The Circleville Mystery (Part II)

(Continued from Part I)

I decided to split the Circleville mystery into two parts for a couple of reasons. First off, if I included everything I wanted to, the article would have become much larger than I had wanted it to. Secondly, because there has been so much reported on this, through traditional news sources, blogs, podcasts, etc., quite a bit of the information that’s out there is, unfortunately, not all that accurate. Now, I am not trying to suggest that anyone is deliberately lying, no matter the circumstance. But, as someone once said to me, “That’s the nature of this business.”

In the first part, I wanted to stick with the basic facts – the things that most sources have reported on. Also, I tried my best to keep things linear in hopes that it will make this twisty and somewhat confusing story make a bit more sense. I have omitted a few details here and there, which I plan on bringing up in part two. The reasons for each one vary a bit, but the overall theme is that I was trying my best to simplify things and just rely on what details propel the story forward. 

As I am writing this (Mid-February 2024) the true identity of the letter writer, and the solution to most of the Circleville Letter Mysteries has not been solved, even though countless television programs, newspapers and magazines, or bloggers and podcasters have tried to claim otherwise. At best, these are nothing more than their theories, and while they may try to introduce new evidence that leads to some new bombshell revelation, they usually seem to fall apart when looking at the much bigger picture.

The bottom line is that I do not know who the letter writer is. I will admit that, personally, I have a few theories on who it could be, and I will admit that some of the theories do make some degree of sense. Although, I have yet to hear a theory that explains everything and where all the pieces of the puzzle come together in a definitive way. Maybe, some day, that will happen and the mysteries will finally be solved. 

A Recap (And A Who’s Who)

If you haven’t read The Circleville Letter Mystery Part 1, doing so now will help make this narrative make a lot more sense. But, just to recap, let’s take a quick look at some of the players in this story.

The Circleville Letter Writer … Simply put, we really have no idea who this is. It could be a man, or a woman, or according to some theories, it could be anywhere from two people to a handful. Let’s just say the jury is still out on this one.

Gordon Massie … He’s the superintendent for the school district, so effectively he’s the boss of all school employees, from bus drivers to teachers and everyone in between. He also seems to be the main focus of the letter writer. He’s married to a woman named Clara, who he ultimately divorced.

Mary Gillespie … She’s a bus driver for the school district and a target of the letter writer. He accuses her of having an affair with Gordon Massie. After Massie’s divorce, the two are dating. Or, maybe they’ve been seeing each other this whole time. Who knows?

Ron Gillespie … He’s married to Mary, and while she’s out of town he dies under mysterious circumstances, but his death is ultimately ruled an accident.

Karen Gillespie (Freshour) … Ron’s Sister. Mary’s Sister-in-Law. 

Paul Freshour … Karen Gillespie’s husband. And the guy who gets arrested for attempted murder and who some people think is the letter writer.

Dwight Radcliff … He’s the sheriff and according to his friends, he has an impressive law enforcement career. According to some other people, he may not have been the good guy his friends seem to think he was.

Dr. Ray Carroll … He’s the coroner for Pickaway County, and if what we’ve learned about him later, maybe that wasn’t such a good thing.

Between the mid to late 1970s to the late 1990s, many of the residents in Pickaway County, Ohio and particularly the town of Circleville began getting poisoned pen letters from an anonymous writer, in envelopes postmarked mostly in Columbus. Gordon Massie is the subject of many of these letters, most of which are accusing him of having an affair with one of his bus drivers, Mary Gillespie. Mary gets a ton of these letters, too. Law enforcement, once they become involved, aren’t able to figure out who is sending the letters. Then, one day, Ron gets a phone call and he tells his daughter it was from the letter writer, and he knows who it is. He was killed shortly after when his car drove off the road and hit a tree. His death is quickly ruled accidental. Seven years later, Gordon and Mary are seeing each other, and Mary spots a sign on the side of the road, only it’s been booby trapped, but it fails to go off. The last known owner of the gun was Paul Freshour, Mary’s brother-in-law and he gets arrested and convicted, but the letters don’t stop and there is no possible way he’s sending them. The entire time he’s incarcerated, he’s protesting his innocence, and once he’s released, he promises to clear his name, only to die (from natural causes) before that can happen. 

