The most damaging female spy in US history (277)

Ana Montes was the most damaging female spy in US history. For nearly 17 years, Montes was one of the government's top Cuba experts, with easy access to classified documents. By night, she was working for Fidel Castro's Cuba, listening to coded messages over shortwave radio, passing US secrets to handlers in local restaurants, and slipping into Havana wearing a wig. Her only sister, Lucy, worked for the FBI helping the FBI flush Cuban spies out of the United States. Little did Lucy or her family know that the greatest Cuban spy of all was sitting right next to them at Thanksgivings, baptisms, and weddings. I speak with investigative journalist Jim Popkin whose book Code Name Blue Wren, weaves the tale of two sisters who chose two very different paths and reveals the making of a traitor- a woman labelled "one of the most damaging spies in U.S. history" by America's top counter-intelligence official. After more than two decades in federal prison, Montes was freed in January 2023. 0:00 Introduction to Anna Montes and her spying activities 10:15 Anna Montes' radicalization and move to Washington 18:10 Anna's trip to Cuba and her spy training 26:12 Anna's entry into the DIA and her unique method of passing information 33:14 Anna's communication methods with Cuba and her siblings joining the FBI 42:01 Colleagues' perception of Anna and her personality changes 49:37 The FBI's success in Cuban counterintelligence operations and suspicions about Anna 54:42 Agent S's identity and the investigation into Agent S 1:02:19 Building the case against Ana Montes and the evidence found 1:07:20 Ana Montes' promotion, arrest, and prosecution 1:15:22 Anna Montes' unapologetic stance and her sentence 1:18:08 Jim's book: Code Name Blue Ren 1:19:07 Cold War Conversations Facebook Group and store promotions Table of contents powered by PodcastAI✨ Buy the book here https://amzn.to/3l9s47k Episodes mentioned Number stations https://coldwarconversations.com/episode239/ Photos and videos relating to this episode https://coldwarconversations.com/episode277/ The battle to preserve Cold War history is ongoing and your support can provide me with the ammunition to continue to keep this podcast on the air. Via a simple monthly donation, you’ll become part of our community and get a sought-after CWC coaster as a thank you and you’ll bask in the warm glow of knowing you are helping to preserve Cold War history. Just go to https://coldwarconversations.com/donate/ If a monthly contribution is not your cup of tea, We also welcome one-off donations via the same link. Support the project! https://coldwarconversations.com/donate/ Follow us on Twitter https://twitter.com/ColdWarPod Facebook https://www.facebook.com/groups/coldwarpod/ Instagram https://www.instagram.com/coldwarconversations/ Youtube https://youtube.com/@ColdWarConversations Learn more about your ad choices. Visit podcastchoices.com/adchoices