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Due to the nature of today's episode, listener discretion is advised. This episode includes discussions of animal death, violence, racism, murder, and death. Consider this when deciding how and when you'll listen. In January 1923, a 40-year-old Osage man named Henry Roane called up one of his closest friends, William Hale.
Henry was in a bit of distress. He'd just learned his wife was cheating on him. William rushed over to Henry's house to comfort him, but it only helped so much. A few days later, Henry turned to whiskey. William tried to get Henry to quit drinking. Not only was his buddy a mess, but in the age of prohibition, if Henry got caught with booze, he could go to jail. Henry basically shrugged off the intervention.
He said he'd be sure to hide the whiskey, but never promised to stop. When the two men parted ways, Henry strolled off into the cold air of the Osage Reservation. It was the last time William saw his friend alive. Henry Roane became the latest victim of what the press would later call "the Reign of Terror."
Hi, I'm Carter Roy, host of Conspiracy Theories, a Spotify podcast with new episodes releasing every Wednesday. And be sure to check us out on Instagram at The Conspiracy Pod. Today, we're continuing our discussion on the Osage murders. I'm once again joined by my friend and host of one of my favorite podcasts, Serial Killers, Vanessa Richardson. Thanks, Carter. Thanks for having me. You bet. 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.
There's a lot going on in his story, so we're going to do a quick recap of the last episode. Let's get into it. Okay.
We were following the Kyles, a family that was part of the Osage Nation, an indigenous American people who in the early 20th century got rich quick off the oil on their reservation. They drew up the contract that made sure they had exclusive rights to the land and all of its natural resources and then split the profits exclusively between the Osage people like the Kyles. Right. And these profit shares were known as head rights.
To ensure the money mostly stayed within the tribe, they made a rule that said head rights could only be passed down through inheritance, family member to family member.
But once the United States government saw how much cash the Osage were raking in, they made this law that essentially gave outside forces, meaning white men, the ability to swoop in and be a so-called guardian to a tribe member's wealth if they deemed that member wasn't competent enough to manage their own funds. Yeah, and competency was directly related to their racial makeup.
The more white someone was, the more likely they'd be able to manage their own money. Right. By the time of Headrights and Big Oil, the patriarch of the Kyle family had already passed. The family was made up exclusively of women: Lizzie Kyle and her four daughters, Anna, Molly, Minnie, and Rita.
You'll remember from our last episode, Molly was the second oldest. In 1917, she married a handsome white cowboy named Ernest Burkhart. Ernest had this wealthy uncle, William Hale, who despite being a cattle rancher from Texas with no direct ties to the Osage people,
was considered the King of Osage Hills. Yes, and when we last left off, Ernest, Molly's husband, seemed like a good guy. A little rough around the edges maybe, but no major red flags yet. However, there had been some strange coincidences. Shortly after Molly married Ernest, her family was torn to pieces.
In the span of only four years, her mother and two of her three sisters died under suspicious circumstances. Now, Molly and Rita are the only ones left. Their mom and sister Minnie died from sudden, mysterious illnesses, and their older sister Anna was found dead in the woods, shot to death by a killer who remains at large. And if that wasn't crazy enough, the Kyles weren't the only ones dying.
Shortly before Anna, another Osage man named Charles Whitehorn was found in the woods, shot and killed in an eerily similar manner.
Before that, Joe Grayhorse was killed, and the body count continued to rise with the death of Anna Sanford, another Osage woman, and Barney McBride, an oilman with connections in Washington, D.C., who'd been trying to help launch a new investigation. And that brings us full circle back to the man who started this episode, Henry Roan.
Right, in February 1923, in the middle of winter, two hunters noticed a car parked in a low-lying stretch of land in a remote area of Oklahoma. They reported it to local authorities. When officials arrived at the scene, they found Henry Roan's body slumped over in the driver's seat, dead, shot in the back of the head.
It didn't appear to be a robbery because Henry still had a gold watch and cash on him.
Much of what we know about this story comes from David Grand's book, Killers of the Flower Moon. In it, Grand says one of the first people notified was William Hale. William and Henry had been good friends. William had helped Henry out a lot in the past, like when Henry found out his wife was cheating on him, or when Henry needed money. See, Henry was 100% Osage.
so he could never access the wealth he earned from head rights. It was all managed for him.
