A seemingly idyllic Ohio town becomes the setting for one of the most mysterious cases of the 20th Century. Sinister letters are sent for years, a life is lost, while others are ruined and the whole matter remains a puzzle to this very day.
EM Hilker is our writer and researcher with additional writing by Cassandra Harold. Jim Harold is our Executive Producer.
CLICK HERE for EM Hilker’s original article.
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It sounds like something out of a story: the pleasant, quiet little town, where everyone knows everyone else, filled with kindly old people, lively yet well-behaved children, and their attractive but not too vain parents. They probably have a quaint library and a diner that serves a really great cup of coffee alongside generous slices of fruit pie made in its very own kitchen. Then, disturbing the harmony: anonymous letters – accusations of affairs, sinister plots, even murders. The town is thrown into turmoil, filled with anger and mistrust and uncertainty. It’s the stuff of short stories studied in highschool literature classes, to highlight hypocrisy and dark truths in society.
And, in fact, it is a story, written by classic horror author Shirley Jackson in 1965: The Possibility of Evil. In this story, a seemingly sweet old woman, Miss Strangeworth, carries out her life as a benevolent and treasured member of the community, descended from the very first members of that community, who retires to her home at night and sits at her writing desk, writing anonymous letters to the townsfolk accusing their partners of infidelity, their doctors of malicious malpractice, their children of terrible things, and turning townsfolk against each other.
Yet in a case of life imperfectly imitating art are the Circleville letters, real life anonymously written letters that Miss Strangeworth would have loved to have written herself, proving that life is indeed stranger and more horrifying than fiction, and often more deadly.
It’s unclear when the first letter or letters were received, but Ohio school bus driver Mary Gillespie’s letters – which would start off the whole mess, beginning with accusations of an affair and ending in a possible murder, and attempted murder, and a jail sentence – began in the summer of 1976. The first letter, unsigned and bearing no return address but postmarked as being sent from Columbus, a short drive from Circleville where Mary lived, demanded that she cease her extramarital affair with Westfall school district superintendent Gordon Massie.
Mary thought she knew who the culprit was: fellow school bus driver David Longberry, who’d expressed his interest in her in the past and hadn’t taken her rejection of him particularly well. Expecting it was just meant to scare her and unwilling to give them the satisfaction, she ignored the letters. Weeks later, her husband Ron began getting his own letters, informing him of the affair and threatening him with death if he didn’t take that information to the school board and demand Massie be fired. Mary swore to Ron that there was no affair, and that it was simply a prank. As the letters continued, the threats changed their tone: stop, or it will be made public. There would be announcements on CB radio, in the newspapers and on billboards. Mary and Ron were at a loss and told their closest friends and family: Ron’s sister, Karen, her husband Paul, and Paul’s sister; as a group, they decided to send letters to their presumed culprit, David Longberry, advising him that they knew who he was and to stop sending letters. The letters – coincidentally or otherwise – did in fact stop for a period, but soon were replaced by signs placed all over town accusing them of all manner of things. Perhaps most damagingly, at least for the moment, were the signs accusing Massie of molesting the Gillespies’ 12 year old daughter. Reportedly, Ron woke up early each morning and drove around town, tearing down signs before his young daughter and her schoolmates could see them. There was no hint of who the culprit, if not Longberry, could be. It came out that other people were also receiving letters, though understandably no one wanted to go into specifics.
In August of 1977, a little more than a year since the beginning of the letter writer’s campaign against virtually all of Circleville but most certainly Massie and the Gillespies, Ron got a telephone call from an unknown person, presumably the letter writer, who told him that he or she was watching the house. Recognizing the voice on the other end, Ron grabbed his gun and stormed out of the house and into his truck with the intent on confronting the unknown person. Moments later there was the sound of a gunshot, and at a nearby intersection Ron’s truck was crumpled, crashed into a tree, with the lifeless body of Ron inside.
Ron was autopsied, and reported to have twice the legal limit of alcohol in his system. His loved ones found this perplexing; he was certainly having a hard time with the campaign of abuse against his family, but he had never been much of a drinker. No one thought he was inebriated when he left the house on the day he died. No bullet casing from the fired shot, which witnesses were positive they’d heard, was found at the scene. County Sheriff Dwight Radcliff investigated the potential involvement of one person, who has never been named, but who evidently passed a polygraph and was dismissed as a suspect. The death was reported as an accident, a tragic loss of control due to Ron driving under the influence.
