Life Will Be the Death of Me with Chelsea Handler - I Am Not Your Enemy with Whistleblower Reality Winner
Episode Date: September 18, 2025Chelsea is joined today by whistleblower Reality Winner, a former linguist and intelligence analyst, arrested in 2017 for leaking classified documents about Russian interference in the 2016 elec...tion. They discuss Reality’s arrest, incarceration and recovery - and why it’s so important to speak out when you see injustice. * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees. This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all. Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice. See omnystudio.com/listener for privacy information.
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Okay, hi.
Hi, Catherine. Hi, Chelsea. Did you see that our friend Boom Boom Hiller won an Emmy?
I did see that Boom Boom Hiller won an Emmy. That's very exciting. Yes, I was very happy for
him. He gave one a great, great speech. I didn't understand what was going on with the Emmys with
the money. What was the money thing? I tuned in like halfway through. I also tuned in like
halfway through. I think they should just let people who won talk, don't you? I mean,
you've hosted these award shows. Like, what's your opinion on that? I just feel like that's
the moment people get to talk. I mean, obviously, within reason, don't go crazy. I thought they were
deducting people. They were deducting
money from a charity for people who were
going over their time. They were taking money back from the
charity? Yeah, that's what they were doing, I think.
I'm pretty sure that they were
basically, they had a set number and anyone who
talked over, it became a
reduction. Oh, they were giving them less? Yes.
So I was like, that's pretty fucked up.
That's rude. But who knows? I mean, I can't really
even track a conversation, so who knows
what I was thinking. I was kind of half-watching.
I went to New York again this weekend,
so I had a quick... Were you in the air?
I had a show actually. I had a show. Oh, I just announced a new tour, you guys.
That's what I want to talk about. I announced the High and Mighty Tour,
which I'm going to start next year. I start in Washington, DC next January or February. I don't
know. It's called the High and Mighty Tour. Tickets are on sale and I'm going to lots of
different cities. And you can check my website, chelseahandler.com for tickets, or you could go
to the link in my Instagram to buy tickets. That's great.
So that's what's happening there.
And we have a very exciting guest.
I, okay, so I saw a movie.
I actually moderated a conversation
for a director named Susanna Fogel
who directed a movie about Reality Winner.
This is a girl's real name.
This is our guest's real name today.
When you first texted me and said,
I want to talk to Reality Winner,
I was like, winner of what reality show?
Like, I did not get it.
Her name is Reality Winner.
And if you don't remember who she is,
she was a whistleblower during Trump's first term.
She was working at the NSA
and she leaked some document to, to the intercept. And then the FBI basically arrested her. They
came, they interrogated her. They went, showed up at her house on a Saturday afternoon. And
anyway, her, she's a former linguist. She's an intelligence analyst. She was arrested in 2017
for leaking classified documents about the Russian interference in the 2016 election.
And there is some backstory that our listeners should know about before we get into this
conversation. Reality was in the Air Force as a linguist. She translated conversations for
government targets. And then when she left, she started a contract with the NSA. And she outlines
that there are certain news sources that people who work for the NSA are allowed to read that are
not available to the general public. But people with security clearance are not allowed to read
mass news the way civilians are. Right. So she explains in pretty great detail in the book
how as a person who has a high security clearance working for the NSA, she had access to a specific
news outlet that was only for people with a high security clearance. But there was also sort of
this rule that she couldn't go look at New York Times. She couldn't go look at Washington Post.
And if they had found something like that, like links to that on her phone, anything like that,
then she would have been in trouble. So there is this sort of weird dichotomy that people with
high levels of top secret clearance do have access to more information, but they also don't
necessarily have what all of the rest of us have access to. So the document, and it was just one
document that she leaked, was from this news source that she had access to as a person with
high security clearance. So she felt that she needed to release this document about Russian
interference in the election so the American people would know it happened. And then the FBI
found out, confronted her in her home in a three-hour interview during which she was not
read her Miranda rights. She also had a dog and cat at her home that were unpredictable.
She describes feeling terrified that they'd hurt her animals
or use their behavior as an excuse to hurt her.
She was taken to jail where she stayed for about a year
before going to prison for four more years.
And then her mom lived in her house nearby
while she was incarcerated, which she says saved her life.
And then once she was out, she had a period of readjustment.
She says even the colors outside were overwhelming for her
after five years of staring at gray walls.
She briefly got married and then quickly divorced
to an old boyfriend who had a child.
This was part of her rebellion
during her readjustment period.
And now she has written a book about her experience,
has moved on romantically,
and is in veterinary tech school.
So there are a few movies out about her.
There was a Broadway show.
There was a Broadway, yes, a Broadway show.
And now she has a book called I Am Not Your Enemy.
That's a little background information for you.
So please welcome reality winner.
Hi, reality.
Hey, Chelsea.
Hi, how are you?
I'm good.
Thanks for having me.
How are you?
Oh, I'm great.
I always want to say we'll commence, but I feel like commence says we're starting.
Does it commence mean we're starting something or we're finishing something?
I'm getting confused with my Spanish.
Yeah, commence is starting.
Commencement speech, though, at a graduation is the end.
Yeah.
Well, you're commencing into life.
Is that right?
Yeah, I guess.
Okay.
We have reality winner here.
Reality, you and I go way back, but you don't know it.
I'm sure a lot of people feel that way about you.
First of all, I'm just happy to see you out of prison.
I actually moderated a conversation between Susanna Fogel.
Do you know Susanna?
I love her, yes.
Yes, okay, great.
She directed a movie, one of the movies.
So there's three movies out about your story.
Reality Winner was a whistleblower in the year 2016
with relation to the Russian interference
in the 2016 election.
