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The Idiot - Chapter 4 - Serial | Wave AI Podcast Notes

The Idiot - Chapter 4

Thu Mar 26 2026

Allen finally agrees to talk … and talk and talk, for 35 hours of interviews. M. wants to understand Allen on his own terms, to try and figure out how this scion of bohemian intellectuals ended up hiring someone to kill his ex. It’s hard for M. to believe everything Allen says, but over the course of their conversations, M. comes to feel for their cousin. And they think they understand what drove him to go so far.

Summary

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.

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Transcript

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M. Gessen (0:33)

In April 2024, my cousin Allen was delivered to federal court in San Francisco for his sentencing hearing. It had been just under a year since a jury found him guilty of hiring someone to kill his ex wife, Priscilla. The maximum sentence for this crime is 10 years. The cast of characters the judge, the public defender, the prosecutor and Allen were back in the same courtroom. All of them seemed the same, except maybe Alan. He was contrite, genuinely filled with regret, or so it sounded to me. He apologized to Priscilla, who was listening on Zoom. He promised that he would never again do anything to harm her or the children. He talked about his decision to reject a plea deal and go to trial, and for a minute he didn't sound like Alan at all. He said that the trial had made him see himself as the jury saw him. It was embarrassing to listen to those recordings, he said. Your Honor, I am prepared to serve any sentence. Allen told the judge, if he got the maximum 10 years, he would be almost 60 when he was released, and it would be hard to start over. But he said he had already suffered the biggest punishment. His voice cracked. He'd lost all access to his children. And he continued, the torture I suffer every day comes from my awareness of the impact I've had on my mom. He was really choking up now. I felt something welling up in my throat, too. Alan was no longer dressed like a dad returning home from work for the sentencing. He was brought in wearing yellow prison scrubs a week over a white thermal underwear shirt and yellow Crocs knockoffs. Allen had his back to me, so most of the time I was watching Judge Curley. She was leaning toward Allen. She was nodding to every affirmative statement he made. Her face reacted to every word, it seemed. Then it was her turn to speak. I didn't see it when you were on the stand at trial, but I can see it now, she said. You acknowledged the harm. The judge had really listened. I mean, she had really listened and observed Allen. And so she focused on the irony. That's the word she used of the story. Allen's relationship with his mother was perhaps the strongest bond of his life, and yet he had been willing to deprive his own children of their own mother. So there's that in itself, judge Corley said. And there were all those times that Allen made the decision to go ahead with the murder for hire plan, not just in that one conversation with the undercover agent. The judge said you didn't have to meet with him the second time. You could have just not shown up. You didn't have to give him the gold coin then you didn't have to wire the $23,000, and you didn't have to send the target package, and you didn't have to tell him when you were going to be on vacations with the kids so they wouldn't be there. Right? So you had opportunity after opportunity after opportunity, but you went forward because that was your intent. Allen's mother, Lena, had gotten dozens of people to write letters to the court on Allen's behalf. All of them attested to Allen's loving, kind and supportive character. Some, including a letter from one of Allen's ex girlfriends, were over the top and praising him. The judge addressed those letters. Now, it's so tragic that you have been such a generous and helpful person to all these other people, she said. But we see that sometimes with domestic violence. She said those last two words to Kato like she was striking the gavel. And finally she said, Mr. Gessen, you are a lawyer. You are a barred lawyer. You took an oath to uphold the law, but by your own testimony, your own testimony, you thought that you were going to bribe some official to have her kidnapped and removed from the United States. The sentence had to reflect this, too. The thing in my throat that had been threatening to make me cry had dissolved. I was following the judge's logic, her righteous outrage. The judge sentenced Allen to the maximum 120 months in prison, followed by three years of supervised release. Like an episode of a TV series. The hearing lasted exactly one hour, took me as a viewer through a range of emotions and deposited me more or less where I'd started. I still had no real understanding of how Alan ended up doing what he did. The court isn't interested in why people do the terrible things they do. The court's job is to determine guilt and apportion punishment. But for me to tell this story, I needed a theory of the crime or a theory of Alan. I needed to imagine what had been going through Alan's head that had made it seem that having his wife killed was a reasonable solution to his problems. For that, I needed to talk to him. I had asked Rilena, and she told me that he wouldn't talk, at least not until after the trial and the sentencing and the appeals. That last part would surely drag on for months or years. More still, When I got back to my hotel after the sentencing, I created an account in the system that facilitates correspondence with inmates and sent Alan a message asking for an interview. Next, Allen would have to agree to correspond with me, and the prison would have to approve my message. But before any of that could happen, Alan reached out to me himself. He was ready to talk. I am M. Gessen and from Serial Productions and the New York Times, this is the idiot.

