Hell in Heaven: A Mysterious Death in Paradise

Episode 7: A Second Chance

Date: November 13, 2025
Host: Becky Milligan
Produced by: Exactly Right Media, iHeartPodcasts, Blanchard House

Episode Overview

This gripping episode, “A Second Chance,” chronicles Ann Bender's dramatic murder conviction, survival in a Costa Rican women’s prison, desperate campaigns for her release, and the high-stakes lead-up to her third trial over the death of her husband, John Bender. Journalist Becky Milligan explores themes of justice, privilege, public perception, and resilience against the vivid backdrop of Costa Rica. The episode features firsthand accounts from Ann’s supporters, especially author and investigative reporter Carol Vaughan, and highlights the extraordinary media frenzy surrounding this notorious case.

Key Discussion Points & Insights

1. The Second Trial and Conviction

• Ann Bender is Convicted of Murder

  • [02:06] Ann is found guilty of murdering John Bender. The judge rules suicide impossible based on forensic evidence.
  • Notable quote:
    "Without a doubt... the court agrees that the death of John Felix Bender was homicide. Ann had murdered him. She was guilty. The sentence was 22 years in prison." – Judge Calderon (as recounted by Becky Milligan, 02:29)
  • Ann faints as the verdict is read, leaving her and her legal team in shock.

• Immediate Aftermath

  • [05:03] Ann is sent to a psychiatric hospital under suicide watch, then transferred to prison.

2. Supporters Rally: Family, Friends, and Greg Fisher

• Family and Public Campaigns

  • [05:37] Ann’s family and supporters are horrified and mobilize quickly, launching GoFundMe and Change.org campaigns.
  • Quote from supporter:
    "An innocent woman is dying, and we can make this right. We can." – Read by actor (06:36)
  • Ann’s brother Ken publicly denounces the trial as a miscarriage of justice.

• Greg Fisher’s Dedication

  • [06:46] Greg Fisher, Ann’s new partner after John’s death, throws himself into advocacy, visiting Ann in prison and running social media campaigns.
  • Twitter bio (actor):
    "Working every day to help save Ann Bender from the terrible injustice done to her by the people she trusted the most." (07:59)

3. Life in Prison: Ann’s Ordeal

• Conditions and Ann’s Frailty

  • [11:47] Ann enters Costa Rica’s only all-women’s jail, a former convent now a fortress with gun turrets.
  • [12:04] Overcrowded dorms, insufficient mattresses, poor food (“maggots crawling out of the rice”), lack of basic necessities, harsh climate, and illness.
  • Quote:
    "I don't know how she survived. I really don't." – Carol Vaughan (12:56)

• Community Among Inmates

  • [14:42] Surprisingly, Ann reports camaraderie and care from other prisoners.
  • Quote:
    "She confessed to me that she was actually well accompanied, that she felt very comfortable with the women that she was living with and that they were taking very good care of her." – Carol Vaughan (14:42)
  • Other prisoners share food and clothing, heat water for her, and offer support.

• Ongoing Health Struggles

  • [13:47] Ann is gravely ill, with a heart port she cannot keep sterile due to prison conditions, compounding her frailty.
  • Carol and her embassy contacts try to get her basic supplies and medical help.

4. Public Perception Turns Hostile

• Media Frenzy and Gossip

  • [21:06] After the conviction, local opinion shifts against Ann; she is widely seen as guilty, labeled a “black widow.”
  • Quote:
    “They say she was a black widow. She was just gunning for him until he died so she could have all those jewels and property to herself... I have never ever heard anyone say Ann was innocent.” – Carol Vaughan (21:06)

• Impact on Expats

  • [21:43] The case puts all Americans in Costa Rica under suspicion.
  • Quote:
    “Americans are so self entitled, they think they own the world... and you watch, we're gonna put a stop to them.” – Carol Vaughan (21:53)

• Unprecedented Media Access

  • [23:04] The trial receives wall-to-wall media coverage, exacerbating rumors and theories, including that Ann hired a hitman.

5. Personal Tragedy: Loss of Greg Fisher

• [24:00] Six months into Ann’s sentence, Greg Fisher dies of an asthma attack. His sudden death triggers further conspiracy theories, but it was confirmed to be natural.

6. A Dramatic Reversal: Ann Freed Pending a Third Trial

• [24:45] After nine months, Ann is unexpectedly freed when her lawyers secure a third trial.
  • Quote:
    "They just told me to get my stuff together and I left the prison. I'm really grateful that the appellate court made the right decision." – Ann Bender (actor) (25:01)
  • The prospect of another trial brings both hope and dread.

