The Spy Who Colluded with Castro
Podcast: The Spy Who (Wondery)
Episode: How Ana Montes Fooled Her FBI Siblings | 4
Date: October 21, 2025
Host: Charlie Hickson
Guest: Jim Popkin, author of Codename Blue
Episode Overview
This episode concludes the series on Ana Montes — an American defense analyst who spied for Cuba for 17 years while hiding her double life from the US military, her FBI agent siblings, and even her closest family. Host Charlie Hickson speaks with journalist and author Jim Popkin, whose book Codename Blue delves into the family dynamics, psychological drivers, and operational prowess that made Montes one of the most consequential spies in US history. The conversation explores the roots of her betrayal, the extraordinary discipline required, and the devastating impact it had on her family — especially her sister Lucy, an FBI counterintelligence agent.
Key Discussion Points and Insights
What Drew Jim Popkin to Ana Montes’s Story
- Popkin, an investigative reporter covering the FBI and CIA, first heard of Montes’s arrest 10 days after 9/11 – an event so overshadowed by world news, even NBC didn't fully cover it.
- Personal connection: Popkin’s college roommate bought Montes’s former condo, where encrypted communications once took place (02:28).
- Popkin: "It's a story about two sisters trying to patch together a relationship while one of them is living a massive lie. It's a family story wrapped around an espionage tale." (03:15)
The Complexity and Personality of Ana Montes
- Montes was “brilliant, highly organized, and attentive,” with both loyal friends and a close relationship to niece and nephew (04:40).
- Described as fun and typical in youth; later became more isolated and emotionally distant as her secret life continued (05:30).
Espionage Impact and Skill
- Montes’s espionage reportedly rendered a billion-dollar spy program useless and compromised US military plans (05:48).
- Popkin: “She kept getting awards and cash rewards from the government for her excellent service… She was relied on by politicians, by US officials, journalists…” (06:15)
Motivation: Political, Ideological, and Personal
- Not a direct “card-carrying Communist,” but driven by opposition to US foreign policy and empathy for Cuba (07:28).
- Personal psychology:
- Sought power and autonomy through espionage.
- Strained, abusive relationship with her military father may have motivated her as a form of rebellion (08:51).
- Popkin quotes CIA behavioral analysis: “One reason is that she wanted to get back at her father. And what better way… than basically attack the US Military.” (09:40)
Family Dynamics: Secrets at Home
- Four immediate family members in the FBI, sitting across the Thanksgiving table while she spied for Cuba (15:08).
- Anecdote: A Thanksgiving dinner filled with FBI agents; Montes had to maintain absolute composure and secrecy (15:08–17:10).
- Lucy (sister) later felt both guilt for her own naïveté and relief at finally understanding their estrangement (17:22).
- Popkin theorizes Montes intentionally withheld all work details from family to protect them if she was caught (18:20).
Life of Secrecy and Isolation
- The stress and psychological toll of sustained double life, including increasing signs of obsessive behaviors and extreme stress (24:00–25:00).
- As the Cubans pulled back their handlers during investigations, Montes’s sense of connection and emotional release evaporated (19:29).
Romance and Human Connection
- Montes fell in love with Roger, a Pentagon colleague tasked with catching Cuban spies, compounding her emotional duress (20:53).
- Popkin: “If you're gonna fall in love, don't fall in love with someone whose job it is to try to catch Cuban spies.” (21:12)
The Endgame: Suspicion, Arrest, and Aftermath
- Montes suspected she was being watched, kept an escape bag and had a plan to flee via Mexico City, but could not bring herself to abandon her family (22:08–22:46).
- Upon arrest, FBI used a ruse implicating her family, hoping to elicit a confession; she immediately asked for a lawyer and later pleaded guilty (28:44).
- Sentenced to 25 years (served less), shared prison with infamous inmates like Squeaky Fromm (29:13).
- Upon release, she returned to Puerto Rico, remains unrepentant, and is rebuilding her life (30:13).
