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July 13, 2023 45 mins

Decorated U.S. Air Force veteran and NSA contractor Reality Winner comes across a top secret document that sheds light on one of the biggest scandals in American history. The White House isn’t telling the truth. Reality must decide: would a true patriot leak it, or look the other way? 

 

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
A quick content note before we get started. This episode
contains talk of self harm. If you or someone you
know is struggling with thoughts of self harm, there are
resources in our show notes for today's episode.

Speaker 2 (00:15):
When you're standing there and everybody's in real clothes and
you're in orange, and you're shackled hands and feet, and
you know you're being told that you committed espionage against
your own country, you regret being born, like you want
to die.

Speaker 1 (00:34):
That's a woman whose name is Reality Winner, and she's
describing what's got to be one of the worst days
of her life.

Speaker 3 (00:42):
Reality Winner leaked a secret report on Russian election hacking
to the media and will now serve more than five
years in prison. That's the longest sentence ever imposed for
this kind of violation.

Speaker 4 (00:53):
Reality thank you for joining us on the phone as
you are there in jail. Let me ask you this,
because it was the document that you late that really
brought everyone's attention to this idea about the Russians trying
to infiltrate and attack our state voting systems.

Speaker 5 (01:09):
What has it been like to see.

Speaker 4 (01:10):
The Russia investigation unfold from behind bars.

Speaker 1 (01:15):
That report from CBS This Morning includes Reality's first TV
interview from the Lincoln County Jail in Georgia. The hosts
of the program they seem sympathetic, but I wasn't. As
an official with the Department of Homeland Security, I thought
what she'd done was plainly illegal and in fact, maybe

(01:36):
even treason US. She deserved a lengthy prison sentence, at
least That's how I viewed it at the time. Then
we met after she was released from prison. I'm Miles Taylor,
and this is the whistleblowers on this show were going

(02:00):
deep into the heart of power to meet people who
spoke out about wrongdoing from inside the Trump administration. Some
were in the President's in her circle. Others were on
the front lines of top agencies. But they all have
a few things in common, the ethical gray areas, the
doubts about whether what they did even made an impact,

(02:23):
and they paid a price. Episode two Reality Before people
debated whether she was a whistleblower, or a trader, or
a spy, or even a friend of the Taliban, and
she was called all of those. Reality Winner was a

(02:43):
six year veteran of the US Air Force. She served
in the ninety fourth Intelligence Squadron. But it's worth going
even further back than that. So I called Reality, who's
now living with her mom in Kingsville, Texas, to talk
about her story from the beginning. I really want to
just art way in the background. When I was reading
up about you, I realized you went into public service

(03:06):
partly because of nine to eleven. Take me back into that.
You know, how old were you? How do you remember
the experience?

Speaker 2 (03:12):
Nine to eleven was just a stressful day for any
nine year old. That night, the first thing I did
was call my dad, because he didn't live with us,
and he always spoke to me and my sister like adults.
He was a psychologist and a theologist, and he was
very interested at that intersection where religion can become toxic

(03:37):
and become extremism and can insight violence. I just remember
he would take us to libraries for fun, and I
would go into the reference section and I would trace
the Arabic alphabet and I would draw him maps of Afghanistan.

Speaker 5 (03:51):
That was the only thing I had with my father.

Speaker 1 (03:54):
Mom and dad were separated, Yes.

Speaker 2 (03:56):
Yes, in fact, my mom had just remarried my stepdad mother.

Speaker 1 (04:01):
Billy Winter Davis remembers watching Reality's growing interest in the
Islamic world.

Speaker 6 (04:06):
We had stickers all over the house in Arabic labeling things.

Speaker 5 (04:11):
But not only did she study.

Speaker 6 (04:13):
The language, she was very interested in the culture as well.

Speaker 2 (04:17):
I would talk to Doubt about language and he would
say that we have to understand basically extremism in its
own terms.

Speaker 5 (04:25):
We can't apply our own terms to it.

Speaker 2 (04:26):
And so that was when I became more interested towards
my latter years of high school in combining this level
of language and understanding how to put the pieces together.

Speaker 1 (04:40):
This is what takes her to the Air Force, where
she could apply her Arabic language skills to intelligence work.
She joins right after high school.

Speaker 6 (04:48):
I think that she went into it thinking that she
was going to help with the war and help eliminate terrorism.
I think that that's what she thought what her role
in the military was going to be.

Speaker 1 (05:03):
Reality serves from twenty ten to twenty sixteen, the War
on Terror is in full effect. The US drone program
is very active. She can't say much about her work
in the Air Force during that time. It's classified, but
it's clear she's really good at what she does. She's
awarded a commendation medal for quote assisting in geolocating one

(05:26):
hundred and twenty enemy combatants and facilitating the removal of
more than one hundred enemies from the battlefield unquote. But
six years in, she starts to feel disillusioned with her role.
She speaks fluent pash To, but she's never been to Afghanistan,
and like a lot of Americans, she's exhausted by the war.

