Serial: "The Idiot" — Chapter 4

Date: March 26, 2026
Host: Masha Gessen (M. Gessen)

Episode Overview

Chapter 4 of "The Idiot" offers a deep—and at times uncomfortable—exploration into the motivation and personal history of Alan Gessen, recently sentenced to ten years for hiring someone to kill his ex-wife, Priscilla. In the aftermath of his sentencing, Masha Gessen, Alan’s cousin and the podcast’s host, embarks on a series of prison interviews with Alan, attempting to construct a theory for why he committed the crime. The episode balances courtroom narrative, personal family history, and psychological analysis, oscillating between Alan’s own accounts and the host’s reflections—culminating in two potential "theories of Alan" rooted in both personal trauma and familial entanglements.

Key Discussion Points & Insights

1. The Sentencing: Regret, Responsibility, and Irony

[00:33 – 06:36]

• Setting: Federal court in San Francisco, April 2024, for Alan’s sentencing—almost a year after his conviction.
• Alan’s Apology: Alan, wearing yellow prison scrubs, expresses contrition and regret, apologizes to Priscilla over Zoom, and says the real punishment is losing access to his children and the emotional burden on his mother.
• Judge Curley’s Response:
  • Irony of Alan’s Actions: Judge Curley observes the tragic irony: "Your relationship with your mother was perhaps the strongest bond of your life, and yet you were willing to deprive your own children of their mother." (05:08, Judge Curley)
  • Repeated Choices: The judge lists each intentional step Alan took in the murder-for-hire plot, highlighting his sustained intent.
  • Reflection on Character References: Judge addresses how domestic violence can coexist with displays of generosity and kindness.
• Sentence: Alan is given the maximum—120 months (10 years) in prison, plus three years' supervised release.

2. Initiating Contact: Alan Reaches Out

[08:13]

• After the sentencing, Masha sends Alan a message hoping for an interview; unexpectedly, Alan initiates contact himself, ready to "provide context missing from the trial."

3. The Prison Interviews: Motive, Memory, and Misdirection

[09:37 – 14:06]

• First Interview: Alan attempts to exonerate himself, referencing complex, peripheral circumstances (Russian assets, IRS, business dealings in Estonia) and downplays the murder-for-hire in the scope of his "bigger picture." Quote:

  "I knew that I was just a relatively small part of a much bigger picture." (10:10, Alan)

• Masha’s Frustration: Masha remains skeptical, pushing past Alan’s evasions, especially regarding the alleged kidnapping of their son and the chain of events that led to their move to the US.
• Confrontation: Masha challenges Alan's version of events about taking the child from Moscow:

  "Well, she was pretty desperately looking for where you had taken her child, and she had no idea where you were." (12:16, Masha)

4. Daily Calls: Patterns of Denial and Glimpses of Humanity

[14:06 – 16:53]

• Ongoing Conversations: Their calls become frequent—almost daily.
  • Alan denies responsibility for any misfortune that befell Priscilla, reiterates his intent was never murder, only deportation.
  • He shares mundane details of prison life, from mixing cottage cheese with cookies to noting the political leanings of prison inmates. Notable moment:

  "I have not met a single Democrat in a jail in the U.S. ...fascinating." (15:14, Alan)

• Developing Rapport: Both note the oddity and unexpected depth of their new connection:

  "We're still more in the past week than we have in the previous 50 years." (15:56, Alan)

5. Alan’s Formative Years: Poverty, Immigration, and Outsiderness

[16:53 – 31:19]

• Childhood in Moscow: Alan remembers being "very happy until he was 15," despite poverty—supported by a close-knit family and bohemian, intellectual social circles.
• Immigration to America: Sudden displacement and loss of status after moving as a teen; feelings of alienation, envy (specifically of his successful cousin), and social awkwardness. Quote:

  "I would pick up a couple of quarters and buy myself chocolate milk in the school cafeteria because I didn't have a couple of extra quarters... very much rich man, poor man situation where I was the poor man." (22:47, Alan)

• Bootstrapping: Describes his journey from bagging groceries to starting a lucrative college "tutoring" business, ultimately supporting himself and his mother.
• Early Adult Success: Through law school, failing to break into elite CIA/FBI, then finding validation and status as a consultant with McKinsey in booming post-Soviet Moscow.

6. Interpersonal Relationships: Need to Be Needed & Patterns of Caretaking

[31:19 – 36:09]

• Macho Persona: Alan claims traditional gender roles abroad made him far more attractive and appreciated than he ever was in America.
• Ex-Girlfriend Testimonials: Letters to the court (and Masha’s interviews) portray Alan as generous, attentive, and supportive—attributes that dovetailed with his need to be needed and validated by others. Letter excerpt:

  "I felt like a goddess... He gave me gifts ranging from the best face cream to my dream car." (31:19, Ex-girlfriend’s letter, paraphrased)

7. Family, Trauma, and the Cycle of Problem-Solving

[36:09 – 41:59]

• Birth of O: Alan details the trauma and helplessness of his son’s premature birth and long NICU stay, reflecting genuine parental love but also his compulsion to "fix" every problem.
• Marriage to Priscilla: Alternates between fond memories and close, supportive periods, and deep pain, infidelity, mutual mistrust, and endless cycles of breaking up and reuniting.
• Alan's Emotional Vulnerability:

  "[She] just told me about one of the times like she cheated on me and I started wailing... I was wailing for about 15, 20 minutes... I just couldn't stop." (37:54, Alan)

• Theory #1 (Masha): Alan’s unraveling is linked to trauma, a lifelong drive to be useful, and his inability to solve the "Priscilla problem"—the first situation he couldn’t control or fix.

