Deep Dive
Shownotes Transcript
Due to the nature of today's episode, listener discretion is advised. This episode includes discussions of racism, violence, murder, and death. Consider this when deciding how and when you'll listen. When you think of the roaring 20s, with all the jazz music, cigarette smoke and flappers, high heels and fur coats, liquor flowing in dimly lit rooms, and gangsters taking chauffeured cars home to their terracotta mansions,
you're probably not thinking of an Indian reservation in Oklahoma, but maybe you should be. This is the story of the Osage Nation, an indigenous tribe who in the early 20th century became enormously wealthy, only to fall prey to a chilling conspiracy that ended in murder and birthed the FBI.
I'm Carter Roy, host of Conspiracy Theories, a Spotify podcast with new episodes releasing every Wednesday. Check us out on Instagram at The Conspiracy Pod. Today's story exists at the intersection of crime and conspiracies. So I'm joined by my friend and host of Serial Killers, Vanessa Richardson. Hi, everyone. Stay with us.
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- Bocas del Toro, Panama.
Scott Makeda's tropical haven becomes his personal hell. A serial killer pretending to be a therapist. A gringo mafia. A slaughtered family. Everybody knows I'm a monster. The law of the jungle is simple. Survive. I'm Candace DeLong. This is Natural Selection, Scott vs. Wild Bill. Available now wherever you get your podcasts.
The Osage nation once went by a different name, Neoconska, or People of the Middle Waters. But in the 1600s, French traders thought they were called Ouijaaji, or Water People, and mispronounced the name as Osage. And for one reason or another, it stuck.
The tribe still uses Osage today, so that's how you'll hear us refer to them. Their people called North America home centuries before the U.S. existed. For most of that time, they lived in the Central American Plains, sprawling as far west as what is now Colorado, east as Pennsylvania, traveled north into Wisconsin, and south into Louisiana. Scholars estimate their population once stood around 17,000 strong.
But thanks to epidemics spread by foreign colonists,
Their number shrank to just about 3,500 people by the 1860s. To make matters worse, the U.S. government continued to displace the Osage people from their ancestral lands whenever and however it benefited them, often by force, sometimes by paying them lump sums of cash. So to protect themselves from more of the same, the Osage people played the American government's game and invested that money in land.
They purchased the deed to a 1.5 million acre plot of land from the Cherokee Nation and created their own reservation in what's now the northeast corner of Oklahoma. Now, at the time of the sale, no one outside of the Osage considered the plot of land valuable. It was mostly rocky and unlivable. But about 20 years after the sale, an Osage man discovered something slick, black, and pungent floating in one of its creeks.
And it changed everything. It sure did. The Osage Nation was now sitting on deposits of what the papers called "black gold." They knew America's oil-hungry corporations would pay almost anything for access.
So they opened themselves up for business and began leasing their land to American oil companies. They drilled for oil over the next decade. In the early 20th century, the U.S. government came knocking on the Osage's door. They wanted to break up Indian Territory and make Oklahoma a state. Thankfully, they were willing to negotiate, and the Osage were savvy. They stipulated in their contract that any oil found on the land would belong to them.
Now, the Osage were the first tribe to hold oil rights on reservation land, and they wanted to protect it. So they created something called the Osage Mineral Estate and handed out a distribution of funds they called "head rights" to a little over 2,000 of the tribe's existing members.
The Osage mineral estate had one crucial rule: head rights couldn't be bought, sold, or traded. The only legal way to pass them on was through inheritance, meaning oil companies couldn't swoop in and buy them up. They had to be passed down to family or through a will. To the Osage, it seemed like a fair way to spread the wealth they made from mining while keeping profits within their reservation.
So, with that settled, the oil started to flow by 1906. And with it, the cash. By 1920, each headright was worth over $8,000 per year.
Well, that may not sound like a lot to us now, but at the time, it put Osage families within the top 10% of U.S. households. According to the Oklahoma Historical Society, the Osage oil boom created more wealth than all the other American gold rushes
By 1923, they were making more than $30 million a year as a tribe. Counting for inflation, that shakes out to about $535 million today. Imagine what you could do with that kind of income. Well, the Osage could only do so much thanks to a 1921 law passed by the U.S. government that
It forced members of the Osage community to pass a so-called competency test to prove they could handle their financial affairs. If they didn't pass, they'd be appointed a white, quote, guardian to manage their money. If that sounds like a legal loophole created for the express purpose of stripping tribe members of their head rights...
There's a reason for that. By its nature, the law incentivized corruption. The more tribe members found to be incompetent, the more money the people making the decisions controlled.
