Into The Dark – Episode 143: The Murder Castle – The True Story of H.H. Holmes

Host: Payton Moreland
Date: October 29, 2025

Episode Overview

In this chilling Halloween episode, Payton Moreland brings listeners deep into the story of H.H. Holmes, one of America’s earliest—and most infamous—serial killers. With her signature blend of true crime, mystery, and horror, Payton unpacks Holmes’s grim legacy, meticulously walking through his childhood, elaborate scams, and the horrors of his “Murder Castle,” a labyrinthine hotel built to snare victims during Chicago's 1893 World's Fair.

Key Discussion Points & Insights

1. Setting the Scene: Hotels, Horror, and the 1893 World’s Fair

• [06:02] Payton uses the relatable discomfort of a bad hotel stay to segue into Holmes’s notorious hotel, contrasting everyday inconvenience with unmatched terror: “It's a nightmare experience. And this next part that I'm going to tell you is true. Okay? This is not false. This is not a made up story.” (Payton, 09:30)

• She briefly recounts the strangeness and scale of the Chicago World’s Fair, highlighting how its transient, chaotic environment provided the perfect cover for Holmes: “All of these people...have to stay somewhere. There is a certain group of people who end up staying in this unnamed hotel in the city. And then these weird things start happening.” (Payton, 08:20)

2. The Origin of H.H. Holmes: Childhood and Early Crimes

• [10:34] Holmes, born Henry Howard Holmes (real name not disclosed), grew up in a wealthy but abusive family. Payton explores his early fascination with death and dissection of animals, suggesting a pattern of emerging psychopathy.

• Notable Quote: “Rumors, all of the wild animals and neighborhood pets tended to go missing when he was home. Apparently, trigger warning. He enjoyed killing them and dissecting them.” (Payton, 11:45)

3. Medical School and Insurance Fraud

• [13:15] Holmes’s med school tenure provides the backdrop for his first significant con: taking out life insurance policies on strangers, then using stolen corpses to claim payouts.

• Insight: Holmes was motivated less by need (he came from wealth) and more by the thrill and psychological satisfaction of deceit and fraud.

• Notable Quote: “He liked the rush of defrauding other people and getting away with it, of tricking people.” (Payton, 13:55)

4. Marriage, Manipulation, and Murder

• [16:04] Holmes cycles through multiple marriages under different aliases, repeatedly marrying wealthy women and absconding with their fortunes.

• He also manipulates investors and business partners, including the suspicious disappearance of a pharmacy owner: “He went to a meeting with the woman who owned the building and she was never seen again.” (Payton, 17:17)

• Notable Detail: Holmes's use of disguises: “Sometimes he even wore fake beards and other disguises when he was flirting with a potential new wife.” (Payton, 19:10)

5. The Birth of the “Murder Castle”

• [20:35] With stolen money, Holmes constructs a massive, three-story building under the guise of a hotel, intentionally designing it with deadly features: trap doors, soundproofed rooms, poison gas pipes, and labyrinthine hallways.

• Notable Quote: “The Murder Castle was designed so the people who went in would never come out.” (Payton, 24:58)

• Payton draws parallels to “American Horror Story: Hotel,” noting the real-life inspiration.

6. The World’s Fair Murders and Body Disposal

• [23:42] Holmes capitalizes on the World’s Fair influx, luring guests and staff into fatal traps and collecting on their insurance—often after listing himself as beneficiary.

• Details on his body disposal methods: Holmes supposedly had a morgue in the cellar, dissected victims, destroyed soft tissues, and sold skeletons to medical schools.

• Notable Quote: “Honestly, there was kind of a thriving black market back then for fresh human bodies.” (Payton, 28:12)

7. The Con Unravels: Insurance Scams, Betrayal, and Murder

• [29:44] Holmes's overconfidence leads him to try the same scam with new partner Benjamin Peitzel. Holmes murders Peitzel for the insurance payout, then lures and murders Peitzel’s three children.

