The Spy Who Colluded with Castro

Podcast: The Spy Who
Episode: Ready to Snap (Episode 3)
Release Date: October 14, 2025
Hosts: Indira Varma & Raza Jaffrey (Wondery)

Overview

This episode continues the gripping story of Ana Montes, a high-level U.S. Defense Intelligence Agency (DIA) analyst who secretly spied for Cuba. It takes listeners inside the tense cat-and-mouse game as suspicions mount, the investigation intensifies, and Ana's world begins to unravel. The episode blends historical research and reconstructed dialogue to capture the emotional stakes and personal struggles faced by those pursuing and betraying their country from within.

Key Discussion Points & Insights

1. The Investigation Hits Bureaucratic Roadblocks

• FBI and DIA Tensions:

  • DIA counterintelligence officer Scott Carmichael and his colleague “Gator” meet with FBI agent Steve McCoy to share evidence that points to Ana Montes as "Agent S," Cuba’s mole inside the DIA. (00:00-04:42)
  • Despite the seriousness of the tip, McCoy is dismissive: “Ana? A woman? You’re way off the mark. The agent we’re looking for is a man.” (02:06)
  • Differences in agency priorities and procedures hobble progress; McCoy remains secretive and wary of sharing operational details.

• Escalation:

  • Carmichael, frustrated, approaches McCoy’s supervisor, Diane Cressman. Still, the FBI is unconvinced:

    “Being in the right place at the right time is not enough to make a case…You can’t just point the finger at someone and ask us to place them under surveillance.” (05:48)

  • Surveilling Montes is seen as a gamble with little legal basis.

2. Ana Montes: Cracks in the Double Life

• Personal Strain and Burnout:

  • In a clandestine meeting in Grand Cayman, Montes pleads with her Cuban handler to let her go:

    “I can’t do this forever. Having to pretend to be one thing and being another and not being able to talk to anyone, not even my therapist. It’s too much. I’m losing sleep and I find it hard to concentrate. I’m afraid I’ll slip up. I need to stop.” (07:49)

  • The handler reminds her of her value, warning her she’s trapped: “If you stop working for us, there is nothing we can do to protect you.” (08:54)

• Isolation Intensifies:

  • Her only solace is her relationship with Roger, but even that is precarious due to her secrets and operational demands.

3. Mounting Surveillance and Close Calls

• Legal Hurdles and Evidence:

  • The FBI finally seeks a surveillance warrant but faces skepticism from a judge:

    “This is weak. What you describe as evidence is largely circumstantial…None of this will stand up in a court of law. Which is why we need a warrant.” (10:30)

  • The bureau is given 90 days to collect hard evidence or drop the investigation.

• Observation and Break-Ins:

  • Agents surveil Montes, search her apartment (finding a Toshiba laptop and shortwave radio), but legal proof remains elusive. (18:00)
  • Internal operations become more daring, including a high-risk purse “snatch and return,” seeking the cipher used to contact Cuba.

4. The Impact of 9/11 and Rising Stakes

• The terrorist attacks of September 11, 2001 change the context dramatically:
  • Montes is promoted to acting branch chief for Afghanistan targets—her access to war plans makes her even more dangerous if undiscovered. (27:49)
  • DIA director Vice Admiral Thomas Wilson expresses his growing frustration:

    “We’re about to go to war. And we’re in a position where our battle plans will likely be fed straight to Osama bin Laden, right via the Cubans. We’re monitoring her all hours…But since the flights have been grounded, her boyfriend has been unable to leave DC…Your Time’s up, McCoy. I’m not going to war with a spy in our organization. If you do not have that woman in cuffs by the end of the week, then I’m firing her.” (30:33)

5. The Final Sting and Arrest

• Ana Suspects Surveillance:

  • During a walk to the National Zoo, Ana spots recurring faces—an elderly woman, a skateboarder—and realizes the FBI is watching her. Nevertheless, she sends an encrypted warning—“Danger Pearl”—to her Cuban handlers. (33:20)

• Arrest and Interrogation:

  • Five days later, Montes is confronted and arrested by McCoy and FBI agent Peter Lapp at the DIA.

