Terror’s Legacy

by Jason Christian


Mark Freeman Jr. was just across the Kansas line from his 3,500-acre cattle ranch. It was in the early 1950s when he and a fellow rancher were bidding on livestock. His buddy nudged him.

“Look down there, you’ll be interested in this,” the friend said. Mark brushed him off. “Son, I’m buying cows.”

“You see that man talking to that old cowboy?”

Mark said yes.

“That’s Bill Hale.”

They both stood and marveled at the man who was never again supposed to see the light of day.

“His hair was still black. He was dressed in a suit and had a tie—that son of a bitch always dressed that way.” Mark laughed. “I got a kick out of it because I was raised on them Bill Hale stories.”

Now 93, Mark lived through the aftermath of the tragedies known in Osage County as the Reign of Terror. He was born in 1920 to a white father (offensively called a “squaw man” in those days) and an Osage mother. He served as a Tribal Council member and as a member of the Osage Congress. As a World War II veteran and lifelong rancher, Freeman is a paradigm of the tough-as-nails, no-nonsense cowboy—a Clint Eastwood type. He didn’t have many good things to say about Bill Hale.


“If he’d have come up on someone like I am,” he assumed a serious posture, “or I was when I was 25 years old—I’d have killed the son of a bitch. Because he was killing my people.”

William K. Hale, known as Bill, was a local legend even before he made the papers. He was born and raised in Greenville, Texas, and moved to Osage County around the turn of the 20th century. It was a time when cattlemen and roughnecks were coming in droves to make it rich, or just to make it at all. Freeman says that Hale “started out in a tent,” alone and ambitious, before he sent for his wife and nephews to join him on the Oklahoma prairie.

If his humble roots didn’t win people over, his showmanship helped. Hale could entertain crowds with the best of them. He told jokes, did rope tricks, and handled a horse like an expert. And then there was his famous gift giving. He liked to cheer the kids up by buying them ponies, and won over townsfolk with brand-new suits. He co-signed loans and visited the sick and elderly. I was told that he brought loads of beef and pork to the yearly Osage dances. I imagine him as a sort of people’s aristocrat, a saintly cowboy gentleman. He even gained a position as reserve deputy sheriff . He was the kind of outsider the locals admired: A self-made man who was everyone’s friend.

In time, Hale’s wealth caught up to his personality. He owned a couple of homes, one in Fairfax and a ranch house in the country. He owned 5,000 acres of grazing land and leased another 45,000 more from Osage landowners. He invested in a bank, a general store, and a funeral home. With so much wealth [1] and influence, he started calling himself “King of the Osage Hills.” And he started to act like it.


William K. Hale, “King of the Osage Hills.” Photo courtesy the FBI.

Headrights and Guardians

When Hale arrived to Osage County, the Osage tribe was not yet wealthy. That story is a marvel on its own. A unique economic arrangement was set up for the Osage. Back in 1906, when the tribe was forced to divide the allotments of its communally owned land, they gave every member—all 2,229 of them—an equal share of land and mineral rights brought in by the tribe. Even as the tribe grew in numbers there would forever be just 2,229 equal shares from then on. Some of the money came from grassland leases, but the vast majority came from the seemingly bottomless lakes of oil beneath Osage County. The royalty payments from mineral income became known as “headrights.” Headright payments began modest but soon everyone was surprised at their incredible gains. The Osage became wealthy seemingly overnight. They built mansions and hired butlers, bought luxury automobiles and hired chauffeurs. But their opulence didn’t sit well with the racist and jealous of America. Apparently, even some newspapers felt the tribe didn’t deserve their new-found wealth.

Because the Osage seemed to be blowing all their money, at least to the passive observer 1,200 miles away in Washington, D.C., action was taken. Congress passed a law in 1921 requiring all [2] Osages of one-half blood quantum or higher to have a “guardian.” The guardians (pronounced gar-deen locally) were there to give Osages their royalty checks every quarter and help them spend it “wisely.” But guardians were only required to pay Osages (under guardianship) $1,000 a quarter, even when headright earnings were three times higher. [3] With little to no oversight, the rest just seemed to evaporate, and almost immediately Osages under guardianship began dying.