Speaker 6 (05:46):
She saw the damage that was being done by this
never ending war, and she really wanted to be on
the ground there to help, and the Air Force wasn't
going to send her there. I'm really proud out of
my time in the uniform, and I'm really proud of
the United States Air Force, But I was getting out
for a reason. I wanted to go towards humanitarian aid.

(06:09):
I was quickly discovering that I didn't have the right
resume for it, that my language training didn't mean anything
on a resume that you needed like a master's PhD
plus plus just to pass out blankets at a refugee camp.
And so like you're really facing like, well, how do
I somehow pivot? And so going into government contracting as

(06:32):
a linguist and then having the freedom as a civilian
to look for other opportunities was what appealed to me most.

Speaker 1 (06:42):
After nine to eleven, the National Security Agency, or the
NSA as it's called, had a vast amount of data
to collect and analyze, so they hired intelligence contractors to
help with the workload. Because these contractors have access to
highly sensitive material, what we used to call the high side,
they need to have top secret security clearance, but they're

(07:04):
still contractors. Hired help from the outside, and that can
make a tight ship a little less so. The most
famous NSA contractor before reality winner Edward Snowden, who exposed
some of the agency's most sensitive surveillance programs. The twenty
sixteen election and the transition into the Trump administration were

(07:28):
awkward times for the US intelligence community, and there was
this one topic that the incoming president just did not
want to talk about. It's like he took it personally.
I spoke to former National Security Advisor Ben Rhoades, who
worked in the Obama administration.

Speaker 7 (07:48):
After the election, we had a meeting in the situation
room with President Obama and the leadership of the intelligence community,
Jim Clopper, John Brennan, the head of the NSA, and
Jim Comey, the head of the FBI kind of laid
out their findings about the scale and breadth of Russian interference.
That was similarly briefed to incoming President Trump, who I

(08:09):
don't think was particularly interested in the facts.

Speaker 1 (08:12):
He's not just uninterested. The incoming president starts to become
actively hostile about the intelligence found inside these briefings. In fact,
Trump vented on Fox News Sunday about the CIA's findings.

Speaker 8 (08:25):
I think it's ridiculous.

Speaker 2 (08:27):
I think it's just another excuse.

Speaker 5 (08:29):
I don't believe it.

Speaker 8 (08:30):
I think the Democrats are putting it out because they
suffered one of the greatest defeats in the history of
politics in this country, and frankly, I think they're putting
it out.

Speaker 7 (08:39):
It wasn't much different than what we all saw publicly
at the time, which was President elect Trump seeing this
as hostile, threatening out to get him, and not at
all engaging in the substance of the information itself. There's
this really comprehensive report that was pretty airtight about the
fact that Russia had done this. That's an incredibly alarming

(09:00):
determination for the intelligence community to make, and an awkward
one given that it was about efforts to help elect
the person that was coming into the office.

Speaker 1 (09:09):
This dismissal and hostility become the story on CNBC. Lester
Holt doesn't get the answer he expects when he asks
Trump directly about Russian hacking.

Speaker 9 (09:20):
Who's behind it and how do we fight it.

Speaker 8 (09:23):
I don't think anybody knows it was Russia that broke
into the DNC. She's saying Russia, Russia, Russia, but I
don't maybe it was. I mean, it could be Russia,
but it could also be China, could also be lots
of other people. It also could be somebody sitting on
that bed that weighs four hundred pounds.

Speaker 1 (09:37):
Okay, it's December twenty sixteen, it's the holidays. Reality is
still looking for a new job and frankly, a new
direction after six years in the Air Force. She's feeling
a drift and she's dealing with a personal tragedy.

Speaker 5 (09:56):
I drive down to Texas to be with my family.

Speaker 2 (10:00):
Day after that is the day that my father died,
and so now I'm just kind of like with a
family over Christmas grieving my father. And then that's when
I got the call and they're like, okay, so we
need you to be at ex Building in Fort Gordon,
Georgia on the state.

Speaker 1 (10:17):
This is how Reality ends up at a company called
pluribis international corporation that provides intelligence services under contract with
the NSA. Now, most people entering that Fort Gordon facility
were not like Reality. Carrie Howley is a features writer
for New York Magazine. She wrote a profile piece on Reality,

(10:38):
and she immediately understood she didn't fit the mold of
a traditional intelligence gatherer.

Speaker 10 (10:43):
She had complicated politics, she was young, interesting and engaged.
She's going to wear two different colored socks. And that
this person, this brilliant, effusive person, so compassionate, so invested
in mostly in the well being of people across the world,
could end up at this strange little contractor that was

(11:08):
selling its services to the NSSA. That story was interesting
to me. How did this person get here?

