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

Chris Hayes talks to New York Magazine's Kerry Howley about Reality Winner, convicted of leaking information about Russian election hacking.

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 it’s 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 célèbre 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?


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?


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.

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.

Image: David Petraeus
Commander of the International Security Assistance Force/U.S. Forces in Afghanistan General David Petraeus shakes hands with author Paula Broadwell in this ISAF handout photo originally posted July 13, 2011.ISAF / via Reuters file

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.


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...


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.

CHRIS HAYES: She confesses in the laundry room and the government seeks 10 years. What is the government's case for why they are throwing the book at her?

KERRY HOWLEY: This is really amazing. They use everything in her life to try to build a case that she is essentially in league with terrorists — this is early in their prosecution. So things like, she would message... She's very sarcastic in a way that would be very familiar to us as young Gen Xers or millennials, right?

CHRIS HAYES: As sarcastic people? As professional...

KERRY HOWLEY: As sarcastic people, yeah, as professional sarcastic people. She'll message her sister, "I have to take a polygraph where they're going to ask if I plotted against the government #goingtofail." And then her sister will be like, "Lol, just convince yourself you're writing a novel." And then she'll be like, "Look, I only say I hate America three times a day. I'm no radical." And the prosecution will be like, "She says she hates America three times a day." Right?


KERRY HOWLEY: Yeah. And this happens over and over with many things that she said. She had written in her diary, in a fit of rage, "After Trump was elected, I think I want to burn down the White hHouse." And they're like, "She wants to burn down the White House."

She taught herself Arabic, I think when she was in high school. I think she had done this because she was very effected by 9/11 — that happened when she was eight or nine — and she'd had these very serious discussions with her father about why had this happened. She was interested in communication, thinking the world would be a better place if we could talk to one another, and so she taught herself Arabic. And in the hands of the prosecution it's like, "Why'd you teach yourself Arabic?" They asked her mother this in this accusatory way, like it's so she can, I don't know, join up with America's enemies.

And things like, she was constantly smashing her phone, she has a temper. And so they'd be like, "Why do you have four smashed phones?" Or, "Why do you have so many laptops in your closet?

CHRIS HAYES: Four smashed phones is a little weird.

KERRY HOWLEY: I don't know if it was four, but it's just a bunch of... I don't know, who doesn't have a bunch of old laptops in the house?

CHRIS HAYES: Yes, totally.



KERRY HOWLEY: And also, those searches she had done when she had left the drone program and was looking for those jobs and refugee camps and nonprofits, those were all searches about going abroad. She was looking for jobs abroad and they took that to be incriminating. So they build this absurd case — which no one buys now — that she was plotting against America, and that was used to deny her bail. She's been in prison since that day.

CHRIS HAYES: Wow. And all these people like... I don't know, like Lev Parnas and Igor Fruman are out walking around, bopping around. Harvey Weinstein had an ankle bracelet that he disabled 57 times. Did I read that in news just today? Michael...

KERRY HOWLEY: And for a while Manafort was just waltzing around.

CHRIS HAYES: He was waltzing around until he literally just kept breaking the law and they had to put him in jail. But like Michael Flynn who ... What Michael Flynn did was like literally work for a foreign government, literally worked for a foreign government while not disclosing that, and then lying about it to the FBI. He never got kept without bail. She had the book thrown at her.

KERRY HOWLEY: Another thing that the prosecution keeps doing during this case is claiming that she's done exceptionally grave harm to national security, for which they offer not one iota of evidence, and none is required. Once you try to interrogate that...

CHRIS HAYES: They assert that.

KERRY HOWLEY: They assert that. And once you try to interrogate that, well, of course, "We can't share that because it would be a violation of national... it would endanger all of us." This happens constantly during the trial, that the defense wants information but that can't be revealed for national security purposes. Also, she has lawyers in Atlanta and Augusta and elsewhere, but they can't talk about the case unless they're in a SCIF, so it's very hard for them to even coordinate.

The classified aspects of this create all sorts of problems. And then Mueller, in an indictment relating to this election interference, an indictment of some of these Russian actors, reveals the exact same information that Reality had leaked, but apparently it didn't cause grave...

CHRIS HAYES: That is what's so insane about this, that independent of her leak and the article about it in The Intercept, this same information — and even a broader set of that information — is independently produced by the Department of Justice, the same entity that prosecutes her. They put into public unredacted, unclassified indictments that are meant for public consumption the exact information — that is supposed to harm national security — that she leaked.

KERRY HOWLEY: Precisely.

CHRIS HAYES: I guess the argument they can make is like, Well, it's already public, but it also seems to me that the other argument is that it wasn't that great of a threat to national security at all, and in fact, probably good for people to know this generally. Even in a national security sense, in the beyond the lookout sense, it seems important. So she pleads and she agrees to a sentence of 53 months you said?

