Fresh Air NSA Whistleblower Reality Winner
10 snips
Sep 11, 2025 
Reality Winner, a former NSA contractor and Air Force veteran, discusses her decision to leak classified documents on Russian election interference, reflecting on the intense moral dilemmas and the repercussions of her actions. She shares her harrowing experiences during incarceration, particularly the unique struggles faced by women in federal prison. Winner also opens up about navigating life after prison, including the challenges of reintegration and her evolving identity as a whistleblower. Additionally, John Powers reviews the MUBI series exploring Mussolini's rise to power.
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Leaking To The Intercept
- Reality Winner leaked a classified NSA document about Russian cyber attacks to The Intercept because she believed Americans needed to know.
- She mailed a five-page printout in a hand-addressed envelope expecting careful handling and redaction.
Reporter Mishandling Led To Exposure
- Matthew Cole, the assigned reporter, mishandled the document and shared scans with an NSA contact.
- That contact recognized the printer crease and digital watermark, which led the agency to identify Winner.
Arrest At The Doorstep
- Two FBI agents arrested Winner at her doorstep, showed a warrant, and said they were looking for classified documents.
- She felt a brief relief because she believed she no longer possessed classified materials.