Speaker 1 (11:16):
Reality is hired as something called a cryptologic language analyst
for this military contractor Pluribus. That sounds interesting, It is not.

Speaker 10 (11:27):
These intelligence jobs tend to be mind numbingly boring. Often
there's nothing to do all day. You feel that your
work is meaningless. I talk to someone who was just
like plotting points on a map, and so you're kind
of desperate for something to do with your time.

Speaker 2 (11:43):
I realized that I could clock in and clock out
and not actually do anything. I had access to YouTube,
and I was watching doctor Sapolski from Stanford would put
up his entire semesters of lectures for free.

Speaker 1 (11:58):
Now one second for context. Doctor Supalski is a neuro
endochronology researcher and author at Stanford University, very well respected,
not most peoples go to when they're bored at work.

Speaker 2 (12:11):
So I was actually taking neurology classes and studying for
a possible massage therapy course instead of my job. There
were so many different contractors there, so I kind of
fell under the cracks. That was when I started freaking out.

Speaker 1 (12:37):
Board at work and reading the news. Reality starts following
the controversy around the construction of the Dakota Access Oil Pipeline,
an underground channel for crude oil opposed by environmentalists and
the Standing Rock Indian Reservation.

Speaker 2 (12:54):
There was going to be a veteran stand at the
Dakota Access Pipeline and it was probably one of the
most violent protests, like the security forces attacking protesters. But
I remember in February twenty seventeen, Kelly and Conway said
nobody was protesting this pipeline.

Speaker 5 (13:12):
And nobody in the room blinked.

Speaker 2 (13:14):
That was when I became concerned, because you said nobody
was protesting and that wasn't true.

Speaker 1 (13:19):
She's disturbed by this latest example of misinformation coming out
of the White House. But I wonder what really pushed
Reality over the edge. Can you give me a sense
about your worries around the twenty sixteen election and what
you were seeing.

Speaker 2 (13:34):
I can't make any comment on any of that. My
concerns in twenty seventeen had to do with the media
holding government accountable, and what would happen if the United
States population were given one set of facts in black
and white, if they could see for themselves how their

(13:54):
media will report.

Speaker 5 (13:56):
Some facts and leave some out.

Speaker 2 (13:58):
My only intention was to give the American people a
litmus test as to the veracity of their media.

Speaker 1 (14:06):
Let's stop here for a second, just so I can
explain something. One of the conditions of Reality's release from
prison is that she can't talk about most of the
details of her case, but journalist Carrie Howley can.

Speaker 10 (14:21):
At the time, there was all this argument in the
press over whether Russia had interfered in the election, and
there wasn't a lot of hard data. So she finds
this document that outlines a specific phishing attack on voting systems,

(14:43):
like the kind of simple thing where you open an
email and someone's like click on this, and then you
have downloaded something undesirable on your computer. And this document said, hey,
the Russian intelligence agency did this.

Speaker 1 (14:55):
To be clear, this report has nothing to do with
realities cryptologically, language analysis, whatever that is. But Pluribis has
access to all kinds of things, and their contractors don't
have a lot in the way of oversight. So Reality
is really bored at work and she stumbles on this
document and everything it allegedly reveals about Russia's attempts to

(15:18):
hack into our elections. But once she has it, does
Reality winner of some sort of political agenda? Well, according
to carry Howley.

Speaker 11 (15:26):
No, there wasn't.

Speaker 10 (15:27):
This sense on reality is part that like, oh, this
proves that Trump did not legitimately win the election.

Speaker 11 (15:35):
Nothing like that.

Speaker 10 (15:36):
She felt like more of a sense of what would
happen if this were out in the world.

Speaker 11 (15:43):
How will the media treat this.

Speaker 10 (15:44):
I'd want to see what happens when they have this
actual concrete document detailing this actual concrete attack.

Speaker 11 (15:52):
How are they going to deal with that?

Speaker 1 (15:56):
It's May ninth, twenty seventeen, the same FBI Director James
Comey is fired by Trumps.

Speaker 11 (16:05):
He wasn't doing a good job.

Speaker 8 (16:06):
Very simply, he was not doing a good.

Speaker 1 (16:08):
Job, not doing a good job of making the Russia
investigation go away. But it's on this day, of all days,
that Reality decides to print out this document she's seen.
And this is a huge no no, Carrie Howley explains,
I mean, I.

Speaker 10 (16:24):
Don't even think she should have been looking at it,
and she shouldn't have been printing it. But if she
had printed it, then it should have gone into the
rules of the NSA, into something called a burnback.

Speaker 11 (16:35):
I mean, she should have just disposed of it there.