“These damn lawyers, and some damn preachers—not all preachers are good—would be guardians for three, four, five people,” Mark Freeman Jr. told me.

The Murders

The first murder shocked the public, but Hale wasn’t yet a suspect.

In 1921 a young full-blood Osage woman named Anna Kyle Brown was found dead in a ravine with a gunshot wound to her head. The local undertaker and two doctors conducted a crude autopsy on Brown, hacking up her body and quickly disposing of it. The tribe was horrified, and many wondered about the integrity of the doctors.



An inquest was held and revealed little. One of the last men to see Anna alive was a man named Byron Burkhart, Bill Hale’s nephew. He was questioned and denied any wrongdoing. Authorities had nothing on him and released him, and the whole matter was dropped. Life went on.

More murders followed. Anna Brown’s cousin Henry Roan was found shot to death. William Stepson, a rodeo star, died in his bed, allegedly of poison. Charles Whitehorn, Joe Yellow Horse, Henry Benet, Hugh Gibson—the list is long, and to this day the number of murders is debated. Nevertheless, Osage County remained relatively quiet—until the explosion.

On March 10, 1923, a house in Fairfax was obliterated by a bomb, sending debris into the trees and yards all over town. A white man, W.E. “Bill” Smith, and his Osage wife, Reta née Kyle (Anna’s sister), owned the home. Reta and their housekeeper, Nettie Brookshire, were killed instantly from the blast. Bill died a few days later, taking to the grave anything he might have known about his wife’s family’s murders.






Something had to be done. The Osage Tribal Council desperately appealed to the federal government for help. [4] Within weeks the newly formed Federal Bureau of Investigation launched a major investigation in which they pioneered the use of undercover agents and informants.

When the feds arrived to Pawhuska, they discovered a complicated mess, and the agents were not welcomed. FBI files say that they found Osage County to be dangerous and full of uncooperative “transient ‘potlickers’ [sic], oil workers, poor whites.”

An atmosphere of fear permeated the area; however, they began to piece together many of the crimes against the Osage people that were happening right under the nose of law enforcement. A conspiracy was unfolding that would have made its murdering mastermind wealthy beyond anyone’s imagination. A whole Osage family was being targeted, it appeared. Anna Kyle Brown had been the first. [5] Her mother, Lizzie, died soon after (maybe from natural causes, maybe not), and then Anna’s cousin Henry Roan (on whom Hale had taken out a $25,000 life insurance policy and later sued to collect). The next in line to die were the Smiths and their unfortunate servant. And the last heir, Mollie Kyle, happened to be married to Earnest Burkhart, Bill Hale’s other nephew.

With the benefit of hindsight, the plan looks simple and obvious: As each member of the Kyle family was killed, his or her headright would pass to the next of kin. Each death would bring all of the headrights closer to Burkhart’s hands, who would either share his spoils with Hale, or else he would surely be eliminated. But still no one had implicated Hale.

Yet more deaths occurred. Like George Bigheart, son of the last hereditary chief of the Osage tribe. And attorney William Vaughn, who was purported to be investigating the recent murders. Bigheart died in his bed, from an unidentified illness. Vaughn, after visiting Bigheart in the hospital, was conveniently thrown off a moving train as he was returning to Pawhuska. These murders happened three months after the FBI began their investigation.

The feds moved sluggishly. Death after mysterious death was marked down as natural or accidental. Autopsies were rare and investigations even more so. Finally, after deaths had reached apocalyptic levels, the FBI and Bureau of Indian Affairs had enough evidence to make arrests. Bill Hale and a few members of his gang—besides the ones who mysteriously died around that time [6]—stood on trial for murder.

