The Why Files: Operation Podcast - 63: The Circleville Letters Mystery

Episode Date: June 26, 2022

MYSTERY OF THE CIRCLEVILLE LETTERS We all keep secrets. For most of us, these are nothing more than minor embarrassing details about ourselves. But some of us have dark secrets which, if discovered, could destroy lives. For years, the residents of Circleville, Ohio, received bizarre, threatening letters; from someone who somehow knew every salacious detail of their personal lives. The letters cost people their jobs, their marriages, their freedom, and sometimes, their lives. Over a thousand letters were sent over *20 years*. Yet somehow, whoever wrote them got away with it. Or did they? Officially this case is closed. But for decades, many people felt that the real culprit is still at large. Let's find out why.  --- Support this podcast: https://podcasters.spotify.com/pod/show/thewhyfiles/support

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This would go a lot faster if you would just let me get through it without... We all keep secrets. For most of us, these are nothing more than minor embarrassing details about ourselves. But some of us, these are nothing more than minor embarrassing details about ourselves. But some of us have dark secrets, which, if discovered, could destroy lives. For years, the residents of Circleville, Ohio, received bizarre, threatening letters from someone who somehow knew every salacious detail of their personal lives. The letters cost people their jobs, their marriages,

their freedom, and sometimes their lives. Over a thousand letters were sent over 20 years, yet somehow whoever wrote them got away with it. Let's find out why. Circleville, Ohio is about 25 miles south of Columbus. In the late 70s, it was the typical small American rural town. With a population of 13,000, Circleville has been described using cliches like nobody locks their doors and everybody knows everybody. A problem with small towns is that it's hard to keep secrets. This story begins in 1976. Circleville residents started receiving anonymous letters, postmarked from Columbus,

handwritten in strange block letters. And the letters were full of details of their private lives. There was never a return address, but the writer was clearly someone with intimate knowledge of the town's residents and their secrets. Gordon Massey was the superintendent of Westfall Schools in Circleville. When he got to work on the morning of March 3, 1977, there was a letter waiting for him.

Dear sir, according to my GF, 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. The 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. And more letters followed, each with escalating threats. One even said they would cut the brake line in his car if he didn't stop sleeping with his employees.

That same day, a letter arrived with a school board describing how Massey approached, assaulted, and sometimes carried on extramarital affairs with the female bus drivers. The writer demanded Massey be fired. He wasn't. He denied everything, and there was no proof of any wrongdoing. But a couple of weeks later, the school's vice principal received a letter. 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 then to be discharged. You'll see that I am telling the truth. That letter was oddly specific. Though he didn't name anyone, he used an employee number. Only someone with intimate knowledge of the school and its employees would have that information.

They looked up the number 62917. It belonged to bus driver Mary Gillespie. Mary Gillespie was not someone you'd suspect of a scandal. She had a nice group of friends and a close family who lived nearby. And according to everyone who knew her, Mary was a good friend, an attentive mother to her two children, and a loving wife to her husband, Ron. Mary led a quiet life. But that would all change in March 1977. Mary opened her mailbox and found a strange anonymous letter,

handwritten in eerie block letters. Stay away from Massey. Don't lie when questioned about knowing him. I know where you live and have 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.

This is upsetting, but rather than tell her husband Ron, she kept this to herself. Over the next few weeks, more and more letters came in, and each one was more threatening than the last, and each revealing more personal information. The writer obviously knew where she lived, but also what bus she drove and the names of her husband and her children. Still, she ignored the letters. So the writer raised the stakes. He wrote directly to Mary's husband, Ron Gillespie. The circle of the letter was gaining confidence. The letter to Ron described his wife's affair with Massey and threatened to kill him if he did nothing about it.

The writer claimed to know where Ron worked and described his vehicle, a red and white pickup truck. Ron and Mary were definitely being watched. And when Ron confronted Mary about the letter, she denied having an affair with Gordon Massey, but she admitted she'd been receiving similar letters for a few weeks. They decided once again to ignore them.

