I try not to be an envious person. The green-eyed monster is the enemy of contentment. But as a cable news commentator, I’ve always been jealous of my fellow talking heads who appear in movies and television shows as themselves. It’s a rather common practice—though it has led to occasional controversy, such as when the head of CNN declared it had been a mistake for its anchors and correspondents to be in Contact, the 1997 Jodie Foster film based on a Carl Sagan novel, reporting on the (didn't-really-happen)
first communication between extraterrestrial aliens and humanity. But usually it seems harmless enough. Oh, look, there’s Rachel Maddow in Ides of March! I always thought it was, well, cool.
Finally, I have made it into a film. At the end of Reality, a new dramatization of the arrest of Reality Winner, the young NSA contractor who leaked an intelligence report about Russian intervention in the 2016 election, footage appears of me on a news show in 2018 commenting on the unprecedented sentence—five years and three months—she had just received for the unauthorized release of national security information to the press. This punishment, I noted, was “exceedingly long” and “obviously there to create a chilling effect so that other people don’t do this, and we stay in the dark.”
Winner, you might recall, printed out an intelligence report detailing that Russian hackers had “executed cyber espionage operations” to target local voting systems in the United States. At a time when President Donald Trump and his Republican comrades were denying that Vladimir Putin had attacked the US election, Winner believed this was important information for the public to know, and she anonymously mailed a copy of the report to the Intercept, which published the document. Unfortunately for her, the Intercept sent a copy of the document to the NSA in order to get a response and published the memo, which contained printer tracking dots. This allowed the feds to identify her as its source.
After hearing of my cameo, I quickly turned on the movie, an HBO production streaming on Max. (Admit it, you would, too.) I expected to watch just the opening 15 minutes or so and return to it later, but I was so gripped by the film I could not push the pause button.
Reality, directed by Tina Satter, is based on a play she wrote called Is This a Room, which itself was drawn from the transcript of the FBI’s interview with Winner when she was arrested. The afternoon the G-men showed up at her rental house in Augusta, Georgia, they made an audio recording of the entire interaction with Winner, a US Air Force veteran who was working at an Army base translating documents from Farsi for an NSA contractor. All the dialogue in the movie comes straight from the transcript of the recording, and the film covers only the few hours between the arrival of the feds and the moment when Winner is hauled off. There are a few flashbacks to her work at the Army facility. But essentially this is a lengthy one-act.
It's utterly fascinating.
The film reveals how the two agents—Justin Garrick and Wallace Taylor—used sly interrogation tactics in an intimidating setting to bond with Winner and eventually compel her to acknowledge she had mailed the document to the Intercept. They display concern for her dog, but do not inform her of her Miranda rights. They do not initially explain why they are there. As the interrogation proceeds—while Winner’s home is being searched by a squad of agents—they whittle away her defenses, revealing what they already know one small piece at a time.
The feds have Winner dead to rights. But they are consumed with the question of why she took this action. Might she be another Snowden? Though a viewer knows where this will end, the movie is 80 minutes of nonstop tension. Sydney Sweeney (White Lotus, Sharp Objects, Euphoria, and Once Upon a Time in Hollywood) is brilliant as Winner, aptly depicting a young woman who is striving to understand the situation and calculating what she should or shouldn’t be saying. Is it best to acknowledge what she did? What can she withhold from her interrogators? Josh Hamilton plays the wheedling and awkward Garrick to perfection. We’re just trying to understand what happened here, he sympathetically reassures her (falsely) over and over, as he fishes for a full confession.
The film functions as a piece of theater—which is hardly a surprise, given its origins. Winner and her inquisitors are isolated in an unfurnished back room of her home. There’s not even a chair. Just three people standing and working through a morality play. It is something of a psychological thriller, as you watch the gears whirring inside the heads of Winner and the FBI agents. This is a detailed and captivating case study of interrogation—going far beyond the usual good-cop/bad-cop routine of Hollywood. Through all the back-and-forth, the tale of Winner’s life and her motivation for this one consequential act is revealed.
I could not tear myself away from the drama, and at the end I was pleased to see that Satter used my soundbite to cast Winner in a positive light. She did break the rules, but she informed the public. Her sentence was excessive. Prior to her conviction, she was denied bail and branded a terrorist-sympathizer by the prosecution. She initially pleaded not guilty but later struck a deal, admitting guilt to one felony count of revealing national defense information.
The movie boasts one of the most important qualities a film can have: good timing. Her case resonates this week, with the indictment of Donald Trump on 37 felony charges for allegedly mishandling classified information, obstructing justice, and lying to the FBI. When Winner in 2018 was sentenced, Trump, then president, tweeted in support of her: “Ex-NSA contractor to spend 63 months in jail over 'classified' information. Gee, this is 'small potatoes' compared to what Hillary did! So unfair Jeff [Sessions], Double Standard." Trump was using her case to bash his attorney general, who by then he despised for having appointed Robert Mueller as a special counsel to investigate the Russia scandal. Trump, though, took no steps to pardon Winner or commute her sentence.
Which brings us to the present. On Friday, Winner, who was released from prison in 2021, said she was “blown away” by the Trump indictment. As NBC News reported:
Winner became the first person to be prosecuted and then sentenced under the Trump administration for defying the Espionage Act by leaking classified information. Now Trump faces 31 counts of willful retention of national defense information in violation of the Espionage Act—as well as other counts related to making false statements and conspiring to obstruct justice.
"This is probably one of the most egregious and cut-and-dry cases," Winner, 31, said in a phone interview.
Winner told NBC News that the Espionage Act, under which Trump, too, has now been charged, has often been used in vague and inconsistent fashion by federal prosecutors. But she pointed out that the Trump indictment was remarkably specific regarding what documents he took and that it made clear he did so for no greater public good. She suggested this case could even be helpful for future whistleblowers:
This is probably one of the most transparent and straightforward indictments that defines national defense information and gives the public a sense of the itemized description of every document, which is not how this particular law has been used against ordinary citizens. So this might set the new legal standard on how it will be used in the future. Perhaps it could give people like myself who were acting out of moral conscience more leverage under the law."
Okay, back to me. With Reality, I can cross one item off my bucket list. But, far more important, it’s an honor to be associated with such a fine piece of art and an important act of whistleblowing. With the nation pondering how Trump’s handling of 31 classified documents will affect the future of American politics, it’s the right moment to watch this all-too-relevant and important movie.