M. Gessen (31:19)

Alan, this is what you took from your bohemian upbringing and your intellectual family? It was hard for me to believe, but yes, it seems that Allen took his macho chivalry act very seriously and that it worked. Women love being doted on by Alan. I interviewed Alan's first serious girlfriend and she told me that she still thought of Alan as one of the best people she had ever met. He made her feel taken care of. Allen's second serious girlfriend wrote a letter to the court. She wrote the way I felt with him. I can wish every woman to experience this. Allen supported her when she lost her dog. He was there for the family when her cousin died in a car accident. And he arranged for the best health care when her grandmother and then her grandfather became ill. It is only thanks to Alexei that my grandparents were alive for many years after. And he was romantic. How did I feel with him as a woman? The ex girlfriend wrote in her letter to Judge Corley. It's fun to imagine Judge Corley reading this one. I felt like a goddess. He gave me gifts ranging from the best face cream to my dream car. Just as a surprise, he made sure I drank more water and went to the gym. He taught me English and faith in myself. Alexei showed me the world and its possibilities. And it wasn't just the women. Other letters to the court mentioned how generous Alan was and how empathetic. When one of O's music teachers suffered a stroke, Alan brought him groceries and also figured out how to help the man out of some tax filing predicament. Allen funded a struggling students film project. When he found out that a woman's husband was beating her, he extracted her and her kids and put them up. He helped build a custom designed port for an injured elephant. This was a side of Allen I'd never really seen. Almost more surprising was that Alan had never bragged about any of this. He portrayed himself to the family as an international man of mystery. A smooth operator at the edges of the legal universe. But secretly he was a universal benefactor. He volunteered to solve everyone's problems and people paid him back with love. Alan was 36 when he was in Zimbabwe in business and met Priscilla for the first time. His gift giving big living ways worked on her too. They were together from the moment they met. A year into their relationship, Priscilla became pregnant. But at just six months, Priscilla went into labor. Rushed to the hospital, she had an emergency C section.

M. Gessen (39:58)

He called me back after he had collected himself. He said okay, maybe Priscilla did love him in her own way. But it wasn't enough. He never felt cared for or supported. Alan had never met a problem he couldn't solve or couldn't at least try to solve. He offered ingenious creative solutions. Once he told me when Priscilla was going to leave him for someone else, he suggested that she go spend a week with the man and decide if she really wants to make a life with him. She didn't leave him that time. Another time, when they reunited after one of their separations and it turned out that Priscilla was pregnant, Alan proposed to stay together through the birth of the child and possibly raise the kid as his own. That pregnancy ended in a miscarriage and when she miscarried again and felt desperate, Allen offered the most inventive solution of move to Russia and have a baby by surrogacy. There was only one problem with all these solutions. They didn't solve anything. At the end of the day, Priscilla and Alan's relationship was Priscilla and Alan's relationship and all the non solution Solutions only added fuel to their fights. By the summer of 2019, Alan was separated from Priscilla, but he was condemned to co parenting o with Priscilla forever. So here's the theory of Alan, a traumatized kid, a guy who has known loneliness and humiliation and has made up for it by making himself useful. A guy who earned people's love by helping them by solving problems. But he couldn't solve his Priscilla problem, couldn't make his wife love him, couldn't bear that she didn't love him, and couldn't figure out a way to be with the son he adored without also constantly being reminded that he had failed to earn her love. So he took the child and ran. And when Priscilla caught up with him, he ran again. And when she caught up with him again, he decided to have her killed. This is a perfectly workable theory, and it's true as far as it goes. But there's always more to his story. And because Alan is my cousin, I know what the more is. It kept coming up in my interviews too, with family members and friends of the family, and of course Priscilla. So I don't think I can end the story here. After the break, my second theory of Alan.