But two weeks later, Ron received another. The letter writer had now changed the handwriting to be even blockier, probably to make it harder to trace. And this letter informed Ron that he knew that he had done nothing about Mary's affair with Massey. And if she didn't admit the truth, the writer threatened to put up signs and billboards and broadcast the truth on CB. CB? Radio? Yeah, theboards and broadcast the truth on CB. CB? Radio?

Yeah, the buses communicated with each other with CB. Wow, CB takes me back. It does? Oh yeah, I used to drive truck in the 80s. Really? If it's a flat or a squeal, a wobble or peel, your dread's worn down or you need a new wheel, wherever you go, you can get it from our tread experts. Toyo's open country family of tires will get you through tough weather in a variety of terrains. Until May 31st, save up to $100 in rebates on select Toyo tires.

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when you purchase Kumho RoadVenture AT52 tires. Find a Kumho Tread Experts dealer near at TreadExperts.ca slash locations. From tires to auto repair, we're always there. TreadExperts.ca You sailed beyond the horizon in search of an island scrubbed from every map. You battled krakens and navigated through storms. Your spade struck the lid of a long-lost treasure chest.

While you cooked a lasagna. There's more to imagine when you listen. Discover best-selling adventure stories on Audible. You searched for your informant who disappeared without a trace. You knew there were witnesses, but lips were sealed. You swept the city, driving closer to the truth while curled up on the couch with your cat. There's more to imagine when you

listen. Discover heart-pounding thrillers on Audible. This is Hicklefish at the Porkchop, and I'm talking to whoever's listening out there. It's like I told my last wife. I says, honey, I never drive faster than I can see. Besides that, it's all in the reflexes. Coke Classic. That was a good one. Anyway, besides the letters, Mary and Ron started getting phone calls from the person they believed was writing them.

They didn't know what to do or who to tell about the threatening letters and calls, so they went to the people they trusted the most, their family. This turned out to be a huge mistake. To fight back against the anonymous letter writer, Ron and Mary Gillespie enlisted the help of Ron's sister and her husband, Karen and Paul Freshour. They put together a list of suspects. From the beginning, Mary suspected another school bus driver named David Longberry. David made a few passes at her and became resentful when she rejected him. So they decided that Paul Freshour would write to David Longberry. In their letters, they told David that they knew what he was doing and threatened to go to the police if he didn't stop immediately. Did the letters stop?

They stopped, and everyone's life went back to normal. Oh boy. What? This is the part where you say everything was fine until... In August 1977, the letters and phone calls had stopped. But now, signs appeared. Suddenly, Ron and Mary began seeing signs posted all over the town, written in the same crude block letters. They accused Gordon Massey of having an affair with Mary.

Some even accused Massey of having an affair with Mary's daughter, Tracy, who was only 12 years old. Yeah, this isn't cute anymore. I hate this guy. I get it. So did Ron and Mary. In fact, every morning, Ron would get up early and guy. I get it. So did Ron and Mary. In fact, every morning, Ron would get up early and drive around town, removing all the signs he could find so his wife and daughter wouldn't see them on their way to school. But things get worse. Mary Gillespie went out of town to clear her head. Ron stayed home in Circleville with the kids. On the evening of Friday, August 19th, the Gillespie's home phone rang. The caller said he was watching the Gillespie house, and he knew what Ron's truck looked like.

This set Ron off. He started ranting that he recognized the voice as the letter writer and was finally going to put a stop to this. So he grabbed his pistol, kissed his daughter goodbye, hopped in his red and white pickup, and tore out into the night. Did he find the guy? Ron Gillespie never made it home. Oh, no. Around 1025 p.m., just a few minutes after Ron Gillespie left his house on his way to confront the letter writer, his red and white 1971 Ford pickup crashed into a tree. Though just a few miles away from his house, on familiar roads, Ron apparently failed letter writer, his red and white 1971 Ford pickup crashed into a tree.

