The Circleville Letters Mystery: Ohio’s Most Chilling Unsolved Case

For decades, a small town in Circleville, Ohio was terrorized by anonymous letters exposing secrets, making threats, and destroying lives. Known as the Circleville Letters mystery, this disturbing case began in the late 1970s and remains one of America’s most puzzling true crime stories.

The harassment initially targeted Mary Gillespie, a local school bus driver accused in the letters of having an affair with school superintendent Gordon Massey. Soon, hundreds of threatening messages began appearing across the town, accusing residents of hidden affairs, corruption, and scandal. The letters were written in strange block handwriting and mailed from Columbus, Ohio, with no clear suspect.

The mystery took a deadly turn when Ron Gillespie, Mary’s husband, died in a suspicious car crash after receiving threatening messages from the anonymous writer. The harassment continued even after his death, escalating into an attempted murder when a booby-trapped gun device was discovered along Mary’s bus route.

Investigators eventually arrested Paul Freshour, Ron Gillespie’s brother-in-law, after the gun used in the trap was traced back to him. He was convicted and sent to prison, yet the letters continued to arrive even while he was incarcerated, leaving many to question whether the real Circleville letter writer was ever caught.

In this video, we examine the timeline of the Circleville letters, the mysterious accusations, the death of Ron Gillespie, the attempted murder plot, and the unanswered questions that still haunt this small Ohio town decades later.