After the death of Ron Gillespie, the letter writer’s campaign continued – letters accusing Sheriff Radcliff of being involved in a coverup of Ron Gillespie’s death, accusing Mary and Massie of having arranged his death, other letters revealing people’s deep, dark secrets, letters complaining of political corruption. Some contained arsenic.
No progress of any sort was made on the case until early 1983. Mary, driving her usual school bus route, came across a vulgar sign about her now teenaged daughter and, angrily, came to take the sign down. She would later report that she’d noticed an odd box attached to it by a string, and so she removed the box and took it home with her. Once home, she opened the box and discovered a gun inside, rigged to shoot if the string that had allegedly been attached to the sign was pulled.
Later that day, Mary took the box and the gun to the police. The gun’s serial number was chiseled off, though poorly, and the police were able to uncover it. They trackdown to its last registered owner. The owner had sold the gun months prior to his coworker, and Mary’s brother in law, Paul Freshour.
Freshour freely admitted when questioned that he had in fact bought that gun, but that it had been stolen months prior. He was open and perhaps naive in his discussions with the police; he did not request a lawyer, willingly took the forensic handwriting analysis that Sheriff Radcliff administered to him, and showed Radcliff personally where he had kept his gun prior to its theft.
Aside from the allegedly missing gun, there were other reasons why the case didn’t look so good for Paul Freshour. The day that Mary had found the gun, February 7th, Paul had taken off work. Paul and Ron’s sister, Karen, had divorced by that point, and Karen was living on Mary’s property in a trailer. Karen, upon being questioned, volunteered that Paul was the author of those letters, which she had found torn up and hidden but hadn’t saved any evidence of, and claimed that Paul had hated Mary. He worked in Columbus where the letters had been mailed from, giving him ample opportunity to mail the letters before and after work. Paul checked himself into the Riverside Mental Health Center for professional assessment, tried to be as helpful to the case as possible, and maintained his innocence.
The trial itself was fairly short – only a week – and Paul was pronounced guilty after only two and a half hours of deliberation by the jury. He had been persuaded by his lawyer to not take the stand, and he would regret that for the remainder of his life. He would spend the next decade in jail for attempted manslaughter. Only a small portion of the letters were included in the trial, and Paul was never charged as the culprit behind the letters.
It was suspicious though. After Ron’s death, Mary admitted to an affair between her and Massie – she claimed it started after the letters began, but there were witnesses to the fact that it had been going on much longer than that, and it’s been reported that few believed that it started as late as she had claimed. There were witnesses to where Paul was on the day Mary allegedly found the boobytrap; he was having repair persons in to fix a few things in his home.
The handwriting test that Radcliff had administered was done incorrectly – Paul had been asked to copy the handwriting with a sample in front of him, which is not at all how the writing analysis was meant to be conducted; it was only natural that they matched, Paul later argued. Karen, who had so willingly announced that her ex-husband was the letter writer and Mary’s would-be murderer, neglected to mention this to authorities at any point during the divorce proceedings and custody battle.
And then there were the letters. They didn’t stop when Paul Freshour went to jail; he even received one himself, the writer boasting about how they’d successfully set him up. This might seem too good to be true – surely Paul was writing these from jail, trying to make himself look innocent? But he was being monitored very closely, at times held in solitary confinement to be very sure that it wasn’t him, and he was cleared by the correctional facility. Radcliff had made claims in the media that he had Paul’s fingerprints on the letters and that people had been caught trying to smuggle letters out of the prison, but evidence of either of those claims never materialized.
The parts of the case involving the Gillespies are by far the most well-known – they received nearly 100 letters, the most of anyone whose involvement is known, and the case involved the tragic death of Ron Gillespie (through murder or an accident remains a highly debated topic) and alleged attempted murder of Mary Gillespie. There was even a twist: the beloved brother in law, behind it all! But there are more than 1000 letters written that authorities know of, sent to virtually everyone in Circleville and a number more in the general area, and who knows how many more that were never reported. It’s known that the letter writer referenced intimate details of their lives, secrets some thought long buried, and that they were oftentimes correct. Perhaps understandably, the citizens of Ohio weren’t eager to have the letters become public knowledge and, because of this, the precise number will most likely never be known.
