William K. Hale gained local prominence in the late 1800s through a vast campaign of bribery, intimidation, and extortion. In 1921, Halle orchestrated the murders of his nephew’s wife and mother-in-law to seize control of their oil rights. Over the next two years, he extended his scheme by ordering the killings of her cousin, sister, and brother-in-law.

In the months that followed, Hale was responsible for the deaths of at least two dozen more individuals who posed a threat by considering testifying against him.

The Osage Tribal Council grew suspicious of Hale early in the investigation but struggled to gather testimony due to widespread fear and silence, enforced by Hale’s bribery and threats. Desperate for justice, the council sought help from the FBI. Four undercover agents were sent to the Reservation and, over the course of several years, managed to earn the trust of the townspeople. This led to a wave of testimonies implicating Hale.

Eventually, Hale’s nephew, whom he had coerced into aiding his scheme, confessed. This confession, along with other evidence, resulted in charges being brought against Hale, his hired contract killer, and his corrupt attorney. In 1929, Hale was convicted for orchestrating the murders and sentenced to prison.

Early Life

William Hale was born on December 24, 1874, in Hunt County, Texas. His mother passed away when he was just three years old. When he was sixteen, he began working as a cowboy in West Texas, and by eighteen, he was running cattle on the Kiowa-Comanche reservation in Indian Territory.

Around the turn of the 20th century, Hale settled in the Osage Nation (then part of the Oklahoma Territory, now Osage County, Oklahoma). By 1900, his wife had joined him, and they lived in a tent while raising cattle. By 1905, he had relocated to Gray Horse, an Osage town, to manage a ranch, and by 1907, he partnered with local bankers to purchase a ranch of his own.

Hale in 1922

Although reportedly uneducated, Hale amassed significant wealth through insurance fraud and exploitative dealings with the Osage people. FBI special agent Tom White, who later investigated Hale, described him in a 1932 memo to FBI Director J. Edgar Hoover as follows:

“Eventually (Hale) became a millionaire, who dominated local politics and seemingly could not be punished for any of the many crimes … His method of building up power and prestige was… by means of gifts and favors.”

Hale styled himself as the “King of the Osage,” owning a controlling interest in the Fairfax bank, part ownership of the town’s general store and funeral home, and serving as a reserve deputy sheriff for Fairfax. He also owned a 5,000-acre ranch and leased an additional 45,000 acres from Osage landowners, further solidifying his influence and wealth.

How did the crimes begin?

In the early 1920s, the western United States was rocked by the mysterious murders of eighteen Osage Indians in Osage County, Oklahoma. Regional newspapers, including those in Colorado, dubbed the events the “Osage Reign of Terror,” reigniting discussions about the lawlessness and boundaries of the western frontier.

The series of killings began on May 27, 1921, local hunters discovered the decomposing body of 36-year-old Anna Brown in a remote ravine of Osage County. Unable to find the killer, local authorities ruled her death as accidental because of alcohol poisoning An autopsy revealed that the cause of death was not alcohol, but a bullet fired into the back of her head. Brown was divorced, so probate awarded her estate to her mother, Lizzie Q. Kyle and her other heirs: Mollie, Rita Smith, and Grace Bigheart. The death of Lizzie Q just two months later left Mollie, who married to Ernest Burkhart, who was no other than Halle’s nephew. and several cousins as heir to the headrights worth several hundreds of thousands of dollars in 1920s.

Unable to find Anna’s killer, authorities put the case aside until February 1923, when another cousin of Brown’s, also known as Henry Roan Horse, was found shot in the head and partially frozen in his car. Roan had a financial connection with Hale, having borrowed $1,200 from the cattleman. Hale fraudulently arranged to make himself the beneficiary of Roan’s $25,000 life insurance policy.

A month later, on March 10, 1923, a nitroglycerin bomb demolished the house of Bill and Rita Smith, located in Fairfax, Oklahoma. The blast killed Rita and her servant girl, Nettie Brookshire, instantly. Before his death, Bill gave a statement implicating his suspected murderers and appointed his wife’s estate.. He died a week later due to massive injuries from the blast.

On June 28, 1923, William Hale and Ernest Burkhart arranged for George Bigheart, who was the son of James Bigheart – the last hereditary Osage chief, to board a train to Oklahoma City to receive medical treatment. Bigheart was Hale’s neighbor and friend. Recently, a court had appointed Hale as Bigheart’s legal guardian. At the hospital, doctors suspected Bigheart had consumed poisoned whiskey. While in hospital, Bigheart contacted attorney William Watkins “W.W.” Vaughan and urged him to come for an urgent meeting. Vaughan arrived that night, and Bigheart shared his suspicions about those behind the murders. He claimed to have incriminating documents that could expose the culprits.