And subsequently went to jail
and then prison because of that.
So there was a documentary about you,
which I also watched. And then there was a movie with Sidney Sweeney. I skipped that one.
And then the one with Susanna Fogel, who starred, what was the, who was the star of that reality?
Amelia Jones.
Amelia Jones, who's fucking phenomenal. Did you love that movie?
I don't watch anything about me because I have a very like physical trauma response.
Okay. I understand that. I understand that. How are you doing today?
I'm doing so good today. My biggest issue was having to get to this studio. I
hate driving on overpasses.
they're my nemesis. Really? Why? They're so high. Why? What about bridges? No. You won't drive over
a bridge? No. Do you know that when I was a little girl, our family used to drive up to Martha's
Vineyard every summer. So you drive from New Jersey. We grew up in New Jersey. We drive to
Woods Hole, Massachusetts, and you would have to drive over a bridge called the Tappan Zee Bridge
that's outside of New York. And it was, you know how big bridges are. They have all of that
iron work over them, right? But that's not the actual pavement. But my brothers and sisters
convinced me that we had to drive up all over the iron work every time. So I would crouch down and
cover my head because I was so scared. I'm like, oh my God, how are we going to stay on? They're
like, we might not let cars fall off all the time. And so anytime, so I have, I have bridge trauma
too. But it sounds like you have lower bridge trauma. Right. There is some bridges out here.
like the only way to get to the beach is on a bridge. And it's not fun to be in the car with
me. I have to drive. I have to be in charge of my own death. But it's horrible. Well, I think after
everything you've been through, it's fine for you to want to be in charge of your own death and your
own life at this point. Right. How long have you been out of prison? Officially, I have been out
for four years. Okay. So you wrote this book, obviously, after that. And the book takes us
through your journey. The book is called I Am Not Your Enemy, Reality Winner. So let's go through
your history because you joined the Air Force and then you decided that you wanted to go work at the
NSA. Correct. And take us through what happened when you started working at the NSA. So in the
transition from the Air Force to the NSA, I already knew it was a temporary position. I had my sights
set on getting a position in Afghanistan proper, but that in order to be eligible for those
deployments, I would have to keep my security clearance current because that's what the
recruiters were looking for. So I was coming up on a very important deadline and I just took any
contract that would have me. So that was the particular position that I was working at
in Georgia at the time of my arrest or at the time I committed the felony,
there was nothing for me to do. I just sat there and watched YouTube all day and planned out my
workouts and my yoga classes. They didn't really know I was there. And looking back,
being so disconnected from any sort of purpose or mission is definitely one of those things that
left me vulnerable to doing something so naive. Naive is the word that you use a lot. And I also
don't really think you're naive. I think that from your books and from what I've learned about you,
that you really just had a sense of right and wrong and that you wanted to share. And I think
that's very admirable. And I think what you did, yeah, you're young. I think you were young and
didn't realize, which you revealed in the documentary, that you didn't realize what
the consequences would be. In fact, you didn't even really consider the consequences of sharing
the information that you were privy to. I didn't. I mean, I just really thought that
at the end of the day, no damage was done. It was very clear that I did what I did
for the greater good and that, you know, I was definitely going to lose my job, but I did not
imagine the statements that the government would then make about me and my character following
this. And at this time in your life, were you familiar with people like Julian Assange?
So on the surface, yes, I knew about Edward Snowden and Chelsea Manning. But because of
the technicality, they were able to keep us from knowing any of the specifics about these
individuals every week or so, especially when the news cycle would be very much focused on
one of those individuals. That if you read this Washington Post article, and it was derived off
of classified information and you read it on your personal device, you are then carrying around
classified information and you could be charged with the Espionage Act. So it was a way to make
sure that we were kept in the dark on what life is like when you're charged with these sort of
crimes and that I didn't know anything about Snowden or Chelsea at all. I didn't know what
their legal defense was like. I didn't really know what they had gone through. I was just kind of
acting in the dark at that point. And the reason that you acted was because you felt what? I felt
like if the American people had the information on that document and they could see it in black
and white, that A, it would answer a question that was, I felt like it was burning a hole in our
Society in 2017. And I wanted to give the American people a way to decode media bias.
If they had the full story, they could see, like, the people I trust on the TV aren't giving me the
whole story. Like, I can see everything right here, and they're leaving half of it out.
And so can you take us through what happened on that Saturday morning
after you had printed that? So you had printed the document, was it on a Friday, right,
in your office? I had actually printed it on like a Monday or Tuesday, and I think I
mailed it out on a Tuesday night. And it wasn't for about two and a half weeks until the FBI came
to my house. And I think we should also point out, you know, the Intercept, which is who you sent
the document to, kind of was like, yeah, they bungled the situation. They have all these high
level people who know how to handle whistleblowers. And your document went to two journalists who did
not know how to do that. And instead, their mistake wound up eventually in your conviction.
Mistake. It was not a mistake. It was on purpose. It's by design. I was the third. Well, actually,
Terry was the third, but there were three of us in a very short succession that were
sort of outed by their incompetence, but then championed by them. So they would create victims
and martyrs and then try to be the only media outlet fairly reporting on them.
So take us through what happened to you on that Saturday when the FBI did show up at your house,
because you were getting ready to go on a date that night anyway.
Exactly. The ultimate ghosting.
