The Creepy Letters That Exposed A Town’s Juiciest Secrets — And Ended In Murder

In the late 70s someone started terrorizing the small town of Circleville, Ohio by spreading gossip and revealing the townspeople’s sexual secrets through the mail. It was a very analog Gossip Girl, but with divorce, murder and false imprisonment. The identity of the Circleville writer is one of the most bizarre mysteries in true crime history. It started in 1976 when people in Circleville began receiving letters that contained information about their personal lives. Many of these letters were about the recipients private sex lives. The letters were postmarked from Columbus, Ohio.

The first letter recipient was Mary Gillispie, a local bus driver who was accused in several letters of having an affair with local school superintendent Gordon Massie. At the time, Mary said the affair never took place. The letter writer said they were “watching” Mary’s house and her children and told her to stop the affair. Later, Mary’s husband Ron Gillispie also received a letter saying Mary was in danger if he could not stop her affair. Another letter said the writer would Kill Ron unless Ron told the school board about the affair. One of Ron’s letters read: “Gillispie, you have had 2 weeks and done nothing. Make her admit the truth and inform the school board. If not, I will broadcast it on CBs, posters, signs, and billboards, until the truth comes out.”

From the beginning, Mary had a suspicion a fellow bus driver named David Longberry was the letter writer. Mary had previously rejected David romantically and he still acted resentfully toward her.

Mary and Ron Gillispie asked Ron’s sister and her husband, Karen and Paul Freshour, for help. Paul’s sister was also informed of the existence of the letters, but no one else knew what was happening. The five people decided that Paul would write the David Longberry a letter of their own. In the letter, Paul said he knew David was writing threatening letters to Mary and Ron. They believed the plan worked as the letters stopped coming for a few weeks.

On August 19, 1977, Ron Gillispie received a call and became angry. He got his gun and told his kids he was going to talk to the person who was writing the letters. A few hours later, Ron Gillispie was found dead as the result of crashing his truck into a tree. Before he died, he had fired his gun. The official police report from Sheriff Dwight Radcliff says that he died as a result of a drunk driving accident, despite Ron’s friends and family saying he rarely drank and hadn’t been drinking that day.

After Ron’s death, other residents in Circleville began receiving letters alleging that Sheriff Dwight Radcliff was involved in a cover-up relating to Ron Gillispie’s death. Sheriff Dwight Radcliff said he thought foul play was involved at first, however, the other person “involved” (unfortunately, there aren’t details about how this other person was involved in the accident or who they were) passed a polygraph test and Ron’s autopsy showed a BAC of .16, so he thought the cause of death was drunk driving.

After all of this, it turns out, Mary Gillispie was having an affair with Gordon Massie, though she claims it started after the letters.

In February 1983, the letter writer had resorted to placing inflamatory signs around Circleville, especially along Mary’s bus route. Many of the signs accused Gordon Massie of raping the Gillispie’s 12-year-old daughter. When Mary Gillispie stopped the bus to tear one of the signs down, she was almost killed. The sign had been crudely booby-trapped to shoot whoever tried to take the sign down. Police discovered the gun in the boobytrap was registered to Paul Freshour.

Paul Freshour said the gun had been stolen, but he had not reported it stolen so there was no evidence of this. He was asked to perform handwriting samples so that his handwriting could be compared to the Circleville letters. The test he was given is not standard and involved him emulating one of the letters, rather than simply being given the words to write in his own handwriting. Paul Freshour was arrested and tried for the attempted murder of Mary Gillispie. During his trial, a handwriting expert testified under oath that he believed Paul Freshour was the writer of the Circleville letters. By that time Paul was divorced from Mary’s sister-in-law Karen and they both believed he was the writer as well.

Paul was found guilty of attempted murder and thought to be guilty of writing all the letters as well. However, while Paul was in prison the letters kept coming. Paul even received a letter from the Circleville letter writer which read “Now when are you going to believe you aren’t going to get out of there? I told you two years ago. When we set ‘em up, they stay set up. Don’t you listen at all?”. Some of the letters were sent while Paul was in solitary confinement with no access to the mail at all. The letters also became more cruel, one accusing the prosecutor in Paul’s trial of having murdered a pregnant woman.

Paul Freshour was released from prison on parole in May 1994 after ten years. He maintains his innocence of both the letter-writing and the attempted murder. The mystery was featured on an episode of Unsolved Mysteries after which the show received their very own letter from the Circleville writer which read: Forget Circleville Ohio: Do Nothing to Hurt Sheriff Radcliff: If You Come to Ohio You El Sickos Will Pay: The Circleville Writer.

What’s especially creepy is how omnipotent the Circleville letter writer seems. They knew so many people’s secrets in town. Some of these secrets are really serious things that people do kill over, if you’ve ever seen an episode of Forensic Files. That rumor about the prosecutor in Paul Freshour’s trial? It turned out to be at least half true. The prosecutor, Roger Kline, was discovered to have had an affair with the dead woman, and he was the father of her unborn child. Dr. Ray Carroll, who performed Ron Gillispie’s autopsy, was outed by the Circleville writer as a pedophile, in 1993 he was officially charged with 12 counts of gross immorality, sex crimes, corruption of a minor, pornography, obscenity, and indecent exposure.

So who was the Circleville letter writer?

There are a few theories:

Paul Freshour. He served 10 years in prison for Mary Gillispie’s attempted murder. He died in 2012 maintaining his innocence and that he had been falsely imprisoned. You can read Paul’s website about the case here.

Mary Gillispie. It almost seems like Mary has to be in on it. How did she know to stop her bus and pull down the one sign that had been boobytrapped? And she was able to discover it was boobytrapped without getting hurt. It was later revealed that Mary was having an affair with Gordon Massie, and then her husband was killed (which she may or may not have wanted to happen at that point). However, some of the signs put up by the writer contained rumors about Mary’s 12-year-old daughter, so it’s unlikely she was the writer.

David Longberry. This is the bus driver Mary Gillispie initially suspected. In 1999, he raped an 11-year-old girl and was on the run before dying by suicide.

Karen Freshour. Paul’s wife and Ron Gillispie’s sister. Their divorce was not amicable and she had access to Paul’s gun and could have framed him.

William Massie. Gordon Massie’s son. The first target of the Circleville letters was Mary Gillispie and the subject of those letters was that she needed to end her affair with Gordon Massie. Some of those letters were signed with a “W”, leading some people to suspect Gordon Massie’s son, William.

El Camino man. A man was seen on the side of the road with a yellow El Camino in the location that Mary Gillispie pulled over and found the boobytrapped sign 20 minutes later. A man Karen Freshour was dating at this time drove a similar vehicle.

It’s also possible that more than one of these suspects, or other residents of Circleville wrote one or some of the letters without being the original or primary letter writer. Perhaps once the letters started, multiple people used the opportunity to air their grievances. In that case, I’m surprised they ever died down. No one has heard from the Circleville letter writer since 1993 when the Unsolved Mysteries segment aired.