8. The Centrality of Alan's Mother, Lena: Enmeshment & Control

[44:04 – 59:32]

• Family & Interview Testimonies: Multiple sources recount Lena’s central role in Alan’s life—her influence, their symbiosis, and her need for (and practice of) exerting control in every sphere, from etiquette books for girlfriends to rearranging apartments.

  "Lena told people how to behave... [She] provided written instructions to Alan’s girlfriend." (45:13, Masha)

• Priscilla’s Theory: Priscilla and others believe Lena’s drive to control her grandson’s upbringing, and Alan’s need to satisfy his mother, were key ingredients in his decision to try to remove Priscilla from their lives—by any means. Quote:

  "If I wasn't there anymore, [Lena] would be free to do what she wanted, which would also give him the freedom... So I think what motivated him actually to go ahead with this plan was to appease his mother." (49:18, Priscilla)

• Masha and Alan Discuss Mother's Influence:

  "My decisions are very much my own in regard to [kidnapping O and leaving the country]… We have been quite independent for the last 20 years until my arrest." (55:52, Alan)

  • Masha gently challenges this, referencing widespread perceptions of Lena as the covert "mastermind."

9. Theories of Alan: Madness for Two and the "Noise in the Head"

[57:32 – 61:16]

• Psychological Parallel: Masha brings up the psychiatric concept of "folie à deux" ("madness for two")—a shared delusion/enmeshment between Alan and Lena, especially regarding Priscilla.
  • The belief their campaign to remove Priscilla was "just."

  "People do horrible things because the noise in their heads becomes intolerable." (57:32, paraphrased advice to Masha from Harriet Clark)

• Conclusion: Alan’s actions were driven not just by his need for parental love or to "solve Priscilla," but by being caught in an inescapable triangle—trying to please both his mother (Lena) and his love for O, with Priscilla as the obstructing force.

10. Epilogue: The Future, the Kids, and Unanswered Questions

[59:50 – end]

• Alan’s Hope: He insists he’s optimistic about his appeal and wants to reclaim a relationship with his children after release.

  "Once I overcome the legal obstacles... I will be able to rebuild a relationship with them. And that's truly... more important than any other considerations." (60:31, Alan)

• Motivation for Talking: Masha realizes Alan’s real reason for doing these interviews is to reach his children—perhaps for their understanding or forgiveness.
• Final Reflections: Masha admits the evidence remains overwhelming, and Alan’s ongoing denial is transparent—leaving both in the same emotional and narrative place as the start.
• Alan's Final Request:

  "If you see me any reasons for concern, just please stay involved. And to the extent you can... look after [my children]." (63:07, Alan)

Notable Quotes & Memorable Moments

• Judge Curley to Alan:
  "You had opportunity after opportunity after opportunity, but you went forward because that was your intent." (~05:27)
• Alan on social status:
  "It was as much about my social status as it was about the money. Maybe it was more about social status than it was about the money." (27:18)
• Priscilla:
  "I think what motivated him actually to go ahead with this plan was to appease his mother." (49:18)
• Masha’s realization:
  "Alan was still guilty and he was lying. And we were done with our conversations." (62:49)
• Alan’s final words from prison:
  "I haven't known peace and quiet for so long, I can't remember what it's like." (66:06)

Timeline / Timestamps for Major Segments

• [00:33 – 06:36] – Alan’s sentencing and court scene.
• [08:13] – Alan initiates contact for interviews from prison.
• [09:37 – 14:06] – Their first, combative interview; Alan's evasions.
• [14:06 – 16:53] – Regular daily calls, rapport builds.
• [16:53 – 31:19] – Alan’s childhood, emigration, and pursuit of social status.
• [31:19 – 36:09] – Debrief on relationships, generosity, and validation.
• [36:09 – 41:59] – Marriage, trauma, and Alan’s “unsolvable” Priscilla problem.
• [44:04 – 49:18] – The omnipresence of Lena and family theories.
• [49:18 – 55:34] – Priscilla’s and others’ perceptions of Alan’s mother as catalyst.
• [55:34 – 59:32] – Alan's pushback and self-assessment of independence.
• [57:32 – 61:16] – “Madness for two,” noise in the head, and closing the loop on motivations.
• [62:49 – end] – Alan’s final request and the lingering family dilemma.

Tone and Language

The episode maintains Masha Gessen’s measured, slightly wry tone—sometimes jaded or direct, often empathetic but unsparing. The interplay with Alan—his self-serving rationalizations, denials, and underlying vulnerability—contrasts with Gessen’s journalistic skepticism and familial proximity, resulting in an intimate, psychological portrait.

For Listeners: Why This Episode Matters

This episode is a turning point in the narrative—moving from external facts and courtroom drama into the murky territory of motive, psychology, and family history. It threads together the personal and the systemic: how trauma, family dynamics, and emotional need can culminate in devastating decisions. Gessen lays bare not just Alan’s psychology, but that of a family—and, perhaps, asks us to reflect on the very human urge to solve unfixable problems, no matter the cost.