Oh, that's funny.
yeah not only did i not show up but he was probably interrogated as well poor guy
so i parked with my groceries and immediately a black vehicle comes up behind my car and parks
me in and garrick and taylor come out they introduced themselves they showed the warrant
and i knew what it was about obviously because i had done the thing but they said they were
looking for documents. And I was like, whew, I only had one document and I sent it out. Like
that's kind of one of the reasons why I was just so compliant. I was just like, okay, search my
house. The only thing that started to get scary was that there were 11 men. I was pretty sure all
of them were armed and the government was very quick to correct me. Of the 11 agents, only nine
of them were armed. Only nine. Only nine. So I was lying again. You know me, I just can't stop
telling lies. And they kept leaving my doors open. And I had just sort of had my early 20s awakening
of the injustices of this country and understood that when the police or the FBI, when someone from
the government kills you, they have the only control of the narrative. And so I knew that
these men were leaving my doors open and interacting with a dog that had previously
been extremely aggressive to men. And that if my cat had gotten out and if I had like run down the
street after her, would they shoot me in the back? If I became emotional about how they were taking
care of my animals, or if I thought they were going to shoot my dog, would they shoot me? And
then, you know, try me, you know, basically posthumously convict me in the news cycle the
next day. They had interrogated me. I did confess. I thought that because they looked like the guys
that I worked with at NSA, if I just was straight with them, that whatever was coming next in a
court or whatever, I could figure out and it would be a normal legal process.
And that was when Garrick told me, we're going to have to take you in. You're going to go in
this vehicle over here. So nondescript, unmarked black vehicle. He said it was going to be okay
because my hands would be cuffed in the front and not the back and that he would be sitting next to
me the whole time and that he wanted to apologize because it would be a bit of a drive what little
I did know about Chelsea Manning was that when they first took her she was in solitary confinement
in Quantico for nine months and nobody knew where she was so when he said that reassuring statement
I understood that I was going to Quantico that night and nobody would know where I was
that was not the case and even if they had intended to drive me to the jail themselves
the last remaining part of the warrant was a search of my person and obviously I was kind of
in between dates so I wasn't wearing much a visual search would have been just fine but a female
a woman had to do it so that was when they called a nearby deputy from the Richmond County Sheriff's
office. And I don't know what it was, but she came and assessed the situation. And she took me to a
private room and patted me down and executed the search warrant on my person. And she came out and
had a conversation that I couldn't hear. And shortly after that, another sheriff's department
vehicle came up and another female officer came out. And she said, hey, I'm going to be the one
taking you to jail so for the first time women were on the scene uniforms were on the scene
marked vehicles were on the scene and the word jail was spoken and I mean honestly that was the
first time I knew that I was going to survive that night because so that's okay so okay there's
a paper trail and a record yes I knew my parents could find me then your poor parents my god I mean
honestly, watching your, I mean, I don't want to make you feel bad because I'm sure you have
enough guilt to deal with about, with regard to your parents, but what your mother and your
stepfather, is it your stepfather? Yeah. Yeah. Went through is just like, I wouldn't wish that
on any mother, you know, and fighting so hard on your behalf and, and having to hear, and, and also,
you know, coming really, there is just nothing better than a good mother. There really is no,
nothing better in life than having a good mother. It's more important than a good father. A good
mother is everything because she wasn't going to let you compromise your values or your goals
either. She wasn't going to let you take a deal, which you were given the opportunity to do.
I was initially upfront. And then later again, like in November of 2017, offered five years.
And we had tried some legal strategies to get that down to four years. And it did not work.
And so when you were given that sentence for basically telling the truth, how did you wrap your mind around that psychologically? I know you talk about in the documentary and in the book you did as well about contemplating suicide. And the one thing you didn't want to do was hurt yourself, kill yourself while your mother was alone in your house, which I thought was just like, oh, my God.
You didn't want your mother to like get that information while she was. Yeah.
Yeah, I think that at that moment in time, the only thing I knew I was going to do it. And the only thing I was in control of was the timing where my mother would be when she got the news. We had just gotten word that I would be denied bail again and that I would probably never leave that jail except to go to prison or to trial.
and I said I can't do this anymore and so I started planning and doing dry runs of my suicide
and the last piece of the puzzle was hey I'm not getting out on bail you need to go back to Texas
you need to go home and get the house in order and you know we'll figure this out later you know
my attorneys will do some stuff and she put it off by a week and then she put it off by another
week and then she put off by another week and then she started like working at a dog shelter
and thinking about adopting a dog in Georgia and it was like those three weeks where I was actively
trying to get her to start driving and doing that other stuff was going on in those three weeks and
I had kind of hit a rock bottom which involved me screaming and punching a door after an officer
and I came out and told one of my attorneys this is what's going on when you guys call me to the
courthouse for this I can't go outside to yard call and I know you guys are sick and tired of
me saying that I want to go outside I'm bulimic I can't do this anymore I'm bulimic I'm not
functioning. I'm not surviving. And, you know, luckily people on my legal team were very close
to that particular illness. And, you know, you think about like, you know, men don't take eating
disorder seriously. They have very intimate knowledge of how deadly bulimia is. And they
said, this is not okay. Like, you are very sick and this has to be taken care of. And when they
started initiating that type of care and that type of consideration, I can't say things got better,
but I feel like the moment I came out, it felt like all the drive in me to kill myself had just
kind of gone away. And then how did that impact your eating disorder when you were in jail or
prison at this point? Once you told everybody, then what happened with your eating disorder?
