Podcast Summary: Click Here — Reality Winner Writes the Next Chapter

Host: Dina Temple-Raston
Date: November 4, 2025
Guest: Reality Winner, former NSA contractor and author of I Am Not Your Enemy
Location: Politics and Prose Bookstore, Washington D.C.

Episode Overview

This episode features an in-depth conversation with Reality Winner, a former NSA contractor famously prosecuted for leaking a classified intelligence report on Russian election interference in 2017. Winner discusses her new book, I Am Not Your Enemy, which weaves memoir with reflection on idealism, government secrecy, and her lived consequences. The discussion explores the pressures of intelligence work, the ethics and fallout of leaking, lessons from her imprisonment, and her assessment of America’s evolving security state.

Key Discussion Points & Insights

1. Background: Who Is Reality Winner?

[00:02 – 02:09]

• Winner was a decorated Air Force linguist and NSA contractor who, disillusioned by events post-2016 election, leaked a classified document detailing Russian attempts to interfere with U.S. voting systems.
• She was prosecuted under the Espionage Act, serving over four years in prison— "the longest sentence ever meted out to someone for sharing classified information with the press." (Host, 01:36)

2. Rules, Secrecy, and the Cost of Leaking

[02:30 – 03:34]

• Winner admits breaking the law, but critiques the Espionage Act’s lack of distinction regarding motive or intent:

  “...the law will treat me the same if I did it for you guys or if I sold that document to North Korea for a million dollars. The consequences are the same. I don’t think that’s right.” (Reality Winner, 02:30)

3. Life in Intelligence: Remote Work, Pressure, and Mental Health

[03:34 – 08:59]

• Winner’s NSA work involved monitoring and translating snippets of intercepted conversations:

  “We really never at any time felt qualified to do what we were doing, but we were required to do it.” (Reality Winner, 04:37)

• She describes intense pressure to produce actionable intelligence, even in the absence of real findings, contributing to a sense of guilt and PTSD among analysts:

  “...the guilt was insane. The pressure was insane. …we thought we would do something important, and it just wasn’t.” (Reality Winner, 07:18)

4. Why She Leaked the Document: The Culture of Secrecy and Viral Intel

[09:37 – 14:08]

• An intelligence report detailing Russian hacking attempts “went viral” on NSA Pulse, the agency’s internal portal.
• Winner was surprised this vital information wasn’t being shared more broadly, especially as media outlets reported on leaks and the Trump administration was itself accused of mishandling intelligence.

  “This report seemed like a bombshell. But one thing confounded me. Why this secret? Why isn’t this getting out there?” (Reality Winner, 10:52)

• She assumed Congress and the public should already know:

  “I thought…Congress saw it…people in power…had seen it and they hadn’t. …Just us.” (Reality Winner, 13:03–13:48)

5. The Leak: Motives, Actions, and Aftermath

[14:08 – 16:33]

• Winner took care to minimize risk to sources and methods, reasoning the dated document was not dangerous.
• Her plan: mail (not transmit electronically) the printout to The Intercept. She hoped public reaction would outweigh consequences but didn’t believe she would escape notice.

  “I was not thinking about what to do after that. That’s why I didn’t have a single attorney in my life when the FBI showed up…” (Reality Winner, 14:08)

Memorable Detail

• Winner mailed the document from a USPS box after subbing a yoga class:

  “Obviously I had to commit a felony in a way that was convenient to me.” (Reality Winner, 15:39)

6. Exposure, the FBI Knock, and Flawed Journalistic Process

[17:43 – 22:28]

• The Intercept’s verification process was botched, with a journalist sending a scan of the leaked document to a direct NSA contact, exposing Winner’s location.

  “He sent it to his buddy…and his buddy’s like, hey, where’d that come from?...It came from Augusta, Georgia…” (Reality Winner, 18:56)

• Three weeks later, the FBI arrived. Winner describes the surreal, frightening process of her arrest and interrogation, including her fear of secret detention:

  “That was when I thought my life was over…just a bunch of non-uniformed armed men...They were just completely incognito, which is what we’re seeing in the country now.” (Reality Winner, 23:23)

7. Legal Process and the Ambiguity of the Espionage Act

[25:26 – 26:39]

• Winner was charged under Section 793E of the Espionage Act, which she criticizes for its vagueness and lack of intent consideration:

  “...there is no legal subtext defining national defense information…It’s just whatever they want to define it in your indictment as being.” (Reality Winner, 25:34)

8. Reflection: Prison, Freedom, and Regret?

[27:29 – 30:15]

• Winner describes the unexpected hardships of release, the constant surveillance, and the loss of normal relationships with family.

  “They don’t tell you when you get out that it’s harder than prison getting out.” (Reality Winner, 28:00)

• Has prison changed her?

  “...Now what I understand is, like, the most dangerous things in America are us.” (Reality Winner, 29:20)

• Any regrets?

  “Absolutely not. …If I have to commit a felony over again, I would be a lot more comfortable…having taken that document straight to D.C.…to someone like Bernie Sanders.” (Reality Winner, 29:49)

Notable Quotes & Moments

• On the Espionage Act’s unfairness
  “The law will treat me the same if I did it for you guys or if I sold that document to North Korea for a million dollars. The consequences are the same. I don’t think that’s right.”
  (Reality Winner, 02:30 & 26:58)

• On being a remote analyst
  “We put on the same uniform as soldiers overseas…But…the guilt was insane. The pressure was insane.”
  (Reality Winner, 07:18)

• On leak culture
  “The whole country knew that Trump had volunteered classified intelligence information to Russia, but this was somehow being kept under wraps, somehow.”
  (Reality Winner, 11:28)

• On aftermath and regret
  “Absolutely not.”
  (Reality Winner, 29:49 — would not go back and change her actions, but would do it differently)

Timestamps for Important Segments

| Time | Segment Description | |-----------|---------------------------------------------------------| | 00:02 | Dina Temple Raston introduces Reality Winner’s story | | 02:09 | Discussion of Winner’s new book / theme of secrecy | | 03:34 | Winner explains the “vague and menacing” NDA and plea | | 04:37 | Winner describes her SIGINT job and feelings of unpreparedness | | 07:10 | Winner opens up about guilt, PTSD, and expectations | | 09:37 | Leak culture and intelligence reports going “viral” | | 13:03 | Winner realizes Congress/the public isn’t seeing vital intel| | 14:08 | Details of the leak: how and why Winner acted | | 18:56 | The Intercept’s failure to protect source anonymity | | 21:19 | FBI interrogation and arrest; reality of the process | | 25:26 | Espionage Act’s vague language and application | | 29:49 | If she’d do it again: Winner discusses choices |

Episode Takeaways

• Winner’s story is about the weight of conscience, the cost of government secrecy, and the legal perils facing whistleblowers—even those who act with public interest in mind.
• Her experience exposes flaws in both journalistic source protection and in legal frameworks meant to rein in spies, not truth-tellers.
• Winner doesn’t regret exposing what she saw as crucial public information, but is now more aware of the systemic consequences for those who dare.
• Her book and public reflections offer personal, sometimes raw insights into sacrifice, justice, and America’s current struggle with secrecy and truth.