KERRY HOWLEY: Mm-hmm. 63 months.

CHRIS HAYES: 63 months. Jesus Christ. So five plus years. Where is she now?

KERRY HOWLEY: She is currently in a maximum security prison in Fort Worth, Texas.

CHRIS HAYES: Maximum security?


CHRIS HAYES: That's really wild. How is she doing?

KERRY HOWLEY: It's tempting to say, She's strong, she's doing well, she's helping people. She wakes up every day in a cage and I think it's really hard. This is her third birthday that she spent in prison — she just had a birthday. I think it's frustrating to see that Russia continues to be in the headlines but she isn't really getting... There's no awareness of her role in this, people don't know who she is. I think it's very hard to be in prison every day and be 28 years old.

CHRIS HAYES: It's interesting you say that because I think that she, because she sort of, you said earlier in the conversation, that she kind of scrambles categories, crosses ideological lines, that she hasn't been kind of called a celeb for her whistle-blowing, essentially — or whatever you want to call it — in the way that others have, certainly like Edward Snowden, because the object of it was not about the U.S. government's excesses. If she had done that, then I think a huge contingent of the folks that celebrate Edward Snowden would be rushing to kind of her defense. But they, generally, are just AWOL on her case as far as I can tell.

KERRY HOWLEY: Yeah. I mean, I think even with Snowden — with any national security whistleblower — there's always this desire to hedge to say, like, Well I'm glad we have the information, but she should have gone through proper channels.


Image: Thomas Drake
Thomas Drake, former senior executive of the U.S. National Security Agency (NSA) turned whistleblower, arrives to testify at the Bundestag commission investigating the role of the NSA in Germany on July 3, 2014 in Berlin.Adam Berry / Getty Images file

KERRY HOWLEY: And it reminds me of the argument that immigration restrictionists make like, Well they should get in line. And, obviously, you and I know there's no line, and the proper channels don't really exist at Reality's level. I mean, other people who have gone through proper channels, like Thomas Drake or William Binney, have been viciously retaliated against. So, that wasn't necessarily an option here. And I think people are uncomfortable just out and out supporting national security whistle blowers for whatever reason.

CHRIS HAYES: Well, but let me sort of give the other side of that argument, right? I mean, let me give sort of an analogous situation. This has much lower stakes.

Occasionally, there will be leaked tape from inside a control room of off-air conversation. And I always have sort of an interesting feeling about it, because at once it's like sometimes that can be newsworthy. The "ABC killing the Epstein story," which was the most... that's newsworthy, right? But, like, the person that did that also, in a kind of deep sense, really betrayed a bunch of people's trust profoundly. That space is a really vulnerable space in some ways, it's both on-camera and not on-camera. And, so I always feel conflicted about that.

And I guess I have that feeling times 100 when the stakes are what we're talking about here, which is that there is just — not even from a national security perspective, just an organizational perspective — there's got to be some rules about people just taking documents out and giving them to people, because you can't run any kind of organization that way. And you certainly can't run the national security apparatus that way.

KERRY HOWLEY: Absolutely, but that's why, when these people are prosecuted, one should be able to consider context, and intention, and effect. And none of that was possible in Reality's trial, right?

CHRIS HAYES: Yeah. I mean I think it's very clear in her case that, like, she should have pleaded to a misdemeanor and done no time. I guess I'm just saying that there has to be some kind of thing that says you can't do that, as opposed to a free-for-all of all people can take all documents and disseminate them however they feel.

KERRY HOWLEY: Right. But one could also argue we're so far in the other direction, right? The secret state is so vast and unaccountable, and outside the democratic process that I'm not sure that's that big of a concern at this point.

CHRIS HAYES: Yeah, I think that's right. And I mean, when you think about the sheer volume of secret documents being processed every day and the amount that we see this is infinitesimally small percentage of those documents are ever being leaked out.

KERRY HOWLEY: Right. And that's why I think Reality's story really starts not with the Trump administration; I don't think it's about Trump. 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, like 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: I mean, there's a big NSA presentation at like the annual hacker conference in Vegas, which i ... I remember when I was young and really into computers and used to read "2600" and stuff like that. And I forget what the name of the conference is — there's been big hacker conference every year in Vegas — and the NSA sends people to that, including (sometimes) the head of the NSA, to go, like, recruit hackers who have a wide variety of anarcho- hacker-ish views that then end up working for the NSA because they need people who have incredibly, insanely good math and hacking skills.

KERRY HOWLEY: Right. And there's, obviously, huge redundancy. There are so many separate agencies doing the same thing, recruiting the same people. I think Reality is such an interesting window into this world because it's exactly what you don't expect, but there must be so much more of that.

