Hare-brained History 34: Disappearance of the Jamison Family
Featuring a history lesson no one asked for, Talladega, Breaking Bad, Pazuzu, "Special Bullets" and My Attempt at Solving The Case
Welcome to the 34th installment of Hare-brained History, a blog in which your intrepid host will treat you with absurdities, follies, mind-fucks, and everything in between from the world of history. Today, we are inspired by an event that transpired on the day I plan for this edition to come out, October 8th. So, you will either know if I succeeded or not, or you are reading from the future. What is that like? Has my short story collection been published yet? That one was my favorite! Have I found the love of my life yet? A boy can hope.
Enough of that. In truth, I have had this one in the docket for the spooky season for a while. But after a good fifteen minutes of thinking, “What the fuck will I do next?” I just so happened to look and see that this event took place on the 8th, as I am writing this, nearly 16 years ago. For the second time, we are dealing with a disappearance. Franklin’s Lost Expedition, though shrouded in mystery at the time, has since been pieced together. We now understand what befell those 129 men and why they perished. But with today’s disappearance, we have no such clarity. No explanations, only speculation. And in my view, we never will. Or maybe not. Fuck if I know, I haven’t jumped into the research yet. Today, join me on a trip to small-town Oklahoma to explore the disappearance of the Jamison Family.
When writing this blog and it focuses on a specific location, I typically consult an expert who has in-depth knowledge of that area, meaning they have been there. I have been doing less and less of this, though we saw it reappear for Hammersmith, and in both of the two recent Massachusetts-based editions. Yes, that means I just called myself an expert. Well, even if I questioned every person in my contacts, Snapchat, or Substack, I would be shocked if any of them had heard of Eufaula, Oklahoma. The seat of McIntosh County, the town is home to some 2,700 people, lying along Lake Eufaula and the Canadian River. This river runs through Oklahoma, Texas, and New Mexico; I have no idea why it’s named after our wonderful northern neighbor. And apparently no one really does. The town’s name, though, is a microcosm of the history of the Oklahoma Territory.
The Muscogee People, also known as the Creek by white people, initially inhabited much of Georgia and Alabama, and had a large village named Eufaula, located along Eufaula Creek, where modern-day Talladega is situated. Yes, of the NASCAR. The Muscogee people, like many Indigenous nations, were not a single unified tribe but rather a linguistic and cultural group composed of multiple tribal confederations. Within Muscogee society, these were traditionally divided into the Red (War) and White (Peace) within their shared political and ceremonial life.
However, after the white people came, which again is never good, tensions arose between the two. Unsurprisingly, the Red, the more traditional and fervent Muscogee, favored resistance and war. In contrast, the White, many of whom had adopted certain European-American customs, sought to preserve peaceful relations. This internal divide erupted into a civil war between 1813 and 1814. General Andrew Jackson intervened, ultimately defeating the Red at the Battle of Horseshoe Bend. Ultimately, it was the Muscogee as a whole who suffered defeat, while the emerging United States gained millions of acres of their ancestral land through forced cession. Piece of Shit Jackson was not done with the Muscogee. After becoming President, our 39th most kissable President, Jackson, played a significant role in the implementation of the Indian Removal Act, which led to the tragic event known as the Trail of Tears. As a result, the vast majority of the Muscogee people were forced to relocate to what is now Oklahoma. There, they established Eufaula, which became an important center of Muscogee life in Indian Territory, at least until the arrival of the railroad. You can guess the rest.
None of that history has anything to do with anything aside from being where the Jamison family lived, but I hope you learned something. Below is Lake Eufuala at sunset, looking very pretty.
