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Life Will Be the Death of Me with Chelsea Handler

I Am Not Your Enemy with Whistleblower Reality Winner

Life Will Be the Death of Me with Chelsea Handler

iHeartPodcasts

Comedy Interviews, Comedy, Society & Culture

4.64.6K Ratings

🗓️ 18 September 2025

⏱️ 50 minutes

🧾️ Download transcript

Summary

Chelsea 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 election.  They discuss Reality’s arrest, incarceration and recovery - and why it’s so important to speak out when you see injustice.  

 

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Need some advice from Chelsea? Email us at [email protected]

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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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.

Transcript

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0:00.0

This is an IHeart podcast.

0:54.2

Okay. Hi. Hi, Catherine. Hi. 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 posted these awards 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?

0:54.9

I mean, I can't really even track a conversation.

1:09.8

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 there? 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.

1:11.4

I announced the High and Mighty tour,

1:13.1

which I'm going to start next year.

1:44.8

I start in Washington, D.C. 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.

1:48.3

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,

1:53.1

she was a whistleblower during Trump's first term. She was working at the NSA, and she leaked some

1:59.6

document to the intercept. some document to the intercept.

2:02.7

Yeah, to the intercept.

2:03.9

And then the FBI basically arrested her.

2:07.7

They came, they interrogated her.

2:09.4

They showed up at her house on a Saturday afternoon.

2:11.9

And anyway, she's a former linguist.

2:14.7

She's an intelligence analyst.

2:16.0

She was arrested in 2017 for leaking classified documents about the Russian interference

2:20.4

in the 2016 election.

2:22.6

And there is some backstory that our listeners should know about before we get into this

2:26.7

conversation.

2:27.9

Reality was in the Air Force as a linguist.

2:29.9

She translated conversations for government targets.

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