M. Gessen (50:36)

Granted, Priscilla is basing this on her own highly specific experience of Lana, but Priscilla is not alone in this view. My father concurs. He thinks that when Alan took the hit out on Priscilla, it was a solution to a persistent problem. What do you think the problem that he was trying to solve was to make my sister happy, so she would have all the time, and she will not hear from Priscilla ever. And what makes you think that that's the root cause? I know Leona's and Alyosha's relationship, and I know that Alyosha would do anything to make her happy. And if that was the way to do it, okay, so let's go that way. He'd do anything to make his mother happy. This came up in a lot of my conversations. It showed up in the letter. Allen's first serious girlfriend wrote to the judge. She wrote that Allen's, quote, main purpose was to make sure his mother, Lena, was well and comfortable. His world began with her, unquote, and, it seems, ended with her. This young woman ultimately accepted that there was no place for her in this closed world. To be clear, Lena was never charged with any crime. She was barely even mentioned during Allen's trial. And I don't have a reason to think that Lena knew about the plot to kill Priscilla before Allen was arrested. But my own conversations with Lena supported my second theory of Alan. It was Lena who first mentioned to me the idea of needing to do something about Priscilla. This was several years before Allan and Lena first took O. At the time of this conversation, O was a toddler. Allan and Priscilla were separated, and Lena and I were at a family gathering in Moscow, helping carry food from the kitchen to the dining room. Lena paused, holding a platter, and said, I want to ask your advice on something. How do I get Priscilla out of O's life? It was clearly an invitation to gather my thoughts on the matter and give Lena advice later. An invitation that assumed I would want to help. You don't, I said. Meaning you don't get Priscilla out of oh's life, I said. She's his mother. We continued carrying food. She didn't raise her question again, and I didn't think about it again until 2019, when the family got that Facebook message from Alan announcing that he and Nana had taken Ode to the United States. Then that scene in the Moscow kitchen flashed in my mind. What struck me the most wasn't the question itself. It was the guilelessness with which it was asked, the certainty that, as Alan would later text the undercover agent, our cause is just. There's a concept in psychiatry which means madness for two in French. It's when two people share a delusion, reinforce this belief in each other and act accordingly. The belief Nana and Alan shared was that Priscilla was a bad mother and it was their right, their duty even, to get her out of O's life. Though, again, there's no indication that Nana wanted Priscilla dead. After Allen was arrested the first time in Canada, Lena wrote to the family chat about what a terrible parent Priscilla was, as though that justified taking O from her. And less than a month before Allen was arrested on murder for hire charges, Lena and Allen met up with an acquaintance and talked at length about wanting Priscilla gone. Not about killing her, just about deporting her. The friend said that Lena and Alan were finishing each other's sentences, talking about how, after Priscilla had gotten Allen arrested in Canada, this is how they saw it. The gloves were really off. Their cause was just. I needed to ask Alan about his mother's role in the series of events that ultimately landed him in federal prison. I needed to tell him that Priscilla suspects that his need to please Leanna played a big role, and I needed to get his reaction, but I wasn't sure how to broach the subject. I thought I might leave it to our last conversation, but to my surprise, Alan brought it up himself. We were talking about the two times he took O away from Priscilla to a different country.