Whatever meager rations trickled down from the top, he spent, so he sometimes turned to William for loans. William actually lent Henry so much money that before he died, Henry made the so-called King of Osage Hills the sole beneficiary on his $25,000 life insurance policy. Which probably didn't cross William's mind as he acted as a pallbearer at Henry's funeral, right?
Henry's death incited further panic among the Osage. Their people, and anyone who seemed to want to help, were being targeted. And no one knew who to turn to. There was already a lack of formal law enforcement systems in place, and the sheriff in charge of everything had been removed from his position, accused of mishandling cases and turning a blind eye to crime. Right, and then William Hale hired a private investigator, but nothing seemed to work.
Which is why Rita's husband, Bill Smith, started his own investigation. So Bill suspected that Rita and Molly's mother, Lizzie, hadn't died from a mysterious illness. He believed she might have been poisoned. He took it upon himself to begin interrogating neighbors and doctors about all the deaths in the Kyle family. Lizzie, Minnie, Anna. And Bill may have been on to something because shortly after he started asking questions...
Bill and Rita heard rustling in the bushes outside their home at night. They knew there was a killer on the loose, and they felt they were being stalked. Bill and Rita lived in fear for a month, then moved across town to what they felt would be a safer location. Many of their new neighbors had guard dogs, which they hoped would deter unwanted guests. But not long after their move, those same dogs
started dying off one by one. Bill suspected poison, which only deepened his concerns about his family's safety. But no one could have anticipated what would happen next. March 10th, 1923 was a quiet and peaceful night. At 3:00 AM, Bill and Rita Smith were asleep in their bedroom. An explosion ripped through the neighborhood.
The blast was so powerful, it bent signposts and shattered nearby windows. Molly and Ernest felt it at their house across town, too. They both jumped out of bed, ran to the window, and saw a huge fire burning in the distance. Ernest got dressed and went outside to investigate. But as he got closer to the blast site, he realized it wasn't just any house on fire. It was Bill and Rita's home. And there were...
No survivors. Molly was now the only surviving member of the Kyle family, and she was certain she was next. With her whole family dead and gone, Molly Kyle Burkhart became a recluse. She locked the doors and closed the windows. She stopped inviting people over for lunch. She stopped going to church.
Her grief consumed her mind and her body. Molly felt so weak she couldn't care for her baby daughter, so she sent her off to live with a relative.
Meanwhile, the investigation into the many suspicious deaths and killings in and around the Osage Reservation had skidded to a stop. After the last couple of people who tried digging into the murders, Barney McBride and Bill Smith ended up dead. People were afraid. The local justice of the peace refused to perform inquests at crime scenes following anonymous threats.
The new sheriff, the one who replaced Har Freas after his scandal, wanted nothing to do with the murder investigations. He basically washed his hands clean of them and said the government should handle it. Now, the tribal council had been turning to the Oklahoma state government for help,
but corruption hindered progress. Yeah. For example, in April 1923, Oklahoma's Governor Jack Walton appointed a private investigator to look into the killing spree. After making no headway on the case,
The PI was arrested and charged with bribery in June. Then a few months later, Governor Walton, the guy who hired him in the first place, was impeached for embezzlement and abuse of power. But just when it felt like the Osage people were running out of road, the U.S. Department of Justice entered the picture. More specifically, their investigative arm, the Bureau of Investigation, or the BOI, which would eventually evolve into the FBI.
And the key word here is eventually, because back in the 1920s, the BOI wasn't well-known, well-funded, or well-staffed. It was small with only a handful of field offices. The BOI mostly worked low-level cases like pornography, prison escapes, people who dodged the draft, that kind of stuff.
Not murder. But when they got the call about what was happening in the Osage Hills, they said they'd do it. For a price. $20,000.
Desperate to solve the killings, the tribe paid the money and the BOI got to work. Albeit with some questionable tactics. The first agents assigned to the case hired a convicted bank robber named Blackie Thompson to go undercover. He was supposed to work the Osage oil fields and gather evidence. Only that didn't go so well. One day Thompson disappeared from his post, robbed another bank and killed a cop.
