In the summer of 2017, a 25-year-old government contractor exposed detailed evidence of Russian interference in the 2016 election. Reality Winner printed out classified U.S. Intelligence documents, hid the papers in her pantyhose as she left work and then put them in the mail to The Intercept. The report they published was the first piece of concrete evidence shared with the public proving that the United States possessed tangible evidence that Russians hackers attacked American voting systems.

After The Intercept published the story complete with scans of the original papers authorities immediately traced the leak back to Reality Winner. She was arrested, denied bail and is now serving five years in a federal prison. Kerry Howley wrote an in-depth profile of Reality Winner for New York Magazine and joins to share the compelling story of who Winner is, why she did it and the severe treatment she's received at the hands of the United States government.

KERRY HOWLEY: It's about, in the wake of 9/11, this massive secret state that we build that's outside of democratic processes. It's not accountable to anyone. We don't even know what it costs necessarily. That's massively geographically distributed and involves 100,000 of our fellow Americans who go to work every day and can't tell their families what they do. And it's like, who are those people, right? And we picture 60-year-old white men who are grim in suits. But no, there are people like Reality Winner. There are young people, people who have been pulled into this world that's completely hidden.

CHRIS HAYES: Hello and welcome to Why Is This Happening? with me, your host, Chris Hayes.

So, there's basically three prongs to Russian interference in the 2016 election two of which we basically have comprehensive knowledge about (or a lot of knowledge about), and one of which remains somewhat murky and occluded.

The first is the hacking of emails, right? They hacked the DNC server, they hacked John Podesta's email who's the campaign chair, I think, for the Hillary Clinton campaign. Those emails then were distributed via WikiLeaks and they drove huge amounts of press coverage, were very damaging to the Clinton campaign. We know about that thanks to both forensic reports from private firms, from statements put up by the intelligence agencies, and also most comprehensively the Mueller indictments that walk through the hacking operation.

There's also the kind of bot network, the Internet Research Agency, which was doing all this stuff on social media, trolling and running Facebook ads, and even in some crazy cases organizing groups of demonstrators, like of Americans from their headquarters in St. Petersburg, I believe. So, that's one

And then the third is in some ways like the most ominous but also the one that's been the least transparently discussed and that is Russian hackers probing various U.S. elections systems. We have some information about that. Some has been made public, some has been made sort of half-public. There's this thing that keeps happening in which the government will say that [the Russians] attempted to penetrate certain election systems, and then not tell us which ones or to what extent.facet.

And the first time that we really learned about the attempts by Russian hackers to get into election software which, let's just keep in mind that this is real kind of apocalyptic stuff, right? I mean, a foreign intelligence apparatus penetrating the software upon which U.S. votes are registered is really scary stuff. I mean, you could imagine them deleting and mass voter registrations causing chaos. You could imagine them in the most extreme setting, changing vote tallies.

None of that happened as far as we know, evidence that any of that happened but they were rooting around those systems, and the degree to which they were able to penetrate them remains somewhat unclear. And in the summer of 2017, June 2017, there was an article about this effort. It was sort of the first big published article, and it appeared in a publication called The Intercept.

The Intercept was an interesting place for it to appear. The Intercept was founded in 2014. It was bankrolled by Pierre Omidyar, who is the billionaire who made a bunch of money in eBay, and its of first three big flagship founders were Laura Poitras, who's a filmmaker who documented Edward Snowden's time in that Hong Kong hotel room. If you've ever seen a movie about that, it's incredible. Glenn Greenwald, who was the person who got the Snowden documents. And Jeremy Scahill, longtime reporter and writer who worked for The Nation, among other places.

And the sort of editorial perspective of the publication has always been deeply skeptical of the intelligence apparatus, intelligence officials, the U.S. military industrial complex has championed whistleblowers folks like Edward Snowden. That term is obviously loaded when you're talking about Edward Snowden, but from their perspective, he's a whistleblower.

