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The Shadow Dossier — The Queen of Cuba · The Shadow Dossier

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  The Shadow Dossier. Act I. No money. No dead
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  drops. Most spies in these files were paid, or
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  blackmailed, or both. Ana Montes was neither.
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  A senior analyst at the Defense Intelligence
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  Agency and the U .S. government's leading expert
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  on Cuba, Montes spied for Cuban intelligence
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  for 16 years. from 1985 until her arrest in 2001,
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  almost entirely without financial compensation.
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  Her motivation, she told investigators after
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  her arrest, was ideological, a conviction that
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  U .S. policy toward Cuba was unjust. Her tradecraft
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  was old -fashioned and, for over a decade and
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  a half, nearly flawless. There was almost no
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  physical evidence to catch. rising while spying.
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  What made Montez so effective was that she wasn't
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  a low -level clerk skimming documents. She rose
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  to become the DIA's top Cuba analyst, trusted
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  to brief senior policymakers and shape official
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  U .S. assessments of Cuban military capability
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  and intentions, all while systematically providing
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  Havana with insight into what Washington knew
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  and didn't know about Cuba. Her access and influence
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  are believed to have compromised at least one
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  U .S. intelligence operation and to have shaped
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  Cuba policy assessments in Havana's favor for
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  years, without her colleagues ever suspecting
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  the woman drafting their briefings. Counterintelligence
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  officials had circulated warnings as early as
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  the 1990s about a suspected mole inside U .S.
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  Cuba policy circles, based on patterns in what
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  Havana seemed to know. Building a provable case
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  against Montez specifically took years of careful,
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  quiet investigation, tracking her movements,
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  and eventually gaining enough evidence to search
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  her apartment. She was arrested in September
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  2001, just days after the September 11th attacks,
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  in an arrest time partly out of concern that
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  the crisis atmosphere might give her an opportunity
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  to flee or that her access might be used in the
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  confusion. Montez pleaded guilty and was sentenced
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  to 25 years, later reduced, and was released
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  from prison in January 2023 after serving about
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  20 years. Unlike many spies motivated by money
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  or blackmail, Montez never expressed regret for
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  her actions, describing her conduct after release
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  as consistent with her convictions about American
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  policy. Her case remains a difficult one for
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  intelligence services to fully guard against.
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  Not a foreign infiltrator smuggled into a position
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  of trust, but an American citizen who earned
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  that trust honestly and then chose, entirely
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  on her own initiative and for reasons she considered
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  principled, to give parts of it away. This concludes
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  declassified file number 069 of the Shadow Dossier,
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  the Queen of Cuba. What dangerous secrets await
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  in our next file? Subscribe on Apple Podcasts,
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  Spotify, RSS .com, and YouTube so you never miss
• 4:34
  an official declassification. This is the shadow
• 4:40
  dossier. Thank you for listening.