It took the BOI months to track him down and arrest him. And that's how the investigation started. It was a huge embarrassment for the Bureau, especially for its new acting director, a guy named J. Edgar Hoover. That's right. Now, Hoover would go on to become a controversial figure and reign over the FBI for nearly 50 years. But at this point,
He was a fresh-faced, ambitious 29-year-old facing one of his first scandals. Hoover managed to keep the Blackie Thompson incident out of the press. But with the federal government breathing down his neck, the pressure was on to solve the Osage murders. So he recruited a Texas lawman named Tom White to lead the investigation.
As a Texas Ranger and Special Agent for the Santa Fe and Southern Pacific Railroads, Tom spent his career roaming the frontier hunting for criminals and murderers.
But this might have been his most dangerous assignment yet. He officially took over in July 1925. His first step was to review at least two dozen murder cases. Except the documents were a mess and some records, including Anna Brown's file, appeared to have been misplaced. And the even bigger issue was there didn't seem to be a regular M.O.
No one knew how the victims were linked, other than their connections to Osage oil wealth, of course. They were all different, almost random. And yet, sifting through the files, White sensed they weren't all the work of one killer. Given the timing and locations, it had to be many, maybe even hired henchmen. The murders seemed to be carefully planned. The bomb premeditated.
Poisonings likely happened slowly over long periods of time. Yeah, according to David Grand's book, Killers of the Flower Moon, White suspected the culprits had been planning the murders possibly for several years, meaning he was dealing with a master manipulator. To catch such a meticulous killer, he thought it best to toss out the old investigation and start over.
He assembled his own team, picking a few cowboys who knew the Wild West and could blend in undercover. One was a former Texas Ranger, another was a local agent familiar with the case, and he selected the BOI's lone indigenous operative, a man named John Wren from the Ute tribe. Some of those agents went undercover in the Osage community. One pretended to be a Texas cattleman, one a rancher, another an insurance salesman,
Wren assumed the identity of an indigenous medicine man searching for some long-lost family members. It was the riskiest covert operation the BOI had ever seen, and the stakes were high. If they succeeded, it would be one of the Bureau's first solved murders. But if they failed, it could ruin the BOI, their careers, and J. Edgar Hoover's reputation in one fell swoop.
It was a daunting task, to say the least. So Tom White focused on one investigation at a time, starting with the death of Molly's sister, Anna Brown. To get to the bottom of it, White's agents had a two-pronged approach. First, go undercover in the Osage community to hear what people were saying behind closed doors. And second, fact check the suspect's alibis. So first up, Anna's ex-husband, Osage.
Oda, who was previously arrested for Anna's murder based on a Czech forger's testimony,
But he turned out to have a solid alibi. He was with another woman at the time and she corroborated his statement. As for the check forger, well, he admitted to lying. He had the naive idea that confessing to the murder might get him transferred to a better prison, which didn't pan out. Well, that leaves one last suspect, Brian Burkhart, Anna's on-and-off boyfriend and Molly's brother-in-law.
Now during the initial investigation, Brian was cleared, but White took another look. So let's rewind four years to May 1921, to the night Anna went missing.
After Molly's luncheon, Brian claimed he drove Anna directly home, dropping her off around 4.30 or 5 in the evening. Then he joined his family at the theater. But a BOI agent came across an elderly farmer who said he saw Brian and Anna in a car together long after 5 p.m.
Tom White and his men didn't want to jump to any conclusions. An old man's eyewitness testimony from four years earlier might be less than accurate. So they kept digging. And that's when they found other witnesses who claimed to see Brian and Anna after 5 o'clock too.
This time at a speakeasy. The witnesses reported that Brian and Anna were there until 10:00 PM, which meant Brian couldn't have been at the theater. - From there, they headed to another speakeasy. According to witnesses, Anna and Brian were drinking until around one in the morning. There were conflicting reports of what happened next.
One witness claimed the pair met up with another man, but after that, Anna's trail ran cold. The agent spoke with one of Brian's neighbors, who claimed Brian asked him not to tell a soul that he was out until 3 in the morning.
It was a breakthrough for Tom White and his agents. But the revelations made room for more questions. Why would Brian kill Anna? And if he had something to do with her murder, was he involved in the other deaths too? Not to mention, who was the other man he and Anna met with that night?