Speaker 1 (16:37):
Reality knows this, but she does it anyway. So why
Maybe she's driven by that same desire that sent her
into the Air Force in the first place as a teenager,
the desire to help America fight this existential threat. Only
instead of terrorism, the threat Reality sees looming is a

(16:58):
loss of truth midst political lies and misinformation in the media.
Or maybe stuck in an office, or she feels useless
she just can't resist the opportunity to do something else,
to do something that could maybe make a difference.

Speaker 2 (17:16):
If you look at the United States foreign policy in
twenty seventeen, it was a fucking clusterfuck. I don't know
if you can say that, but it was a shit show.
I just cared way too much about this country and
our place in the world. I don't really have any
specific sympathies. It was probably just something on Fox News,
like more of their like constant lying, and it was like,

(17:36):
there's a whole other set of facts here, and so
it was more triggered by that, more triggered by the
way Americans are getting information and that they're on any
given side of the conversation, you're only getting half the truth,
and somebody needs to just for once give everybody the
whole truth and let us decide as a people without

(17:59):
core media interest involved.

Speaker 1 (18:01):
So she should not be accessing this document. It has
nothing to do with her job, and she probably doesn't
have the right security authorization anyway. She should definitely not
be printing it, and if she did, she should put
it in a burn bag and destroy it. But you
know what she really should not do.

Speaker 10 (18:20):
She folded it up, put it in her panteos and
walked out of the building.

Speaker 2 (18:26):
Yeah, I really am the world stummist criminal. I didn't
think it through. I didn't even have an attorney. I
I didn't know anything about whistle blowing or leaking. The
only other two I had for reference were Chelsea Manning
and Edward Snowden. And I'm like, this is not really
anything like that. So if everybody sees that I meant

(18:48):
good intentions, maybe I'll be fired, but I won't go
to prison forever.

Speaker 1 (18:53):
Carrie Howley again.

Speaker 11 (18:55):
She puts it in her car.

Speaker 10 (18:57):
It stays in her car for maybe a few days,
I can't remember precisely, and eventually she puts it in
a Manila envelope. She addresses that envelope to The Intercept,
and she drops it in a standing mailbox in a
streetmall parking lot in Augusta, Georgia.

Speaker 1 (19:15):
The Intercept is a news organization co founded by Glenn
Greenwald and Laura Poitris, the journalist who had worked with
Edward Snowden to expose the nssa's surveillance program in twenty thirteen.
It's an obvious choice for reality. She assumes it's the
perfect place to anonymously send the top secret information. And

(19:35):
she's also a fan.

Speaker 2 (19:37):
The Intercept is really masterful at having their audience believe
that they are the only independent journalistic outlet that speaks
truth to power. You can tell they're really good at
inciting action and making you feel like you are the

(19:57):
gatekeeper to this knowledge that's going to help set America right.
They had done a ninety minute Intercepted podcast on racist environmentalism.

Speaker 9 (20:11):
And this is episode ten of Intercepted. This is nothing
short of a declaration of war on the planet that
is coming directly from the Oval Office. And they know
damn well that climate change is real. They know it's
not a hoax, So why do they lie?

Speaker 2 (20:26):
Lie? Lie?

Speaker 1 (20:27):
Reality even goes to the trouble of emailing the Intercept
to ask for a transcript of a podcast episode hosted
by the other Intercept co founder, Jeremy Scahill, a move
that will eventually come back to haunt her to the
extent that you remember those hours and the days afterwards,

(20:47):
What does it feel like, Where was your head at,
where you scared, where you resolved?

Speaker 2 (20:52):
So I was pretty much used to having breakdowns, having
days where I couldn't keep food down and physically shaking
for days at a time. So that's how I felt
for a couple days after I mailed a document and
then nothing happened. Seven days, super nervous.

Speaker 5 (21:09):
Nothing happens.

Speaker 2 (21:11):
Two weeks later, nothing happens. So I was like, whooh,
that was really stupid. Let's never do that again.

Speaker 1 (21:19):
Then the FBI shows up. June third, twenty seventeen. It's

(21:47):
been twenty five days since Reality Winner put a Manila
envelope containing a classified document into a mailbox and a
strip mall in Georgia addressed to the intercept. Nothing has happened.
Then one afternoon she arrives home from the grocery store
to find she has some visitors.

Speaker 2 (22:08):
When the FBI showed up at my house, it was like,
Oh my gosh, I'm gonna get disappeared to Quantico, like
this is it. This is the Chelsea Manning treatment. I
was scared for my life.

Speaker 1 (22:18):
US Army intelligence analyst Chelsea Manning was arrested for leaking
classified documents in twenty ten. Authorities held her in solitary
confinement for over a year. The FBI questions Reality at
her home that day and they made a transcript of
the conversation. Tina Satdter is a playwright and filmmaker, and

(22:39):
a few months after Reality was arrested, Satur was able
to track down the FBI transcripts of that interview. In fact,
she was so fascinated by the dialogue that she decided
to adapt the transcript into a theater piece, and the
result is a play called Is This a Room?

