Column: The story of whistleblower Reality Winner is stranger than fiction

Reality Winner arrives at a courthouse in Augusta, Ga. on Aug. 23, after she pleaded guilty in June to copying a classified U.S. report and mailing it to an unidentified news organization.
(Michael Holahan / Associated Press)

At a which-side-are-you-on moment in American politics, some of the most intriguing figures are the most ambiguous. One of these is so ambiguous that the binary brain can hardly take her in: Reality Winner.

The very normally named Reality Winner might be a Rorschach test for … something.

Perhaps it’s a test for whether you consider Islamic terrorism or Russian cyberattacks the greater geopolitical threat. Or whether you prioritize government transparency or national security. Or whether you see a naive young woman with a big brain who inserted herself into international affairs as enterprising — or suspicious.

It would be a good Rorschach test if it featured an inkblot that evoked nothing but a hallucinatory kaleidoscope of more inkblots.


Reality Winner is a prodigiously intelligent former National Security Agency contractor and Air Force vet who, at 25, exposed significant classified details of the 2016 Russian attack on U.S. voting software and Russian spear-phishing of local voting officials. She did so almost a year before the Justice Department issued the blockbuster indictment that fleshed out her findings.

Not one person who has aimed to suppress the facts of Russian election interference is in jail. The only one in prison is Reality Winner.

She accepted a plea deal and on Thursday was sentenced to more than five years in prison.

Winner has been scathingly critical of the president for selling out the United States to Russia.

But Trump, who believes the Russia affair is a witch hunt, has expressed support for her. And journalist Glenn Greenwald, who believes Democrats are using the Russia affair to distract attention from their electoral losses, has also expressed support for her.

(Greenwald’s employer, the Intercept, has been accused of being careless with documents that Winner shared anonymously, putting her in legal jeopardy. The publication’s parent company, First Look, has a Press Freedom Defense Fund, which supported Winner’s defense.)

Is Winner a patriot or a traitor? And what does it even mean anymore to be a patriot or a traitor? Those terms are as confusing and mysterious as Winner.


When every day seems to bring one more tale of jaw-dropping corruption or treachery or personal eccentricity, Winner is stranger than most of the truth that is itself stranger than fiction.

She is a yogi and CrossFit trainer born on the coastal bend of South Texas who is also a prolific cryptologic linguist, fluent in Arabic, Farsi, Pashto and Dari.

She was honorably discharged from the Air Force. Beginning at age 21, she worked in the drone program and provided the U.S. with intelligence gleaned from intercepted polyglot chatter. Winner’s efforts won her a medal of commendation for “aiding in 650 enemy captures, 600 enemies killed in action and identifying 900 high-value targets.”

Yet in a diary she recorded support for Taliban leaders and Osama bin Laden, according to a U.S. magistrate judge. And prosecutors tried to paint her as anti-American; they cited a shocking, if deeply ambiguous, line in that diary: “It’s a Christlike vision to have a fundamentalist Islamic state.”

The inkblots multiply into inkblots that multiply into mayhem.

She gathered documents relating to Russian election interference, which she acquired using her top-secret clearance while working for government contractor Pluribus.

The Winner documents sketched out — before indictments by the Justice Department decisively confirmed — that Russian intelligence carried out a cyberattack on at least one supplier of voting software and spear-phished more than 100 local election officials days before the November 2016 presidential election.


She is the first person prosecuted by the Trump administration for leaking classified information. In legal parlance, for “gathering, transmitting or losing national defense information.”

Finally, Winner is the beloved daughter of Billie Winner-Davis, a stalwart at #KremlinAnnex, the antic and long-running demonstration against what protesters see as the president’s treason.

Trump may not have known this history. On Friday, he seemed to praise Winner on Twitter — if “praise” is the right word for leveraging a mention of Winner into a clumsy broadside against Atty. Gen. Jeff Sessions and former Secretary of State Hillary Clinton. “Ex-NSA contractor to spend 63 months in jail over ‘classified’ information. Gee, this is ‘small potatoes’ compared to what Hillary Clinton did! So unfair Jeff, Double Standard.”

Oh, Trump. Winner-Davis took his tweet as a chance to ask him, whom she has faulted for treason, to pardon her daughter. Naturally, she solicited this pardon on Twitter. Because all statecraft and geopolitics now take place in 280 characters with bluebird logos flitting around. Or are those logos inkblots?

Not one person who has aimed to suppress the facts of Russian election interference is in jail. The only one in prison is Reality Winner, who sought to expose Russian military operations against the U.S.

“I don’t think any family — I don’t think anyone — could ever imagine something like this.” said Winner-Davis last year. She was wearing a T-shirt that said, “I stand with Reality.”


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But it was something else Winner-Davis said that struck me as useful for elucidating the how-did-we-get-to-Reality-Winner question.

“Our family was a very regular, normal family,” she said. Then a beat. Then a reversal.

“No, we weren’t normal,” she concluded.

Nice honesty. It’s time to stop saying anything is regular or normal anymore. America has shipped way, way out from shore. We have Russian cyberattacks, a president who denies them, and a hero-antihero embraced by no one — neither resistance types, because she worked in drone intelligence, nor Trumpites, because she blew the whistle on the Russia affair. We were once a regular, normal America. But, no, we aren’t normal anymore.

Twitter: @page88

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