Two films, one real-life National Security Agency (NSA) whistleblower, and a story that blurs the line between truth and fiction. In part two of our season finale, we dive into two very different films: Reality (2023), the HBO American crime drama directed by Tina Sater and staring Sydney Sweeney, and Winner (2024), the black comedy directed by Susanna Fogel, staring Emilia Jones, Connie Britton, and Zach Galifianakis. The films offer two very different cinematic interpretations of the life and arrest of Reality Winner, a former US Air Force linguist turned NSA contractor who leaked top-secret documents about Russian interference in the 2016 presidential election.

We unpack how each film portrays Winner’s character, choices, and the forces that brought her from military service to a leak that made national headlines. Next, we contrast those portrayals with the real events – from the NSA leak and Federal Bureau of Intelligence (FBI) investigation to her 2018 guilty plea and five-year sentence under the Espionage Act, the longest such punishment for unauthorized media disclosure in recent history. Whether you’ve seen the movies, followed the headlines, or are just curious about the real woman behind both scripts, this episode peels back Hollywood’s layers to reveal the truth beneath.

Primary Sources:

Howley, Kerry. Bottoms Up and the Devil Laughs: A Journey Through the Deep State. Knopf (2023).
Winner, Reality. I Am Not Your Enemy: A Memoir. Spiegel & Grau (2025).
NSA Document

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