You know, it's so difficult. Like even in normal daily life, like you come out about something
like that, like obviously you can't just like not eat. You know what I mean? It's not like,
it's not like being like, oh, I'm addicted to meth. You know what I mean? People are going to
watch you to see if you're doing meth. If you're like, oh, I have bulimia, people want to see if
you're eating, right? It's never really like a relief. It just cuts some tension. And I was
medicated. And my legal team altered their interactions with me in a way that would not
disrupt the daily schedule of the prison. Then they understood that when they came to have
legal meetings with me, or when they were calling me to the courthouse and I would miss yard call
or being able to go outside, they stopped doing that. They said, we are going to meet her on her
own terms, and we're only going to try to meet with her after she's gone outside to go run or
exercise. And just things like that, it made enough of a difference to get me through the
winter of 2017. And you talk a lot about the exercise and that kind of replacing your addiction
in a sense. I mean, were you able to actually stop throwing up at that point or did you continue on
for a while? I was able to not throw up and to continue to exercise at an intensity that allowed
me to eat. And that was another pressing issue of, with my disordered eating, having very severe
OCD as to what I would even put into my body. I don't even think clinically I could get my
hands on enough food that I was willing to eat to do a proper binge. So it was pretty much just
trying not to throw up the one meal I would eat that day. Right. Right. Because you talk about
how it was difficult to get not only like kosher meals, but like meals that didn't have meat or
had things that you could eat that you were okay eating? I mean, it's crazy, but as a federal
inmate, that county jail was required to give me a substitute protein and not just more rice or more
corn. When I got to federal prison where it is regulated, there's fried chicken or there's
baked beans, right? They have to have that on the line. It didn't make it easier because you would
be discriminated against if you dared hold up the line to ask for the alternative because they're
just throwing chicken on trays and trying to push everybody through. You just got to have a thick
skin. And there were several really tense standoffs with officers because, like I said, I dared to ask
for the beans. This week, we're looking for questions from writers. Whether you're an
up-and-coming writer, or you do it for a living, please write in to DearChelseaPodcast at gmail.com.
Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat
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i was kidnapped and held captive for nine months i survived and i've spent my life exploring how
other people survive what should have destroyed them i'm elizabeth smart and these are the
survivor files. I just remember this low taunting voice next to my ear saying shut up don't say
anything. Every week I'm with survivors who live through the unthinkable. I knew if he woke up
without a doubt he was going to hurt me. I started feeling that there was someone at the end of my
bed and I just started screaming. They are abducted, stalked, controlled and nearly silenced.
but these aren't stories about what's taken from them.
They're stories about what it takes to make it out alive.
Listen to The Survivor Files with Elizabeth Smart
on the iHeartRadio app, Apple Podcasts,
or wherever you get your podcasts.
If your bookshelf and your For You page
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I'm going to have to look up this story. I'm obsessed. I'm obsessed.
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Hey, this is Hayes Davenport.
And Sean Clements.
We host the podcast Hollywood Handbook on the Big Money Players Network.
Our show is extremely accessible to first-time listeners.
Each week, we talk to someone in show business, a.k.a. the biz, and try to help them with their careers and see what they have to offer us.
Everyone has a good time, and no one gets mad at their publicist for letting them do our show.
We've had a lot of great guests like Sarah Sherman, not that great.
Actually, can you help me shape this?
How about we flip it on its head?
How about we flip the script?
What if the surprise woman, who actually you think is the straight man, is actually the one who's acting weird?
Adam Scott, this entire time, you've been expecting Adam Sandler to come to visit the show.
I would never let go of that.
I have never set expectations for something like that.
If the universe allows for something like that to happen, I'm open to it.
I'm always going to accept, you know, Danny McBride.
Fine.
Yeah.
It's all this fragile masculinity exuding.
exuding i could smell it walking down the hallway to be honest with you
i was like is that weed nope it's fragile masculinity ben stiller no because a lot of
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On the new podcast,
Solita, we share the messy reality
of traveling alone as a
woman. I can wait four hours for the next bus
or this random dude
is offering me a ride on his motorcycle.
I chose option B. I'm Julie
Pinheiro, and I travel by myself
because it's a rare space where I can say yes
without asking anyone else first.
I'm on a mission to reclaim the word solita,
trading the pity for possibility.
Every time I tried to be alone, I kept meeting people
and they were like, you smiled at us.
Not a lot of people smile around here.
It's when you're alone that you're most receptive
to the world as it is and not the lies you're sold about it.
It can be a time where you push your limits,
change your mind, or wake up to a new version of yourself.
So whether you're a solo travel veteran or you're too nervous to book your first trip,
I hope you listen to Solita on the iHeartRadio app,
Apple Podcasts, or wherever you get your podcasts.
Did you make any friends in prison?
Lots, yeah.
People you still keep in touch with?
Absolutely.
I went and ran a half marathon with one of my friends, Stephanie, and my family got to
meet her and they added her on Facebook.
She's great.
She's doing so well.
I'm so proud of her.
Oh, wow.
Yeah.
So talk to us about what it was like to come out of prison after spending that much time
there when you did come out four years ago.
Talk to us a little bit about leading up to that moment and then the actuality.
I know you have ideas.
People talk about these kinds of huge changes that you have ideas of what it's going to
be like, and then the reality of what it is like can be kind of counterintuitive to a degree.
Absolutely. I mean, when you're inside those four walls of the prison, it's like,
give me an ankle monitor. I don't care. I would do anything just to be home.
And in the year leading up to my release, the COVID pandemic had happened. We had had several
unwarranted lockdowns and being put in county jail-type conditions all over again.