And there had also been, I think, sort of prominent editorial voices there: Greenwald chief among them, had been very skeptical of stories about Russian election interference and manipulation, that that should be taken with a grain of salt, that perhaps it was being overstated and manipulated. And so when this story appeared in The Intercept, it was both a huge scoop.

The story had actual U.S. intelligence documents that showed that Russian hackers had attempted this spear phishing which is the way they got into Podesta's email against a variety of American election software firms. Again, big deal, and it was the first, if I'm not mistaken, first time that we really had concrete evidence that there was tangible intelligence info that the U.S. government had possession of that showed the scope of the ambitions of what Russian hackers were doing in 2016.

That story was published. It was very notable and interesting. It appeared in The Intercept when what it demonstrated seemed to be in some tension with the kind of posture of some of the most prominent editorial voices there. And then a few days later, the person who leaked this information, a contractor with the NSA, a woman by the name Reality Winner, was arrested by the FBI. She was denied bail and ultimately sentenced to five years in federal prison.

Now, what she did was a violation of law. It was classified information that she leaked. That's illegal, but the treatment of her has been honestly insane. There is no credible evidence that the publishing of this information harm national security in any way. In fact, a lot of it hasn't been made public subsequently. In fact, there's a good case to be made it's information we should know as an informed public.

She is serving a five year sentence in federal prison and she is a really interesting case because she's the kind of person that you could imagine being kind of cause clbre as happens often with whistleblowers. People who come forward to distribute information they feel the government is hiding that the public should know about. But she's a strange case because she doesn't have a kind of natural ideological cohort backing her.

The folks on the left, who are very skeptical of intelligence agencies, and the so-called deep state, fit awkwardly with what she was trying to demonstrate in her leak, which was to convince the folks at The Intercept that the Russia thing is real. It's really happening. They really, really did do some gnarly stuff and you should take this seriously. So, there's not this sort of like built-in kind of base to support Reality Winner on the elements on the left ideological spectrum, that have been the sort of base for support of intelligence, whistleblowers and leakers.

And on the right, she was showing that Russia really was putting it some on the scale on behalf of Donald Trump. And there's no ideological appetite on that side either.

And so her case, I think, has been caught in this kind of shameful limbo. And what's been done to her is just to my mind, insane. I mean, what she did was rash. It was impulsive, it was a violation of both the law and what the oath she had taken in her job. All of that is unquestionably true, but five years in federal prison for what she did is just an unbelievable penalty.

And the government's treatment of her, as you'll hear in this conversation, has been just relentlessly punitive at every single turn. And the human story of who she is and why she did what she did is a super compelling one. I first kind of came upon the full human story in this fantastic profile that was written about her back in 2017 by a phenomenal nonfiction writer named Kerry Howley. It's called Who Is Reality Winner? And subsequently Kerry wrote a screenplay about Reality Winner that has now been acquired, and I think it's going to go into production. It can be an upcoming film called Winner.

And I had been wanting for a while to take a deep dive on Reality Winner's case, because it's stands at the nexus of so many of the issues that kind of run through our discourse right now about who to trust, about the so-called deep state, about the ways in which career government officials are wrestling with the Trump era and the Trump moment and when to go against their bosses and when to make information public and what we know and don't know and what secrets lurk out there. All of which kind of hangs over the entirety of our political discourse in the moment of Trump, particularly in the wake of the manipulation of the 2016 election and the criminal sabotage conducted by a foreign intelligence agency in Russia.

So, Kerry Howley very kindly agreed to come on the podcast and talk about who Reality Winner is, what happened to her, what her story is and I think it is both an incredible story about the moment we're in in this country and also just a really, I think, moving human story about the complex motives that go into a person who decides to take a risk like Reality Winner did.

I want to just start at the most basic level with the story because I think the details of it are not very well known despite the fact they are fascinating and unnerving in many ways. Maybe just tell me: Who is Reality Winner?

