The Spy Who Colluded with Castro | How Ana Montes Fooled Her FBI Siblings | 4
The Spy Who
Audible
4.6 • 891 Ratings
🗓️ 21 October 2025
⏱️ 37 minutes
🧾️ Download transcript
Summary
How did Ana Montes spy for Cuba for 17 years while surrounded by FBI agents, which included her own relatives? Investigative journalist Jim Popkin joins spy novelist Charlie Higson to reveal how the Pentagon's top Cuba analyst maintained her double life, and shared Thanksgiving dinner surrounded FBI family members while feeding America's military secrets to Havana. Having spent extensive time with Montes’ own siblings, Popkin knows this remarkable story of deception inside out - from Montes’ risky romance with an intelligence officer, to the psychological discipline that kept her hidden in plain sight. It's a tale that shook US intelligence to its core, wrapped around a family drama that still reverberates today.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Wonderry plus subscribers can binge full seasons of the Spy Who early and add free on Apple |
| 0:06.8 | podcasts or the Wondery app. |
| 0:12.2 | From Wondery, I'm Charlie Hicksons, Spy novelist, actor, comedian, and this is The Spy Who. |
| 0:24.2 | Thank you for joining us for our final episode of The Spy Who colluded with Castro. |
| 0:29.2 | The real art of espionage is to stay hidden. |
| 0:32.9 | And Arna Montes remained hidden in plain sight for 17 years. |
| 0:38.4 | Working at the Defence Intelligence Agency, the nerve centre of US military strategy, |
| 0:44.1 | Anna shared its secrets with its closest enemy, Castro's Cuba. |
| 0:48.9 | Eventually, her actions earned her the title, |
| 0:51.9 | The Most Dangerous Females Spy in US history. From a young age, |
| 0:56.8 | the army was a defining part of Arna's life. Her controlling father was a US army colonel. Her |
| 1:02.9 | brother and sister both became FBI agents, with her sister Lucy specifically tasked with |
| 1:09.2 | finding Cuban spies in the US. |
| 1:12.1 | Little did she know there was one on the opposite side of the dinner table. |
| 1:16.5 | To hear how her story unfolded, make sure you've listened to episodes one to three of this season. |
| 1:23.7 | In this episode, I'm going to talk with author and investigative journalist Jim Popkin. |
| 1:29.5 | He wrote the book, Codename Blue Ren, the true story of America's most dangerous female spy, and the sister she betrayed. |
| 1:38.5 | Jim knows the world of Anna Montes. |
| 1:40.7 | He knows the family, he knows the agents who worked with Anna, the ones who trusted her, |
| 1:45.8 | the ones who eventually took her to her sentencing. I want to understand how Anna was able to work |
| 1:51.2 | undercover for so long, how she could sit across the dinner table from her family and loved ones |
| 1:56.1 | and not crack, and whether he thinks the Cubans really cared for at all. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Audible, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Audible and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.

