The Spy Who Colluded with Castro | In This Building | Episode 2

Podcast: The Spy Who
Hosts: Indira Varma, Raza Jaffrey
Date: October 7, 2025
Duration: ~45 minutes (excluding ads, intros, outros)

Episode Overview

This mesmerizing second installment of "The Spy Who Colluded with Castro" charts the high-stakes cat-and-mouse game unfolding within the heart of U.S. intelligence. The episode dives deep into the double life of Ana Montes—a Defense Intelligence Agency (DIA) analyst covertly passing America’s most sensitive military secrets to Cuba. As suspicion steadily mounts and investigative nets tighten, the episode weaves through tense interrogations, secret intelligence briefings, and the psychological toll of treason. Key rivalries and suspicions among NSA, FBI, and DIA bureaucracies amplify the drama, showing not just how one woman outmaneuvered the U.S. security apparatus, but also how cracks within America’s own agencies enabled her deception.

Key Discussion Points and Insights

1. Immediate Suspicion: Interrogation at the DIA

(00:00 - 04:57)

• Setting: November 1996, Clarendon, Virginia.
• Action: Ana Montes is summoned by the DIA's senior counterintelligence investigator, Scott Carmichael, for questioning regarding suspected Cuban connections.
• Dynamics:
  • Montes maintains composure under questioning, using plausible deniability, e.g., defending her work hours and challenging weak evidence ("8pm is not early. I had come in at around 8 in the morning and I was completely exhausted." – Ana Montes, 02:09).
  • Carmichael clarifies she's not officially under investigation, which temporarily allays her fears.
• Insight: The U.S. intelligence community’s initial suspicions lack depth, relying on circumstantial behaviors rather than hard evidence, allowing Montes to evade trouble.

Notable Quote

“If this is the sort of evidence they're throwing at her, it's incredibly thin.”
— Indira Varma (narration), 03:57

2. ESPIONAGE AT THE HIGHEST LEVELS: The Misty Satellite Program

(06:36 - 14:00)

• Setting: February 1996, then May 1997, at NRO and DIA briefings; followed by Ana’s therapist’s office and confidential actions at home.
• Action:
  • The NRO launches a covert multi-billion-dollar spy satellite, Misty, faking its destruction to deceive rival nations.
  • Montes, privy to this information after her clearance is increased, debates leaking it to Cuba, understanding the severity ("This is a secret so big that if she were caught sharing it with the Cubans, she could face the death penalty." – Indira Varma, 11:43).
  • In therapy, Montes struggles with loneliness, guilt, and familial scars influencing her choices.
  • Eventually, she sends the Misty satellite intelligence to her handler, Ernesto, using a wiped floppy disk.

Notable Quotes

“It would be a tremendous aid to Fidel Castro's regime, a chance to rebalance the geopolitical order.”
— Indira Varma (narration), 12:37

"Because what I just gave you is big. Really big."
— Ana Montes to Ernesto, 18:34

3. THE HUNTERS CLOSE IN: U.S. Agencies Intercept Clues

(20:24 - 27:00)

• Setting: April 1998, NSA headquarters; later in field offices and at meetings between U.S. agencies.
• Action:
  • NSA officer Elena Valdez briefs 20 FBI counter-espionage agents on intercepted Cuban communications indicating a spy (codenamed "Agent S") has penetrated the upper ranks of U.S. intelligence.
  • Friction and dismissal: The FBI is skeptical; Valdez, who takes the case personally, faces resistance and bureaucratic inertia.
• Insights:
  • Inter-agency competition and skepticism hinder swift responses to emerging threats.
  • Valdez's backstory (her family fleeing Cuba) animates her relentless pursuit.

Notable Quotes

"We all know how the Cubans operate. They recruit naive students who think Che Guevara is some sexy guy on a poster, not a vicious killer."
— Elena Valdez, 24:48

"If they have someone high up in our agencies, we need to find them."
— Elena Valdez, 25:15

4. SPYCRAFT ADAPTS: Loss of Human Contact

(27:00 - 31:00)

• Setting: September 1998, Washington, D.C., at Ana and Ernesto’s final in-person lunch.
• Action:
  • With a Cuban spy ring busted in Miami, Ernesto tells Ana they can no longer meet face-to-face; all communication must shift to encrypted pages and rare Caribbean rendezvous.
  • Ana is devastated but determined—loneliness and paranoia now intensify.