And the word competency here is extremely misleading. These tests weren't based on acumen or acuity. The biggest barometer was something called blood quantums, which was tied to ancestry. And it's as weird as it sounds. Essentially, the more native you were, the more likely your rights would be stripped away. The more white you were,
the more likely you'd be found competent. So yeah, you can see how this opened the door for outside businessmen and lawyers to step in as "guardians" and, I'm using air quotes here, "manage" their funds. Not only did these "guardians" skim money from the head rights, but they then tightened their grip by passing another law, allowing them to restrict how much money an Osage could withdraw per year.
Didn't matter if they needed life-saving medication or wanted a car. Everything was completely controlled. As we know all too well, big money often leads to big conspiracies. And today's story has no theories. All the conspiracies are real. They happened. And unfortunately, they targeted one prominent Osage family in particular. The Kyles.
Most of what we know about the Kyles comes from journalist David Grand's book, Killers of the Flower Moon. It was adapted into a film in 2023 by Martin Scorsese, starring Leonardo DiCaprio, Robert De Niro, and Lily Gladstone.
And as you may have guessed, Kyle wasn't their given last name. For the most part, the Osage didn't use surnames until the early 20th century, when white merchants gave them western-sounding first and last names to use instead of traditional ones. For instance, the family patriarch of the Kyle family, Nekeshay, received the name Jimmy.
His wife became Lizzie. Since they continued to use their Western names themselves, that's how we'll refer to them moving forward. Jimmy and Lizzie had four daughters, but today's story mainly focuses on their second oldest, Molly. Molly was 10 when the Osage Nation discovered oil on their land, so her family was among the first to reap the benefits. She planned to marry a nice Osage man and settle down, but that all changed when she met...
Ernest Burkhart Ernest was a handsome white cowboy with brown hair and blue eyes. He grew up poor in Texas, but when he turned 19, he went to Osage Hills to live with his uncle, a powerful cattle rancher named William K. Hale. Ernest ran errands for William and at some point started spending time with Molly and driving her around.
To Molly, Ernest was different from other guys. Beneath his rough exterior, he was soft. He learned the Osage language so he could speak to her in her native tongue. He consoled her when she was sick. In time, Molly Kyle became Molly Burkhart. The couple married in 1917. They stayed on the Osage reservation and by 1921, they had two kids. For a while, everything seemed like a dream.
But the honeymoon period didn't last forever. Only one year after her wedding, Molly's 27-year-old sister Minnie died suddenly. Doctors blamed a vague disease they called "wasting illness." But that didn't make sense to Molly. Wasting illnesses usually took years to run their course. But Minnie had been perfectly healthy and then suddenly she was gone.
Molly sensed something strange had happened to Minnie. She just couldn't prove it. Yet. After Molly Kyle married and became Molly Burkhart, her younger sister Minnie died unexpectedly. It happened all at once, and Molly suspected she may not have died from a disease like the doctor suggested. Adding to her suspicions, a few months after Minnie's untimely death,
her husband Bill Smith got remarried to their younger sister Rita. And that wasn't the only red flag. Besides the quick remarriage to another Kyle sister, Bill drank excessively and had assaulted Rita, his new wife, more than once. Now,
Now, you might be thinking, this Bill guy must have had a hand in Minnie's death. He was obviously after the head rights. That was my first thought too. But actually, Bill didn't stand to inherit Minnie's head rights because he and Minnie never had children. They reverted to Minnie's mother, Lizzie, not Bill. So the situation was more complicated than it seemed.
And Minnie's death wasn't the only problem the Kyle family was dealing with at the time. The family patriarch, Jimmy, had died in 1913, and Lizzie, their aging mother, needed someone to care for her. Lizzie's first option was to move in with her eldest daughter, Anna Brown. But Anna was dealing with her own issues, including a divorce from her husband, Oda. Anna reportedly coped with the separation by drinking whiskey,
and partying every night until dawn. So in short, she was in no shape to care for anyone, let alone their elderly mother. So Lizzie moved in with her second oldest, Molly. With a husband, two kids, and a mother to take care of at home, and multiple sisters to worry about, Molly had her hands full. Her life was more than a little chaotic, and that chaos came to a head on May 21st, 1921. ♪
That morning, Molly's eight-month-old son and her mother Lizzie woke up sick, and Molly was supposed to host some of Ernest's family for lunch. Even with the help of servants, she was overwhelmed, so she called the only person she thought could help, Anna. Molly quickly regretted the decision. Anna arrived looking ready for a night on the town. She wore a fancy skirt, alligator purse, and bright red shoes. And she was drunk.
really drunk. To make matters worse, she showed up at the same time as Molly's lunch guests, including Ernest's racist aunt.
who loved to talk about how much she hated the fact that her nephew married an Osage woman. Molly tried to salvage the lunch as best she could, but Anna walked right up to Ernest's relatives, holding a flask of whiskey, then proceeded to flirt with Ernest's younger brother, Brian. Okay, to be fair, Brian and Anna had dated on and off, but at the time, their relationship status was unclear.