There are a lot of theories on who the letter writer is and I would like to share some of them with you now.

Law Enforcement’s Theory – Paul Freshour

According to local law enforcement, Paul Freshout was, in fact, The Letter Writer. Their only problem was that they had no proof. At best, they could connect him loosely with the letters. He had, at times, expressed a hostile attitude toward Mary Gillespie. And, as far as law enforcement could tell, Paul Freshout was the last registered owner of the gun used in the booby trap (although Freshour had told a few people before the trap was found that the gun had been stolen). He also had taken the day that Mary found the booby trapped sign off from work, although he said he spent the entire day doing repairs on his house. 

The bottom line here is that the case against Freshour was entirely circumstantial. They also had nothing directly connecting him to any of the letters. This was a time when DNA testing was at its infancy and couldn’t really be used with any of the materials in this case. Still, there was no fingerprint evidence, and nothing to link him (and him alone) to any of the crimes.

There is, still, one piece of evidence that was used to convict Freshour, and most experts I’ve heard from say that it never should have been allowed in court.

While investigators were interviewing or interrogating Paul, they asked him for a writing sample. At first, he wrote in his normal, every day handwriting, but this card ultimately got thrown away. They then asked Paul to write using block letters, just like the Circleville letters – and they gave him one of the letters to copy. Paul tried to copy the letter as best he could, thinking that this would somehow exculpate him from the crimes. Instead, it was used to “prove” his guilt.

He was convicted of the attempted murder of Mary Gillespie, and served his time. And, from the time he was arrested to the day he died, he swore he was innocent of all these crimes.

Paul Freshour’s Theory #1 – Mark Freshour

Mark Freshour was the son of Paul Freshour and his wife, Karen Sue. During the mid-1970s, when the letters began, Paul and Karen’s relationship wasn’t exactly the greatest. They were having problems, which ultimately led to their divorce. To say this divorce was contentious would be an understatement.

In most matters, Mark sided with his mother, much to Paul’s dismay, as the two of them had a much closer relationship than he had with his father. After the divorce, Mark wanted nothing to do with his father. This easily could have been on account of his mother’s near constant verbal bashing of Paul, or maybe there were more issues at play, he never said one way or another.

A week before the booby trap incident, Paul discovered that his son had been in his house while he was at work and that a few of his (or Karen’s) belongings had been taken. This was fine with Paul as it was just a few less things for the two to fight over. But, it was this time when Paul realized that his gun was missing. When it was later used in the booby trap, the first person he thought of was his son – but even with the rift between them, he didn’t want to publicly accuse Mark or bring up his name to the sheriff. 

The other problem with the Mark Freshour theory is that while it might explain why someone possibly framed Paul, and how a few of the events played out … It offers no explanation why everyone else received the letters they did and based on everything known at the time (or now) it doesn’t make much sense.

There was, however, a renewed interest in this theory later, after in 2002, Mark Freshour was found in the Scioto River, the victim of an apparent suicide. Some suggest that he couldn’t live with the guilt over what he had done to Mary, and so many other Pickaway County residents, 

Mary Gillespie’s Theory – David Longberry

If you read the first part, you may remember that at one point, after the letter writing business had been going on for nearly a decade, Mary Gillespie was at her wits end because law enforcement couldn’t stop the campaign of terror that oddly seemed focused on her. She gathered a few close friends to discuss the issue and see if there was anything they could do. We’re not entirely sure who all, exactly, at the meeting, but we know it included Mary, Paul Freshour, Karen Gillespie, and quite possibly one or both of Mary’s parents, and maybe one or two other close personal friends. As they reviewed everything that had happened, they were able to come up with a few ideas, but they were far from proving that any one of them could have been responsible.