Later that evening, Vaughan boarded a train to return to Pawhuska. By morning, he was missing. Vaughan’s body was discovered near the railroad tracks close to Pershing, about five miles south of Pawhuska. His skull had been crushed, and the incriminating documents he had taken from Bigheart were missing. Due to the severe disfigurement of the body, the coroner could not determine whether Vaughan had fallen from the train or been attacked and pushed off. The death was ruled “suspicious,” but no official determination of murder was made. That same morning, Bigheart died in the hospital.

With Anna’s mother and several cousins dead, Mollie and Ernest Burkhart became the heir to Anna Brown’s estate.

Hale’s connection to Anna Brown’s family was clear. His weak-willed nephew, Ernest Burkhart, was married to Anna’s sister, Mollie. If Anna, her mother, and two sisters died, then all of the “head rights” would pass to the nephew this giving Hale control. The prize? Half a million dollars a year or more. Hale’s goal was to gain the headrights and wealth of several tribe members, including his nephew’s Osage wife, Mollie Burkhart, the last survivor of her family. Now Mollie Burkhart, became a prime target. Her relatives were shot and poisoned. And it was just the beginning, as more and more members of the tribe began to die under mysterious circumstances.

Mollie, a devout Catholic, had told her priest that she feared she was being poisoned at home. The priest told her not to touch liquor under any circumstances and he alerted one of the BOI agents. Mollie recovered from the poison she had already consumed and divorced Ernest after the trials. Following her recovery, she divorced Ernest, and later married again. Her estate was passed down to their children. Mollie Burkhart Cobb died of unrelated causes on June 16, 1937.

It is believed that Hale’s ultimate plan included the intended murders of Mollie, Ernest, and their children, which would have left the entire Kyle-Burkhart estate in his hands.

Mollie Kyle
Molly Kyle, Survivor of Osage Indian murders

Between 1921 and 1923, thirteen more Osage men and women, all full-blooded tribal members, were murdered. Frustrated by the lack of progress and growing violence, the Tribal Elders of the Osage Nation sought help from the Bureau of Investigation (now the FBI) to uncover the truth and bring the perpetrators to justice.

The investigation

In March 1923, the Osage Tribal Council, alarmed by the escalating number of murders among their people—including Joe Grayhorse, William Stepson, Anna Sanford, and others outside the Kyle family—requested intervention from the U.S. government. In response, the Bureau of Investigation (now the FBI) dispatched agents to Osage County. Among them were special undercover officers who spearheaded the investigations, focusing on the murder of Henry Roan, which had occurred on restricted Indian land and fell under federal jurisdiction.

As the agents gathered evidence and shared their findings, they noticed recurring connections to William K. Hale, Ernest Burkhart, and John Ramsey, marking them as key suspects in the growing case.

Hale was a segregationist and a prominent figure in the Democratic Party in Osage County. His influence extended to the local prosecutor, who sought Hale’s endorsement during an election campaign. With Hale’s support, the prosecutor secured victories in every precinct near Hale’s ranch. Leveraging this political connection, Hale was able to collaborate with local investigators during the initial inquiry into Anna Brown’s murder.

When Henry Roan’s body was discovered in a ravine, Hale personally accompanied the deputy and marshal to retrieve it. In 1921, he also hired a private investigator to look into the series of murders. However, the investigator later admitted to federal agents that his real task was not to solve the crimes but to fabricate evidence and coach witnesses to create alibis for Hale and his accomplices.

A report by the Bureau of Investigation (BOI) ultimately concluded that key local authorities, including the chiefs of police in Ponca City and Fairfax, the Osage County prosecutor, and a local Office of Indian Affairs agent, were all under Hale’s sway, rendering them incapable of aiding in the investigation.

The Bureau of Investigation deployed undercover agents to Osage County to probe the murders. Initially, investigators struggled to find witnesses. The only living informant they located was Dick Gregg, a former member of the Al Spencer gang. Gregg revealed that Hale had tried to hire the gang to kill Bill and Rita Smith. Gregg directed investigators to Al Spencer, Henry Grammer, and Curley Johnson for more information.

The investigation gained traction when Burt Lawson, an inmate at McAlester prison, testified that Hale and Ernest Burkhart had instructed him to plant the explosive device that killed the Smiths. During interrogation, Ernest Burkhart implicated John Ramsey in the murder of Henry Roan. Ramsey, a local farmer and cowboy, confessed that Hale had hired him to kill Roan. He also admitted his role in the Smith murders, identifying Hale as the mastermind behind those crimes as well. Ramsey further implicated Henry Grammer and Asa “Ace” Kirby in the scheme.