Though just a few miles away from his house on familiar roads, Ron apparently failed to make a turn. He was partially thrown from the truck and declared dead on arrival at the hospital. When Pickaway County Sheriff Dwight Radcliffe arrived at the scene, something looked strange. A bullet had been fired from Ron's gun, but there was no bullet hole anywhere and no actual bullet, just an empty casing.

The Gillespie family was convinced this was no accident. They believed Ron had caught up with the letter writer, took a shot at him, and lost control of his truck while in pursuit. Or they thought maybe Ron was run off the road. But an autopsy showed Ron's blood alcohol level was 0.16, twice the legal limit. As far as the sheriff was concerned, this was the answer.

Ron had too much to drink, left the house in a rage, and lost control of his vehicle. Case closed. The Gillespie family wasn't having it. Ron wasn't much of a drinker, and he wouldn't leave his kids in the house alone unless he was dealing with something urgent. They wanted the sheriff to investigateer, and he wouldn't leave his kids in the house alone unless he was dealing with something urgent. They wanted the sheriff to investigate further,

but he wouldn't. Sheriff Radcliffe called the whole thing an accident. Ron's family demanded to look at the truck, but they couldn't. It was sent to a junkyard and crushed just days after the incident. It was later learned that there was a suspect in custody, but they passed a polygraph test.

It's assumed the suspect was David Longberry, but his name was never released. The town now had more questions than answers. Why did the sheriff suddenly change his mind? Who was the suspect? Why was the car quickly disposed of? And why is the sheriff refusing to investigate? The town of Circleville now had a conspiracy on its hands. And the letters kept

coming. Now people were receiving letters claiming the sheriff was covering up the truth. Nobody was more vocal about this than Paul Freshour, Ron's brother-in-law. But Sheriff Radcliffe wouldn't budge. And two years later, we get a twist. Two years after the death of her husband, Ron, Mary Gillespie finally admitted to having a relationship with Gordon Massey. But, but, but, but, but, but she said the affair started in 1979

after receiving the letters. Oh, come on. She said the stress and the trauma brought them together. Look, I ain't buying whatever she's shoveling. Hey, that's what she said. Well, she did the time. Might as well do the crime, eh? That's one way of looking at it. Mary hoped that finally being open about her relationship with Gordon Massey, the letters

would stop. They didn't stop, did they? They kept coming. Over the next seven years, Mary Gillespie received almost 40 letters. She was called a cheater, a homewrecker, a murderer. Some letters threatened the lives of her children. The signs continued, too. Graphic images and vulgar language about her were posted all over town,

specifically placed on her bus route so she and her children would see them. In 1983, Mary had enough. She was driving her school bus near the intersection where her husband Ron died a few years earlier. There she saw a sign posted that talked about Massey and an inappropriate relationship with Mary's daughter, using very obscene language. She stopped the bus and went to grab the sign. Then she noticed a piece of string connecting the sign to a box about the

size of a shoebox. And inside the box was a handgun propped up by styrofoam blocks. And the string was connected to the trigger. When the police examined it, they told her the gun was loaded and set to fire. If Mary had pulled on the sign by standing in front of it, she would

have been shot in the face or chest point blank. The Circleville letter writer was no longer just a nuisance. He wanted to trade ink for blood. But whose gun was this? Don't tell me. The serial number was filed off. It was. But one of the forensics technicians was able to recover it. The gun belonged to a man named Wes Wesley. Who the hell is Wes Wesley? Wesley worked at Anheuser-Busch in Columbus.

When police asked him about the gun, he said, yes, it was his, but he recently sold it to his supervisor at work. Who's his supervisor? Paul Freshour. What? So the gun belonged to Paul Freshour, the man who kept trying to find answers to Mary's husband's death.

The man Mary and Ron first went to to help with the letter writer. When the police questioned Ron Freshour about the gun, he freely admitted that it was his, but it had been stolen a few weeks earlier. He just forgot to report it. According to company records, Paul had taken the day off the day the trap was placed, but he had an alibi. Still, the sheriff brought him in for questioning. Paul insisted he was being framed, and the letter writer was behind everything.