And I had just become so disruptive and violent and using drugs, getting girlfriends,
getting into fights, that by the time that version of me walked out of that prison,
I was almost unrecognizable to my family even mild disagreements would get loud with me
I didn't know how to relate because the things that I thought were funny were like you know I
mean they were so inappropriate all the time like which was fine but I don't think anybody gave me
or my family the vocabulary to sort of talk through the process of decompressing
a huge trauma i'm right leading up to my release is that i spent 23 days in a single hospital room
as part of a covid quarantine procedure it was just so de-socializing to a certain extent and i
feel like not ashamed but just like god the person i had to become to get through that
with any type of stability or you know we were we were literally like okay you're gonna put us
in a room like mental patients we're gonna act like mental patients I mean we did and then to
come out the pressure was if your parents do anything public if they announce that you're home
we might not be able to keep you at home at every step of the way that halfway house threatened my
ability to be on home confinement. I did two drug tests a week. I was not ever authorized to drive
myself. So my parents had to take off work to drive an hour and an hour back. Just constant
drug testing when I didn't even have a drug charge. Like, yes, I know I did drugs, right?
Like we can all say like, oh, she did drugs while she was in. It's in the memoir. At that point in
time, like the federal government had zero documentation of substances being in my body.
but I'm being tested constantly
if the ankle monitor would buzz
if it would be on low battery
one time I missed a phone call
because I was on the phone with my boss
and I called the guy back
and he was like
oh okay well I had already documented
as having escaped
I was constantly under so much pressure
from the top down
from the government down
that the only way that pressure could come out
was sideways
And so my family were, they were the sideways. They were in my line of fire since I couldn't do anything to ease the government pressure off of me. So things were really toxic those first six months.
Wow. How about your sister?
Luckily, she was protected out of the picture.
She was in North Carolina.
She did bring my niece down, her daughter.
She brought her down to visit.
I got to meet my niece for the first time, or second time, because they surprised me
getting out of prison.
She and baby were there waiting outside the prison for me.
I know for her it was hard, but she also had a one-year-old daughter, so that probably
gave her a really nice little buffer zone between the absolute dumpster fire that I was.
And what do you think, what was the shift that happened after about six months? Just did it
start to depressurize like everything surrounding your case and your kind of like their oversight of
I think a really big part of it was, yes, I secretly married Carlos in my backyard. And then 67 days later, that relationship fell apart. And, you know, my parents didn't talk about it, but I think that once it had completely fallen apart, you know, day 67, I said, okay, like, his shit is out of this house.
I made him come get it and was like, I'm going to start figuring out how to secretly get divorced
from my living room, right? It felt like one of the biggest barriers between me and my parents
was lifted. And honestly, it's really ugly to say this, but a big part of it was the fact that he
had a daughter who was, she was four at the time and he would bring her over. And my mother felt
like I wasn't supposed to bond to this child while my sister and her baby existed. Like,
oh, you got out of prison. You got to meet your baby niece. Oh, but now you're playing
stepmom to a four-year-old. Like, I thought you wanted to be an aunt for your sister's baby.
Or were you in any condition to be in that role in the first place?
Well, I was fucking better than he was at it. That's for fucking sure. But
when I found out he was getting high again and stuff like that I mean
you know it and part of getting married I knew he was terrible but I thought again like
this girl was brilliant four years old taught herself how to read her mom really didn't want
to be a mom which is why she was she spent 90 of her time with her alcoholic high you know piece
a shit father and I just thought well goddamn like even with this ankle monitor I'm better
than both of them combined and isn't it amazing though when you think back and look at that kind
of decision making like marrying Carlos in the first place like when you look at your the state
that you were in how newly out of prison you were what your parents must have thought about that I
mean, you know, you discussed that too, and it's obvious. But when you look back at that decision
making, don't you just know that you were in no position to make any of those decisions? Like,
you were dealing with so much trauma that you hadn't even begun to unearth. Yeah. And I think
that when someone's drowning in trauma, the worst thing you can do is point out that they're
traumatized. And that I was, I hate it when people say this, but they do say it. Inmate
thinking patterns, the way you think and operate as an inmate is you find what you want and you
find a way to secure it in a way that an officer or a position of authority cannot take it away
from you. So I knew that I wanted to be with Carlos and I wanted to be a family to that little
girl. And I was just thinking like, A, my parents can't say anything if we're married, but B,
if I do wind up back in custody, the government can never deny me access to the two of them
if we're legally married. Okay. So it was the absolute, like you just grab something and you're
just like, no, you can't take this away from me because I have this legal document. And you're
constantly trying to be two steps ahead of the police. And that's where that decision-making
was from. And again, as a family unit, nobody had that sort of, nobody had the vocabulary to sit me
down and say, nobody's going to take him away from you. We don't like him. We don't agree with
him. We're not going to let you go back into custody, but nobody's going to make it illegal
for you guys to interact. And because I didn't get that assurance, I married him secretly.
And once that disintegrated, I felt like everything got better with my parents.
Obviously, like the way relationships go, we did see each other one more time.
and that was when i saw firsthand the way he was going to use access to his daughter
to get behavior that he wanted from me yeah and that was when i walked away permanently
and um i never saw either of them again wow it's like trauma on top of trauma on top of trauma
i just keep asking for it i make shit decisions no no no you're gonna get better at making life
decisions you already have. You're going to get better. That's just a period in time. That's not
permanent. Nothing's permanent. You know, look, you're out. This is different. I mean, I have a
lot of faith in your future. Do you? I mean, I guess. I think you just lead. You're just such
a heart leader. You know, you lead with your heart so much that that's been your issue. I think,
you know, with when you say you're terrible at making decisions, you're you're making decisions
with your heart rather than using your head. But with all of this experience that you now have,
you're going to make better decisions. It's like a math equation. You're smart. You're too smart
to keep repeating those decisions. And I don't think the first decision was necessarily framed
as a bad decision. It was based on the courage of your convictions. Exactly. It was what you
believed in. I wouldn't frame that as bad. You just didn't realize the consequences. So it was
it was naive, as you say, it was young, but it wasn't like you did something wrong. You didn't
do something wrong. You know, I would like to think that I would have those same convictions
in your situation. So now where are you? Where are you with all of your trauma? How do you feel
about everything? And how do you feel about your life moving forward? And how do you frame the
past? So one of the best parts about being back in my hometown is I get to be anonymous. People,
when they've realized that i'm reality winner it's usually like oh you're billy's daughter
and so everybody wants to know how my mom and my sister are doing people don't really make the
connection to what i did the people down here are very conservative but they also don't follow
national news there which has kind of been my hiding place i'm just coach re and i've been
coaching CrossFit now for four years. It's a cult, but it's also what keeps me from being
bulimic. It's like the only cure that I've ever found so far. And, you know, I rescue dogs and I
recently started a veterinary technology program at the local university, which is the hardest
thing I've ever done. And the travel restrictions are even more like, I'm not traveling. I'm not
going anywhere. Like I basically signed up for three more years of federal probation.