KERRY HOWLEY: Right. Reality Winner was a 25-year-old NSA contractor working in Iranian aerospace at NSA, Georgia in Augusta. One day she walked into her job and she had come across a document that detailed Russian election interference at a level of detail that we hadn't yet seen publicly at that point.

She prints it out, that document, folds it up, put it in her pantyhose and walked out, and sometime later mailed it to The Intercept, where it was subsequently published and she's currently serving a sentence of 63 months in a maximum security in Fort Worth for that crime.

CHRIS HAYES: That is a pretty long sentence.

KERRY HOWLEY: It's the longest sentence ever for a leak prosecution...

CHRIS HAYES: The longest ever?

KERRY HOWLEY: Yes.

CHRIS HAYES: Let's go back. I mean, the first thing when I heard about this story, and this is a dumb surface thing, but her name. The first thought was like, "Who is the kind of person who's named Reality and to which household does a baby come that then gets named Reality?"

KERRY HOWLEY: I think that has actually been a problem for raising awareness of Reality's case and the analysis does tend to stop there. Like, really? In this age in which everything seems so absurd we're going to add the name Reality Winner to the pile? But another hilarious aspect of this is that she has a sister named Brittany. Brittany and Reality. Her father gave her that name. Her parents had decided that her mother would get to name the first and her father would name the second.

The larger question of who is Reality Winner is a fascinating character study. I mean, as soon as I started researching this, I was hit with just how hilarious this person is. The legal documents that I was accessing just to begin the story, to begin the process of telling the story, involved her FBI interrogation. She's hilarious in her FBI interrogation. Her Facebook messages, which were brought up in court with her sister are very funny.

She's a vegan, she's a social justice activist. She is a gun rights supporter. She's just one of these millennials who crosses lines, right? She doesn't fit easily into any particular box. That made her really fun to write about.

CHRIS HAYES: How did she end up working as a contractor for the NSA?

KERRY HOWLEY: That's a really good question. And it's really the animating question, I think, of the profile and in some ways the film. How does this person who is so invested in social justice, thinks of herself as someone who raises awareness about all these causes, about what she has great anxiety, like global warming and Syrian War orphans and African elephants? How does this person end up, not just at the NSA, but a contractor for the NSA?

It's a very complicated question to answer. It starts with her joining up with the Air Force, which is something that I think she saw as a humanitarian act. She didn't see the goals of her idealistic humanitarianism and joining up with the military to be intention at all. And I don't think many people in Kingsville, Texas, where she's from necessarily do.

And so she signs up and she ends up actually in the drone program. She's trying to go abroad. She ends up a linguist. So, the Air Force trains her as a linguist. She's fluent in Farsi, Dari, and Pashto...

CHRIS HAYES: Wait, let me just stop you there. I mean, the armed services always need more people who speak languages like those. It's very hard to train people to speak them because those languages are difficult to learn if you're a native English speaker, and the world of people that can train and learn Dari and Pashto is fairly small. It's not like learning Spanish. She must have some considerable aptitude if she's able to acquire some level of mastery or competence in those.

KERRY HOWLEY: Absolutely. I mean, I think she was very good at her job. All of this is classified. It's very hard to get people to talk about their participation in the drone program. But those who would talk to me said things like, "She was excellent and very professional," and she clearly had an aptitude for languages and she had this job where all day long she's listening to communications and she knows she's eavesdropping on people in Pakistan, transcribing. And those translations were used for military actions, right? People, it seems, would have died due to her translations. It's a very serious, troubling job that I think caused her a lot of anxiety and guilt.

CHRIS HAYES: She goes into the air force with this kind of... She's someone who's very animated by social justice, really cares about global causes particularly, she goes into the Air Force with a kind of view that this would be a means to that end. She ends up training as a linguist and then she's surveilling folks in Pakistan and using the product of that surveillance to target people that will then be blown up by airstrikes.

