Conspiracy Theories, Cults, & Crimes

Episode: The Circleville Letters

Host: Vanessa Richardson
Date: November 26, 2025

Episode Overview

Vanessa Richardson guides listeners through the twisted true crime mystery of the Circleville Letters—a decades-long campaign of anonymous, threatening letters that terrorized an entire Ohio town, destroyed families, and allegedly led to murder. The episode examines key suspects, botched investigations, escalations to attempted murder, and the unresolved debate over who was truly responsible for the campaign. The episode further explores the broader damage wrought by secrets, gossip, and paranoia.

Key Discussion Points & Insights

1. The Beginning of the Harassment Campaign

• First Letters Appear (1976)
  • Mary Gillespie, a school bus driver, and Gordon Massie, superintendent, receive anonymous letters.
  • Mary’s letter (00:35):
    • “Stay away from Massey. Don't lie when asked about knowing him. I know where you live and have been observing your house and know you have children. This is no joke.”
  • Letters accuse Gordon of inappropriate relationships with female employees; Mary is accused of having an affair with Gordon.
  • The aggressor dubs themselves “the Circleville Writer.”

2. Escalating Threats and Paranoia (1976–1983)

• Impact on Gillespie and Massie Families (05:10):

  • Increasingly detailed letters sent to Mary, Ron (her husband), their family, friends, and coworkers.
  • The stalker demonstrates intimate knowledge of their lives (vehicle details, work schedules, children).
  • Local sheriff Dwight Radcliffe dismisses pleas for investigation.

• Attempted Counteraction (08:20):

  • Mary, Ron, and Paul Freshour (Mary’s brother-in-law) suspect coworker David Longberry and send him warning letters.
  • The letters stop briefly then resume, escalating further ("the calm before a much deadlier storm").

3. The Death of Ron Gillespie (August 19, 1977)

• Lead-up and Event (15:15):
  • Mary is away. Ron receives a phone call, retrieves his revolver, tells his family:
    • “I know who the letter writer is and I’m going to make it all stop.” (15:38)
  • Ron dies in a mysterious car crash shortly after, with puzzling forensic evidence:
    • His gun had been fired, but no shell casing or bullet found.
    • Autopsy shows elevated blood alcohol, but family disputes he was a drinker.
  • Community suspicion mounts that the letter writer caused Ron’s death, possibly with sheriff involvement.

4. Communitywide Psychological Attack (late 1970s–early 1980s)

• Letter Writer Expands Offensives (19:22):

  • Hundreds of threatening, secret-revealing letters surface across Pickaway County.
  • Some letters contain poison (arsenic); content varies from obvious falsehoods to frightening truths.
  • Local official Dr. Ray Carroll is accused of abuse—and years later is, in fact, exposed as a predator.

• Public Turmoil (20:50):

  • “It was like psychological warfare. Marriages grew strained under suspicion. Friendships dissolved. Business relationships crumbled.”
    — Vanessa Richardson

5. Attempted Murder and Key Evidence (February 7, 1983)

• Booby Trap Incident (30:40):
  • Mary discovers a graphic sign about her daughter Tracy attached to a bus stop.
  • Upon inspecting, finds it’s rigged to a box—a loaded handgun meant to discharge if the sign is yanked.
  • Police trace the gun to Paul Freshour, Mary’s former brother-in-law.

6. The Case Against Paul Freshour (16:40, 32:45)

• Investigation and Arrest (32:10):
  • Paul denies involvement; states the gun was stolen but hadn’t reported it.
  • Polygraph and unorthodox handwriting tests (33:40), both implicating him.
    • Handwriting test error: Paul asked to imitate letter style—not forensically valid.
• Trial & Conviction (36:08):
  • Sentenced to 25 years for attempted murder, largely on circumstantial evidence and disputed testimony.

7. Letters Persist After Imprisonment (38:18)

• Paul’s Incarceration Doesn’t Stop Letters
  • Letters about the Circleville case, now sent statewide, continue despite Paul being under surveillance and solitary confinement.
  • Paul receives his own threatening letter in prison:
    • “Now when are you going to realize that you are not going to get out of there? ... No one wants you out there. The joke is on you. Ha ha.” (40:12)
• **He’s eventually paroled; remains adamant about his innocence; creates a website to proclaim he was framed.

8. Lingering Theories & Unsolved Mystery (42:10)

• Paul’s Theory:
  • Claims Sheriff Radcliffe framed him, but no conclusive evidence.
• Alternative Suspects:
  • Karen Sue (Paul’s ex-wife) — had motive, financial gain, and possible links to the booby trap via her boyfriend and son.
  • Multiple letter writers or a community conspiracy.
• FBI Profiler’s Take: Letter writer may have been a local woman, “a bully in her daily life.”
• Ultimate Takeaway (43:00):
  • “The letters stopped as mysteriously as they began, leaving behind questions, fractured families, and the sense that nothing stays hidden for long ... except for the Circleville writer’s identity, that is.” — Vanessa Richardson

Notable Quotes and Memorable Moments

• Vanessa Richardson summarizing the town’s panic: (20:50)
  “It was like psychological warfare. Marriages grew strained under suspicion. Friendships dissolved. Business relationships crumbled. The mere possibility of being targeted kept residents on edge.”

• Paul Freshour’s prison letter: (40:12)
  “Now when are you going to realize that you are not going to get out of there? ... No one wants you out there. The joke is on you. Ha ha.”

• On privacy and gossip: (43:02)
  “If our most intimate and embarrassing moments were smeared across social media for everyone to gossip about? These days, that can happen with one wrong click or one mistaken download. In our digital age, privacy is no longer a right, it’s a privilege. And we should guard it very carefully. Because once it’s lost, there’s no going back.”

Important Segments & Timestamps

• The first Circleville Letters and the threat to Mary Gillespie: 00:35–04:50
• Gordon Massie’s letter and the expansion of targets: 04:50–10:15
• Mary, Ron, and Paul try to fight back: 10:15–13:45
• Ron's mysterious death: 14:59–17:50
• The community-wide spread and escalation of the letters: 18:50–25:30
• Crude public signs and the booby trap incident: 27:30–30:40
• Investigation into Paul Freshour: 32:45–36:08
• Paul’s conviction and the mystery deepening: 38:18–40:12
• Review of major suspects and enduring theories: 42:10–43:30
• Societal commentary on secrecy and privacy: 43:00–43:30

Conclusion

This episode delivers a meticulously structured chronicle of the Circleville Letters—one of America’s most bizarre and unresolved criminal harassment cases. Richardson’s storytelling blends slow-building suspense with deep empathy for the victims, while presenting the tangled theories that have perplexed law enforcement, profilers, and the community for nearly half a century. The Circleville Letters reveal the dark power of secrets, small-town suspicion, and the ways in which unchecked paranoia can destroy lives.

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