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

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Episodes mentioned

Number stations https://coldwarconversations.com/episode239/

Photos and videos relating to this episode https://coldwarconversations.com/episode277/

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