𝗧𝗲𝗻 𝗧𝗵𝗼𝘂𝘀𝗮𝗻𝗱 𝗗𝗼𝗹𝗹𝗮𝗿𝘀 𝗗𝗲𝗮𝗱 𝗼𝗿 𝗔𝗹𝗶𝘃𝗲: 𝗧𝗵𝗲 𝗛𝘂𝗻𝘁 𝗳𝗼𝗿 𝗗𝗶𝗰𝗸 𝗚𝗿𝗲𝗴𝗴
On the morning of May 21, 1924, word crackled like wildfire across Osage County: Dick Gregg, a notorious outlaw with ties to the feared Al Spencer gang, had been captured. Just hours earlier, the Farmers State Bank in Burbank, OK had been robbed in a brazen daylight heist. Now, one of the men believed responsible was in custody following a dramatic and violent confrontation deep in the Osage Hills—a region long known as a safe haven for outlaws.
𝗚𝘂𝗻𝗳𝗶𝗿𝗲 𝗶𝗻 𝘁𝗵𝗲 𝗢𝗶𝗹 𝗙𝗶𝗲𝗹𝗱𝘀
Burbank, a booming oil town about 25 miles west of Pawhuska, was left shaken by the robbery. Witness accounts quickly tied Gregg to the scene. But it was swift action by two unlikely lawmen—John Henderson, a former deputy sheriff working as constable of nearby Lyman, and Freddie Graves, a deputized postal worker and son of the town marshal—that brought Gregg to justice.
The showdown unfolded in Lyman, a rough-and-tumble town in the heart of the Burbank oil field. Acting on reports of a disturbance near the Cadillac Rooms, Henderson and Graves approached a boarding house suspected of harboring outlaws. Graves circled back while Henderson knocked on the front door. There, Graves suddenly found himself face-to-face with Dick Gregg. Before he could draw, Gregg had him covered at gunpoint.
Moments later, Henderson entered the scene. Gregg spun around and opened fire. A bullet tore into Henderson’s hip. Despite the injury, both men returned fire. Henderson’s revolver eventually clicked empty, and Graves’s pistol misfired. Gregg pistol-whipped Graves, disarmed both men, and marched them at gunpoint toward a waiting car. "I'm taking you out to the prairie," Gregg warned, "and I'm going to shoot you both."
But fate—and a fearless taxi driver—intervened. As Gregg forced the wounded lawmen into the car, the driver struck the outlaw’s hand, knocking his revolver loose. Henderson lunged forward, locking Gregg in a half-nelson. The car exploded into chaos. A violent struggle ensued inside until Gregg was overpowered, shackled, and dragged from the vehicle.
When Marshal Arthur Graves and Deputy Smith Leahy delivered Gregg to the Osage County Jail in Pawhuska that night, he was beaten so badly that jailers couldn't immediately confirm his identity. His eyes were swollen shut beneath heavy bandages.
Gregg wasn’t alone. Authorities also arrested Wendall Powell, an alleged ex-convict, and Alta Gregg—reported as either Dick’s sister or his wife. She was described as a small woman with black hair and dark eyes and was said to be the getaway driver behind the wheel of the Cadillac sedan.
𝗧𝗵𝗲 𝗠𝗮𝗸𝗶𝗻𝗴 𝗼𝗳 𝗮𝗻 𝗢𝘂𝘁𝗹𝗮𝘄
Dick Gregg was no stranger to law enforcement. Born in Nowata, Oklahoma, his rap sheet was long and violent. Two years earlier, he’d been arrested near Bigheart (now Barnsdall) by Deputy Ted Strong alongside associates I.E. Berry and another gang member. Their car was loaded with firearms and ammunition. Strong, unaware of their identities, brought them into Pawhuska alone, where they were placed in the Osage County Jail. Gregg was soon extradited to Kansas, but jumped a $20,000 bond and vanished.
He resurfaced later in Pawhuska, where he engaged in a shootout with Pawhuska police during another attempted arrest. Officer C.E. Van Noy was wounded; Gregg escaped yet again.
