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The Spy Who Colluded with Castro | How Ana Montes Fooled Her FBI Siblings | 4

The Spy Who

Tuesday, 21 October 2025 - 36 minutes

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.

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