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The Enduring Mystery of the Circleville Letter Writer

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Written by   50
2 months ago

Starting in 1976, Circleville, Ohio, with a population of only around 13,000, began to be plagued by the unsolved mystery of the Circleville Letter Writer. Sound like a dumb name? Well, it was certainly a serious matter to all who lived there. You see, a series of anonymous letters were sent to many residents, accusing them of everything under the sun, and sometimes right on the money. The letters threatened to expose them, though they never demanded hush money. The entire affair sent shock waves throughout the town, even continuing after a murder and an apparent framing.

How it All Began

This whole, crazy thing started in December 1976 when a letter arrived at the Westfall High School. It was addressed to then-superintendent Gordon Massie, accusing him of having an affair with the married school bus driver Mary Gillispie. Written in block letter style, it was the first sign of bad things to come.

The next day, another letter came, this time addressed to the Westfall School Board, telling them of the alleged affair. The strange thing is, the letters, and all of those to come, were postmarked Columbus, Ohio, 25ish miles north of Circleville!

Despite the initial letters being sent to the superintendent and the school board, the main target of the anonymous writer’s harassment campaign would be none other than Mary Gillispie herself. Mary found a handwritten letter in her mailbox not long after the initial letter with the same accusation the superintendent had received. The writer claimed to have been observing her and her children. The writer insisted that this was a serious matter and also stated that “everyone concerned had been notified and everything will be over soon.” Perhaps this was in reference to the previous two letters sent to Gordon Massie and the Westfall School Board.

Anyway, Mary shared the letter with her husband, Ron Gillispie, but denied having an affair with the superintendent. However, in March of 1977, Ron got a letter of his own telling him that he needed to admit that his wife was cheating on him. Instructions in the letter told him to inform the Westfall School Board of the affair.

Ominously, the letter also warned that he’d be killed if he didn’t.

Both Ron and Mary decided to keep the letter quiet, however, another letter was sent two weeks later. Again, this letter was addressed to Ron, saying, “You have had 2 weeks and done nothing. Make [Mary] admit the truth and inform the school board.”

By now, both husband and wife had received letters threatening them and their children, but now there were also phone calls coming in.

Mary believed the letters to be coming from a fellow bus driver named David Longberry. Longberry had flirted with her before, but she’d rejected him. Was this revenge?

Mary and Ron reached out to Ron’s sister, Karen Freshour, and her husband, Paul, for help. Paul’s sister was also told about the letters, but no one else knew about the harassment campaign against them. Paul was a former prison guard, and when Mary told him that she suspected David, Paul decided to write a letter to him explaining that the Gillispies believed he was writing letters to harass and threaten them and ordered him to stop.

...And, for a time, the letters did stop. But then came the signs. Posted along Mary’s bus route, the signs alleged that Mary’s 12-year-old daughter was in a relationship with Gordon Massie. Ron would reportedly drive around early in the morning to collect the signs before his daughter could see them.

Then, on August 19, 1977, Ron received a phone call in which the caller said he was watching the house and knew what kind of car Ron drove. Ron thought he recognized the caller’s voice, grabbed his gun, and rushed outside to confront him. Getting into his truck, he drove off.

A shot was heard, but Ron didn’t return. His truck was found at 10:35 PM, smashed into a tree. Ron was dead from major internal injuries.

Many Circleville residents believed that Ron had been murdered, that the anonymous writer/caller had made good on his dangerous threats. His brother-in-law, Paul Freshour, also believed he’d been murdered. After all, his gun was found under his body. Moreover, it appeared that one round had been fired off, explaining the shot some people claimed to have heard.

Initially, Sheriff Dwight Radcliff suspected foul play, but the coroner, Dr. Ray Caroll, found a high blood-alcohol level of .16, or twice the local limit. As such, the sheriff changed his mind and claimed that Ron had driven drunk and crashed. The problem was that no one knew Ron to be a heavy drinker. Then again, a harassment campaign like that could have driven him to the bottle.

However, Sheriff Radcliff also had reason to cover up Ron’s possible murder. He was running for President of the National Sheriff’s Association, and it would look bad if this letter-writer hadn’t been caught before turning to actual murder.

Funnily enough, the letter-writer was also frustrated by the complete lack of investigation into Gillispie’s death and soon letters were circulating to other residents of Circleville as well. They alleged that Radcliff had covered up the murder and that Mary Gillispie and Gordon Massie had conspired to kill poor Ron. The letters also accused Dr. Caroll, the coroner who’d examined Ron, of sexually abusing young children. Strangely, he would eventually be charged with doing just that in 1993. Twelve counts to be exact.

The letters continued to be sent to residents throughout Circleville, including local businesses, the newspaper, and even schools. Terror gripped the town as residents were taken aback by the fact that the unhinged letter-writer seemed to know details of their lives that no stranger should’ve known.