KERRY HOWLEY: Yes, and I think her vision had been, "Okay, I'm going to go in for a little while. I'm going to learn these languages and then I'm not going to use these languages to eavesdrop. I'm going to use them to go over to Pakistan and work in a refugee camp," or some direct kind of helping.

CHRIS HAYES: She saw this as sort of a step on the way and then she has these language skills and she can go help these folks directly.

KERRY HOWLEY: I think so, and she's constantly trying to deploy. She's trying to go abroad, but there just isn't that opportunity. When she finally gets out, she's searching, and this later it comes up in her trial. When the DOJ attempts to characterize her as some nefarious terrorist sympathizer, she's searching for jobs in Afghanistan and Pakistan with nonprofits, but she doesn't have a college degree because she's gone straight into the Air Force.

KERRY HOWLEY: And there is this pipeline from the military into these contractor jobs because these military contractors are always desperate for people who have security clearance. When she cannot find a job that she wants, she ends up at this contractor, which was never, I don't think, the future she envisioned herself.

CHRIS HAYES: Wow. That's fascinating. She gets these language skills. She's on the drone program. She wants to go do nonprofit working. She ends up sort of through this kind of inertia.

KERRY HOWLEY: Right, this conveyor belt, this machine. Yeah.

CHRIS HAYES: Because they need people that are already... have clearance, and she finds herself doing... What is the work that she does for the NSA contractor?

KERRY HOWLEY: What we know is that she was working in the field of Iranian aerospace. I don't know more than that or really what even that means.

CHRIS HAYES: She's there. At this point, do we know what her sort of feelings are about, I don't know, the war on terror, the American state, the American military industrial complex, her role in all of it? Does she have kind of... in the case of, say, Edward Snowden, there's this kind of trajectory of a kind of dawning awareness in which he starts out thinking like, "I'm gung-ho about this," and then being, "There's serious abuses and this is too much." And kind of having this sort of crisis of conscience. Does she have an arc like that here?

KERRY HOWLEY: It's not so clear. I mean, I think it's complicated. I think that she was deeply troubled by atrocities that she was listening to and hearing about that were committed by ISIS. In some way she saw herself as protecting the vulnerable when she was at the NSA... or in the drone program, excuse me. But she also... she was no fan of Donald Trump. She mostly had very progressive politics. She has this compulsion to help. She's one of these people who is constantly trying to improve everywhere she is.

She's not great at compartmentalizing. She, like many 25-year-olds, believes very strongly in her own capacity to see right from wrong. And that is really... it's a great character to write because if you are determined to improve everyone you meet and every situation you find yourself in, that's a recipe for conflict. And it's like a disaster for the NSA, which depends on conformity and compartmentalization.

CHRIS HAYES: Yeah. The whole point is you do what you're told and you do it competently and quietly, but you're not like... no one's looking for Joan of Arc, right?

KERRY HOWLEY: Right.

CHRIS HAYES: ... in those situations, that's not what you're looking for.

KERRY HOWLEY: I think one of the things that attracted me to this story is ... I can remember being 25 and the intellectual rigidity of that time. It's a time, I think, of great intellectual fulfillment and certainty, and to confront a 25-year-old with a question of, "Are you going to respect the oath you made to this federal agency or an obligation you think you have to the American electorate?" I think that's a great burden to put on an intellectually engaged 25-year-old.

CHRIS HAYES: Why is that the question she faces?

KERRY HOWLEY: The document she came across detailed a spear phishing attack on a provider of election software which had been successful. The Russian intelligence had attained login credentials and was then able to email a bunch of state level election officials. And this was a time we forget that this ever happened but this was a time when people on the left and the right were saying things like, "There is no hard evidence that the Russians attempted to interfere in our election." She was hearing that on Fox News, which was played consistently at her job at NSA Augusta, to the point where she actually filed a formal complaint asking them to change the channel.

CHRIS HAYES: Are you serious?