What do you mean basically signed up?
Literally, if you miss more than two days, you're out of the program.
The vet tech program?
Yes. I felt more nervous asking for one day of missed class to go on book tour,
the week of publication, than I ever did asking my probation officer to travel.
You said you were surprised that they used the dog in the movie,
that they had the dog in the movie. Why did that surprise you?
Or that they had you stealing a dog in the movie, which you had never done at that time?
Oh, yeah.
I hadn't actually never stolen a dog.
My friends stole a dog for me back in May, and I just thought that was like a funny continuation
of like how that movie played out.
That was the only scene I've ever seen from that movie.
I just thought it was so delightful.
It is delightful.
It is.
It's so funny.
I wasn't even really into animal rescue at the time of my arrest.
You know, it's just kind of been a self-fulfilling prophecy.
Like, the more people talk about it, the more I started doing it in my own life.
And what do you think are, like, some of, like, what do you think is your biggest takeaway from spending all that time locked up and being treated as a criminal?
Like, what do you think that did to your spirit?
Like, do you feel stronger now?
I don't necessarily feel stronger.
I do feel a little bit more brittle, kind of like I know if you hit this glass against a table the
right way, it's going to shatter, you know? I know what can take me down really quickly.
You know, I've often said, like, what doesn't kill you just doesn't kill you.
But I do think that getting to interact with people from a background that I never would
have before and sort of breaking down. Like, I mean, when I was growing up, I was constantly
just around other brilliant children. Even in high school, you know, all my friends right now
are like, they're all doctors. They're just insanely successful people. And even in the
military, being around other people like me that could learn languages, I've never been around
normal people until I was in that county jail. And that's kind of what burst my bubble and helped me
understand my own country. I thought I was interested in social justice in the United
States. And then I got locked up and I got really interested in it very fast. Because you do realize
that what is happening to millions of other Americans can happen to you at any time. And that
all of us are one interaction with law enforcement away from being in solitary confinement without
legal justification. And what we're seeing now with, you know, these ICE raids going on and,
you know, citizens getting detained under immigration law, which is ridiculous. Like,
it's so scary right now to the point to where I never thought that this is
where we were going as a country, my basic understanding was, yeah, if they charge you
with a crime, they can do anything to you after that. And now they don't even have to charge you.
Oh, it is. Yeah, that's very scary to think about, especially when you put it like that.
What do you want out of life now that you have won?
honestly i just want to know that my community is a better place because i'm in it and like most
people i want to be comfortable in my life i want enough to get by i want to fence in my 10 acres
and open a dog sanctuary you know i mean my view of the world has gotten a lot smaller with this
criminal conviction, not being able to have the high positions that I wanted to do. I can't even
coach troubled kids, you know. I can't be a mentor yet. You have to have 10 years clearance from your
last day of your sentence. My sentence didn't end until last November. So in 2034, I might be
eligible to be a mentor for children caught up in the criminal justice system. I'm surprised they
allowed you to write a book? I am allowed. I can't make any money from it. And the NSA took
two years to clear that manuscript. Really? So where does the money go?
So I gave everything to my agent because I love him. Not in a weird, like creepy way,
but he found me and he didn't even know I couldn't make money from it. This was all
conversations we had later on once we found a publisher. As of right now, I don't have any
documentation to say otherwise, but proceeds from this book will go to charity. We just,
we waited two years for the NSA to clear the manuscript. When the time comes, we will make
a statement on which charities are and, you know, what percent of proceeds and how that works out
legally, but I do plan on being as transparent as possible. And do you want to have a family?
I have eight dogs, three cats, and somebody named Eddie. So. Is that a man in your life
or is that another animal? He's a man, unfortunately. No, no, no, no. That's not
unfortunate. I'm glad that you have someone that you care about. I want that for you.
and i also just want you to like you're an inspiration you know i hope you do you feel that
way um i don't i just i'm like looking back like i could have done things so much better
and i could have been somebody that the government couldn't say these terrible things about even
though 99 of them weren't true you know it's really hard to continually absorb the things
that were said about you in the courtroom that are like, there's just enough truth in that
statement, like to where you actually just believe everything they said about you. And I'm still
reckoning with that today. Like I said, I don't use my name in a lot of social situations. And
just admitting that I went to prison, you know, the biggest compliment that I get is if I bring
it up. People just think I went for like meth. And I'm like, I'm willing to go along with that.
Like, yeah, sure. It's so much more than that. Because I mean, I don't think you're taking into
account that you survived all of this. You know, of course, it's not ideal. Of course,
you don't want anyone to be saying, you know, to be propagating lies or perpetuating lies about you.