Speaker 12 (22:56):
Is This a Room? Stages verbatim word for word everything
from the first word of the transcript, which is when
these two FBI agents start talking to Reality, to the
very last word when they note the date and time
and turn off their recorder.

Speaker 1 (23:12):
That play has now been adapted to an HBO film
starring Sydney Sweeney. So we open on a scene.

Speaker 12 (23:21):
First, these two lead FBI agents surprise Reality like she
does not know they're coming.

Speaker 5 (23:27):
She is literally just.

Speaker 12 (23:28):
Doing Saturday afternoon errands. They start talking to her, alluding
to the fact that they have some information on something
she may have done, and so they let her go
into the house with them watching her and companying her
to put her groceres in, but she's brought back out
into lawn. All that conversation that happens out in the
lawn is kind of like vamping by the FBI until

(23:50):
they can ensure that her house is clear.

Speaker 11 (23:52):
She does have firearms.

Speaker 12 (23:54):
That's an amazing reveal that she does own three firearms,
including automatic weapons.

Speaker 1 (23:59):
By the way, one of those automatic weapons is a
pink Ar fifteen. It's just a great detail.

Speaker 12 (24:06):
Then they get her into the back room and no
one in the rest of her whole life knows that
she is in having this happen to her.

Speaker 1 (24:11):
Right now, the FBI are done with small talk. Now
it's an interrogation. Her first reality denies even leaking the document.

Speaker 12 (24:20):
Becomes sort of this circular questioning because she keeps trying
to sort of evade the corner they are trying to
back her into. She's really very masterfully trying to keep
her cool and probably both protectingly maybe the information she
leaked and how she leaked it. Her most raw emotion
seems to come about the animals, and she was wildly
concerned that the cat was going to escape and either

(24:44):
get shot, or if she ran to get the cat,
she would get shot. And these men aren't quite equipped
to deal with this woman's emotion that is actually about
something so tender and intimate and Real as her pets.

Speaker 1 (24:56):
The FBI finally tells Reality they have cut and dry
evidence that she printed a top secret document and send
it to the media. It's then that she confesses.

Speaker 12 (25:06):
The agents say, you don't seem like the kind of
person who would do this, and Reality gives this, like
to me, it always gives me goosebumps. Now she says,
I'm not and then they're like, then, why did you
do it? Did something just snap? And she basically gives us,
I mean, it's incredible monologue. She says, what am I
doing at this job if I'm not here to help
the way I thought that everything in my life was

(25:29):
leading towards like learning these languages, joining the military, and
it said I'm seeing information that means me and my
entire country or being lied to. I just I did
sort of like lose it. But she ends that amazing
thing saying why can't this be public?

Speaker 1 (25:49):
Here's Billy Winner again.

Speaker 6 (25:51):
She called my husband. The kids always call Gary when
there's an issue. When there's a problem, they don't call
Mom because I might overreact. So she called Gary and
she was there with the FBI agents at her home,
and she let Gary know that she was in trouble.

Speaker 2 (26:09):
The experience lasted about three and a half hours before
I was transported to a county jail. When an actual
uniformed police officer showed up to take me to the jail.
She was the one that said, Hey, I have to
be the one to take you to jail. That was
when I realized I was under arrest, because the FBI
never said you're under arrest. She called later after they

(26:31):
had booked her in the jail, and I asked her
if we needed to travel up to Georgia to be
with her, and she said yes. That's when I knew
that things were serious.

Speaker 1 (26:40):
But hold on a second, how did this anonymous document
send to the Intercept lead to reality getting exposed and
arrested in just twenty five days? Like what happened there?
Not that I support her decision, but shouldn't the news
organization protect their source? Journalist Kerrie Hollicks.

Speaker 11 (27:00):
It actually sat in a mailbox for a while.

Speaker 10 (27:03):
No one even checked this mailbox because like, you don't
like if you're working in media, you're not.

Speaker 11 (27:07):
Like using the mail, you know what I mean.

Speaker 10 (27:09):
So it just sat in the mailbox for a long time,
and then someone checked the mailbox and they were like,
what is this. So they have the document, they assign
it to your reporter. The first order of business and
a big problem for the Intercept at this point is
is this document real?

Speaker 11 (27:26):
How do we even know if this is real?

Speaker 10 (27:28):
And so the way that they went about authenticating the
document ultimately exposed reality.

Speaker 1 (27:36):
The Intercept reporters reach out to a representative with the
NSA to confirm its validity, but instead of describing what
was in the document say over the phone, the reporters
provide an actual copy of the document to the NSA
rep and they say it was postmarked from Augusta, Georgia.