• The horrifying sequence follows Alice, Nellie, and Howard—sent to Philadelphia by their mother—into Holmes's clutches.

• [35:18] Carrie, Benjamin’s widow, suspects the worst, triggering a nationwide manhunt.

8. Arrest, Trial, and Infamy

• [38:33] Holmes is captured in Boston. He initially only admits to fraud but, as evidence mounts (including bodies found in his properties), he is convicted of murder.

• The media frenzy paints him as a supernatural evil, even suggesting he could be Jack the Ripper.

• Notable Quote: “He was kind of painted as this evil monster or demon rather than just a human serial killer.” (Payton, 41:14)

9. Confessions and Execution

• [43:11] Awaiting execution, Holmes confesses to 28 murders, but authorities suspect the true number may be as high as 200—uncertainty due to poor recordkeeping and forensic technology.

• [45:18] Holmes is executed by hanging on May 7, 1896, at age 34.

10. Legacy: The Murder Castle’s Fate and Lasting Mystique

• [46:06] After his death, Holmes’s “castle” becomes a tourist attraction until it burns down; its existence cemented in true crime lore.

• Notable Quote: “People were fascinated by H.H. Holmes’s life and his crimes and by the hotel where he had killed so many terrified employees and people.” (Payton, 46:15)

Memorable Moments & Quotes

• [09:50] Payton: “You guys, doors that go nowhere, trap doors—it’s a nightmare experience. And this next part I’m going to tell you is true. Okay? This is not false. This is not a made up story.”
• [11:45] Payton: “Rumors, all of the wild animals and neighborhood pets tended to go missing when he was home.”
• [13:55] Payton: “He liked the rush of defrauding other people and getting away with it, of tricking people.”
• [19:10] Payton: “Sometimes he even wore fake beards and other disguises when he was flirting with a potential new wife.”
• [24:58] Payton: “The Murder Castle was designed so the people who went in would never come out.”
• [28:12] Payton: “Honestly, there was kind of a thriving black market back then for fresh human bodies.”
• [41:14] Payton: “He was kind of painted as this evil monster or demon rather than just a human serial killer.”
• [46:15] Payton: “People were fascinated by H.H. Holmes’s life and his crimes and by the hotel where he had killed so many terrified employees and people.”

Timestamps for Important Segments

• 06:02 – Transition to hotel horror, World’s Fair context
• 10:34 – Holmes’s childhood and early symptoms of psychopathy
• 13:15 – Medical school scams and insurance fraud
• 16:04 – Multiple marriages and disappearance of business partner
• 20:35 – Construction and design of the Murder Castle
• 23:42 – Fair influx, murder methods, body disposal
• 29:44 – New insurance scam, Benjamin Peitzel, and the children’s fate
• 35:18 – Nationwide manhunt, Holmes pursued
• 38:33 – Arrest, trial, and media frenzy
• 43:11 – Holmes’s confessions and estimated kill count
• 45:18 – Execution and legacy
• 46:06 – The castle’s destruction, lasting mythos

Tone & Language

Payton employs a conversational, sometimes playful tone (“I now know that UConn is in Connecticut. Don’t worry, guys. When I first talked about… I was very early into the fandom.” (05:20)) with sudden shifts to somber gravity when discussing Holmes’s atrocities. Her delivery is at once approachable and chillingly vivid, heightening the horror and the mystery.

Final Thoughts

Payton frames Holmes’s story as the ultimate real-life horror, perfectly suited to the Halloween season. She emphasizes that, despite sounding like fiction, these events are all too real—a potent reminder of the darkness that can lurk behind everyday facades:

“Holmes just goes to show that you never know what frights are hidden just out of sight, what monsters dwell among us, and how terrifying the world can actually be.” (Payton, 48:12)

This summary covers all major content in the episode, focusing on narrative flow, thematic highlights, and significant segments, preserving the original tone for those seeking a detailed account without listening to the full podcast.