No, but you survived all of this. You have a job and you care about your like place in the
community look at all these animals that you're helping like your parent you're with your fam you
know like there's so many good things even though this is not an ideal situation and you would
if you had to repeat it you would not have repeated it you are here with us today and
there are lessons for you to still continue to learn and and and your story like sharing this
book with the world is going to be tremendously helpful I think and cathartic for your healing
process. I mean, I'm assuming you're already in therapy. I mean, you'd have to be, right? You
have been in therapy for a while. Yeah. Therapy and me don't get along well because for three
years of probation, I was court ordered to do it. I had to be in a program without being provided
the healthcare for it. So I was like a lot of paying out of pocket. So like for me, it just
led such a bad taste in my mouth, but I have been able to kind of get my veterans benefits back up
and running. Oh, that's great. Yeah. So I was properly diagnosed last fall and have been doing
a lot better with my mental health and a sort of regimen for that. And you need to reclaim that,
too. You know, you need to reclaim therapy because that's yours for the taking, not theirs to leave
a bad taste in your mouth. Yeah. I mean, I'll just do a bunch of podcasts till I feel better
about myself. Absolutely. Just keep talking and talking and spreading the good word. Well,
Chelsea, I think you're so right. This book, I feel like, is such a turning point where 10,
20 years down the road, you may have a better understanding of why you went through
what you went through, but this is just the beginning of that. This feels like a starting
point, a commencement, like we talked about earlier. We have to figure out what commencement
means because I keep looking up that word. I'm like, is it a beginning or an end?
Behind every night spent making the kids' lunches, there's a lot of suspense. Will they
finally eat the veggies will the pesto survive the first bite will the lunchbox come home empty
half full or come home at all and will you finish episode eight before you're done slicing the
cucumbers get bell pure fiber internet with crave netflix and disney plus from 94 a month price
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for details and to check availability bell connection is everything when i was 14 years old
I was kidnapped and held captive for nine months.
I survived, and I've spent my life exploring
how other people survive what should have destroyed them.
I'm Elizabeth Smart, and these are The Survivor Files.
I just remember this low, taunting voice
next to my ear saying,
shut up, don't say anything.
Every week, I'm with survivors
who live through the unthinkable.
I knew if he woke up,
Without a doubt, he was going to hurt me.
I started feeling that there was someone at the end of my bed, and I just started screaming.
They are abducted, stalked, controlled, and nearly silenced.
But these aren't stories about what's taken from them.
They're stories about what it takes to make it out alive.
Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app,
Apple Podcasts, or wherever you get your podcasts.
If your bookshelf and your For You page are equally important to your personality,
welcome home. This is Prose Society, the weekly podcast that's part book club,
part group chat for thought daughters, pop culture obsessives, and anyone who thinks
Pride and Prejudice and Love Island deserve the same level of discourse. I'm Eli Rallo,
and every week we're connecting the dots between books, the internet, and the conversations
everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed.
From best-selling authors and your favorite book talk creators to the latest pop culture moments, nothing is off the table.
It's like if you can hide some real messages inside compelling characters, then that is a Trojan horse.
Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place.
Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
See you between the pages.
On the new podcast, Solita, we share the messy reality of traveling alone as a woman.
I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle.
I chose option B.
I'm Julie Pinheiro and I travel by myself because it's a rare space where I can say yes without asking anyone else first.
I'm on a mission to reclaim the word solita, trading the pity for possibility.
Every time I tried to be alone, I kept meeting people and they were like, you smiled at us.
Not a lot of people smile around here.
It's when you're alone that you're most receptive to the world as it is and not the lies you're sold about it.
It can be a time where you push your limits, change your mind, or wake up to a new version of yourself.
So whether you're a solo travel veteran or you're too nervous to book your first trip,
I hope you listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your
podcasts.
hey this is Hayes Davenport and Sean Clements we host the podcast Hollywood Handbook on the
Big Money Players Network our show is extremely accessible to first-time listeners each week we
talk to someone in show business aka the biz and try to help them with their careers and see what
they have to offer us everyone has a good time and no one gets mad at their publicist for letting
them do our show we've had a lot of great guests like Sarah Sherman not that great actually can
Can you help me shape this?
How about we flip it on its head?
How about we flip this around?
What if the surprise woman, who actually you think is the straight man, is actually the one who's acting weird?
Adam Scott.
This entire time, you've been expecting Adam Sandler to come to visit the show.
I would never set expectations for something like that to happen.
It seems like you did.
universe allows for something like that to happen i'm open to it i'm always going to accept you know
danny mcbride fine yeah it's all this fragile masculinity exuding i could smell it walking
down the hallway to be honest with you i was like is that weed nope it's fragile masculinity
ben stiller no because a lot of times in out of context people don't get it or even know what a
circle is you know what i mean like you're like oh what's this david everyone's so dumb and fake
right fake and and also not interested or just like oh i've got my life i don't care about your
life and a lot of other big shots that wouldn't be where they are without us oh and by the way
will ferrell told us personally he loves the show and he wants to be a guest on every episode but
he's just so busy listen to hollywood handbook on the iheart radio app apple podcasts or wherever
you get your podcasts but no reality i think that it's so funny that your name is reality winner
i mean honestly try to be anonymous with a name like reality winner right but i really do think
like you haven't seen i know you've been out for four years but you haven't seen the lessons that
are going to come from this just yet and to be open to whatever comes your way and the fact that
you're so open and so willing to share your story and that you don't yes of course there's bitterness
but you don't come across as someone who is bitter and enveloped in your bitterness. Do you know what
I mean? You're loving and you're sweet. And to have those things remaining within you is quite
a feat. And it speaks volumes about your true character and who you really are, as opposed to
all of the things that have been said about you that are not true. Yeah, I think 2025 for me has
been difficult because we're right back in the same position we were in 2017 yeah of course it's
very triggering for you so triggering I mean one of the jokes we have is like you know the last
time around I only made it four months before I broke the law um and I think right now you've
already doubled your time you've already done it it's eight months I know I have little tick marks
you know what i mean like but it's like the guilt of that then was like last time i was willing to
act and now like so many millions of americans i don't want to lose everything all over again i
don't right you know am i supposed to be out there i mean and of course where i live in the middle of
nowhere you know we're not in a big city we're not in la we're not chicago right now what am i
supposed to do? Am I supposed to drive to Chicago and put my body between victims and masked agents,
masked kidnappers, you know? I mean, what am I supposed to do? You've done what you're supposed
to do. You're not supposed to be involved in anything else. You need to keep yourself safe
and sane. That's your main objective and take care of all of your animals and have a good time
with your boyfriend. That's what I want you to do. Those are doctor's orders. I'm a medical
professional. I'm actually not, so I can't say that, but I think I am. So, but that's, you've
done your, you've done your time literally, and you've done your contribution to society. Leave
that up to everybody else and just focus on getting yourself healthy and as happy as possible.