Actually, during the gathering, Brian asked one of Molly's servants out on a date. When Anna caught wind of it, she threatened to kill him. And that was in between fighting with nearly everyone at the house, including her bedridden mother. Needless to say, the day was a total disaster.
Ernest eventually took his family to the theater to remove them from the situation. Meanwhile, Molly stayed behind to clean up and look after her mother and sister. But there's someone else who stayed behind. Ernest's brother, Brian. Even after everything that happened earlier, he ended his visit by offering to drive Anna home. And she said yes.
Cut to two days later. Molly hadn't heard from Anna, and it wasn't like her sister to not stay in touch. She became worried. Was Anna alright? Was she on a bender? Did she get hurt? Her sister was missing, and she couldn't bear to lose another loved one. But she didn't know who to call for help. See, formal police departments hadn't really made their way to the western states yet, so Molly decided she'd launch her own investigation.
First, she retraced Anna's steps after the luncheon. She called Brian to make sure her sister made it home that afternoon. He swore she did. After a third night of not hearing from Anna, Molly sent Ernest to Anna's house to check on her, only to find out the servants hadn't seen her either. And Molly's worry may have been compounded by the fact that earlier that month, another member of the Osage had gone missing.
30-year-old Charles Whitehorn. His body was discovered decomposing in an oil field with two gunshot wounds in his head. Molly thought it was possible her sister was just partying at one of her favorite jazz clubs in Oklahoma City. Ernest assured her that Anna would be home any day now. A week later,
The phone call came. It was Anna's financial manager, Scott Mathis. He told Molly Anna might have been found, but not in the state anyone hoped. Squirrel hunters had stumbled upon a decomposing body in a forest creek. It was a young indigenous woman who'd been shot in the head.
just like Charles Whitehorn. The gunshot wounds and decay had mangled the woman's face, making it impossible for the hunters or Mathis to identify her. There was a chance it wasn't Anna, but they needed the family to rule it out.
The extended family traveled to the creek to see for themselves. As Molly, Rita, and Rita's husband, Bill, slowly approached the body, they shielded their noses from the smell of decomposition. They stared at the misshapen face, searching for signs of Anna. At first, they couldn't tell. Then, Molly noticed the skirt and red shoes Anna had worn to the luncheon.
Bill grabbed a stick and nudged the woman's mouth open. She had gold tooth fillings that matched Anna's. Rita broke down in tears and ran into Bill's arms. All Molly could say was, yes, yes, the body was her sister. But no, she couldn't be sure if it was a coincidence or if someone was picking her family off one by one.
A coroner's inquest was held to determine Anna's official cause of death. Remember, law enforcement was very informal at this time, so the only people tasked with the inquest were the police chief, Sheriff Harv Frias, and a handful of civilian jurors.
Jurors were selected by the Justice of the Peace and were typically prominent white men. In this case, it included people like Anna's finance manager, Scott Mathis. The group convened at the crime scene where two doctors performed the autopsy. It is really hard to imagine showing up for jury duty at a creek in the middle of the woods to watch a coroner slice open a murder victim firsthand. But back then, that's how it worked.
Unfortunately, the inquest was a dead end. They were able to rule the death as a homicide, but the doctors failed to locate the bullet in Anna's skull, so they couldn't tell the make or model of the murder weapon. Even worse, Sheriff Frias now had two murder victims and no leads. Instead of bringing closure for Molly and the Kyle family, the inquest raised more questions.
Given the similarity between Anna and Charles' deaths, people wondered if they were killed by the same person. Possibly someone who wanted their head right. Or maybe a serial killer. Or maybe they were one and the same.
Sheriff Frias started his investigation by looking into the most likely suspects, namely Anna's ex, Oda Brown. According to one investigator, Oda seemed a little too upset over Anna's death, like he might have been pretending to grieve. Especially because after their divorce, Anna made sure Oda didn't get a dime in her will. Her head right was split between Molly, Lizzie, and Rita.
According to David Grand's book, Killers of the Flower Moon, one detective remarked Oda was, quote, "...capable of doing almost anything for money."
