Hell in Heaven: A Mysterious Death in Paradise

Episode 3: The Ambush

Host: Becky Milligan
Date: October 16, 2025

Overview

In this gripping third installment, host Becky Milligan unpacks the dramatic "ambush" that heightened the Benders’ paranoia and led to the couple’s transformation of their Costa Rican paradise into a heavily fortified and fear-filled enclave. Through interviews, first-hand accounts, and chilling new revelations—including the apparent involvement of mercenaries—Milligan sheds light on how a routine-seeming business errand erupted into armed chaos, exposing the deepening sense of threat surrounding John and Ann Bender. The episode scrutinizes the ambiguity of the supposed police intervention and the darker currents below, raising new questions about who was after John and why.

Key Discussion Points and Insights

1. Retracing the Benders’ Journey to Rosemary Bradley (02:01–08:25)

• Becky and her producer Poppy visit Rosemary Bradley, a British soil microbiologist living in Costa Rica, to revisit the critical 2001 visit by the Benders.
  • They recreate the journey across a treacherous hanging bridge, evoking the perils and isolation of the area.
  • Rosemary’s business sells native seed blends designed to combat erosion, a significant issue due to hillside building.
  • The Benders, intent on ecological solutions for their new mansion, sought Rosemary’s expertise.
  • Rosemary recalls Ann’s ongoing health struggles (Lyme disease) and notes John’s charisma.

"She limped a lot. She used a walking stick because of the Lyme disease. ... She was kind of shy, timid, whereas he was less so. I would say deep, deep voice. Yeah, yeah, nice guy. I mean, he was good looking too. I was fascinated by them, fascinated."
— Rosemary (08:25)

• Rosemary sympathized with the couple’s desire for privacy and isolation, reflecting her own experience as a foreigner in Costa Rica.

“I think you can get quite paranoid here as a foreigner and feel that everybody's against you and just live your own little private life. And I think that's what they were doing. You create your own bubble. I mean, we've done that here.”
— Rosemary (09:24)

2. The Ambush Event: Chaos on the Bridge (11:12–15:58)

• As the Benders return to their car after making the purchase, shots ring out—Anne screams for help through the intercom.
• Marco recalls how he rushed to the scene, crossing the dangerous bridge to find a white pickup truck blocking the drive, armed men jumping out, and John infuriated.
• Initial panic gives way to confusion as Rosemary and Marco recognize one of the armed men as someone they knew—a revelation that the "attackers" are police, not robbers or kidnappers.

“He fired the gun between John's legs and held it up to John's head. Anne was terrified.”
— Becky Milligan (13:12-13:49)

• John and Anne, shaken, are informed that the incident is merely about "documents" and are forced to accompany police to the station, language barriers compounding their distress.

3. Unpacking the Police Encounter and Its Aftermath (16:06–19:09)

• At the police station, the focus is on John and Anne’s Grenadian passports—a notorious tax haven. The oddness of the strong-arm tactics and their targeting grows.

“Apparently, the passports had aroused the police's interest. John's father, Paul, says that he was worried about his son's decision to give up U.S. citizenship and move his fortune abroad.”
— Becky Milligan (16:08)

• John’s father Paul expresses his disapproval:

“I guess the one thing that bothered me about what he was doing was when he started thinking about moving offshore and not living in the United States. And I said, why are you doing that? And he said, to avoid taxes and stuff. And that I did not like.”
— Paul Bender (16:45)

• Despite the police saying the incident was about IDs, suspicion lingers that something else was at play—possibly the police acting on behalf of a creditor.

• The assault triggers a surge of paranoia: John is traumatized, believing people are after him and Anne, prompting an escalation in personal security.

4. The Security Response: Enter “El Toro” (19:09–22:09)

• Jose Pizarro, former chief of Costa Rica’s police (nicknamed "El Toro"), is hired as Benders’ head of security.
  • He finds the couple traumatized and quickly fortifies their estate with armed guards and new protocols.
  • Jose senses that the police operation was highly irregular and possibly not “routine” at all, further fueling suspicions of a setup, perhaps related to a lawsuit filed against John by a former associate.