One of the people they looked at was a man named David Longberry. He was a bus driver for the school district, just like Mary. And he had what some might call an unhealthy obsession with her. At the very least, he made it known that he had the hots for her, wanted to hook up, and by today’s standards he sexually harassed her – but, in the 1970s and 1980s, most sexual harassment was viewed as “boys just being boys” so other than a supervisor telling David to knock it off, there wasn’t much anybody could do. 

The reason Mary and her gang thought David could have been the letter writer were mostly circumstantial. David was fixated on Mary, and so was the letter writer. They saw David as being totally creepy, and so was the letter writer. Okay, there was a bit more to it than just that, but not so much as to actually change anything.

Mary and her meddling kid gang knew they didn’t have enough to take to law enforcement, so they came up with another plan to make the letters stop. If, they reasoned, this all started with a letter, maybe it could end with one, too. They drafted a sternly worded letter letting David know that they knew he was the letter writer, and they included a few of the reasons why. They went on to say that if the letters did not stop, every last piece of information they had on him would be handed over to the cops and that just might be enough to have him arrested. 

For the first week after the letter was delivered, neither Mary nor any of her friends got any letters. As the following week slowly crept by, and they still hadn’t gotten any letters, they were almost to the point where they thought it was finally over … but, then Mary gets another letter, it doesn’t mention anything connected to David at all, and pretty soon they’re not as convinced as they had been that David was the guilty party.

At some point in the near future, the David theory would be tested again and finally put to rest. This theory didn’t work for a number of reasons. One of the bigger ones being that at times when it was known the Letter Writer was in Circleville, such as the days when he posted signs around town, David could prove he spent the entire day far enough away that it would have been impossible for him to post the signs, or do whatever they knew the Letter Writer had done. He was also over a thousand miles away the day that Ron Gillespie died, so if anyone believed that he was killed by the letter writer, there was no way that could have been David.

The 48 Hours Theories – A Mean Girl, no, wait, it was Paul Freshour

The 18th episode of Season 35 of the show 48 Hours was centered around the Circleville mystery. While the show did do a fairly decent job recounting most of the events and a couple of the theories, at the very end of the show they tried to solve the mystery themselves. First, they relied on a Document Examiner and Profiler, who suggested, among other things, that the letter writer was likely a female, one who does not mind hurting people just to make a point, someone who is active in society but also does not stick out – so your typical Regina George (the head of the mean girls in the movie Mean Girls.)

They then turned to another Document Examiner, who concluded “One Hundred Percent” that the person who wrote all of the letters was Paul Freshour and she knows she is not wrong. The main thing the show focuses on is the letter “G” which she claims is written in a very unique style that nobody else could possibly use, but it appears to be the same way that I write the letter “G” which she says clearly looks like a number “6” except it’s clearly a “G” and … yeah, I’m not buying either one.

Another Theory – Karen Sue’s Brother, Bob, Maybe? Maybe Karen Sue, too? Or someone?

On the morning the booby trap was discovered, one of Mary’s fellow bus drivers just happened to be driving past the area where the sign was found and happened to spot something unusual. She spotted a large man with sandy hair standing near where the sign was found. But, as her bus neared, the man turned and acted as if he was urinating, which she concluded the man could have been doing. She never saw the man’s face and therefore felt like she couldn’t identify the man. But, she hoped, maybe the El Camino could point in a new direction.

As far as we can tell, investigators never looked into the El Camino theory, or if they had they haven’t released any information about it. 

However, a little investigation by people not in law enforcement has raised an interesting issue or two. 

First off, Karen Sue Gillespie was dating a man named Bob, who was not only a large man with sandy hair, but he had recently come into possession of an El Camino. While this is far from a smoking gun that points to Bob, or maybe Karen Sue and Bob, it does at the very least point to a possible suspect (or two).

There are also those who want to claim that Karen Sue was acting kind of weird around the time the booby trap was found. One of the things a couple commented on witnessing was how she would sit in front of the school and write down the arrival and departure times of all the buses. Others have said her acting weirdly extended beyond just that, and a few have commented that she had the hots for Gordon Massie. 