Speaker 2 (27:54):
I may as well have just mailed the document to
the FBI with my name on it and a hair sample,
because the Intercept gave it straight back to NSA.

Speaker 1 (28:03):
Hindsight is twenty twenty Carrie Howley.

Speaker 10 (28:05):
Again, there is a digital security team at the Intercept,
and that security team was probably at that time the
best in the world, and nobody consulted them.

Speaker 11 (28:17):
Nobody ever said what should we do with this?

Speaker 10 (28:20):
That particular misstep is extremely mysterious to everyone who looks
at this case, but I think it's atributable just to
the fact that there weren't good protocols in place at
the intercept, that they weren't used to dealing with anonymous documents,
that they're really tied to this machine of the Snowden documents.

Speaker 1 (28:37):
The NSA sends the document to the FBI, and they
see creases that suggest it was printed and folded. It
contains water marks showing it was printed on May ninth,
and included a serial number of the exact printer that
had been used. From there, it wasn't hard to put
together a full list of people who printed that document

(28:59):
on that printer, and of those six people, only one
of them had ever emailed the intercept asking for a
podcast transcript. Billy Winner again.

Speaker 6 (29:10):
Reality probably would have gotten caught either way, but the
intercept made it so so easy for the government to
have an ironclad case against her.

Speaker 2 (29:26):
I learned from the wikileak stump that Chelsea Manning had
done that Fox News did not care if something was
top secret. They were going to put up a scan
of the document on the TV, and so my ultimate
goal was to have Fox News do that again and again.
I wanted the document to be the story. I knew

(29:48):
it would come back to me, but I just thought
it would wake Americans up enough to where by the
time the FBI knocked on my door and said, hey,
we kind of know you did it, the public consensus
would be we needed to see this, And instead I
was indicted on Monday morning, and that afternoon the Intercept
dropped the documents and it was too late. Ever since then,

(30:13):
the story has been about Reality Winner and who Reality
Winner is, and how much she hates Trump and that's
not really true, and how much she hates America, which
obviously everything I've ever done has been for America.

Speaker 1 (30:28):
Reality is spot on about the media coverage. They don't
seem to really care about the revelations in the leaked
document or that it adds further proof the White House
is downplaying the Russia threat. Three days after the arrest,
trefor Noah sums it all up perfectly on his show.
Instead of Russia, the media focuses on just well her name.

Speaker 13 (30:50):
Someone leaked top secret information about Russia to the press,
and that person's name is Reality Winner. Their real name
is Reality Winner, and Trump has to be one of
the luckiest people around because this new leak shows that

(31:11):
the Russian military actually tried to gain access into the
Florida vota system. But we can't concentrate on those facts
because reality winner.

Speaker 1 (31:21):
Reality are the show Box and Friends goes with unsubstantiated
claims that make reality seem like a member of the
radical fringe and a Grade A manipulator. And by the way,
people like me did not second guess that characterization.

Speaker 14 (31:37):
The government contractor accused of leaking top secret NSA documents
also wanted to burn down the White House. Prosecutors revealed
handwritten notes about plans to join a taliman. She also
told her sister she'd played the quote pretty white and
cute card to get out of trouble.

Speaker 1 (31:54):
The media narrative that focused on reality worked just fine
for the White House. It was a welcome distraction from
the facts that Russia attempted to hack our elections. But
those facts inevitably raised some pretty uncomfortable questions, like why
at a televised Senate hearing, Senator Claire mccaskell reels my

(32:14):
former boss, White House Chief of Staff John Kelly, about
the report and what it shows about Russian hackers' intentions.

Speaker 4 (32:21):
It's clear they were trying to get into that votor files,
and I don't think they were going there to try
to just hang out.

Speaker 1 (32:28):
As mccaskell notes, the information is pretty useful to understanding
just how far the Russians were willing to go to
meddle in our elections. But despite the importance of that information,
I still felt at the time that it was wrong
to leak it. Ben Rhodes was of a similar mind.

Speaker 7 (32:44):
The problem to me is actually less probably to do
with that specific document. It's more that, well, then you're
telling everybody it's okay to do this, and then why
wouldn't more people do it. It's problematic for anybody to
mishandle classified information or to put in the public domain,
because then you open up a spigot and you get
ten other Reality winners, and one of those documents might

(33:06):
be something that really is something that puts people's lives
or risk.

Speaker 1 (33:12):
Reality is being held in a Georgia County jail for
the trial, and it's bleak. Not even her family offers
her much comfort because the prosecution is listening in on
the phone calls here's Billy again.