KERRY HOWLEY: Yes. This is her, right? She gets to a place and she's like, "Things need to change."

CHRIS HAYES: Like, for instance, "You need to shut off the Trump TV on my television."

KERRY HOWLEY: Yeah. She's also hearing it at The Intercept, which is a publication that she was following. She asked for a transcript of a podcast that The Intercept had done in which someone states, "Literally there's no hard evidence that the Russians have attempted to interfere in our election." And so you can see one way to tell this story is that she was responding to that statement.

CHRIS HAYES: Around what time is this, that this is happening?

KERRY HOWLEY: This was May 2017.

CHRIS HAYES: Right. What's frustrating about that is that it had been pretty well established by May 2017. You've got the intelligence agencies saying back in 2016 that that's their determination, but I can understand people being skeptical of them. But you also have private security actors who say pretty quickly, "Look, we've done a forensic review and the Russians were in these systems, they were definitely in the DNC." There's a fair amount of evidence by May 2017, but it's an important point I just want to stay on, which is that there are lots of people denying that for a very long period of time, on the left and on the right.

KERRY HOWLEY: Right. And the Obama administration I think was... they were worried about being too loud about this, because they didn't want to be seen as sewing paranoia about the election in a way that looked like they were trying to rig things for Hillary Clinton. And so they would send out these very vague notices to state level election officials, "Be on high alert," the kind of thing where it's like you're getting a notification to change your password, but what really didn't came across was a level of specificity that was new.

And, in fact, after the document appeared, the Election Assistance Commission which is the federal agency whose job it is to communicate with state level election officials sent out an alert saying, Hey, look at this. This is new to us. State level election officials were upset, they said, No one told us about this attack and we would've like to have known about it.

CHRIS HAYES: So her specifically, you're saying she's watching Fox News and she's listening to The Intercept podcast, and The Intercept had some folks who are skeptical about Russian interference. She gets a transcript of a podcast in which someone is saying there is no hard evidence, and then she comes across this not just hard evidence, but truly astoundingly unnerving hard evidence which is like, they didn't just get into the inbox of a dude named John Podesta (which itself was massively destructive to the entire election) but a log in into an election software company. It's pretty scary stuff.

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KERRY HOWLEY: Yeah. The potential to change voter rolls is scary, and I think she felt... What she said during her FBI interrogation was, "I can't believe this wasn't already out there, that someone else hadn't already leaked it."

CHRIS HAYES: And it's funny because subsequently there's been reporting on precisely this, independent of her leak. Right? It has sort of come out through different reporting, that it's been the subject of tremendous controversy. You have a situation in Florida in which Bill Nelson was running for Senate and sort of said... mentioned offhandedly that their state election system had been penetrated, or at least attempted to be penetrated, and people were like, What are you talking about crazy old man? And then it turned out that he was right.

KERRY HOWLEY: Yeah. Yeah. If you talk to election security experts, they'll say, This is precisely the kind of thing we've been worrying about publicly for a long time, but nobody listens because who wants to talk about election... people get bored immediately when you say the words "election security." But this idea of the vulnerability of vendors apparently had been a weakness that people knew about, and now those experts can say, Look, it's actually happened, here's the evidence.

CHRIS HAYES: Is it an impulsive situation where she prints this thing out? Is it a plant? Is it, she's like, I'm going to set these people right ? Because what's so crazy to me about this leak is that she is trying to correct the false sense of media figures that she trusts. She's like, No, you guys, I like you and you're right about so many things, but you're wrong about this and I want to just show you that you're wrong.

KERRY HOWLEY: Yeah. My impression and something that she does say in a jailhouse phone call is that it was impulsive, but I think we can say it was impulsive and came from good intentions.

CHRIS HAYES: Right. I guess my point is that she's a strange sort of figure because this is not whistle blowing, in the sense she's not like, Oh, look at this abuse that's happening in the surveillance agency I live in. Or like, Look at these civilians that we the U.S. government killed. It's, No, actually the attack against the Americans by the Russians is a real thing, you skeptics of Russian interference.