Meanwhile, Paul Freshour took Ron’s death into his own hands, filing a report requesting that the FBI get involved in the investigation.

A messy divorce between Paul and Karen ensued during this time, and Karen moved into a trailer on Mary’s property. Mary told her that after Ron died, she and Massie did start to have a fling, and that’s when things get even crazier.

The Even Crazier Stuff

We rejoin Mary Gillispie on February 7, 1983. She’s been targeted for years by now and her husband gone for six years. Without him to take down the nasty signs targeting her daughter, she’s left to do it on her own as she encounters them on her route.

Driving near Five Points Pike, she saw one of the offending signs. Pulling over to remove the obscene sign, she saw that it was attached to a box with some twine. Unable to pull the sign down, she decided to take the entire rig home with home, but when she opened the box, she found a gun inside.

Bringing the gun to the sheriff’s office, it was determined that the sign was meant to be a booby trap. When the sign was pulled down, as the perpetrator clearly knew Mary would try and do, the gun would fire, killing her. However, for some reason, the trap didn’t go off when Mary first tried to pull down the sign.

For the police, this was the first break in the case, but it gets complicated at this point. The gun belonged to Paul Freshour, Ron’s brother-in-law who’d been trying for years to get someone to investigate Ron’s death. According to Paul, the gun had gone missing weeks before and he denied setting a trap for Mary. He didn’t report the gun missing, though.

The police asked Paul to copy one of the many Circleville letters and to try and emulate its handwriting. This practice is definitely not proper procedure for obvious reasons, but it helped build the case against Paul Freshour. Aside from this, however, there was still more evidence coming.

Mr. Freshour failed a polygraph test, and then his embittered ex-wife told the police that he was behind the letters. She even claimed that she had access to letters Paul hadn’t yet mailed, but then said that she couldn’t produce said letters because she’d already disposed of them.

Paul also took time off of work on the 7th so he could stay home, for there was work being done on his house. However, he fully cooperated with law enforcement, and it’s not like other witnesses weren’t coming forward, they were just ignored by police.

For example, some people claimed to have seen a large man with sandy hair in a yellow El Camino standing at the site of the booby trap designed to kill Mary. This description doesn’t fit Paul at all, but it does fit the man Karen was dating at the time.

Over 1,000 letters had been sent to residents by this point in time, complaining of corruption and some even containing arsenic. However, Paul was charged only with setting the trap designed to kill Mary Gillispie, though the letters were entered into evidence against him at his trial.

After just two-and-a-half hours, the Jury returned a guilty verdict. He was sentenced to 7-25 years in prison for the attempted murder of Mary Gillispie.

Whew, Glad That’s Over, Right? ...Right?!?

Are you kidding? I probably wouldn’t be writing this article if it didn’t get even weirder!

The thing is, the letters continued being sent after Paul Freshour was thrown in prison. Paul himself even received a letter saying, “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?”

The prison had taken numerous measures to make sure that Paul wasn’t writing these letters while imprisoned. He was kept in solitary confinement with no access to pen, paper, or any mail. He was strip-searched regularly and his cell searched. Yet the letters kept coming, all still postmarked from Columbus 25 miles north. The warden himself eventually wrote a letter to his ex-wife telling her that there was no way Paul was writing letters from his cell.

The letters finally ceased in 1994.

48 Hours Tackles the Case

In August of 2021 (how do you think I heard about this case?), 48 Hours decided to take the case, airing an episode that they claimed would identify the writer. Yeah, that didn’t happen, but there was some interesting stuff revealed.

Document examiner, Beverley East, compared the Circleville Letters to Paul Freshour’s handwriting and found links between them. In particular, she focused on the way he wrote his numbers, so even though there were numerous differences in writing, there were also what she called ‘quirks’ of Paul’s handwriting that matched.

However, former FBI profiler Mary Ellen O’Toole doesn’t believe that Paul Freshour was the letter-writer. Not only did the letters continue while he was imprisoned, she believes the letters were written by a female, and not a well-educated one at that. Paul Freshour, however, was a man with three college degrees.

The Theories

I’m interested in reading what all of you think of this case, but here are some theories.

1. It wasn’t Paul, it was Karen. He and Karen went through a tumultuous divorce that ended when she moved onto Mary Gillipsie’s property and he gained custody of their three children. Between the FBI profiler believing the writer was a woman and Karen having access to Paul’s gun, the pieces just click. She was bitter and angry at their failing marriage and subsequent divorce that robbed her of her children, so she set him up.

2. There were a lot of letter-writers. This would be a realm for handwriting experts, but one theory is that David Longberry did write the initial string of letters, but others picked up where he left off. Everyone with grievances decided to air everyone’s dirty laundry. The Circleville Letters was a social phenomenon, not the result of one or two terrorists.

What do you all think?

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