Cause I want you to have a really full life and you, you know, you're still young. You have a
whole life ahead of you. And this guy's not going to be president for the rest of our lives. This
is only a four-year stint, even though, you know, other things have, so just don't even, you know,
that's not your problem anymore. But I do want to thank you. I want all of our listeners to pick up
a copy of I Am Not Your Enemy by Reality Winner. This book is really important and it's important
to just, if you care about your country, it's important to read. And if you care about being
a strong woman who has, stands up for something and has convictions, it's important for you to
read. And it's a story about surviving. It really is. You're a survivor and you went through hell
and you're still here to talk about it. And that in and of itself just shows that you have a
purpose. And so thank you for coming on the podcast. And I really wish you all the best.
Thank you so much for having me. I mean, like I'm such a huge fan and I just really appreciate
you taking the time. Absolutely. It was my pleasure. And I was just when I met Susanna
and she's like, oh, will you moderate this film?
I just, I was like, oh my God, yes, I know that story.
So I was just, yeah, thrilled to be a part of that as well.
And I'm gonna text her right now as soon as we get off
and let her know that I got to meet you.
I can't wait to see her next week.
Oh, good, you're gonna see her.
Okay, tell her I say hi, will you?
I will.
Okay, okay, bye, reality.
Thank you so much.
Sending you huge love.
Bye, thank you.
Bye.
I put up New Vegas tapes, by the way, for next year.
This year, I will be there November 1st and November 29th.
Those are my last two dates this year.
Then I start up again January 31st, March 7th, April 18th, and May 30th.
And tickets are now on sale for all of those dates.
Do you want advice from Chelsea?
Write into DearChelseaPodcast at gmail.com.
Find full video episodes of Dear Chelsea on YouTube by searching at Dear Chelsea Pod.
Dear Chelsea is edited and engineered by Brad Dickert.
Executive producer, Catherine Law.
And be sure to check out our merch at chelseahandler.com.
I survived nine months in captivity,
and I've spent my life exploring how other people survive what should have destroyed them.
I'm Elizabeth Smart, and these are The Survivor Files.
Every week, I'm with survivors who lived through the unthinkable,
abducted, stalked, controlled, and nearly silenced.
These are stories about what it takes to make it out alive.
Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app,
Apple Podcasts, or wherever you get your podcasts.
If your bookshelf and your For You page are equally important to your personality,
welcome home.
Pro Society is a weekly podcast that's part book club, part group chat for anyone who
thinks Pride and Prejudice and Love Island deserve the same level of discourse.
Each week, we're connecting the dots between books, the internet, and pop culture.
with your favorite writers, book talk creators,
and plenty of overthought opinions.
Yeah, I'm obsessed. I'm obsessed.
Listen to Pro Society on the iHeartRadio app,
Apple Podcasts, or wherever you get your podcasts.
Did you hear the new episode of the Hey Jonas podcast?
We are at D23, so we'll see who stops by.
The cast of Frozen stopped by.
Kristen Bell, Josh Gad, and Idina Menzel.
I auditioned for Frozen.
What?
For Kristoff.
They said, okay, what are you going to be singing today?
I said, I don't know.
That must have been why you didn't get in.
Plus, John Stamos, Hayden Christensen from Star Wars, and more.
And I guess I can share that, uh...
No way.
Listen to the latest episode of Hey Jonas on the iHeartRadio app,
Apple Podcasts, or wherever you get your podcasts.
Hey, this is Hayes Davenport.
And Sean Clements.
We host the podcast Hollywood Handbook.
Each week, we talk to someone in show business
and try to help them with their careers and see what they have to offer us.
Everyone has a good time, and no one gets mad at their publicist
for letting them do our show.
We've had a lot of great guests like Sarah Sherman,
Adam Scott, Danny McBride, Ben Stiller,
and a lot of other big shots
that wouldn't be where they are without us.
Listen to Hollywood Handbook on the iHeartRadio app,
Apple Podcasts, or wherever you get your podcasts.
On the new podcast, Solita,
we share the messy reality of traveling alone as a woman.
I can wait four hours for the next bus
or this random dude is offering me a ride on his motorcycle.
I chose option B.
I'm Julie Pinheiro and I travel by myself
because it's a rare space where I can say yes
without asking anyone else first
I'm on a mission to reclaim the word solita
trading the pity for possibility
listen to solita on the iHeartRadio app
Apple Podcasts or wherever you get your podcasts
this is an iHeart Podcast
guaranteed human