7. Building to the Third Trial: New Evidence and High Drama

• Preparation and Public Spectacle

  • [27:52] Ann, her family, and supporters stay at a local hotel, guarded by security and joined by international media.
  • Quote (on trial media circus):
    "Reporters were from that corner to here... all day long, just sitting there..." – Santiago, Hotel Manager (29:30)

• Ann’s Physical State

  • [30:29] She is visibly weak, always dressed in black, walking with crutches, and surrounded by an air of sadness.

• Court Testimony

  • [31:11-34:41] Ann testifies in detail about John’s mental health, previous suicide attempts, their deteriorating health, and the origins of their wealth.
  • Notable quotes:
    – "We were looking to set up the shelter to live a calm and peaceful life here." – Ann Bender (31:06)
    – “He was talking about suicide every single day.” – Ann Bender (34:05)

• Forensic Re-examination

  • [36:16] CBS brings in renowned forensic experts who dispute the prosecution’s theory, lending weight to Ann’s claim of innocence.
  • The new experts’ testimony becomes a turning point, casting doubt on key evidence like wounds and earplugs.

• Logistics for Escape

  • [38:21] Carol Vaughan coordinates with the US Embassy to ensure Ann can obtain a replacement passport if freed.
  • Quote:
    "I knew that she didn't have a passport and you know, get out of Costa Rica without a passport. So talked to the embassy and the embassy said, relax, we're going to get her a replacement passport." – Carol Vaughan (38:21)
  • The passport is secretly delivered, representing Ann’s literal ticket to freedom.

• Cliffhanger: Awaiting the Verdict

  • [39:01] As the third trial concludes, all sides anxiously await the judges' decision, the outcome still uncertain.

Notable Quotes & Memorable Moments

• "She was overcome. It was awful. And we were all looking at each other just in total disbelief."
  – Carol Vaughan, describing Ann’s reaction to the guilty verdict [04:46]

• "It's so embarrassing. I became possessed and obsessed with the story of the Benders."
  – Carol Vaughan, on her deep involvement with the case [10:05]

• "She was a wounded birdie... She was like a birdie with a broken wing."
  – Carol Vaughan, on Ann’s vulnerability and why inmates sympathized with her [15:56]

• "Americans are so self entitled... we're gonna put a stop to them."
  – Carol Vaughan, reflecting Costa Rican resentment of the Bender case [21:53]

• "She looks devastated every day... always dressed in black... using the crutches."
  – Santiago, hotel manager, on Ann’s state during the trial [30:29]

Important Timestamps

• 02:06–04:43 – Second conviction, Ann’s immediate reaction, insights from Carol Vaughan
• 05:37–07:59 – Family and Greg Fisher’s advocacy, fundraising, and campaign efforts
• 11:47–14:42 – Prison conditions, Ann’s day-to-day survival, support from inmates
• 21:06–23:04 – Public perception shifts, media circus, effect on the expat community
• 24:45–25:09 – Ann’s unexpected release pending retrial
• 27:52–30:41 – The hotel as command center, Ann’s physical/mental state
• 31:11–34:41 – Ann’s testimony: John’s decline, their motives for moving to Costa Rica, and financial woes
• 36:16–38:21 – Forensic evidence re-examined, role of CBS experts, Carol’s passport intervention
• 39:01 – The episode closes on cliffhanger before the third verdict.

Tone and Atmosphere

Milligan maintains a tone of empathy, curiosity, and suspense, painting a rich portrait of both Ann Bender's personal turmoil and the fevered public atmosphere around her trials. Carol Vaughan’s colorful and candid interjections add dimension and a sense of personal investment, while interviews with locals ground the story in the fabric of Costa Rican society. The episode is marked by its blend of true crime investigation and almost cinematic drama.

Summary for New Listeners

This episode brings new intensity to the saga of Ann Bender, exploring not just her legal jeopardy but the human costs and cultural fallout of her husband’s death. From the notorious conviction and dire prison experience, through mass mobilization to free her, we see Ann both isolated and surprisingly supported. The episode intertwines legal drama, personal tragedy, and media spectacle, building to a nail-biting wait for a final verdict. Listeners are left suspended in the crowded courthouse beside Ann and her supporters, awaiting either her liberation or a return to the hellish prison from which she’s just escaped.