CHRIS HAYES: It's also, like, the sort of ferocious vengeance of the state when it's crossed that is so unnerving here. That we have these rules, we set them up, we've got this ancient, outdated and sort of awful piece of legislation called the Espionage Act, which was passed — we should note — it passed in 1917. It's right around the time of the first Red Scare, and what's called the Palmer Raids, in which you have the Bolshevik Revolution that happens in Russia and there is huge fear about American communism. There's a huge purge of them. The Palmer Raids is our sort of FBI raids of subversives. There's also actually quite a bit of anarchist violence at the time. There's bombs being set off on people's lawns, but that's the context in which this act is passed that she's being prosecuted under.

KERRY HOWLEY: Right. And there's also this constant — going back to, in the wake of 9/11 — there's this invocation of the words "national security" more as an incantation than as an argument that's used to just shield everything from questioning.

And so there's this huge absence, right? We don't know anything about this world. It's so hard, as a journalist, to get inside. And then when you have a demagogue come to power, maybe it's not hugely surprising that he's able to say, This is actually a vast conspiracy meant to unseat me and deny you the man that you voted for.

CHRIS HAYES: Right. The idea that there's this deep state, this secret government that secretly... I mean the funny thing about it as the secretly liberal state.

KERRY HOWLEY: Right, exactly.

CHRIS HAYES: God knows the FBI, bastion of liberalism.

KERRY HOWLEY: But if you build this absence, then, like, Trump can project his fantasies onto it, right?

CHRIS HAYES: Yeah. I think that's true. Although, I also think that he can project his fantasies onto anything, but yes.

I mean it's funny to watch the current politics of, like, I wrote a piece in The Nation in 2009, which was when Obama was president and there was unified control of it. It was a really important moment to have essentially something like a Church Committee — which is started in the wake of Watergate, led by Frank Church, who's a liberal Democratic senator, to sort of overview and reform the practices of the secret government, the CIA, the FBI, a lot of hugely important reforms, like statutory reforms, come out of that. The FISA process, for instance, which is obviously still broken — but this idea that we can't have this metastasized, unaccountable universe in which we try to assassinate foreign leaders by like sending them poisoned toothpaste and things like that, a thing that actually happened.

And we've never had that reckoning; we've never had that reckoning. There was the kind of look-forward, not back, of the Obama administration, this sort of continuation of most of the major institutional structures on the war on terror. And now that's been — in this crazy way it's been — inherited by Donald Trump, who has both proliferated it, continued it.

Look, I mean, this is the thing that drives me crazy. It's not like Donald Trump or any Republicans have pushed on any serious structural reforms to surveillance, to FISA, to oversight, none of that. No. Instead, they've continued all of it in their votes and in actions, but they have rhetorically turned against it as a kind of convenient scapegoat for whatever political problems he faces.

KERRY HOWLEY: Yeah, and now it's entrenched. I mean places like Augusta, Georgia or Tampa, Florida are full of contractors, private organizations that are making a lot of money off of surveillance doing... well, we're not really allowed to know what. It's just become mundane, but they continue to recruit people and the secret state continues to grow.

CHRIS HAYES: It's interesting to watch, when we watch sort of the whistleblower situation play out, which is what prompted the impeachment is that just, like, looking at, though there is an IG for the director of national intelligence (which is a position created post-9/11), but we haven't had any big wave really of serious comprehensive reforms to the post-9/11 secret state.

KERRY HOWLEY: It's interesting. I'm not a national security reporter, so I came to this material very fresh, and what I was reading it was so abstract. It was like everything you read about surveillance either it descends into computer science jargon, or the finer points of the Fourth Amendment, right? It's not character-driven, it's kind of unclear what surveillance is, like what it's made of. It's made of waves, and like it's made of flesh and bone. It's made of these people who go to work every day. And there's this like massive infrastructure, right? But people never talk about it with that kind of specificity and solidity.

And so I think it just, like, passes through our consciousness, the way that we're all a little bit anxious about privacy, but we're not going to think about it hard enough to actually like update our phones on time, because that would be stressful.

CHRIS HAYES: Right. I mean that, to me, is the other part of this conversation, which is there's a broader conversation about the sort of sprawling growth of the sort of security state, people's anxiety about that. But that also sort of like pales in comparison to our other anxieties. Like, part of the reason I think it continues to perpetuate is just that there's a lot going on, and a lot that's scary.

And I don't know: Alexa, there's someone in Amazon listening to every moment of me losing my patience with my son saying his socks are uncomfortable as we're trying to leave the house, which, by the way, for the love of God, please, please...)

KERRY HOWLEY: The seams, the seams.

CHRIS HAYES: I can't take it anymore. Please, we've gone over this. Your socks, these are the comfortable socks that I'm giving you. These are the ones you specifically told me were comfortable. How are they uncomfortable right now? Anyway, that's it.