For weeks, Sheriff Freus pursued Oda Brown as the prime suspect. And interestingly, he wasn't the only one on his trail. Ernest's uncle, William Hale, offered to track down the killer too. As we mentioned earlier, William was a powerful rancher with deep ties to law enforcement. He'd even become known as the King of the Osage Hills.
despite being a white man from Texas. But it was Sheriff Frias who had the first big breakthrough. In July 1921, the sheriff received a letter from a prisoner in Kansas
The man, who had recently been locked up for forging checks, claimed to have information about Anna's murder. The sheriff and a team of officers raced across the state border to get the scoop, except someone else showed up at the jail too. William Hale. Sheriff Frias might have received the lead first, but someone in the sheriff's office apparently tipped William off. He came down to personally interrogate the check forger on behalf of Molly and her family.
That's why when the prisoner offered to point them to Anna's alleged killer, both William and the sheriff were present, but neither one expected his answer. The man said it wasn't Oda Brown. It was him acting on Oda's orders. He claimed that Oda paid him $8,000 to shoot his ex-wife and leave her body in the creek. Based on the man's testimony, Oda Brown was arrested.
But the sheriff couldn't corroborate the Forger's story, so within days of the arrest, officials had to let Oda go. That put Anna's case back at square one, and no one was more heartbroken than Molly's mother, Lizzie. Within a few weeks, Lizzie's health declined rapidly. It might have been her grief, but something about the sickness seemed off.
Molly called a few doctors to check on her mother, but they didn't have any solutions. Neither did the Osage medicine men. Nothing seemed to help. In July, only two months after Anna's murder, Molly found her mother unresponsive. She tried unsuccessfully to revive her. The only members of the Kyle family left were Molly and her younger sister, Rita.
To make matters worse, Sheriff Frias' office was forced to stop all criminal investigations
The Oklahoma Attorney General charged him with, quote, failing to enforce the law and accused him of turning a blind eye to local bootlegging and gambling operations. Frias denied the charges, but it kicked off a long, complicated legal battle and basically left the Osage community on their own. Fortunately for the Kyles, their powerful uncle-in-law, William Hale, had another solution.
hire private detectives to continue working on Anna's case. They started by combing through Anna's house and phone records and pursuing any leads the sheriff may have missed. - The local investigation had stalled out, but the murders hadn't.
Ten months after Anna's murder, another Anna died under mysterious circumstances. This time it was Anna Sanford, an Osage woman who had recently wed a white man named Tom McCoy. According to author Donald Lee Fixico, weirdly enough, after Anna's death, Tom married William Hale's niece. And remember Charles Whitehorn, the man who disappeared shortly before Anna Brown?
He was thought to have been the first murder in this reign of terror,
But Fixaco also discovered a few weeks before Whitehorn's death, a man named Joe Grayhorse was killed after buying some land from Hale. Osage Nation tried to appeal to the United States government for help. Their best foot forward was Barney McBride, a wealthy white oilman with connections in Washington, D.C. He traveled to the capital to see if he could convince them to launch an investigation into the Osage murders.
He checked into his hotel on August 9th, 1922, and then went to play pool at a nearby Elks Club. As he exited the club, someone grabbed McBride and threw him into a car. McBride's body was found in Maryland the next day. He'd been severely beaten and stabbed more than 20 times. The murder made national headlines.
For most, it was a shocking story about a government official caught in some mysterious crossfire. But for Osage Nation, it was so much more. It felt like their last chance at a resolution was now dead.
Thanks for tuning in. Join us next time for part two of our story. You can catch new episodes of Serial Killers on Mondays and Conspiracy Theories on Wednesdays for free on Spotify or wherever you like to listen. Of the many sources we used, we found Killers of the Flower Moon by David Gran helpful to our research. Until next time, remember, the truth isn't always the best story and the official story isn't always the truth.
The Osage Nation Foundation supports their community by preserving the history and culture of the Osage people.
Funds benefit Osage members, particularly artists and youth. If you'd like to donate, visit osagefoundation.org/donate. Serial killers and conspiracy theories are Spotify podcasts. This episode was written by Mallory Cara, edited by Adam Da Silva and Lori Marinelli, researched by Bradley Klein, fact-checked by Kevin Johnson, and sound designed by Alex Button.
Our head of programming is Julian Boisreau. Our head of production is Nick Johnson. And Spencer Howard is our post-production supervisor. Conspiracy Theories and Serial Killers are hosted by Vanessa Richardson and me, Carter Roy. This episode is brought to you by Hills Pet Nutrition.
When you feed your pet Hills, you help feed a shelter pet, providing dogs and cats in need with science-led nutrition that helps make them happy, healthy, and ready to be adopted. It's an initiative that Hills has supported since 2002. And since then, the Food, Shelter, and Love program has helped more than 14 million pets find new homes, changing their life forever so they can change yours.
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