“This was totally out of line. That wasn't the proper protocol. ... In the end, John sued the police and they were all fired.”
— Jose Pizarro via Becky Milligan (22:09)

• No conclusive evidence of a true kidnapping or extortion plot is uncovered by Jose, though he admits his own investigation was limited.

5. Mercenary Revelation: “Michael” and a Parallel Plot (24:39–29:20)

• Milligan tracks down a shadowy figure known as “Michael,” a retired “private contractor” (mercenary) with a past in covert international ops.
• Michael claims he was contracted to intercept John Bender and send him to the US—a clandestine extraction seemingly unrelated to police activity.
  • He describes arriving at Rosemary's property with three associates, only to find Costa Rica’s equivalent of the FBI already there.
  • A tense standoff ensued, but Michael receives the order to abort after about 30 minutes; he never captures Bender.

“Basically that's what it is. … So wherever the army can't go in or won't go in or whatever, they usually send us. ... I was contracted by a third party to kind of intercept Mr. Bender and send him to the States.”
— “Michael” (24:56–26:07)

“I don't know if it was a fluke or it was coincidence or what happened exactly, but that day, we actually bumped into local law enforcement, kind of the equivalent of the FBI Costa Rica. … It was kind of pretty intense for a few minutes.”
— “Michael” (26:30–26:50)

• Michael will not reveal who hired him, but says the employer was “very interested” in extracting Bender, possibly over owed millions.
• There is no corroboration that Michael was present—Rosemary saw no other car, staff refused to comment, and the claim remains unsubstantiated.

6. Aftermath and Ongoing Questions (29:44–31:36)

• The attempted abduction—whether by police, mercenaries, or both—explains the Benders’ descent into fearful isolation.
• The podcast teases further investigation: Were police serving papers or acting for shadowy creditors? Was “Michael” genuinely involved, and who wanted Bender taken out of Costa Rica?
• Emphasis on the psychological toll: the incident marks a turning point toward extreme paranoia and defensive measures.

Notable Quotes & Memorable Moments

• On paranoia as a foreigner:
  “You create your own bubble. I mean, we’ve done that here.” — Rosemary, (09:24)

• John and Anne’s terror:
  “They were trembling. They were terrified.” — Rosemary, (14:00)

• Jose Pizarro on the scale of police action:
  “This was totally out of line. That wasn’t the proper protocol.” — Jose Pizarro via Becky Milligan, (22:09)

• Michael the mercenary describing his work:
  “I don’t like the term [mercenary] … but basically that’s what it is. ... I was contracted by a third party to kind of intercept Mr. Bender and send him to the States.” — Michael, (24:56–26:07)

• The episode's haunting question:
  “What kind of man would let this happen to his family?” — Repeated by Becky Milligan, (10:00, 18:00)

• On John Bender's mentality (preview for next episode):
  “Is that what he believed himself to be? A sort of genius of sorts?” — Becky Milligan (31:19)
  “Oh, absolutely. … There was not a question about it.” — Interviewee (31:21)

Important Timestamps

• 01:31: Episode narrative begins after adverts.
• 02:01–05:53: Arrival at Rosemary’s; revisiting the seed farm and backstory.
• 07:55–09:39: Initial Bender meeting with Rosemary; mutual isolation.
• 11:12–13:49: The day of the ambush—gunshot, panic, confrontation.
• 14:00–16:06: Realization it was police; aftermath and trip to station.
• 16:45–17:12: John's father, Paul Bender, discusses his concern.
• 19:09–22:09: Jose "El Toro" Pizarro fortifies the Benders’ estate.
• 24:39–29:44: Interview with “Michael” the mercenary; claims of extraction attempt.
• 29:44–31:36: Reflection on the fallout; ongoing fears, next episode preview.

Conclusion

This episode peels back the layers of the Benders' growing fear and isolation in Costa Rica, revealing how much more was at stake than simple cultural misunderstandings or legal confusion. Through tension-filled reenactments, interviews, and the shadowy confession of a supposed mercenary, it suggests that John Bender may have had very real reasons to feel hunted in his jungle refuge. The narrative ends with lingering uncertainty about who was truly pulling the strings, encouraging listeners to follow the investigation further in the episodes to come.