Tom White assigned that question to a BOI informant named Kelsey Morrison. Meanwhile, White dug further into Brian and his uncle, William Hale. Even though the men remained tight-lipped, the BOI found one source willing to talk, one of William Hale's own private investigators, a man named Pike. Now, remember how Hale offered to help Molly investigate Anna's death?
Well, it seems there was more to it than that. Pike explained that Hale never wanted to solve Anna's murder. Hale only wanted to fabricate an alibi for Brian. So during the cover-up, Pike claimed he regularly met with three men, Hale, Brian, and Molly's husband, Ernest.
By the end of the summer, Agent Tom White felt he had his ringleader, William Hale. But why would a powerful man like Hale do all this? He was a wealthy rancher who everyone seemed to respect. He had tight relationships with lawmen. The motive mystified White and his men. And since Hale seemed to be an upstanding citizen, well, they needed more than a shady private eye's word. And soon...
They got it. In September 1925, one of the undercover BOI agents got some serious dirt on Hale. Someone in town told him Hale hired men to burn thousands of acres on his farm to collect an insurance payout of $30,000. White's agents also found out Hale paid Anna's finance manager, Scott Mathis, to spy on her.
Plus, Hale bribed a local police chief to turn a blind eye to whatever he was doing. So what did all this have to do with killing members of Osage Nation? Well, remember that pact the Osage made when oil was first discovered? Their oil head rights could only be sold to Osage members, not outsiders. But there was a glaring loophole.
White non-Osage people could inherit head rights after an Osage owner died. So White theorized that William, Ernest, and Brian killed off the Kyles one by one, transferring all the family's head rights to Molly. That way, when she died, Ernest would receive them all.
There was just one problem. The BOI had no proof. Everything was hearsay. They couldn't risk embarrassing J. Edgar Hoover with a half-baked case, which meant White and his agents had to keep digging, hoping for another big break. One month later, in October 1925, they got it. An inmate at the state penitentiary seemed to know too much about the Osage murders. His name?
was Burt Lawson. Lawson had worked for Molly's sister Rita and her husband Bill Smith, but when Lawson found out Bill was having an affair with his wife, he couldn't stand to work for the Smiths any longer. Understandable. And a year later, Lawson got a job offer from Bill's brother-in-law, Ernest Burkhart. It wasn't the sort of work he expected. According to Lawson, Ernest said, quote,
"I want you to blow up and kill Bill Smith and his wife." Initially, Lawson said he refused the job. But then William Hale entered the picture and sweetened the deal with $5,000. Almost a year's salary for an average worker at that time. That was supposedly enough to convince Lawson. Lawson planted the bomb that killed Rita and Bill Smith.
He made a full confession. It was the testimony Tom White and the BOI were waiting for. They finally had a witness to tie Ernest and William to the murders. So now the case was coming together. White knew the motive was greed, and he knew the next target.
Molly Burkhart. Well, luckily they could probably get to Molly. Agent John Wren found out about a local priest who was apparently still in contact with Molly because remember, she's in hiding basically.
Wren was tasked with tracking Molly down before something bad happened. In the meantime, White rushed to get arrest warrants for Ernest and William Hale. In January 1926, authorities captured Ernest at a pool hall. Hale, on the other hand, apparently wanted to surrender on his own terms.
He walked into a sheriff's office and turned himself in. While in custody, Ernest stonewalled authorities. So White searched for another witness to give him the leverage he needed. And he found one right under his nose. Right. Remember the BOI's bank robber informant, Blackie Thompson? He was in jail and ready to talk. He told officials that Ernest and William had also approached him to kill Bill and Rita.
But he refused to go along with it. The next chance he got, White sat Blackie down across from Ernest in an interrogation room. Blackie told Ernest that he'd given the BOI everything. And that's when Ernest broke his silence. Ernest basically pinned the blame on his uncle William. He said he grew up idolizing him. When Hale came to him with a plan to kill Bill and Rita, he just went along with it.
Together, they hired an outlaw to plant the bomb. Now, interestingly, that outlaw turned out not to be Burt Lawson, the guy who originally said he did it. Instead, it was a man named Asa Kirby. Lawson falsely confessed for reasons that are still unclear, but possibly to get his sentence reduced for an unrelated crime. But Lawson's false confession didn't change the end result.