On August 4th, 1965, Bobby Dale Jamison was born, the son of Bob Dean Jamison, somewhere in the Oklahoma City area. I must tell you, in all honesty, we don’t know much about the family. We do know that Bob Dean was a man with a temper, allegedly linked to criminals, and possibly involved in such behavior himself. Regardless, by all accounts, Bobby did not follow in his father’s footsteps. Sherilynn Leighann Jamison was born on November 5th, 1968. We don’t know her maiden name. Maybe they were cousins? I mean, I hope not, we just don’t know. I’m going to say they were not. Regardless, Sherilynn at some point in time had been diagnosed with bipolar disorder. Sherilynn also had an older son, 12-year-old Colton, from a previous marriage.
At some point, Bobby and Sherilynn met and began a relationship. In 2003, Bobby was in a serious car accident that left him with chronic back and neck pain. The resulting settlement and disability benefits meant he no longer needed to work. I once had a coworker who was hit by a ninety-year-old woman who fell asleep at the wheel. She plowed into him, then into a Dunkin’ Donuts. His recovery took over a year, but in truth, he never had to work again if he didn’t want to. I think about that trade sometimes.
Sherilynn, too, was on disability due to her bipolar. Her sister had died in a freak accident, stung on the tongue by a bee, and her throat swelled until she choked to death. The loss left Sherilynn devastated, deepening a depression that worsened her bipolar symptoms. It was also noted that she didn’t always take her medication. In the same year as Bobby’s accident, their only child, Madyson Stormy Star Jamison, was born on August 1, 2003. The following year, in 2004, Bobby and Sherilynn were married. Below is the family.
While it is unknown exactly how the Jamisons acquired their money, they outwardly appeared to have it. The family lived on the shore of Lake Eufuala and had several timeshares in both the United States and Mexico. Several sources believe they were living above their means. However, part of the reason we know so little about the Jamison family is that they largely kept to themselves and didn’t have the best relationships with some of the few people they did.
In 2009, family friend Kenneth Bellows stayed with the family. Bellows was a white supremacist (Meaning he sucks… understatement), and Sherrilyn had a trace of Native American heritage. The volatile Sherilynn and Bellows got into a discussion about this, to put it mildly, and Sherilynn fired shots at his feet using her .22 caliber pistol to get him to leave. You go, Sherilynn. Suffice to say, they were no longer friends.
Their relationship with Bobby’s father was worse, to say the fucking least. Bobby claimed his father had promised him money in a business venture, only to renege on the deal, leading Bobby to sue him. Then, in mid-2009, Bobby filed a petition for a protective order against his father, Bob Dean Jamison. In that petition, Bobby described his father as “a very dangerous man who thinks he’s above the law” and said Bob Dean had threatened the family’s lives twice, once in November 2008 and again in April 2009. He even alleged his father was connected to gangs involved in meth production, like something straight out of Breaking Bad. The judge ultimately dismissed the protective order.
By the fall of 2009, things had grown stranger. Bobby and Sherilynn withdrew Madyson from school for reasons that remain unclear and threatened to sue the school district. No one knew what the supposed lawsuit was about; perhaps it was meant to keep the school from looking too closely into their lives. That is my speculation. Below is the family’s home.
Speaking of the home. What was life like for the family? By this point, the marriage was in trouble, and so was Sherilynn. In July, her ex-husband was awarded custody of their son, Colton. The boy told the court he preferred living with his father because his mother was “very depressed” and acted “very strangely.” The loss was not only a financial blow to the family, as they stopped receiving child support, but an emotional one that hit Sherilynn especially hard. In September, her mental health took a darker turn. Diagnosed with bipolar disorder and possibly off her medication, Sherilynn attempted suicide and was hospitalized. Little else is known about that episode, but by the end of September, she was back home. Colton stayed with them for a while afterward and later described the visit as uneventful.
The family was also very religious. Well, religious might not be the right word. Much of this did not come out until later, but I am choosing to tell you now that the Jamisons went to their pastor and explained that dark spirits had invaded their home. What’s more, they expressed their belief that they needed the man to conduct an exorcism. This was because Madyson had started talking to an imaginary friend named Emily. Sherilynn believed that Emily was a demon, much like Pazuzu. Bobby asked the pastor if he knew of anywhere he could purchase “special bullets.” The Pastor, confused, asked what he meant. Bobby explained he needed special bullets to kill “the two to four ghosts” on their roof. The Pastor declined to comment on whether he had directed Bobby towards the special bullets. Bobby added that he had acquired a Satanic Bible and intended to try to exorcise the spirits himself.