And if the sheriff had done his job and caught whoever was writing the letters, Mary would have never been in danger and Ron would still be alive. Well, the sheriff showed Paul Freshour a few of the Circleville letters. He asked Paul to copy them as best as he could, which he did. He then asked Paul to write a few sentences using that same handwriting if he could. So Paul did. The sheriff looked at what Paul had written and claimed this was a perfect match and placed Paul Freshour under arrest for the attempted murder of Mary Gillespie.

Wait, wait, wait, wait, wait, wait. What? The sheriff told him to copy the letters? Yep. And that's how the handwriting matched? Uh-huh. Now any judge would throw that evidence right out. Well, Paul Freshour was found guilty and sentenced to 7 to 25 years in prison.

What? That's some sloppy police work. But at least they finally got the guy. And, while Freshour years in prison. What? That's some sloppy police work. But at least they finally got the guy. And while Freshour was in prison... Don't tell me. The letters kept coming. Oh, no! While in prison,

Paul Freshour continued to claim that he was innocent. He was imprisoned in Lima, Ohio, over 100 miles from Circleville. Yet somehow the letters kept coming. And like always, they were anonymous, written in that weird blocky handwriting and postmarked Columbus, Ohio. By now, the letters were going all over central Ohio, not just Circleville. The prosecutor in Paul's case was accused of corruption. The coroner who did Ron Gillespie's autopsy was accused of child abuse, which actually turned out to be true.

So who knows? Maybe there was a cover up. Over a thousand letters went out and some were even dusted with poison. Sheriff Radcliffe demanded that the warden get Paul Freshour under control. The warden insisted there was no way Paul could be writing these. Not even putting Paul in solitary confinement stopped the letters. So in 1990, after being in jail for seven years, Paul Freshour was up for parole. The parole board said that his ongoing campaign of hate mail

proves he's not ready to enter society. The warden even spoke up for Paul and said he was a model prisoner and absolutely could not be writing the letters. Still, his parole was denied. And shortly after that, Paul received a letter of his own. Fresh hour. Now when are you going to believe you aren't getting out of there? I told you two years ago, when we set them up, they stay set up. Don't you listen at all.

No one wants you out. No one. The joke is on you. Ha ha. Tell no one of this letter. I saw the paper. Great news. Wait, wait, wait. Did they say when we set him up? Yeah, it did. Interesting. Isn't it? They finally released Paul Freshour from prison in 1993 after 10 years. He proclaimed his innocence until his death in 2012.

Around the same time Paul was released from prison, the Circleville letters stopped, and there hasn't been one since. When Paul Freshour was arrested, this case was officially closed. But there are so many unanswered questions that even after all these years, the case is still fascinating. Every major true crime TV show, blog, and podcast have covered the Circleville Letters case. Even the show Unsolved Mysteries did two episodes on it. In 2021, the CBS program 48 Hours had two FBI experts examine the letters. One said Paul definitely wrote them. The other said Paul definitely didn't write them. So let's look at the evidence and see if we can figure out who done it. You searched for your informant, who disappeared without a trace.

You knew there were witnesses, but lips were sealed. You swept the city, driving closer to the truth. While curled up on the couch with your cat. There's more to imagine when you listen. Discover heart-pounding thrillers on Audible. You sailed beyond the horizon. In search of an an island scrubbed from every map. You battled krakens and navigated through storms. Your spade struck the lid of a long-lost treasure chest.

While you cooked a lasagna. There's more to imagine when you listen. Discover best-selling adventure stories on Audible. There are a few theories. Here are the primary suspects. Some think the answer is simple. Paul Freshour did it. It was his gun, his handwriting,

that's it. Now, could Paul have sent hundreds of letters from prison, unnoticed, all postmarked Columbus, Ohio, over 100 miles away? No. Sure, I guess it's possible. No. Some think it was David Longberry, the bus driver who made a pass at Mary, who rejected him. Longberry was troubled. He got caught abusing a young girl and left town in 1993 to avoid prosecution. It was around this time that the letter stopped. But there was a large group of people, including professional investigators like Martin Yant,