    “We know what you’ve done. … But if you don’t [cooperate], we’re going to visit your brother and sister and end their FBI careers…Your life as you know it is as good as over. But you can stop theirs being ripped apart. And Roger’s, too.” (35:11)

  • Montes invokes her right to counsel and is marched out in handcuffs as colleagues watch in shock.

6. Guilty Plea, Sentencing, and Legacy

• Courtroom Drama:

  • At sentencing, Ana makes a defiant speech:

    “I am here before you because I obeyed my conscience rather than the law. Our government’s policy towards Cuba is cruel and unfair. I felt morally obligated to help Cuba defend itself from our efforts to impose our values and our political system on it.” (38:27)

  • Her sister Lucy is stunned and disappointed by Ana’s lack of remorse.
  • The judge responds sternly:

    “If you can’t love your country, you should at least do it no harm.” (39:00)

• Outcome:

  • Ana is sentenced to 25 years in prison, five years parole, and 500 hours of community service.
  • She was released in January 2023 after serving 20 years.

Notable Quotes & Memorable Moments

• “The FBI is the only intelligence agency with the power to arrest. Without them on board, Carmichael's hands are tied.” – Narration (04:30)
• “Being in the right place at the right time is not enough to make a case…you can’t just point the finger at someone and ask us to place them under surveillance.” – Diane Cressman (05:48)
• “I’m losing sleep and I find it hard to concentrate. I’m afraid I’ll slip up. I need to stop.” – Ana Montes to her Cuban handler (07:55)
• “This is weak. What you describe as evidence is largely circumstantial... None of this will stand up in a court of law.” – FISA Judge (10:30)
• “We’re about to go to war. And we’re in a position where our battle plans will likely be fed straight to Osama bin Laden, right via the Cubans.” – Vice Adm. Thomas Wilson (30:33)
• “Your life as you know it is as good as over. But you can stop theirs [her family’s] being ripped apart.” – Steve McCoy to Ana (35:13)
• “I am here before you because I obeyed my conscience rather than the law. Our government’s policy towards Cuba is cruel and unfair.” – Ana Montes in court (38:27)
• “If you can’t love your country, you should at least do it no harm.” – Judge Ricardo Urbina (39:00)

Timeline / Timestamps for Important Segments

• FBI & DIA Confrontation: 00:00 – 04:42
• Carmichael Escalates to Supervisor: 05:48 – 07:31
• Ana in Grand Cayman / Wants Out: 07:35 – 09:18
• FISA Judge Reluctance to Issue Warrant: 10:15 – 11:52
• FBI Apartment Search: 18:00 – 21:10
• Tension after 9/11: 27:49 – 32:00
• Ana Realizes She’s Being Watched: 33:10 – 34:18
• Ana’s Arrest: 35:11 – 36:30
• Sentencing and Final Reflections: 38:27 – End

Tone and Storytelling

The tone is tense, meticulous, and empathetic, weaving together the procedural aspects of counterintelligence work with personal drama and moral ambiguity. The narrative does not shy away from Ana's own perspective, capturing her emotional exhaustion and conflicted motivations.

Closing Notes

The episode closes by reflecting on the broader impact of Ana Montes' betrayal, its effects on her family, and the open questions surrounding her motivations and legacy. A preview announces the next episode's deeper dive into Montes’ psychology and familial dynamics, featuring author Jim Popkin and comedian/writer Charlie Higson.

Sources referenced in the episode:

• True Believer by Scott Carmichael
• Codename Blue Wren by Jim Popkin
• Queen of Cuba by Peter Lapp

For more stories from the shadow world of espionage, visit Wondery’s The Spy Who.