Memorable Moment

"You’re the best we have. That’s why I must leave to protect you. If I stay, they might locate me, and that would put you in danger."
— Ernesto to Ana Montes, 29:09

5. CLOSE CALLS AND PROMOTIONS: Escalating Tension

(31:00 - 34:45)

• Setting: May 1999, DIA headquarters, and subsequent months.
• Action:
  • Ana, fearing she’s about to be exposed, is instead blindsided with a prestigious promotion (GG14) ("I. I don't know what to say. Thank you, sir." – Ana Montes, 33:45).
  • The existential dichotomy—she’s lauded as an exemplary analyst while betraying the institution—augments the psychological strain.

6. AGENCY STONEWALLING AND BREAKTHROUGHS

(34:45 - 41:00)

• Setting: Early 2000–September 2000; Fort Meade, DIA, NSA.
• Action:
  • Valdez is repeatedly stonewalled by the FBI: “Other priorities? We have a Cuban spy high up in US Intelligence. What could be a higher priority?” – Elena Valdez, 36:30.
  • Frustrated, she begins probing the DIA directly, uncovering that Ana Montes—"the Queen of Cuba"—holds excessive power and secrecy.
  • In a key conversation with DIA analyst Chris Simmons, the critical connection is made: technical clues about "Agent S" (laptop purchase, Guantanamo visit, access to 'SAFE' database) all point to a mole active inside the DIA.

Notable Quotes

"If your Agent S has access to safe, it means—they’re in this building right now."
— Chris Simmons to Elena Valdez, 40:46

7. THE NET TIGHTENS: Closing in on Montes

(41:00 - 43:50)

• Setting: September 2000, Washington, D.C., and surrounding areas.
• Action:
  • Personal toll: A rare romantic relationship prompts Montes to contemplate a life beyond espionage, but her secrets preclude intimacy and normalcy.
  • DIA counterintelligence officer Scott Carmichael, using Valdez and Simmons’ clues, combs through Guantanamo visitor logs and identifies Ana Montes as the prime suspect. The hunt is on—with Carmichael, “triumphant,” staking a Coke bet on catching the mole.

Memorable Moment

"Oh no, buddy. This ain't no guy."
— Scott Carmichael to 'Gator', 44:25

Highlight Timestamps

| Time (MM:SS) | Segment | Summary | |:--:|:------------------------------------|:-------------------------------------------| | 00:00–04:57 | Montes' Interrogation at DIA | Ana sidesteps counterintel suspicions | | 06:36–14:00 | Misty Satellite Briefing | U.S. satellite deception; Ana’s moral crisis| | 20:24–27:00 | NSA Tips FBI/Inter-Agency Clash | Valdez struggles to get the FBI engaged | | 27:00–31:00 | Ernesto’s Departure | Ana loses her Cuban handler, feels isolated| | 31:00–34:45 | Tense Promotion | Ana receives career honor while spying | | 36:00–41:00 | Valdez Investigates DIA | Inter-agency breakthrough—focus on Montes | | 41:00–44:25 | Carmichael Zeroes In | U.S. counterintel closes in on Ana |

Tone and Language

The episode is narrated in a suspenseful, cinematic style, blending dramatic reconstructions with factual investigative prose. Characters’ emotions are artfully drawn: Ana’s nerves and rationalizations, Valdez’s indignation and persistence, Carmichael’s mix of skepticism and exhilaration, and even the understated tragedy of Montes’ personal sacrifices.

Memorable Quotes (With Speaker Attribution & Timestamps)

• Montes’s Internal Calculation:

  "This is a secret so big that if she were caught sharing it with the Cubans, she could face the death penalty."
  — Indira Varma (narration), 11:43

• Valdez on Cuban Recruitment:

  "They recruit naive students who think Che Guevara is some sexy guy on a poster, not a vicious killer."
  — Elena Valdez, 24:48

• Carmichael’s Triumph:

  "Hot damn, Gator. You better have some change for that Coke machine... Oh no, buddy. This ain't no guy."
  — Scott Carmichael, 44:20

• Ernesto’s Farewell to Montes:

  "You're the best we have. That's why I must leave to protect you."
  — Ernesto, 29:09

Conclusion

Episode 2 deepens the intrigue and emotional stakes of the Ana Montes story. It underscores the vulnerabilities of sprawling intelligence agencies, the psychological burden shouldered by covert operatives, and the critical importance of inter-agency vigilance. By episode’s end, U.S. counterintelligence is closing in—but Montes’ story is far from over. The drama’s momentum is tightly wound, promising even bigger revelations to come.

For listeners who missed this episode:
The narrative interlaces technical details of espionage, the emotional toll of betrayal, and the bureaucratic pitfalls of U.S. counterintelligence in a tightly scripted true story. Be prepared for a rich, tense exploration of trust, deception, patriotism, and personal cost—set against the battlefields of the Cold War's twilight years.