A Government Whistleblower Trusts a Newsroom, Ends Up in Prison
Question Everything
Brian Reed
4.6 • 707 Ratings
🗓️ 6 November 2025
⏱️ 39 minutes
🧾️ Download transcript
Summary
When NSA contractor Reality Winner leaked proof that Russia had tried to break into the U.S. election system, she thought she was helping her country. Instead, she got the longest federal prison sentence ever for giving information to the press. While prepping for her trial, she found out that the journalist she had trusted with the leaked document, accidentally exposed her. The Intercept, once known for protecting sources like Edward Snowden, bungled their vetting process in a way that led investigators straight to Reality’s front door.
As Reality releases her new memoir, “I Am Not Your Enemy,” This American Life host Ira Glass joins her in a live conversation, where she explains what happened and how the media turned her life into fodder for tabloid TV.
“Question Everything” is a production of KCRW and Placement Theory. And don’t forget to sign up for our newsletter.
Guests:
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Reality Winner, government whistleblower
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Ira Glass, host of This American Life
Show Notes:
During Reality’s conversation with Ira Glass, she said she thought the world record for holding an abdominal plank position is around 18 hours. According to Guinness World Records, the record is 9 hours 38 minutes 47 seconds.
Transcript
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| 0:00.0 | Today on the show, a conversation with someone who lots of people view as a patriot and others see as a traitor. |
| 0:12.3 | Some of the biggest turning points in our country's history have come thanks to whistleblowers who broke the law and risked everything to get information out to the public. |
| 0:21.9 | Daniel Ellsberg leaked the Pentagon Papers, revealing how leaders had misled the country about Vietnam. |
| 0:27.5 | Edward Snowden exposed the government's vast surveillance of its own citizens. |
| 0:31.6 | Chelsea Manning revealed human rights abuses by the U.S., including soldiers in an Army Apache helicopter shooting at Iraqi civilians and |
| 0:39.0 | journalists, because they allegedly mistook them for insurgents. |
| 0:43.1 | And in 2017, a 25-year-old NSA contractor, a linguist, named Reality Winner, leaked proof |
| 0:50.1 | that Russia had tried to break into U.S. election systems. |
| 0:55.2 | I just wanted people to see the truth for once |
| 0:58.5 | and not what their relative media platform was going to tell them. |
| 1:05.8 | For that, reality got the longest prison sentence |
| 1:09.0 | ever imposed on a whistleblower for leaking information to the media. |
| 1:13.1 | Reality speaks Dari and Pashto, loves working out, really into yoga and CrossFit. |
| 1:18.2 | When FBI agents came to arrest her at her home in Georgia, she had a Pikachu bedspread, which then got reported in Rolling Stone. |
| 1:25.2 | You might remember her story because it's been documented in three films. There was a documentary plus two feature films, one on Hulu called Winner, starring Zach Alphenakis and Connie Britton as her parents and Amelia Jones as reality. And then there was an HBO film called Reality, which starred Cindy Sweeney. We had the director and writer of that movie on our show last year. |
| 1:45.8 | Up next, reality winner tells her story, in her own words, to Ira Glass. From KCRW in |
| 1:52.0 | placement theory, this is Question Everything. I'm Brian Reed. Stick around. In order for our system |
| 2:00.2 | to work, however imperfect, where whistleblowers feel comfortable taking such a huge gamble to give sensitive information to a reporter, they have to trust reporters. |
| 2:10.1 | And what happened to reality winner was a massive breach of trust by journalists, a huge failure. |
| 2:15.8 | I've always wanted to hear reality talk about that if she has regrets |
| 2:19.3 | about her experience, anger, and what lessons she takes from it. I recently went to an event here |
| 2:25.3 | in New York moderated by my former boss and mentor, this American life host, Ira Glass. He was |
... |
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