Speaker 6 (33:24):
We're a family that survives off of humor. Like I
remember telling her, I bet you rock those oranges, because
she told me, Mom, I'm wearing orange and I bet
your rock in it. Well, the prosecution used all of
that against Reality. All of our telephone calls, all of
our visits were recorded, and they were being used against her.
If we laughed about something, we would hear about it

(33:46):
in court the next hearing.

Speaker 1 (33:49):
As things progress, it's clear that the prosecution is creating
its own narrative about this Reality Winner character.

Speaker 6 (33:57):
They took all of her strengths, like you know, my
daughter had books in her house about Afghanistan, about the Taliban,
and they took that and made it into something cynical.
What the prosecution said was that Reality Winner actually joined

(34:19):
the Air Force for the sole purpose of getting exposed
to classified information so that she could betray her country.

Speaker 1 (34:30):
The Justice Department is poised to prosecute Reality to the
full extent of the law, like come down very hard
on her. But given the nature of what Reality has done,
I mean, didn't they have to Carrie Howley, you can.

Speaker 10 (34:45):
Imagine a situation in which this just gets shrugged off.
That's just an administrative decision. Are we going to prosecute this? No,
it's dumb, let's ignore it. Let's not draw attention to it.
That happens all the time there are leaks, and like,
it's not in the interest of the government to talk
about it or create a new story about it, so
they just look the other way.

Speaker 11 (35:00):
And that easily could have happened here, but it's not
what happened.

Speaker 1 (35:03):
Given the President's sensitivity to the subject, it does make
sense that he'd pressure the Justice Department to make an
example of Reality. But Carrie thinks the push to punish
her was maybe driven by a simpler motive.

Speaker 10 (35:18):
I imagine it was something like, hey, this is like
a really easy case. We have a lot of evidence
that this was leaked, and from somebody's position in the
Department of Justice, it would be good for a promotion,
It would be good for their personal prestige to go
after this person as hard as possible, to get the win,
to impose the longest ever sentence against a whistleblower. And

(35:41):
I think it's these like little, these smaller incentives.

Speaker 1 (35:46):
Reality is facing up to ten years in prison. Meanwhile
friends of the president are facing a very different type
of justice. Tina Satter talks about that disparity.

Speaker 12 (35:58):
When you've me the nine bail Paul Manafort out on
bail by his pool and mansion.

Speaker 1 (36:04):
Paul Manafort, political lobbyist and chairman of the Trump presidential campaign,
charged with eighteen counts of tax evasion, bank fraud, and
hiding foreign bank accounts. He's convicted on eight of those charges.
But while Reality Winner is rocking those oranges in state jail,
Manafort is in a luxury condo in Virginia. I don't know,

(36:27):
maybe the fifteen thousand dollars Ostrich jacket that Buzzbeed News
reported about. Anyway, Reality doesn't have friends in high places, and.

Speaker 12 (36:37):
So like a year and two months after being in jail,
she makes a plea deal because the writing seemed to
be on the wall that she could get the ten years,
which and I think she was for a range of reasons,
and mostly her health and mental health, was really.

Speaker 5 (36:51):
Not wanting to do that.

Speaker 1 (36:53):
Reality is sentenced to five years in prison. She spends
three and a half years at the Federal Medical Center
Carswell in Fort Worth, Texas. She's twenty six. Her time
at Carswell happens at the intersection of the COVID pandemic
and the racial reckoning over the murder of George Floyd.

(37:14):
It makes an already bad situation a whole lot worse.

Speaker 2 (37:19):
My entire time incarcerated was a lesson in never admitting
that you've hit rock bottom, because there's always a new
rock bottom. I thought County Jail was rock bottom, and
then COVID happened and we were, you know, immediately put
on lockdown, and I thought, oh my god, this is
rock bottom. And then Derek Chauvin murdered George Floyd in

(37:41):
front of the entire world, and then we were put
on our first real, real lockdown for in nine days,
where you can't leave yourself, Billy Winner, having somebody in prison,
it's so very, very difficult. You have no idea because
you feel so powerless, and when that person calls you
and they're upset something happened, you can't do anything to

(38:03):
help them. There's there's absolutely nothing that you can do
to help that situation, but just be there, to be
there on the other end of the line. When they called,
I internalize everything and I saw the bigger picture of
what was being done in our country, and it was
like that pain, like I started cutting myself and by

(38:23):
the end of it, you know, my neighbors the cells
next to us are like, dude, Winter, You're going to
get your ass locked down if you don't calm down.
And so that was when neighbors started passing, you know,
pills and drugs to keep me, to keep me sane.
Within a month, we were on another lockdown. This time

(38:43):
they revealed that there were active COVID cases on our unit.
That was a thirty three day lockdown, and I stayed
high for thirty one of those days.

Speaker 1 (38:58):
In June twenty twenty one, after a public campaign for clemency,
Reality is released early from prison. Initially, she's placed under
a gag order, banned from using social media, and under
constant supervision as part of her home confinement. The government
says good behavior is the main reason behind her early release.