There’s a bit here that mirrors the theory that Karen and Paul’s son was responsible, such as maybe Karen blamed Gordon Massie or her sister-in-law for some of her marital issues, but that seems like a stretch.

The Giorgio A. Tsoukalos Theory – (Sigh)

The Circleville Letter writer was likely to be, if Giorgio Tsoukalos would ever comment on it … He doesn’t say it was aliens, but … Yeah, probably aliens. (Sorry for the bad joke.)

Paul Freshour’s Theory – A Whole Bunch of Law Enforcement and Government Corruption

Before he passed away, Paul Freshour came up with a fairly elaborate theory, one that is easy to dismiss at first, but the more you look into it, the more sense it starts to make. The people who he felt were behind everything – the letters, the murder of Ron Gillespie, the booby trap, everything … lies somewhere between Sheriff Dwight Radcliffe and a corrupt system of law enforcement.

Freshour had never been a big fan of Sheriff Radcliffe before the letters, or during them. So, while we’re tempted to just dismiss his comments because he likely hated the guy, we still have to ask ourselves … What if he was right?

Paul’s theory was that the letters began as a way to punish (for lack of a better word) certain people in town that he was not fond of, people like Westwood School Superintendent Gordon Massie, the Gillespie and Freshour families, among others. It is also worth noting that some of the other people were sent letters instructing them to vote for Radcliffe, or one of his associates, in local elections and maybe that was a factor, too.

Dr. Ray Carroll was a personal friend of Ratcliffe, and his role as coroner for Pickaway County means there was a professional relationship, too. He was also the one who rather quickly signed Ron Gillespie’s death off as accidental, which you may remember reading about in Part 1. For that reason, he’s already included in the story … but, what if there is more to it than just that? Was it possible that he did so on Ratcliffe’s suggestion (or order) because the sheriff had something to hide?

But, there is one further thing that needs to be discussed regarding Dr. Carroll – he was a bit of a monster. And, by “monster” I mean that in April 1994, he was stripped of his medical license after fourteen different individuals presented evidence to the state licensing board showing how he sexually abused children in his care. 

Several of these women, and many more who were not a part of that fourteen, had tried to present their cases to various law enforcement agencies, most of which were transferred to the Pickaway Sheriff’s office to investigate. Not a single criminal case was ever brought against Dr. Carroll and I have to wonder if his relationship with Sheriff Ratcliffe was the reason why. (Or, part of the reason.)

Shortly before his death, Paul Freshour started collecting evidence against Ratcliffe and for his own innocence, which he wanted to use inside a courtroom, however Paul passed away before that could happen. Paul put much (if not all) of that information onto the web via a WordPress Site, and it is still available today. Among the contents of that website is a 164 page document which would have gone on to become part of his ultimate appeal, and quite possibly charges brought against Ratcliffe. 

Through this document, and the other info on the website, Paul gives his side of the whole story, and at some key places he makes some very compelling arguments. He often lists unfair practices made during his trial, including but not limited to missteps taken by law enforcement, such as hiding evidence that would be exculpatory for Freshour, or failing to turn over discovery evidence that would be used in trial. He points out witnesses and established facts which were ignored by both the sheriff’s office as well as the court … and if what he says is true, it certainly does put this story into a whole new light.

My Theory – It’s Not What You Think

I have probably spent what my psychologist would call an unhealthy amount of time looking into The Circleville Mystery and all I can say is that I have no clue who did it. But, there is one thing I think I know, for sure, without any shadow of any doubt. And it’s this:

Circleville, Ohio is quite a lovely place. 

The people I have spoken to that are from either Circleville, or Pickaway County have all been nice, lovely people. And while the solution to this puzzle still hangs in the air over the entire town, it really can’t be blamed for the actions of a single individual (or a team of … cough snort … writers). I have been to Circleville a couple of times now, and I don’t regret either trip. Perhaps later this year I’ll finally get to check out the annual Pumpkin Festival I’ve been hearing so much about.

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