A long battle of jurisdiction between state and federal courts ensued. After wading through tampered juries, bribed or threatened witnesses, perjured and falsified testimonies, and several grueling trials, justice finally prevailed—kind of. William Hale and a hired gunman got life sentences, though they were paroled after just 20 years. [7] Hale’s nephew Earnest Burkhart only served 11 years and was inexplicably pardoned by Governor Henry Bellmon, and everyone else either got a slap on the wrist or walked free. [8] The sensational case made national headlines; the FBI website has more than 3,200 pages dedicated to it. Reading like bad noir, the FBI describes the details of Hale’s plan and the Bureau’s success in thwarting it. The Bureau considered the Hale case a triumph of justice, even as corpses were surfacing during and after the trials.


“The FBI, once Bill Hale was convicted, dropped the whole case. Didn’t go on any further,” Mary Jo Webb, a retired teacher, told me. “There were many murders that weren’t taken up by the government.” And she went on to tell me about her own grandfather’s controversial death after the Hale conviction. A full-blood, one of the original allottees with a full headright, Webb’s grandfather was killed in a hit and run accident, resulting in a third of his headright landing in the lap of his former wife, a white woman.

“History’s going to remove all the fullbloods,” Webb said. “That’s the modern day history of how the Osages have been decimated by greed. There’s a lot more stories that never made the paper.”

The FBI tallied at least two dozen murders. Others claim hundreds of Osages were killed, if one looks back before the 1920s. Webb admits, “It’s a long story. It would take days.” There is no way of calculating the damage done to her people, she says.

Webb, a former member of the Osage Constitutional Commission, has been trying to bring these facts to light all her life. At 79, she has a reputation as Fairfax’s expert on the Reign of Terror. “They [the killings] were labeled as ‘accidents.’ Or they were poisoned and they said, ‘He had a bad stomach.’ ” Some Osages were drugged or whiskey-ed, only to find themselves married to a swindler the next day.

Even now, Webb told me, there are white descendants who have inherited “a piece of some full-blood’s estate [and] they think, ‘I’m probably part Osage, or I’m close to this family.’ Of course, that’s just not true.” People don’t know the history, and that is part of the problem, she says. “I made sure my family knew who was responsible [for my grandfather’s death].”

Mary Jo Webb pulled out a box of files (she had two more in the other room) and began showing me newspaper clippings, photographs, and other material on the subject. She had a reputation for doing independent research, but nothing ever materialized into a book. However, she did put together an exposé on some of the killings and some of those responsible who never went to jail. Around 20 years ago, she placed the document in the Fairfax library and it eventually went missing.

Not long after that she received an anonymous phone call from a man threatening to kill her. I asked her why someone would give her anonymous death threats and she replied candidly, “I named names.”

In Osage County today, you see a few elegant buildings boarded up and a few mansions in shambles. Th e only indicators of an oil economy that I saw were some scattered derricks in the wide open prairie that was once forested them, and a company on the edge of Pawhuska selling oil field parts and used pump jacks. Signs of a legacy of murders are less tangible. The oldtimers
know it in their bones. And the younger ones seem to be just trying to get by and move on from the haunting past that traumatized their elders nearly a century ago.


1.The New York Times reported in 1926 that he was worth half a million dollars ($75 million today).

2. If Osages could prove they were “competent” to an unsympathetic court, they could get out of having a guardian. Many gave up or didn’t try.

3. In 1923, the peak earnings for every headright shareholder was $11,800.

4. The price the FBI took for their services amounted to $20,000.

5. Anna Kyle Brown was pregnant when she was murdered and it was widely believed that Bill Hale was the father.

6. The most well-known of them was Henry Grammar, a world-champion roper turned bootlegger and criminal. He died mysteriously in a car accident shortly after the FBI began their investigations. Many suspect he was killed by Bill Hale.

7. Hale was known to consort with organized crime bosses from Kansas City (“thieves and bounders,” according to Mark Freeman Jr.), and Mark also believes that that his eventual parole came from an underhanded relationship with President Harry Truman, of Kansas City.

8. Kelsey Morrison received a life sentence for Anna Brown’s murder but was paroled after just a few years. He was later involved in other crimes and was killed in a shootout with the police in 1937.

Originally published in This Land, Vol. 4, Issue 15. August 1, 2013.