White had Ernest and his uncle backed into a corner and admitting that the motive for their murder conspiracy was money. With Rita and Bill out of the picture, Molly would inherit their head rights and if Molly died, Ernest and his uncle would get their hands on them.
Oh, and Ernest didn't stop at one confession. He also told White about other murders. He outlined how his uncle hired a hitman to kill Henry Roan for his life insurance policy payout. And as for Anna Brown, Ernest knew who killed her, too. It wasn't his brother, Brian.
It was the man the BOI had originally assigned to investigate Anna's case, Kelsey Morrison. Morrison was a double agent for Hale the whole time.
Around the same time that White was connecting all the dots, the BOI finally tracked down Molly. She was alive, but just barely. They rushed her to the hospital and kept her under their supervision. With Hale and Ernest behind bars, Molly quickly recovered, which seemed to indicate she was being poisoned.
White suspected that someone may have been paying her doctors to spike her insulin shots with unknown toxins. But Molly refused to believe Ernest was involved. She still wrote him letters while he was in jail. Everything changed at the trial. In March 1926, Ernest Burkhart pleaded not guilty and refused to testify against his uncle. It seemed that after Ernest admitted the truth to Agent White,
Hale and his attorneys intimidated him into recanting his confession. Ernest discreetly told a lawyer that if he testified, quote, they'll kill me. But then something unexpected happened. In June, Ernest fired his defense attorneys and changed his plea to guilty. When Ernest was sentenced to life in prison, Molly didn't cry. She just stared at her husband, numb.
Over the next few months, Molly returned to the courtroom for the trial of William Hale. At the end of it all, he was found guilty in the murder of Henry Roan. He and his hired gun were both sentenced to life in prison. As for Brian Burkhart, he was offered immunity to testify against Kelsey Morrison, which helped convict Kelsey of Anna's murder.
As for the rest of the victims, Charles Whitehorn, Anna Sanford, Joe Grayhorse, and Barney McBride, well, they never got their day in court. The number varies, but some sources estimate 24 Osage were killed during the Reign of Terror. There's no telling just how many murders Hale had a hand in, or how many hired killers got away scot-free. When the trials were all said and done,
Molly divorced Ernest. She remarried and even had her competency restored. She was finally free to spend her own money. Even after the case, the legacy of the Osage murders lived on. The BOI was kickstarted to national headlines. Only a few years later, it would chase down famous criminals like Al Capone and John Dillinger.
And in 1935, the agency was given a new name, the one we know now, the FBI. Ah, so that's how it all started.
And in the years since, Osage Nation's funds looked very different. The oil stopped flowing as much as it once did. In peak oil years, Osage wells were producing over 200,000 barrels per day. By 2016, that number had dropped to 12,000. Plus, the Great Depression took its toll on the tribe, like the rest of the U.S.,
According to Gran, the price of a barrel of oil dropped from $3 to just 65 cents in 1931. Even so, the original headright system prevailed and continued to be exploited for many years.
More head rights payments were transferred to non-Osage people, including entities like schools and churches. By 2000, Osage Nation had filed two lawsuits against the U.S. government, alleging that the head rights system was being mismanaged.
11 years later, the lawsuit settled for $380 million. As of 2021, Molly's granddaughter Margie was living in Tahlequah, Oklahoma, where she sat on an Osage healthcare board.
She spoke openly about the murders to Gran and the press, hoping to remind people of the tragedy that occurred and the ripple effects that still affect the Osage Nation today. She told the magazine Tulsa Kids, quote, I think for the next generation of my family, they're going to be okay just because of the way we talk about it. We don't put any shame on anything. It was a tragedy and we're strong because of it.
And they'll be strong because of it, too. Thanks for tuning in to Conspiracy Theories, a Spotify podcast. Episodes release every Wednesday. Of the many sources we used, we found David Grand's book, Killers of the Flower Moon, to be helpful in our research. The movie of the same name is out October 2023. 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 slash donate.
Conspiracy theories and serial killers are Spotify podcasts. This episode was written by Mallory Cara, edited by Adam DaSilva, Lori Marinelli, and Chelsea Wood, researched by Bradley Klein, fact-checked by Lori Siegel, and sound designed by Alex Button. Our head of programming is Julian Boirot, 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. Science did that. Learn more at hillspet.com slash podcast.