Henry Grammer identified Asa Kirby as the bomber responsible for the Smiths’ deaths. However, before agents could question Kirby, he was shot and killed during a “failed jewel heist.” Investigators suspected that Hale orchestrated Kirby’s murder by tipping both Kirby and the store owner about a potential diamond shipment, setting up the heist. This led investigators to believe that Hale was systematically eliminating witnesses. Accusations also arose that Hale had tampered with Grammer’s car brakes and poisoned Johnson.

Both Grammer and Kirby, known for their own notoriety, met suspicious deaths shortly after the Smith murders, raising further suspicions about Hale’s involvement in silencing potential witnesses.

Hale raised further suspicion when he sought to collect on a life insurance policy for Henry Roan. In 1921, after his initial application was denied, Hale reapplied through a different company, submitting a note allegedly signed by Roan, claiming that Roan owed him $25,000. This time, the application was approved. During the required medical evaluation for the policy, the examining doctor reportedly asked Hale, “Bill, what are you going to do, kill this Indian?” to which Hale bluntly responded, “Hell yes.”

Investigators also uncovered a deliberate strategy behind the sequence and methods of the murders, designed to maximize Mollie’s inheritance. For instance, Anna Brown was murdered shortly after her divorce, ensuring her inheritance remained within the family rather than passing to her ex-husband. Similarly, Reta and Bill Smith were killed together in a bombing, triggering the simultaneous death clause in their will and consolidating their assets within the family.

Arrest and conviction

On January 4, 1926, a warrant was issued for the arrest of William Hale and Ernest Burkhart for the murders of Bill and Rita Smith. Ernest was apprehended immediately, but Hale initially evaded capture. According to David Grann, Hale later turned himself in but proclaimed his innocence, prompting federal agents to focus on interrogating Ernest. Under pressure, Ernest broke and agreed to turn state’s evidence after being confronted with testimony from Blackie Thompson, an outlaw in custody for murdering a police officer. Thompson claimed that Ernest had approached him to carry out the killings. Despite this, Hale continued to deny any involvement.

William Hale in 1926 (second from the left) and John Ramsey (third from left) flanked by two U.S. Marshals

The Department of Justice sought to try Hale in federal court, concerned about his sway over Oklahoma’s state judiciary. However, a federal judge ruled that the killings, which occurred on unalienated allotment land, fell under the jurisdiction of Oklahoma courts. Hale’s legal team included Sargent Prentiss Freeling, a former attorney general of Oklahoma. The case was subsequently moved to state court, with Hale’s first hearing scheduled for March 12.

In July 1926, William Hale was tried alongside John Ramsey in federal court for the murder of Henry Roan. This trial, held in Guthrie, Oklahoma, followed the U.S. Supreme Court decision in United States v. Ramsey (1926), which established federal jurisdiction over the case. By this time, Ernest Burkhart had already been sentenced to life imprisonment by the Oklahoma courts.

The jury for Hale and Ramsey’s first trial began deliberations on August 20, but after five days, they were unable to reach a verdict, resulting in a hung jury. In the aftermath, several witnesses were indicted, tried, and convicted for accepting bribes or providing coerced testimony. A second trial for Hale and Ramsey was scheduled for late October and transferred to Oklahoma City.

During the second trial, Ernest testified that Hale had paid Ramsey with a new Ford and $500 to kill Roan. Hale denied the allegations, claiming he had no motive to harm Roan and asserting that he was in Fort Worth at a livestock show during the bombing of the Smiths’ house. On October 28, the jury began deliberations, and by the next morning, both Hale and Ramsey were found guilty of first-degree murder and sentenced to life in prison.

Hale appealed the verdict, leading to a retrial in federal court in Guthrie, Oklahoma. However, this trial also ended in a hung jury. A subsequent trial in Oklahoma City resulted in another guilty verdict, this time sentencing Hale to 99 years in prison. Hale appealed again to the United States Court of Appeals for the Eighth Circuit, which ordered a new trial. His final trial took place in federal court in Pawhuska, Oklahoma. He was convicted in federal court on October 29, 1929, for the murder of Henry Roan and sent to the Leavenworth Penitentiary in Kansas.

Henry Roan, Osage NationIndian Territory,

Parole and death

Hale was sentenced to life in prison but was paroled on July 31, 1947. Hale’s relatives said he once remarked, “If that damn Ernest had kept his mouth shut we’d be rich today.” He moved to Phoenix, Arizona around 1950 and died in a nursing home there on August 15, 1962. He was buried in Wichita, Kansas.

FBI Documents

Osage Indian Murders Part 01

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