Notable Quotes & Memorable Moments
On Montes’s Talent as a Spy
Jim Popkin:
“She did really well in her job. You have other spies like Rick Ames… who had a drinking problem and a lot of other issues. Ana kept her personal problems kind of in check most of the time when she was at DIA. And so she kept getting awards and cash rewards from the government for her excellent service.” (06:15)
On Motivation
Jim Popkin:
“She was offended by the very muscular US Foreign policy… She just saw the United States as playing a bully role… She also had this very complicated relationship with her father, who had been in the military and was physically and psychologically abusive… One reason is that she wanted to get back at her father. And what better way… than basically attack the US Military.” (07:49–09:40)
On Family Irony
Jim Popkin:
“In a matter of years, Ana has four family members who all work at the FBI… The place is just creeping with feds. In walks Ana Montez. It must have been extremely uncomfortable for her.” (15:08)
On the Burden of Secrecy
Jim Popkin:
“I think she did at first… but as Ana's career progressed… her handler went dark for a long time. That really took a toll on her.” (19:33)
On Isaac’s Arrest
Jim Popkin:
“They walk in… and they say, Lucy, we have bad news for you. Moments ago, your sister Ana was arrested in Washington, D.C. Your sister is a Cuban spy. Lucy couldn't believe it, and she fought it at first… But she felt relief… Oh, my God, now I understand… why Ana has been so weird to me for 17 years.” (25:32)
On Whether the Cubans Cared
Jim Popkin:
“I think they used her over time… In the end, she wants to get out. She wants to… have a normal civilian life… and they won’t let her… They got what they needed out of her and they seemingly moved on.” (27:18–28:37)
On Meeting Ana
Jim Popkin:
“If you did meet her, what would be your first question?”
“I think I'd want to go deep on the why. Your sister has said that it was ultimately about power and ego. Is that fair? Is that a fair presumption to make about why you took this enormous risk?” (31:47)
On the Reality of Espionage
Jim Popkin:
"It's a life of discipline and sadness to me. And, you know, there were moments of joy… but that's what strikes me about her. Just the day to day, boring, disciplined element of spying." (32:30)
Timestamps for Key Segments
- 02:28 – Why Jim Popkin wrote about Ana Montes, and his personal connection
- 05:30 – Montes’s early personality and psychological profile
- 06:15 – Analysis of Montes’s espionage effectiveness
- 07:28–09:40 – Her motives: political, personal, and psychological
- 15:08 – Family Thanksgiving anecdote: Surrounded by FBI agents
- 17:22 – Lucy's reaction and family secrecy fallout
- 19:29–20:53 – The toll of isolation and the ill-fated love affair
- 22:08–23:45 – Planning escape, stress behaviors, and approaching arrest
- 25:32 – Lucy’s feelings upon learning her sister is a spy
- 27:18 – Relationship with Cuban handlers and lack of support after arrest
- 28:44 – The FBI sting and plea deal
- 30:13 – Life after release, social media support, and future plans
- 31:47 – Popkin's hypothetical questions for Ana
Tone and Style
- Conversational, highly personal, and nuanced – balancing factual intelligence history with family psychology.
- Direct and honest; Popkin and Hickson do not romanticize espionage, instead emphasizing the emotional and ethical complexities.
Summary
This episode provides a detailed, humanized portrait of Ana Montes, revealing her as diligent, intelligent, and deeply conflicted. Jim Popkin's insights illuminate the overlap of personal trauma, ideological conviction, and operational discipline that allowed Montes to conceal her treachery, even as her family worked to thwart people like her. The discussion exposes espionage’s tragic banality — far removed from cinematic glamor — and confronts the enduring mysteries at the heart of betrayal, loyalty, and motivation.
Quintessential Takeaway: Montes’s story is less about Cuba or classified documents, and more about the invisible fractures within families and the excruciating solitude of living a lie.
End of summary.