KERRY HOWLEY: Well, then he has to put on his shoes...

CHRIS HAYES: Yes. And then that's uncomfortable too. But like Alexa has all that information, clearly. Is someone sitting in listening there at Amazon?

The sort of scope of our paranoia is so big and you're right that, like, the secret state is so formless, and sort of opaque and gray, and there's these people doing something, and I don't know if it has to do with me or not, but I don't know, it just seems like a remote risk.

KERRY HOWLEY: But that's what became so clear to me when in reporting this story, I drove up to NSA Augusta — which you're not supposed to do. And before I was escorted out, I'm in this vast parking lot, right? So I'm driving through Fort Gordon, which is like a very dilapidated, just normal looking military base. And then, rising up before me is this spaceship-like, smooth white building, gleaming, multi-million dollar construction. Clearly new, clearly very well-funded, and it's surrounded by this vast parking lot full of cars. And it's like, "Oh, people work here. It's full of Camrys and Jettas. It's like all of these middle class people come to this building every day and conduct secret business."

CHRIS HAYES: Yes, it's an industry. It is, like, it's its own industry. It's spread out across the country and people just have nine to five.

KERRY HOWLEY: They go to work.

CHRIS HAYES: Yeah, they punch in and they, I don't know, like, listen to people's conversations. I don't know what they do. I genuinely don't know what they do either.

KERRY HOWLEY: Right. And that solidity is interesting to me. There's this $1.5 billion data center that exists in Utah. It's the size of nine city blocks. It's in the middle of nowhere. And all day long, it collects every kind of information, emails and love letters, and health records, and parking tickets. And it's all amassed in this physical building. In this physical building, it's very hot, and requires millions of gallons of water to cool it down to protect the data that's being collected. All of this is going on, but just kind of filters past our consciousness somehow.

CHRIS HAYES: Is there any hope for Reality Winner getting out early, or she is just going to, barring a pardon which doesn't seem forthcoming, is going to have to serve out the sentence?

KERRY HOWLEY: I can tell you that her family would love for your listeners to go to, and she has a lawyer who's collecting letters of support for clemency. I don't know what the prospects are for that, but I think just kind of talking about her story, her family's very grateful for that, because it really hasn't broken through for whatever reason.

CHRIS HAYES: Yeah, I mean, I personally feel like she has done more than enough time for what her infraction is, and it's just absurd and outrageous for her to be kept behind bars. I mean, I feel that way about, like, hundreds of thousands of people too, I should note.

KERRY HOWLEY: Right, she's not alone there.

CHRIS HAYES: As I often say on this program, so I don't want anyone to mistake me that this is a... there are so many people, but her case really is pretty outrageous.

Kerry Howley wrote a 2017 New York Magazine article called “Who is Reality Winner?” And she has a biopic in the works. She's writing the screenplay for it, called "Winner," which I'm very, very excited about. Thank you so much for joining us.

KERRY HOWLEY: Thank you so much for having me.

CHRIS HAYES: Once again, my great thanks to Kerry Howley. You can read her fantastic profile “Who is Reality Winner?” in New York Magazine. It's on the internets, and she's got a screenplay for an upcoming film, "Winner," which you should look for as well.

We had a great time doing the mailbag and we always love to hear your feedback. Even when we're not doing mailbags, you could tweet us #withpod, email

If you're listening to this in the week in which we publish it — which is not everyone — but if you are and all this stuff is happening in the Middle East right now. there's two podcasts we did that I think are really useful for understanding some context for the fallout from the US air strike that killed Qassem Soleimani, there's a podcast we did with Dexter Filkins. It was one of the first three podcasts we put out back in May of 2018 in which Dexter (from the New Yorker) talks about Qassem Soleimani, and the Quds force, and the sort of Iranian activity in the region, and the kind of escalating proxy war between Iran and Assad and Hezbollah, and this kind of Sunni access of Saudi Arabia, and the United Arab Emirates and sometimes with the U.S. and Israel as well. It's a really useful context for what happened.

There's also a podcast we did just in November of last year with James Verini about the Battle for Mosul, which was how the Iraqi army took Mosul back from ISIS, and that's really relevant too because James does incredible reporting about just the reality of life during war — a period of uninterrupted, unending war for the Iraqi people for decades now — and what it's meant for that society, what it's meant for the people on the front lines of that, which is all of course extremely relevant right now as everyone is bracing for further escalation in the region. So definitely check those out.

Why is This Happening? Is presented by MSNBC and NBC News, produced by the "All-In" team, and it features music by Eddie Cooper. You can see more of our work, including links to things we mentioned here by going to


Who Is Reality Winner?,by Kerry Howley

The Secret Government, by Chris Hayes

Untangling the Middle East with Dexter Filkins: podcast & transcript

Looking back at the Battle of Mosul with James Verini: podcast and transcript