parent company helped fund Winner’s legal defense, no one appeared to face professional consequences for their role in outing Winner to the government. Strangely—and perhaps troubling for a former investigative journalist who worked on national security stories—Richard Esposito now works as a spokesman for the New York Police Department, a job that practically requires stonewalling and otherwise misleading journalists.
But the truth of Winner’s arrest is secondary to what brought her to that position. A lively personality and heterodox thinker—an animal-loving yogi critical of U.S. foreign policy, who owned a pink AR-15 and helped translate communication intercepts for drone strikes—Winner sublimated her own interests in service to a state that, as soon as she strayed a millimeter from the law or shared ideology, had no use for her. The same happened to DeHart, who was discharged by the Air National Guard for depression—a decision he unsuccessfully challenged. One gets the feeling that DeHart, a technically talented computer obsessive who followed in his parents’ footsteps by joining military intelligence, simply wasn’t suited to being part of a regimented military machine, not when his own instincts told him that classified information should be set free. And although the film doesn’t suggest it outright, one wonders if Winner’s service—which included a commendation for contributing to bombing missions that killed hundreds of alleged enemy combatants—proved similarly disillusioning. She may have leaked that document to The Intercept in part because she saw that her own government wasn’t telling the truth about what it knew.
In a sign of their moral maturity, Kennebeck’s films exhibit sympathetic concern for her human subjects and deep skepticism at the systems that rule over them. With DeHart, there are too many unresolved questions not to think that some injustice occurred. Why was the FBI so keen to interrogate him without ever charging him? (DeHart’s parents claim that the FBI wanted to cover up its knowledge of CIA involvement in the anthrax attacks.) Why was DeHart drugged and tortured in custody, to the point where he collapsed in court and, in another instance, landed in an emergency room? Why would the FBI interrogate DeHart’s grandmother about the political loyalties of her daughter, DeHart’s mom?
While their stories differ in the particulars, Winner and DeHart belong to a growing club of whistleblowers, dissidents, political prisoners, hackers, information activists, former intelligence officers, and other distinctive characters who have come under the withering gaze of the national security state. Some have been prosecuted and jailed; all have suffered materially and personally. The very facts of their stories are sometimes subject to debate, but each story must be told, because each is an outrage, a civil libertarian nightmare that persists long after the camera goes dark.
The somber truth at the heart of Kennebeck’s films is not just that agencies like the FBI or NSA operate according to their own logic of secret governance; it’s that the problems they produce might be insoluble. As Matt DeHart’s father suggests, there is practically nowhere a person can go to protect himself from the United States—unless he has the bizarre misfortune, as Edward Snowden did, to end up stuck in the Moscow airport, passport canceled, while in flight from American authorities. There is no easy escape from the watchful gaze and political influence of a globe-straddling empire. But no matter how many times the U.S. government makes an example of people like Reality Winner, it’s clear that some insiders will only feel more emboldened to risk their safety to leak information in the public interest. Or as Snowden put it, simply and hopefully, “There will be others.”
