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 activities10:15 Anna Montes' radicalization and move to Washington18:10 Anna's trip to Cuba and her spy training26:12 Anna's entry into the DIA and her unique method of passing information33:14 Anna's communication methods with Cuba and her siblings joining the FBI42:01 Colleagues' perception of Anna and her personality changes49:37 The FBI's success in Cuban counterintelligence operations and suspicions about Anna54:42 Agent S's identity and the investigation into Agent S1:02:19 Building the case against Ana Montes and the evidence found1:07:20 Ana Montes' promotion, arrest, and prosecution1:15:22 Anna Montes' unapologetic stance and her sentence1:18:08 Jim's book: Code Name Blue Ren1:19:07 Cold War Conversations Facebook Group and store promotionsTable of contents powered by PodcastAI✨

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