He was a suspect in the June 7, 1922, murder of William Lockett, the night marshal of Ochelata, Oklahoma. Lockett was shot through the heart during a burglary that reportedly involved both Gregg and Al Spencer. Weeks later, Gregg and Spencer robbed a bank in Elgin, Kansas, escaping with over $20,000 in bonds and $1,500 in cash, taking hostages and fleeing back across the Oklahoma border.
𝗔 𝗞𝗲𝘆 𝗪𝗶𝘁𝗻𝗲𝘀𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗥𝗲𝗶𝗴𝗻 𝗼𝗳 𝗧𝗲𝗿𝗿𝗼𝗿 𝗢𝘀𝗮𝗴𝗲 𝗠𝘂𝗿𝗱𝗲𝗿𝘀
By fall 1925, the Osage Indian Murders—also known as the Reign of Terror—had sparked national outrage. Despite Bureau of Investigation agent Tom White making progress, J. Edgar Hoover, still forging his national profile, was demanding results. Fear gripped the Osage Nation, and families began fleeing their homes—some even leaving the country.
In a desperate bid for new leads, Tom White arranged a meeting with Dick Gregg, then serving time in a Kansas penitentiary. Through a local attorney, Gregg was transported to Pawhuska under guard to meet with White at the county jail.
In exchange for a sentence reduction, Gregg offered explosive testimony: he claimed that William Hale, the powerful rancher at the heart of the Osage murder conspiracy, had paid the Spencer gang $2,000 to kill Bill and Rita Smith. Gregg said he refused the hit, insisting he would not murder a woman. Even by the brutal standards of the era, Gregg maintained that killing an Indian woman crossed a moral line.
But before he could testify in open court, Gregg pulled off another sensational escape. In 1927, while being held in Pawhuska for the trial, he escaped the Osage County Jail and vanished into the hills once more.
𝗙𝗶𝗻𝗮𝗹 𝗥𝗲𝗰𝗸𝗼𝗻𝗶𝗻𝗴
Gregg remained a fugitive for over two years. During that time, he was linked to a string of robberies across the region. The last confirmed sighting came after a robbery of the Peoples State Bank in Wichita, Kansas, on July 26, 1929.
His criminal saga ended weeks later, on August 29, 1929, in a deadly shootout outside Sand Springs, near the Tulsa-Osage County line. After a car accident, Gregg and an accomplice attempted to flee. When Tulsa Highway Patrolmen Ross Darrow and Abraham Bowline tried to make an arrest, Gregg opened fire, killing both officers.
As Patrolman Darrow fell from his wounds, he summoned the strength to return fire—his final act of duty. His bullet struck Gregg, who collapsed and died at the scene, ending one of the most violent outlaw careers in Osage County history. Nearby, officers arrested Bob Dyer, a 29-year-old Indian cowboy from Pawhuska, in connection with the shooting. Dyer told authorities that he and Gregg had traveled to Tulsa the night before to have Gregg’s car repaired at a local mechanic's garage. With no prior criminal record and insufficient evidence tying him to the crime, Dyer was later released.
The deaths of Patrolmen Darrow and Bowline left behind grieving widows and children—and marked the grim closing chapter of Dick Gregg’s long and bloody reign across the Osage Hills.
𝗟𝗲𝗴𝗮𝗰𝘆 𝗼𝗳 𝘁𝗵𝗲 𝗢𝘀𝗮𝗴𝗲 𝗛𝗶𝗹𝗹𝘀
Author Gerald Moore once wrote that, since the days when Abilene, Arkansas City, and Dodge City were young cow towns, the Osage Hills had served as a “haven of the fugitive.” The tangled scrub oak, deep canyons, and rocky ridges formed a natural fortress for those hoping to evade the law.
It was in this unforgiving wilderness that outlaws like Dick Gregg disappeared—and where, sooner or later, justice caught up with them.
… See MoreSee Less
2 days ago