A friend of Sherilynn revealed that Sherilynn would often invite her over to conduct seances, which Sherilynn took seriously, while the friend did not. By all accounts, the Jamisons thought their house was haunted, and in truth, so did some of their friends. Another friend of Sherilynn’s would say, “In all seriousness, that house was haunted. I don’t want to sound crazy, but whenever I went there, I felt a horrible presence. I would leave feeling down and depressed.” Sherilynn was also outspoken about her belief that someone in their neighborhood had been poisoning black cats. Whether it was the ongoing disputes with Bobby’s father, financial strain, frustrations with the local school district, the haunted house, or the poisoned cats, by October 2009, the family had decided to leave Eufaula behind. They said they wanted a quieter, more peaceful place to live. A reminder that Eufaula is a town of less than 3,000.
The family eyed a 40-acre plot of land in Red Oak, a town of just 500, though in truth this plot was far off the beaten path of the town and lay up in the forested San Bois mountains. There was no house on this property. What the Jamisons did have, though, were storage containers, and for whatever reason, they planned to move these shipping containers to their new property and live out of them. It is unknown why this was the plan. They did not want the real estate agent who was selling the property to attend the showing. Again, we have no idea why that was the case. Sherilynn spray-painted the storage container they planned to make their home. I know this is blurry and does not appear definitive that she wrote it, but I can tell you it says, “Witches do not like it when their cats are killed.”
October 8th, 2009, was a chilly day in Oklahoma, with temperatures around 40 degrees Fahrenheit (4.4 degrees Celsius, Marlene). On that day, the Jamison family drove to Red Oak to view a section of the land they hoped to buy. They met briefly with the landowner, then parked their truck nearby and went for a walk. At some point afterward, they were seen driving away. It would be the last time anyone saw them alive. Because the Jamisons were a private and somewhat reclusive family, their absence went unnoticed for several days. Even their few close contacts knew they had the propensity to disappear for a period of time. Nothing seemed amiss until October 16th, when hunters discovered their pickup truck abandoned at a remote well pad site south of Kinta, Oklahoma, roughly a twenty-minute drive down dirt and back roads from the property they had planned to purchase in Red Oak.
The hunters peered inside the truck and immediately knew something was wrong. The Jamisons weren’t there, but their dog, Maisy, was. I haven’t mentioned her until now because, frankly, she wasn’t important until now. And I’m glad to say she was alive, emaciated, but alive. What was left inside the truck, however, was both troubling and baffling. The family’s coats were still there, as were their cell phones, wallets, IDs, GPS device, and bags of clothes. The police had no answers for any of it. Nor could they explain the $32,000 in cash found inside. The Jamisons weren’t known to carry large sums of money; no one knew where it came from or why they had it. Additionally, Sherilynn’s gun was not found in their home or in their truck.
There were no signs of foul play. In fact, there were barely any signs of anything at all. The only clue, if it can be called that, was an eleven-page letter written by Sherilynn and found in the truck. It was part manifesto, part rant, page after page criticizing Bobby, calling him a “no-good hermit,” and declaring that she wanted a divorce. An extensive search began, with dogs scouring the woods, men on horseback combing the trails, and helicopters circling overhead. But nothing was found.
Given the strange circumstances, police initially suspected a drug deal gone wrong, but why would they bring their six-year-old daughter and their dog to something like that? Latimer County Sheriff Israel Beauchamp said, “I think they were forced to stop and get out of the truck to meet with someone they recognized. And I think they either left willingly, or by force.” Investigations uncovered some more disturbing findings, including the last photo taken on Bobby’s phone of Madyson. Somehow, I think it is the most horrifying thing I have ever seen in connection with this blog. And I saw the needles in Albert Fish.
