Educational Media Reviews Online

This documentary is a portrait of Reality Winner, a retired U.S. Air Force veteran and military contractor who leaked a classified intelligence report on Russian interference in the 2016 United States elections. She was only 25 years old when arrested by the FBI in 2017; she was 26 years old when she decided to plead guilty to the charges of espionage in 2018.

There are two key aspects to the documentary: one covers who she is and the other considers what she did and the consequences. The one that covers the real Reality Winner dominates: her devoted family, her home in Texas, her beloved pets, her personal feelings and reflections, her mental health, and her American dream. We spend time with her mother, Billie Winner-Davis, her sister, Brittany, and her stepdad, Gary, as they stand by her through her trials and tribulations. This portion of the film is quite emotional and will persuade viewers to empathize with her as a person of integrity. One of the film’s strengths is in showing unconditional mother-daughter love. Billie rallied behind her daughter and built support for her daughter’s case in every way possible. There are scenes of her at rallies, talking to lawyers, packing up t-shirts, and learning to work social media. Reality Winner’s parents divorced when she was seven years old. Her birth father, who named her Reality as he wanted “a real winner” (as told by her mother), also greatly influenced her character and that is covered in the film. He died in 2016 before her arrest and trial.

The second aspect concerns her being charged with the Espionage Act, a law from 1917. The original intent of the law was to prosecute spies during World War I. However, in recent years it has been used against whistleblowers who leak security secrets. Winner explains how the law is binary – you did or you didn’t share intelligence – and does not allow for the consideration of the ethical reasoning of the whistleblower. The film features three representative government workers who were prosecuted under the act: Edward Snowden (whistleblower on the National Security Administration’s mass surveillance programs), Thomas Drake (NSA executive and whistleblower on government corruption), and John Kirakou (CIA officer who disclosed torture). They were all interviewed but Drake actively advocated for Winner; he was seen at rallies with Billie to show his support. Drake’s case was compared to Winner’s as she initially pleaded not guilty to the charge and was hopeful of a lenient sentence (Drake received one year probation and community service). The U.S. government decided to charge Winner harshly to make an example out of her; she was given five years and three months in prison, more than any comparable conviction. Snowden expressed that, nonetheless, people of conscience will continue to do the right thing regardless of consequences.

Documentaries have been made about the cases of her predecessors; to name a few: The Most Dangerous Man in America: Daniel Ellsberg and The Pentagon Papers (directed by Judith Ehrlich and Rick Goldsmith, 2009), director Robert Greenwald’s War on Whistleblowers: Free Press and the National Security State (2013), and Citizenfour (Laura Poitras’ 2014 Academy Award winning documentary about Snowden). In these documentaries, viewers consider the ethical tension is between the conscience of the whistleblower, the government’s power to silence dissent, and the free press.

Poitras co-founded The Intercept with Glenn Greenwald and Jeremy Scahill in 2013 with the media organization First Look Media (Poitras left the in 2015 and Greenwald in 2020). The publication’s mission is to “expose corruption and injustice” and one means to do that is to intercept government information. The Intercept’s then editor, Betsy Reed, appeared in the documentary, recognizing that the publication failed Winner. To verify the document, Reed shared it with the government; yet the document contained coding that revealed Winner’s identity. Proper measures were not taken to protect their source. While First Look Media assisted Winner with her legal fees, she expressed resentment at their mistake.

In addition to Ines Hofmann Kanna of Codebreaker Films, some of the listed producers are familiar names: Abigail Disney (grandniece of Walt), Tony Hseih (late CEO of Zappos), Roger Waters (of Pink Floyd), and Wim Wenders (esteemed filmmaker). Director Kennebeck used crowdfunding platform Kickstarter to re-edit, license footage and distribute the film after Winner was released from prison for good behavior in 2021. Winner was in the fourth year of her sentence when she was released; she continued to serve home confinement with an ankle bracelet (there are close-ups of it as she exercises). Some of the credits may be from large donations (IMDB links out to the Kickstarter page with a funding period from November 2022 to January 2023 and lists major funders). Considering the funding may be of interest to students studying documentary filmmaking.

The documentary is well crafted with Sonia Kennebeck as director and Maxine Goedicke editing. To their credit, the filmmakers obtained audio recordings from the FBI through FOIA requests. One key scene that employed reenactors is the tense interrogation of Winner by the FBI agents. The scene is dramatic. In addition to this documentary on Winner, the story has inspired a play (Is This a Room and later an HBO Film called Reality). In the documentary, most of Winner’s story is told directly by her shot from the shoulder up and provides a sense of talking to someone across a table from you.

Because this film addresses a problematic law, a sympathetic character who sacrifices for a decision of conscience, and the importance of a free press, it is innately provocative. Students can wonder if they would decide to leak information to the public if it was important for the public to be informed. They can consider whether the Espionage Act should be repealed or amended.

During the post-production of the film, news came that former President Trump is charged with 31 criminal counts under the Espionage Act for illegally keeping government documents upon leaving office and not returning them; in his case, he could have evaded charges by returning the documents, but his refusal resulted in an indictment (the filmmakers were able include a note about the documents found in former President Trump’s Florida home).

Additional questions can be posed in the classroom: Why are whistleblowers of the government being charged with spying? What is the legal difference between a leaker and a whistleblower? Should there be protection for those who share classified national security documents to inform the media? How can the press best protect its sources when government surveillance is pervasive?

I regard this film as an important story of a brave individual who, not in opposition to her country, but in service to it, shared information with the press about dangers to our election process. Since the document about Russian hacking efforts against the election infrastructure of the United States was made known, efforts to secure it have taken place. It also informed a debate at the time as to whether foreign interference was happening (former President Trump’s connection to it was later investigated by special counsel Roger Mueller from 2017 to 2019). That said, government officials of both parties would not agree given their accountability for national security.

If I had a criticism, it would be to spend more time considering the Espionage Act and what could be done to amend or repeal it. Have there been efforts to repeal it? Are there bills in Congress? Who advocates for reform? Who opposes it?

As we enter the 2024 election season in the year of this review, the documentary could also serve as a history of foreign affairs and a probe of current problems of our democracy. The “Trumps Documents Case” is currently in the U.S. District Court for the Southern District of Florida. The trial has been postponed. Reality Winner was sentenced to five years for one top secret document that was shared to help the country. Such comparisons raise more questions of justice. Will Donald Trump be tried before the election? Why did he not return multiple boxes of classified documents (he is being charged for 31 specific documents that are marked as either secret or top secret)?

One final related story broke as I submit this review: on the 24th of June 2024, Julian Assange, founder of WikiLeaks, agreed to plead guilty to the Espionage Act. The Justice Department recommends a 62-month sentence, but he would be credited with time spent in a U.K. prison. He worked with Chelsea Manning who received 35 years in prison but whose sentence was commuted by President Obama. The film can be considered in the context of similar and ongoing cases.

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