Transcript

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A small town in Ohio, two decades of psychological horror and a legacy of death. Today's video is about the Twisted Circleville letters, one of America's most tragic and eerie true crime mysteries. In the 1970s, Circleville, Ohio, only had a population of about 13,000 people. It was the classic American little town where nobody locked their doors. But things were about to change fast. In 1976, the residents started receiving bizarre letters from a mysterious sender. The chilling part was that the sender was somehow aware of the victim's dark, life-changing secrets. The centerpiece of the whole story was Mary Gillespie, a school bus driver and a mother of two. Mary would continue to receive threatening letters for years. All were posted from Columbus, Ohio, and written in strange block letters with no return address. The letters contained intimate details about people's lives and alarming threats, and so began a cycle of letters and rumors that would lead to nothing but death and ruined lives. Over a thousand letters were received in 20 years, yet, somehow, the sender got away with it. Who was the Circleville letter writer? Why weren't they caught? Stick around as we pick apart this web of revenge plots, police cover-ups, and more in pursuit of the Circleville letter writer. Mary Gillespie lived in Circleville with her husband, Ron Gillespie, and two daughters. One day, an ominous letter appeared in Mary's mailbox, accusing her of infidelity with Superintendent Gordon Massey. The letter read, Mrs. Gillispie, stay away from Massey. Don't lie when questioned about meeting him. I know where you live. I've been observing your house and know you have children. This is no joke, please take it serious. Everyone concerned has been notified, and everything will be over soon. The writer knew where she lived, where she worked. He also knew about her kids. You can only imagine how frightening it must have been when she'd hear something at night or when one of her children got home late. Despite that, Mary chose not to alarm her husband or children and ignore the ominous letter. She continued to receive more of these letters. Each one was more vicious than the one before. Sadly, she continued to ignore them for a long time. This brings us to March 3rd, 1977. Gordon Massey was the superintendent at Westfall, the school district Mary worked for. On the morning of March 3rd, when Massey arrived at work, he found a letter waiting for him in his mailbox. The writing on the letters was in all caps. A return address was nowhere to be found. The mailing address was Columbus, Ohio. But what was written inside the letter made the superintendent's blood run cold. Dear sir, according to my girlfriend, you have asked her to go out many times and have asked the other female bus drivers too. This must stop at once for the good of the school and families. If they are not stopped, I will be forced to write to the school board, and I would hate to do that. To prey on another man's girl is untouchable. I suggest you find yourself a pimple-faced whore and start up with her and leave my girls alone. On the surface, Massey had the perfect small-town life: a nice job, a teenage son, and a wife, but the letters seemed to suggest otherwise. The Circleville letter writer would continue to accuse the superintendent of having affairs with his female bus drivers. With each letter, the threats grew more intense. One letter said he'd cut the brakes off Massey's car and slash his tires if he didn't stop pursuing his female employees. The writer demanded Massey admit his crimes and be penalized. But he wasn't. There was no proof of the allegations, and Massey continued to deny them until much later. Massey failed to heed the writer's warnings. Maybe he antagonized him further. But a few weeks later, the school vice principal also received a suspicious letter. A rambling four pages accusing Massey of multiple accounts of sexual harassment, demanding that he had to be fired. Later that day, the school received another letter. The writer claimed he was keeping tabs on Massey and knew exactly which bus drivers Massey was having affairs with. On March 18th, the school would receive another one of these accusatory letters. Frighteningly, it contained details that only someone who knew the school system very well would know, something he couldn't have pulled out of thin air. Dear school, talk to Gordon Massey about his affairs. I shall warn you. I know the truth. I want to protect your school. It has a good reputation. You should keep it like that. I shall send you proof about driver number 62917. She has a child in school there now. I shall prove this shortly. I expect him to be discharged. You'll see that I am telling the truth. Gordon Massey and Mary Gillespie did end up admitting that they were, in fact, having an affair. Ironically, they claimed the affair only began after the letters started arriving, not before. Did Mary and Gordon lie to keep themselves out of trouble for as long as possible? Or did the writer get it wrong? By the end of April, the writer decided to target Ronald Gillespie. He did so by informing him of Mary's infidelity and threatening his life if Ron didn't do something about it. Ron would receive another letter, a message that would force the family to take action. Ron and Mary turned to their nearest and dearest to determine their next course of action. With the help of Ron's sister and husband, Karen Freshhour and Paul Freshauer, the Glispys came up with a list of possible suspects. Their prime suspect was one of Mary's colleagues, David Longberry, another bus driver who had made a pass at Mary and gotten bitter upon being rejected. The family sent Longberry artful letters of their own. In these letters, they threatened to go to the police if Longberry didn't stop his reign of terror. After a long time, the nightmare at the Gillespie seemed to be over. The letters had finally stopped. That's until, after two weeks, things would take a turn for the worse. One afternoon, on his way home from work, Ron witnessed something sinister. Right there on a signboard was a message in that same all-caps block-like handwriting. It read that Massey had been having an affair with the then 12-year-old Tracy Gillespie, Ron and Mary's daughter. Over the course of weeks, more disturbing signs kept popping up, all harassing Gordon Massey and Mary Gillespie. Ron was distraught. Paul Freshour, his brother-in-law, reported that Ron wasn't getting much sleep during this period. He would drive around Mary's route every morning to remove any obscene signs that might be there. He was determined to solve the problem once and for all. On August 19th, Mary Gillespie accompanied her sister-in-law Karen Freshhour to Florida to take her mind off things. However, while they were on their way, they received tragic news. Not far from their home, the wreckage of Ron's 1971 Ford pickup was crumbled into a tree on the side of the country road. They later found out that Ron had received a mysterious call. The caller had frustrated him and he left the house with a 20-caliber revolver. Interestingly, the police found out that Ron had fired his gun during the car ride. Investigations also revealed that his blood alcohol level was at the time of the crash 0.16, which is way above the driving limit. He wasn't wearing his C-belt and had died from the impact of the tree. Was it a case of driving under the influence or was he chasing the letter writer? Whatever the case, the letters didn't stop. The ones that followed Ron's death blamed Sheriff Dwight for covering up Mary Gillespie's and Gordon Massey's affair. He said that the investigation of Ron's death was done in a way to prove it was an accident. They asserted that the sheriff was involved in corruption and mishandling of previous cases as well. The Circleville writers' obsession didn't end with Ron's death. Sadly, even after his death, Mary kept receiving the obscene letters. In February 1983, Mary discovered a sign involving her daughter on her regular bus route. She decided to take it down. What she found this time was more than just a message. It was meant to end her life. The Sheriff's Department report said that a cardboard box accompanied the sign. Within the box was a 25 caliber handgun ready to go off. The slightest mistake in removing the sign would have triggered the gunshot and killed Mary instantly. Investigation stated that the sign was positioned in a way that the gun was at the level of her chest and head. Intriguingly, the culprit had made a rather sloppy attempt at rubbing off the gun's serial number. A little detective work led to a very unlikely suspect. Someone very close to Mary. The serial number on the gun was traced to Paul Freshhour, Ron's brother-in-law, making him the prime suspect. But here's where things get interesting. Paul admitted the gun was his, but it had been stolen before the incident. Questioning revealed that he even had a solid alibi for most of the day. Sheriff Dwight Radcliffe then asked Paul to copy the original Circleville letters as best as possible. On the basis of this copy, Paul's handwriting was deemed to be an exact match to the letters. Based solely on the fact that the gun was registered to Paul's name and a handwriting test designed to make Paul fail, the state of Ohio sentenced him to 7-25 years in prison. What's creepy is that the Circleville letters continued to arrive without delay, even when Paul was in solitary confinement. Paul Freshour died on June 28, 2012, age 70, still unable to prove his innocence. In an interview with Robin Yochum, he said his notoriety as the Circleville letter writer would long outlive him. Was Paul Freshour really the evil mastermind behind a plot that haunted Circleville for two decades? Or was he an innocent man sentenced unjustly, where their copycats or someone else is doing Paul's bidding on his behalf while he was in jail? 50 years later, these answers we'll never know for sure. Like I always say, guys, remember to stay safe out there.