Then there was the security footage from October 8th. That morning, Sherilynn and Bobby can be seen moving in a slow, trance-like state, making several trips between the house and their truck. They move almost mechanically, carrying bags back and forth in silence. It’s more than simple grogginess. At one point, Sherilynn places a brown briefcase in the truck. Unlike nearly all of the family’s other belongings, that briefcase was never found. Below is a still from the footage.
When I say they looked like they were in a trance, I don’t mean anything supernatural. Sorry, ghosts aren’t real. I mean, drugs, most likely. The police seemed to think the same. Their attention turned to the most obvious suspect: Bobby’s father, Bob Dean. He allegedly had ties to crime and the drug world and a long, troubled history with his son. But by the time the Jamisons disappeared, Bob Dean was frail and living in a nursing home. He died just a few months later. Investigators could find nothing linking him to the disappearance, and to this day, he’s not considered a suspect. Interestingly, Madyson was the sole beneficiary of his estate. After that, the leads went cold.
Four years later, on November 16th, 2013, another pair of hunters, Oklahoma has a lot of those, discovered severely decomposed remains. The discovery consisted of three skulls, several bones, numerous bone fragments, and scraps of clothing. The remains were found just 2.7 miles from where the Jamisons’ truck had been abandoned. Almost immediately, it was widely suspected they belonged to the missing family. Anthropological and forensic testing takes a lot of time, apparently, but on July 3rd, 2014, the Oklahoma State Medical Examiner’s Office confirmed the remains were those of the Jamison family.
Now, first, you may, like me, wonder why these remains had not been found in the initial search. Many at the time asked the same question. An Assistant Special Agent with the Oklahoma State Bureau of Investigation later explained, “Falling leaves potentially obscured the bodies.” Hmm. It was October, sure, but that feels like a flimsy excuse. The area where the family vanished is densely forested and rugged, bordering on mountainous terrain. So, in fairness, I don’t suspect police malpractice or even incompetence. Still, it’s hard not to wonder why the bodies weren’t found sooner. By the time they were recovered, decomposition made it impossible to determine the cause of death. One of the skulls did have a small hole that hunters believed to be a gunshot wound, but the medical examiner disagreed.
And, in all honesty, that’s where the case stands to this day. As Sheriff Beauchamp put it, “A lot of investigators would love to have as many leads as we do. The problem is, they point in so many different directions.” We still don’t know what happened to the Jamisons between leaving their prospective property in Red Oak, leaving their truck, and ending up 2.7 miles south of it, or whether they were killed elsewhere and their bodies left there later. Returning a segment from the last “mystery” I covered, I will now outline several theories:
Murder-Suicide
As dark as it gets, the truth is that neither parent seemed to be doing well, especially Sherilynn. Just a month before their disappearance, she had been hospitalized following a suicide attempt and was reportedly off her bipolar medication. She was trigger-happy as well, though that asshole white supremacist deserved it.
The couple’s marriage was crumbling; Sherilynn’s eleven-page manifesto made that painfully clear. Perhaps the two were fighting, and in some charged moment, one of them snapped; maybe that haunting photograph of Madyson was taken amid that chaos. Investigators leaned toward Bobby as the more likely of the two to have committed a murder-suicide, though personally, I find Sherilynn the more probable.
Still, that theory raises as many questions as it answers. Where was the gun? Why would one of them lead the other and their daughter, 2.7 miles from the truck? Even accounting for the decomposition, the medical examiner found no clear signs of trauma or gunshot wounds.