(39:19):
For Reality, that's pretty ironic. What was more difficult to
grapple with the incarceration and the effects of that, or
the public scrutiny.

Speaker 2 (39:33):
In order to deny me bail, the prosecution alleged that
I was a Taliban sympathizer. That was never a charge,
and it never came up again once I was denied bail.
It was only useful for that one SoundBite, and that
SoundBite haunts me to this day. Everything we've done since
then in the public domain has been to refute that,

(39:55):
and has been to clear my name, and has been
to get my my veteran status back. It's like, well, damn,
I'm not even a veteran anymore. Like they took my
military service from me, and I'm extremely bitter about that.

Speaker 5 (40:07):
You had no right to say that.

Speaker 1 (40:12):
At the time that your story came out, I was
in government working on these issues, and of course my
reaction was, she shouldn't have done that, or she shouldn't
have done it that way. What would your advice be
to a prospective whistleblower?

Speaker 2 (40:30):
So I say this as somebody who almost lost their
life over two pieces of paper. The personal cost of
releasing these documents is absolutely not going to be worth it,
simply because once you release that document, you cannot possibly

(40:51):
control the narrative. You will be crushed, You will be investigating,
and your name will be tarnished and you will do
hard time in prison. However, the actual change in legislation
that you are hoping will be done by simply revealing
these documents will not happen. You're going to hurt yourself,
you're going to hurt your family, and you're going to

(41:13):
give the media talking heads something else.

Speaker 5 (41:15):
To talk about.

Speaker 1 (41:17):
Maybe there's another question Reality's case raises, like, is the
government overclassifying information that maybe doesn't even need to be
secret in the first place. And I saw this all
the time in government, information that didn't need to be secret,
and if it was in the open, potential leakers might
be less of a problem. Kerry Howley to me.

Speaker 10 (41:41):
As like a citizen, there was no cost to sharing this,
that no one was put in danger. What she did was,
in a part made clear how much is pointlessly kept
from us. And so the idea that this was a
felony that deserves five years in prison, I think is absurd,

(42:03):
and I think most people who look at the story
clearly will agree.

Speaker 1 (42:06):
I'm closer to Reality's opinion about her decision that it
was a mistake at least the route she took, but
the destination what she was ultimately trying to achieve, That's
what really surprised me. I didn't think I'd changed my
mind about her until we met, But honestly, how could
I not like me. She's a child of divorce, she

(42:28):
was inspired to go into government after nine to eleven.
Then she blew the whistle after she saw something wrong,
something very wrong. In the end, we had more similarities
than I was ready to admit. But if you ask
her now, Reality says she doesn't see herself as a
whistleblower or a major leaker. She tells the FBI and

(42:51):
her interview quote, I wasn't trying to be Snowden or
anything unquote. Here's Carrie Howley once more.

Speaker 10 (43:01):
To me, the most important part of this story is
not the document itself. I think what's really interesting is
what Reality Winner tells us about the way the intelligence
system works, about the way the media works, about the
way a life can just take these crazy twists and turns,

(43:24):
and you can end up at this single moment of
decision saying, am I going to do whateverone around me
is doing? Or am I going to do what I
feel is right?

Speaker 1 (43:38):
Next time? On The Whistleblowers, the head of the FBI,
Andrew McCabe, is thrown into the center of the biggest
political scandal since Watergate. As he races to lead the investigation,
he finds his agency and his own family in the crosshairs.

(44:04):
The Whistleblowers is a production of iHeart Podcasts in partnership
with Best Case Studios and ARC Media. It was hosted
by Me Miles Taylor and written by me Isabel Evans
and Adam pinkis. Isabel Evans is also our producer. Associate
producers are Hanaliblwitz Lockhart and Ashley Warren. Darcy Peakele is
consulting producer. Zach Herman is the VP of Development of

(44:24):
ARC Media. This episode was edited by Michael Odebark with
assistance from Max Michael Miller. Original music is by James Newberry.
Executive producers are Me Miles Taylor, Adam Pinks for Best
Case Studios and Barrick Goodman for ARC Media. Beth Ann
Mcaluso is our executive producer for iHeartMedia, along with Ali Perry.
Special thanks to Kevin Famm, all of our contributors and interviewees,

(44:46):
and our intern Anna Levitt, and a big thanks to
the teams at Government Accountability Project and Whistleblower Aide, two
of the best organizations for government and private sector whistleblowers
seeking legal support. Follow and rate the whistle blowers on
the podcast site of your choice to hear what these
whistleblowers and others have to say about what they believe
will happen under a second Trump administration or in the

(45:09):
White House of AMaGA Successor you can pick up my
new book, Blowback from Simon and Schuster
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