Podcast Summary: Hell in Heaven: A Mysterious Death in Paradise

Episode 5: The Night Of

Host: Becky Milligan
Date: October 30, 2025
Duration: ~42 min

Main Theme

This episode delves into the fateful night of January 7-8, 2010, when John Bender, a wealthy former Wall Street trader and animal lover, died of a gunshot wound in his remote, fortress-like Costa Rican mansion. The show reconstructs the couple’s last moments, the immediate aftermath, and the rapidly spiraling suspicions. Listeners are drawn into a web of mental illness, isolation, paranoia, and tragedy—and the beginning of a mystery that will lead to multiple murder trials and persistent doubts about what really happened that night.

Key Discussion Points & Insights

1. Background: The Bender Dream Crumbles

• [01:37-03:52]
  — John and Anne Bender invested their fortune in a massive, wall-less mansion, creating a jungle sanctuary.
  — Over time, dreams of paradise collapsed under fear, violent encounters, and growing neurosis.
  — Their isolation and mental health challenges intensified amid reports of attempted kidnappings and gunfights.
  — “They wanted to live in the clouds and not have to deal with anything.” — Carol Vaughan [02:03]

2. The Day and Night Leading to John’s Death

• [04:01-07:07]
  — On January 7, 2010, John worked on a mineral garden while Anne, frail and nearly immobile from illness, stayed close.
  — Their tightly-routined, insulated lives: sunset-watching, video games, and elaborate bedtime rituals.
  — The bedroom is secured by a locked elevator, filled with hundreds of Tiffany lamps—switched off that night, plunging the room into darkness and jungle noise.

• Quote:
  “He slept on a stack of three pillows…with ear buds in because he couldn’t stand noise. And the jungle at night is hugely noisy.” — Carol Vaughan [06:42]

3. The Moment of Crisis

• [07:07-10:14]
  — At 12:15am, a guard hears a gunshot; Anne, frantic, radios for help.
  — Security head Aguila scrambles to unlock the elevator, finding Anne covered in blood and John motionless with a gun near his head; chaos and horror ensue.

• Quote:
  “She is just completely falling apart. ...The guard immediately started trying to help Anne, saying, how can I help you?” — Carol Vaughan [10:00]

4. Emergency Response & First Reactions

• [14:02–17:49]
  — Head of security Jose Pizarro (the “Colonel”) is woken and speeds toward the estate, overwhelmed with questions. — Ambulance driver Carlos, maintenance man Osvaldo Rojas, and police head towards the mansion; all are shocked.

• Quote:
  “I was impressed because there was a lot of security. Two guards were standing at the front gate and as we got closer, we saw this huge illuminated house. It looked like a flying saucer.” — Carlos [18:48]

5. Scene in the Bedroom

• [19:43–22:50]
  — Paramedics and staff describe a surreal, tense atmosphere; Anne appears calm to outsiders, prompting suspicions. — Many compare the luxury and security to a “Pablo Escobar soap opera.”
  — John’s body is found with a gunshot wound, his gun nearby, among dazzling wealth and odd silence.

• Quote:
  “I could see the gun on the floor. The trail of blood. ...It seemed to me like we were walking into a Pablo Escobar soap opera.” — Carlos [21:52]

6. Family Notification & Mental Health History

• [22:50–25:50]
  — Anne contacts her family, saying “he finally did it” [17:09]. — John’s parents are confused by Anne’s call and account. — Anne later tells reporters both she and John had been spiraling into depression, with John obsessing about Anne’s illness and suspected financial betrayal.

• Notable Quotes:

  • “Such a total fucking loser for ever getting involved with those scumbags... Today is a total fucking nightmare and tomorrow will get worse. ...I want to be dead.” — John’s email, read by actor [25:05]
  • “He was talking about suicide every day.” — Anne Bender [25:53]

7. Anne’s Account of the Shooting

• [26:48–27:50]
  — Anne claims she woke to John saying, “You’ll now know what it’s like to wake up next to your dead husband” [27:07].
  — She says she lunged for the gun to stop him; her hands closed over his, the gun went off, killing him instantly.

8. Police Investigation & Doubt

• [32:48–36:14]
  — The police scene investigation raises doubts about suicide:

  • John’s earplugs were still in; would a person wear those before killing themselves?
  • The gunshot entered from the right, but John is left-handed.
  • John’s hand tests negative for gunpowder residue; Anne’s is positive. — Anne insists she didn’t shoot John, but police begin building a case against her.

• Quote:
  “It doesn’t look like a suicide because of the way that we found the gun in the wound. There’s something really weird going on here.” — Osvaldo [34:48]

9. Aftermath and Emerging Motive

• [39:14–40:09]
  — In the days following, police discover over 3,000 precious gems hidden in a suitcase.
  — Speculation arises: Were the gems smuggled to hide fortune? Did Anne have a financial motive?

• Quote:
  “I remember the police found a small suitcase filled with jewelry... From that moment on, they began to whisper among themselves how strange that was.” — Jose [39:56]

10. Anne’s Health Fails; Police Tighten Suspicion

• [41:42] — Anne’s physical and mental health rapidly deteriorate; she is hospitalized and barely alive as suspicions and tensions mount.

Notable Quotes & Moments with Timestamps

• “They wanted to live in the clouds and not have to deal with anything.” — Carol Vaughan [02:03]
• “He slept on a stack of three pillows. ...nude. ...ear buds in because he couldn't stand noise.” — Carol Vaughan [06:42]
• “You’ll now know what it’s like to wake up next to your dead husband.” — Recap of Anne’s account [27:07]
• “Such a total fucking loser for ever getting involved with those scumbags... I want to be dead.” — John’s email [25:05]
• “She kept saying this. It was very tough.” — Jose Pizarro on Anne repeating “I tried to stop him, I tried…” [32:09]
• “It doesn’t look like a suicide because of the way that we found the gun in the wound…” — Osvaldo [34:48]
• “There’s too much money in here. It seemed to me like we were walking into a Pablo Escobar soap opera.” — Carlos [20:43]
• “The truth is, I was very sad. It was a terrible loss of a good friend, a great person.” — Jose [39:14]

Timestamps for Major Segments

| Segment | Timestamp Range | |---------------------------------------------------|----------------| | Warning/disclaimer (content) | 01:37 | | Bender background, paranoia grows | 01:37–03:52 | | The night unfolds in mansion | 04:01–07:07 | | Gunshot, security response, scene discovery | 07:07–10:14 | | First notifications, Anne’s reaction | 14:02–17:49 | | Medics, staff arrive, police on scene | 18:00–21:52 | | Family & staff descriptions of aftermath | 22:50–25:50 | | Anne's night-of account | 26:48–27:50 | | Police doubt, key evidence emerges | 32:48–36:14 | | Gems found, police develop motive theory | 39:14–40:09 | | Anne’s health collapses, next episode preview | 41:42–42:06 |

Tone & Style

The episode maintains a tense, immersive, and suspenseful tone, drawing listeners into both the emotional world of the Benders and the procedural world of the investigation. The language alternates between factual reporting, vivid sensory details of the jungle mansion, and clipped, sometimes anguished quotes from key participants.

Conclusion

Episode 5, “The Night Of,” is a pivotal chapter—recounting the last hours of John Bender amidst growing paranoia, culminating in his death under deeply mysterious circumstances. The police quickly shift suspicion onto Anne, and the podcast sets the stage for legal battles and contested narratives. The episode raises haunting questions about isolation, mental illness, wealth, and the dark side of paradise.