who think Paul's wife, Karen, deserves a closer look. While all this was going on, Paul and Karen Freshour were going through an ugly divorce. Really, really nasty. When Martin Yant was investigating the case, he said he'd never seen someone hate another person as much as Karen hated her ex-husband, Paul Freshour. Yant discovered a witness that could have possibly exonerated Paul, and she made herself available to the defense, but was never called. She was also a bus driver who had the same route as Mary. About 20 minutes before Mary found the trap,

this witness says she saw a tall man with sandy brown hair near the sign, and parked next to the sign was a yellow El Camino. Why is this important? Well, first of all, Paul was short with dark hair, but at the time, Karen Freshour was dating someone, and he was described as tall with sandy brown hair. Any chance Karen's boyfriend had an El Camino?

No, but Karen's brother did. Oh no, the wife did it. Paul was framed. Maybe. Karen had multiple motives. Mary had cheated on her brother Ron, who is now dead. And if she could frame Paul for the murder, well, that solves two big problems for

Karen. If you read the divorce decree, Paul pretty much got everything. The house, retirement savings, the kids. But if Paul goes to jail, Karen gets everything. In fact, Paul insisted this was her plan all along. Paul even believes his son Mark stole

his gun a few weeks before the incident. And Paul didn't report it because he didn't want to see his teenage son go to jail. And Paul's son Mark became severely depressed and took his own life in 2002. And some have speculated that he just couldn't deal with the guilt anymore. And Karen testified against Paul that she had found dozens of letters in her home that she claimed Paul wrote. When the court asked her to produce those, she said she threw them away. Also, during the divorce proceedings, Karen visited Paul's sister and asked to borrow a typewriter, and Paul's sister thought this was an odd request.

Yet at about the same time, the Circleville letters were no longer handwritten. They came typed. Martin Yant does not paint a very nice picture of Karen Freshour, but others come to her defense, saying she was a victim of domestic abuse, and that Paul was the culprit all along. Okay, so who did it? Well, nobody really

knows, but I think it started with Gordon Massey's son, William, and potentially David Longberry. The early letters were very specific and contained details that you'd only know or even care about if you worked in the school district. Karen and Paul Freshour knew Mary, but they wouldn't know her employee number.

And once Mary and Ron Gillespie shared the letters with the Freshours, I think the Freshours found a way to wage an anonymous war against each other while going through their bitter divorce. Things quickly got out of control, as they tend to do, and lots of people got hurt. But I can understand why all the players in this story are portrayed the way they are. The story of the Circleville Letters has so many layers of mystery, it's only natural

that if we can't solve the puzzle, let's at least try to put some pieces in place. And every good story needs a hero. That's Paul Freshour, a husband, a father, wrongfully accused and sent to prison. The villain is Karen, a vindictive wife obsessed with destroying her husband. Mary is cast as deceitful and unfaithful, who had an affair that set the entire story in motion. Ron is a victim, a man trying to protect his family, who had the courage to confront his attacker,

and whether by accident or not, was killed. But the more you look into the story, and I encourage you to do so, there is a ton of material about it, you'll see that each of these characters is not so black and white. Everyone is a shade of gray. Now, I have a hard time believing Paul Freshour was the only letter writer, but also he wasn't the saint that a lot of the podcasts claim him to be. And Karen isn't as awful as is widely reported. In my opinion, the Circleville mystery has no villains.

It also has no heroes. All the story has is victims. And if you want to solve this mystery because of curiosity, I think that's okay. Everyone loves a puzzle. But there are some people who want to solve the Circleville letters because they think justice wasn't served and they want someone to pay. I'd encourage those people to really think about what these families and the community endured for 20 years. And before demanding punishment, they should ask themselves, haven't these people been through enough? Thanks so much for hanging out with me today.

My name is AJ. That's Hecklefish. This has been the Y-Files. If you had fun or learned anything, do me a favor and like, subscribe, comment, share. All that stuff really helps a small channel. Until next time, be safe, be kind and know that you are appreciated. I hit that. Is that

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