In 2017, former Air Force specialist Reality Winner was working as a contractor for the Department of Defense, and she leaked classified intelligence to the online publication The Intercept revealing that Russia’s cyberwarfare division had intended to hack our elections in 2016. Because she leaked this information, Winner, whose politics skew left or at the very least anti-Trump, was arrested and eventually pled guilty to 63 months in prison. The documentary argues that Winner should be freed and celebrated because she was a good-hearted veteran who only wanted to let her fellow citizens know that the Russians were trying to hack our elections and the Trump Administration was possibly trying to cover up that information because Trump hated anything that cast doubt on his surprise 2016 victory.
Kennebeck’s portrait of Winner is frequently confusing and only serves to raise more questions. If Winner was such a brilliant linguist and voracious reader, then why did she make so many obvious mistakes in leaking intelligence? She went to The Intercept rather than a more established publication that had a history of protecting sources (one could argue that because The Intercept was founded by journalists who worked with Edward Snowden, who is in the documentary and another advocate on Winner’s behalf, Winner decided to trust them, but also Edward Snowden is in exile in Russia for the rest of his life seeking a pardon he’ll never receive, so ask yourself how well it worked out for him), and when FBI agents came to her door, she talked to them freely without seeking any kind of legal representation, thus indicating a stunning amount of naivety of how much trouble she was in or a failure to consider the full consequences of her actions.
There’s no interview with Winner (we get the interrogation tape from her June 2017 arrest, but everything after that comes from letters and calls to her parents rather than a one-on-one with Kennebeck, who, after her 2020 movie Enemies of the State, seems to be making an unfortunate habit of doing documentaries absent a central figure whose direct input would make the project come together), so we don’t know exactly what she was thinking or if she assumed she could remain an anonymous whistleblower. It’s also unclear what Winner’s larger goal was here. In the Snowden case, you can see his argument that if the government is spying on its own citizens, then that’s a violation of the 4th Amendment. Winner’s leak concerned the actions of the Russian government, and in December 2016 the Obama Administration had already sanctioned Russia for election hacking.
Kennebeck never gets into this level of detail because her entire case is built on Reality Winner being a good 25-year-old woman whose private texts were misconstrued, and her service to her country overlooked. That’s an incredibly weak argument because we don’t have a legal system based on personal morality; it’s based on laws. Now if you want to argue that the laws themselves are unjust, then that’s a case you can make, but Kennebeck fails to do so beyond showing that the government holds all the cards, which, no shit. Rather than laying out a better system for if and how classified information should be leaked to the public, Kennebeck retreats to trying to make us root for Winner as an individual, which means the entire case falls apart because the central tension here is not about Winner’s personality. It’s about law, classified intelligence, and the role of whistleblowers. Anything beyond that purview is largely irrelevant beyond getting people to donate to Winner’s legal fund.
This review isn’t to say Winner is a “good or bad” person or that her actions were “good or bad.” This review is to say that the movie about Winner and her case is bad. Kennebeck failed to recognize the larger implications of this case, failed to address her subject directly (it feels like Kennebeck started this documentary before Winner pled guilty, and when that happen, she lost her entire narrative arc of “Free Reality Winner”, not dissimilar to how Kennebeck also lost her main subject in Enemies of the State, which is why that film also fell apart), and failed to even create sympathy in this particular case by making Winner look shockingly ignorant of what may happen to her. If you believe that Winner is a good person and doesn’t deserve the fate that has befallen her, then you certainly don’t need a feature-length documentary to tell you that. For anyone looking for an investigation into the larger issues raised by Winner’s case, you’ll be left wanting.
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