Drugs
Of course, this theory could easily overlap with others. Because of the family’s strange behavior, drugs became one of the most widely suspected explanations for their disappearance, and not just drug use. The $32,000 in cash found in the truck couldn’t be accounted for, leading some investigators to believe the Jamisons might have been connected, in some way, to drug activity. Oklahoma’s rural areas, including where they lived, were known for methamphetamine problems at the time (Maybe still, who’s to say). One theory suggested that the Jamisons weren’t dealers or manufacturers at all, that they had simply gone to buy drugs, and the deal went bad.
However, the details don’t quite fit. Why bring Madyson and their dog, Maisy, to a drug deal? Why would the supposed dealers leave the cash in the Jamisons’ truck behind? If they had killed the family, why not then break into the truck? And if violence was involved, why were there no gunshot wounds? The Jamisons also had no known history of drug abuse, which may not mean much considering their secrecy and the, well, everything about them, but a search of their home turned up no drugs or paraphernalia.
Bob Dean
Again, this theory isn’t mutually exclusive from the last. Bob Dean, Bobby’s father, was rumored (principally by his son) to have criminal connections and a reputation for being a dangerous man. He and his son had serious conflicts, and although he was frail and dying in a nursing home, if he was truly the man Bobby claimed he was, it’s not impossible to imagine him orchestrating his family’s demise from afar.
But the police found no evidence linking Bob Dean to organized crime or to the disappearance itself. And why would he have harmed Madyson, who was the sole beneficiary of his estate? In my opinion, this is the weakest of the credible theories (Please hold).
Kenneth Bellows
Then there’s the family friend, the racist piece of shit Sherilynn once fired shots at. He certainly would’ve had a motive. After the incident, the ties were cut completely. While he had a rock-solid alibi, some have speculated that he might have arranged a hit through white supremacist circles, an idea that isn’t impossible, considering those networks do exist.
Still, police found no evidence to support that theory and cleared Bellows. And truthfully, it’s barely mentioned in discussions of the case. Personally, I think it’s possible, but, like the supposed drug connections, I find it hard to believe investigators wouldn’t have uncovered something if that were true.
Accidental Death
Because the medical examiner found no apparent signs of trauma on the decomposed remains, some have suggested the Jamisons simply went for a hike, became disoriented in the rugged terrain, and died of exposure.
But that theory doesn’t quite hold up. Bobby suffered from chronic neck and back pain that made hiking nearly impossible. And then there’s the $32,000 in cash found in the truck, money that didn’t fit any clear purpose. Maybe it was meant for the land purchase, but no such transaction was planned for that day. What’s more, the three bodies were found lying face down, side by side. Some have speculated they might have been praying, but to me, that positioning feels deliberate. The medical examiner may have left it open, but I’ll say it plainly: I think the Jamisons were killed.
This theory centers on the final photo found on Bobby’s phone. Family and friends insist Bobby didn’t take it. One remarked, “In the picture, Madyson is looking away from the camera. She looks unhappy, and her arms are crossed. If that had been Bobby or Sherilynn behind the lens, she wouldn’t have looked like that.” From that image, some have speculated the family may have been kidnapped, possibly by a pedophile or a group targeting Madyson specifically.
But there’s no evidence to support that idea. None. It’s a theory built entirely on one unsettling photograph.
Satanic Cult/ Witchcraft
Not witchcraft or magic in the literal sense, but ties to those who believed in it. It seemed the Jamisons did. Between the Satanic Bible found in their home, Bobby’s request for “special bullets,” Sherilynn’s graffiti referencing witchcraft, and additional writing found by her about demons, it’s clear that the occult held some significance to them. Sherilynn’s mother, Connie Kokotan, later claimed, “That part of Oklahoma is known for that… cults and stuff like that,” she said. “I was told that she was on a cult’s hit list.” An abandoned car near where the Jamisons’ truck was found was used for target practice and was covered in Satanic graffiti. Together, these details have been cited as evidence that the family may have become entangled in a cult, or at least occult activity that led to their deaths.
That’s all intriguing, and much of it is factual, but none of it proves anything. Police found no trace of an active cult in the area, no connection linking the Jamisons to one, and Connie never provided the name of any specific group.