The number of secrets the letter-writer was privy to seems almost occult: the affair between Gillespie and Massie was apparently true. In two of the better known examples of other letters, one contained accusations of child molestation by Dr. Ray Carroll, for which he was never formally charged but victims have since come forward with accusations of precisely that. In another letter, prosecutor Roger Klein, who would to on to become judge Roger Klein, had been accused of murdering a woman and the unborn child she was carrying. It’s unknown whether that part was true, but under investigation it was found to be true that he’d had an affair with the dead woman, and that the child she carried was his. Even without Klein’s guilt, the knowledge of the affair and paternity of the unborn child is still a lot of intimate information to come by.
In truth, framing Paul Freshour would have been easy for someone who knew him well – and we know that the letter writer knew an awful lot about everyone in town. In Circleville or any other small town, it wouldn’t be hard to find out that Paul wasn’t working that day – his boss and coworkers would have known he wasn’t scheduled to work, the people Paul hired to work on his house knew he wasn’t working; anyone Paul mentioned it to in passing knew that Paul wasn’t working. And how sincere was the attempt to chisel serial numbers from the gun? Were they meant to be uncovered?
There’s no shortage of suspects; some think that Paul Freshour was indeed guilty, either alone or with the aid of an accomplice to keep the letters going and to make it appear as though they’d arrested the wrong man. Others think it was his ex-wife and Ron’s sister, Karen, who hadn’t mentioned Paul as a letter-writer once during their divorce, during which she’d been trying to secure custody of their children, and who had a boyfriend that matched the description of the man spotted with the El Camino (which Karen’s brother was known to drive) in the area of the boobytrapped sign that very morning, and who would presumably have known whether or not Paul was working on that February day. Paul, prior to the laying of the boobytrap, had suspected that it was his own son that had stolen the gun and had talked about that with friends.
Paul himself believed that the murder of his former brother in law, Ron, was covered up by Sheriff Dwight Radcliff, who was at that time in running to become the National Sheriff’s Association president, and that he was intentionally framed by Karen and Mary for the attempted murder. He observed on his website that no one saw the Boobytrapped box until Mary presented it to the authorities several hours after allegedly finding it. There’s a lot in Ron’s arguments, still posted on his website “The Circleville Letters,” that warrants a closer look.
But the truth is, we can’t know. A decent case can be made for nearly anybody involved in this case, and dozens and dozens of people who went about their daily lives in between their poison pen letters, much like our false, fictitious Miss Strangeworth did. People who have never come to the attention of authorities. People whose names are notes in yearbooks and on wedding registries, obituaries in papers, photos in family albums. Paul Freshour died in 2012, Radcliff in 2020, Gordon Massie in 1996. As time passes, fewer and fewer people who know the truth remain. The last known letter sent by the letter writer was to Unsolved Mysteries, warning them away from the case, in 1993, and he, she, or they have not been heard from since.
“Circleville Writer.” Unsolved Mysteries Wiki. Retrieved 9 August 2022.
Freshour, Paul. “Circleville Letters.” Circlevilleletters, 23 October. 2011. Retrieved 8 August 2022.
“Gordon R Massie.” AncientFaces. Retrieved 8 August 2022.
Jackson, Shirley. “The Possibility of Evil.” The Possibility of Evil by Shirley Jackson, 1965. Retrieved 9 August 2022.
Moriarty, Erin. “Has the Anonymous Author of the Infamous Circleville Letters Been Unmasked?” CBS News, CBS Interactive, 6 August 2022. Retrieved 7 August 2022.
Rossen, Jake. “Unknown Sender: The Mystery of the Circleville Letters.” Mental Floss, Mental Floss, 27 August 2021. Retrieved 7 August 2022.
Stockton, Chrissy. “The Creepy Letters That Exposed a Town’s Juiciest Secrets – and Ended in Murder.” Thought Catalog, 10 August 2021. Retrieved 7 August 2022.