KERRY HOWLEY: Right. And I think it's been really frustrating to her family that not only other leakers like say, Petraeus, or the president has also shared classified information, have not been punished in the same way.

CHRIS HAYES: Yeah. We should say the president is different constitutionally because all classification authority flows from him, so he can declassify anything he wants to.

KERRY HOWLEY: Sure. But take the example of Petraeus. He was charged with a misdemeanor and never did any jail time. Other people, like say, Michael Cohen or Maria Butina people who did not have the best of intentions have done less jail time or been sentenced to less jail time, and I think that's been of great frustration to her and her family.

CHRIS HAYES: I want to get into the chain of events that led to her arrest and sentencing and we'll do that after this break.

So she prints this out, she smuggles it out and what does she do with the printout?

KERRY HOWLEY: She snail mails it to The Intercept.

CHRIS HAYES: And they get it and they write a story based on it?

KERRY HOWLEY: They get it, and this becomes quite murky, we've never gotten a full accounting of what happened and why, but... I'm not an investigative reporter but my understanding is when you get a leaked document, you never share the image of that document with the agency from which it was leaked, because that has traceable information.

CHRIS HAYES: Right.

KERRY HOWLEY: That someone at The Intercept sent an image of the document to a contractor who was then legally obligated to show it to the NSA, which then immediately located Reality. Only a few people had printed this out. Only one of those people had downloaded a transcript from The Intercept. And...

CHRIS HAYES: She did that on her government account, on her contractor account?

KERRY HOWLEY: I believe so.

CHRIS HAYES: Oh, God. There's traceable information because there's actually... My understanding is there's a security system on the printer. That it's built in. That there's traceable signals embedded in the document that say who printed out the thing.

KERRY HOWLEY: Yeah, that's my impression too. So it's not entirely clear why that happened from a publication that prides itself on supporting whistleblowers, and of course was founded with the intention of disseminating information that Snowden had acquired, but she was basically immediately apprehended after that.

CHRIS HAYES: So in the course of reporting, they share the document; the document makes its way back to the NSA. The NSA does not have a very tough detective trail to trace down until they find that this contractor who's working for them in Augusta, Georgia printed this out and apparently leaked it. What's the timing between... from how long The Intercept gets it to her being arrested?

KERRY HOWLEY: I think it's a while before The Intercept publishes it because they think it's probably fake, because it's postmarked Augusta. I think it took them a while to trust that this was legitimate. But once they published it, it was a matter of hours before [the authorities] were at her house.

CHRIS HAYES: Oh wow. So it gets published and they're there in a matter of hours.

KERRY HOWLEY: I think so.

CHRIS HAYES: What is the government... what do they charge her with and what's the case like that they build against her?

KERRY HOWLEY: They charge her with willful retention and transmission of national defense information, which is under the Espionage Act which is, of course, an act intended to punish spies, but which really the Obama administration used very zealously to punish whistleblowers and leakers. And so she has almost no opportunity to mount a defense because, under this act, intention doesn't matter. She's already confessed in her laundry room to the FBI...

CHRIS HAYES: Wait

Kerry Howley and all they have to do is... She confessed.

CHRIS HAYES: Wait. OK, let's step back. She confesses in her laundry room? Take me through that.

KERRY HOWLEY: They show up at her door... It's a riveting transcript, which has actually been turned into a stage play in which she's really charming, and funny and intelligent and vulnerable, but she deflects for a while and then she says basically, I felt helpless. I wanted to know why this information hadn't already been leaked.

And so, when it comes time to mount a defense, there's very little available to her defense team. And every motion they made to kind of broaden the case to questions of the First Amendment was rejected, so she basically had to take a plea deal because they were seeking a full 10 years.

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Explaining why Reality Winner is still in prison with Kerry Howley: podcast and transcript - NBC News