Random, or at least, Unknown Targeted Killing
Random murders do happen. Still, you’d think whoever did it would have taken the money or at least the Jamisons’ truck. Then again, sometimes people kill simply to kill. Maybe the family was meeting someone, someone still unknown to the police, family, or friends. Maybe.
But once more, the same issues arise: there were no signs of a struggle around the truck, no trace of anything, really. The same problems that undermine every other theory undermine this one, too.
Supernatural/ Paranormal
Well. I don’t believe in ghosts, demons, or spirits, but many people do. They argue the family was possessed, and that this somehow led to their deaths. The Jamisons’ supposed interest in the occult is cited as proof. Others have even suggested UFOs were involved. For the record, I do believe in aliens. I just can’t imagine why they’d bother with a weird family in rural Oklahoma. Why abduct the Jamisons? Why leave their bodies behind?
Obviously, I don’t buy any of these theories, but in fairness, nothing about their disappearance makes sense. So why not demons or aliens?
It has now been sixteen years to the day since the Jamison family vanished, and we are no closer to an explanation than we were then. It remains one of the strangest missing person cases I’ve ever come across. Unless someone comes forward with a confession, I doubt we’ll ever know what truly happened to them. My speculation counts for little, but here’s what I think happened.
Bobby and Sherilynn were living beyond their means. While it’s unclear how much Bobby received from his accident settlement, I doubt it was enough to sustain a lakeside home, timeshares across the U.S. and Mexico, and their general lifestyle. At some point, they fell into debt. To get out of it, they may have entered not only into a business venture with Bobby’s father, but also into dealings, or perhaps loans, with people connected to him or at least known by Bob Dean, possibly with criminal ties.
The business venture soured, or the deadline to repay those debts came due. Around this time, or perhaps earlier, both Bobby and Sherilynn may have turned to drugs to cope: not only with the stress, but Bobby with his chronic pain, Sherilynn with her mental health struggles. Bobby filed a protection order against his father, possibly to distance the family from mounting pressure, though I think their problem with Bob Dean was the least of their troubles, and planned their move into isolation as a way to escape it all. The Hare-brained (!) nature of the scheme is due to their substance abuse.
On October 8th, the Jamisons had arranged to meet someone near the well-pad site. They brought $32,000 in cash as well as either drugs or more cash inside the brown briefcase, hoping to buy their peace. But whoever they met had other plans. Strung out, frightened, and desperate, the family packed their truck with their daughter and dog and drove into the mountains. There, at gunpoint, Sherilynn was disarmed, and the brown briefcase was taken; then they were led into the woods and executed. The killers likely left the truck untouched as they got what they wanted, the brown briefcase. The Jamisons’ talk of hauntings and spirits wasn’t supernatural at all, but the product of two people unraveling under addiction and stress. As for why no drugs were found in the home, they were preparing to sell it and had removed all paraphernalia and used all they had.
I think that’s a good theory, a wrong one, but fuck if I know what happened. But what do you think? Please let me know. Three lives were lost. Regardless of Sherilynn and Bobby’s faults, the Jamisons didn’t deserve whatever happened to them, least of all poor little Madyson. May they rest in peace. Also, let me know if I have a future in murder porn. I think I did good.
Note: Thank you for making it to the end! What began as a farcical blog for a depressed, history-loving nerd to mess around with, an escape from the hole I’d dug, has grown into something more. As I’ve said before, this was always meant to be entertaining rather than academic. I’m not doing the deep-dive research that kept me from pursuing a career in history, but the work I put in here is careful, thoughtful, and, yes, work. And while it often doesn’t feel like work because I love it, it still takes time and effort. So if you’ve enjoyed this, please consider tossing a few bucks my way. My goal is to make history both educational and entertaining, the kind of history that first captured my imagination as a kid. Thank you for reading, and thank you for coming along on this journey. If you’ve made it this far, just know, I love you.
So well written!