Train robbers, bank robbers, and other gun-toting outlaw gangs are a part of the heritage of Oklahoma. Also part of that heritage are the lawmen who pursued those outlaws. The daring exploits of men on both sides of the law often were the subject of sensational news stories. But the grim reality is that law and order in the early days of Oklahoma was a deadly business, and shootouts between outlaws and lawmen were common.
Infamous gangs such as Frank and Jesse James, the Youngers, and the Daltons all sought refuge at one time or another in the Indian Territory. The federal court for the Western District of Arkansas had been established in Fort Smith by Congress. The court had jurisdiction over all lands between Kansas and the Red River, the largest jurisdiction in the world. In 1875, Isaac C. Parker was appointed judge. Parker, the "Hanging Judge," took on the outlaws who hid out in the Indian Territory, hiring almost 200 deputy marshals to track down the lawbreakers who robbed and killed in both Oklahoma and the surrounding states. Indian Territory was a favorite hiding place for outlaws wanted elsewhere because there was no law to extradite a badman for his crimes in another state or territory. During the years of Judge Parker's court, 160 offenders were sentenced to die by the "Hanging Judge." Seventy-nine of them were hanged in Fort Smith. But the cost for bringing them in had been high. More than 100 deputy marshals died at the hands of the outlaws during the years of "Hell on the Border."
The land run of 1889 opened Oklahoma to settlement. Oklahoma Territory was organized in 1890 and the territorial capital was established at Guthrie. In 1892, the notorious Dalton gang was gunned down just across the border in Coffeyville, Kansas, while attempting a double bank robbery. Gang member Bill Doolin escaped and returned to start a new reign of bloodshed with his own gang, known as the "Wild Bunch." Deputy United States marshals riding out of Guthrie went after the Doolin gang in the small community of Ingalls in 1893. In what became known as the "Ingalls Raid," more than a dozen lawmen surrounded the tiny town east of Stillwater where the Doolin gang was holed up. A fierce gun battle ensued in which three marshals were killed. Bill Doolin escaped.
Leading the fight for law and order in the territory were Deputy United States Marshals Bill Tilghman, Heck Thomas, and Chris Madsen, known as the "Three Guardsmen." Tilghman went after Bill Doolin, tracked him down in Eureka Springs, Arkansas and captured him single-handedly without firing a shot. Doolin was returned to the federal jail in Guthrie, but later led a daring jailbreak and escaped. Heck Thomas took to the trail of the outlaw and, in 1896, found Doolin in Lawson on the Payne/Pawnee county line east of Stillwater. Doolin fired on the lawmen and was killed in a hail of bullets. The next year, Deputy United States Marshal Bud Ledbetter captured outlaws Al and Frank Jennings. By the turn of the century, the lawmen began to win the battle.
In 1914 and 915, a wave of bank robberies swept across the state. The man behind them was believed to be Henry Starr, a relative of the infamous Belle Starr, the "Queen of the Outlaws." Henry Starr had begun a life of crime in 1890 which lasted for 30 years. In March 1915, Henry Starr attempted to rob two banks at the same time in Stroud. Starr was shot during the robbery attempt and captured by townsmen. He was sentenced to 25 years in prison, but was paroled after serving four years. Starr was killed in Arkansas in 1921, attempting another bank robbery. Starr did, however, illustrate the changing style of the outlaws. Starr had ridden into Stroud on horseback armed with a six-shooter, but when he was killed in 1921 he had driven into town in a high-powered automobile. Outlaws were beginning to use automobiles and machine guns.
The early 1920's also saw the discovery of oil in Oklahoma, and "boom towns" began to spring up around the state. These oil towns became the scene of much violence. One such town was Cromwell in Seminole County. Oil had been discovered in October of 1923 and by 1924, Cromwell had 10 unsolved murders. Governor M. E. Trapp called upon former deputy United States marshal Bill Tilghman, now retired, to take on the job of town marshal and clean up the boom town. But in November 1924, the famous lawman died at the hands of a drunken federal prohibition agent. His murderer was tried, but found not guilty, and lived to slay another lawman a few years later. Tilghman's body was taken to the rotunda at the state capitol, where thousands of Oklahoman citizens paid their respects to one of the "Three Guardsmen" who had fought the badmen in the territorial days.
The renewed wave of violence prompted Governor Trapp to propose to the legislature in 1925 an "agency of special special investigators or state police to combat bandit gangs and dangerous criminals who have terrorized banks of the state." The new agency was named the Oklahoma Bureau of Criminal Identification and Investigation, better known as the State Crime Bureau, and was the first state law enforcement agency in the nation to combine an identification bureau of fingerprint experts with a staff of field operatives to track down and apprehend outlaws across the state. In its first year of operation, these state lawmen killed 11 bank robbers. But the battle between lawmen and bank robbers in the 1920's was not without it's price.
In August of 1926, brothers Mathew and George Kimes robbed two banks in Covington, a small town in Garfield County. They headed for their home near Van Buren, Arkansas, and successfully eluded lawmen across the state until they reached Sallisaw, where they encountered a road block set up by Sequoyah County Deputy Sheriff Perry Chuculate and Sallisaw Chief of Police J. C. Woll. In a fierce shootout, Deputy Chuculate was killed and Woll was captured and held hostage by the outlaws. Woll later was released. The Kimes brothers were tracked by State Crime Bureau operative Lee Pollock to the family farm outside Van Buren. Pollock shot it out with the bank robbers, captured them, and returned them to Oklahoma. George Kimes was sent to prison at McAlester. But Matt Kimes was still in jail in Sallisaw in November, 1926, when members of his gang forced their way into jail at gunpoint and rescued him. The Kimes gang escaped following a wild shootout. The next month, State Crime Bureau operative Luther Bishop was brutally shot to death in the middle of the night at his home in Oklahoma City. Some lawmen speculated that Bishop was murdered by one of the many outlaw gangs the officer had chased during his career. The case never was solved.
Shootouts with badmen continued. In 1929, in Tulsa, oulaw Dick Gregg and officers Ross Darrow and Link Bowline were involved in a bloody shootout. Three years later, in 1932, the state witnessed what may have been the bloodiest year in Oklahoma's fight for law and order. In January, bank robber Charles "Pretty Boy" Floyd robbed the banks in Paden and Castle on the same day, and robbed the bank in Dover the next day. Floyd eluded police in February, and in April "Pretty Boy" killed lawman Erv Kelly, who was waiting to ambush the outlaw at a farm belonging to Ruby Floyd's father near Bixby. In June, a gun battle between "Pretty Boy" Floyd and lawmen took place near Stonewall. Floyd escaped.
In July, the man who had killed famous marshal Bill Tilghman in 1924 pulled a gun on a lawman in the Corner Drug Store in Madill. State Crime Bureau Agent Crockett Long returned fire, and when the smoke cleared, both men lay dead. A month later, Clyde Barrow and Raymond Hamilton of the "Bonnie and Clyde" gang shot Atoka County Sheriff C. G. Maxwell and killed deputy E. C. Moore near Stringtown. Also in August, the bank in Bixby was robbed by Fred Barker of the "Ma" Barker gang. In September, State Crime Bureau operatives shot it out with fugitives in the Cookson Hills. In November, "Pretty Boy" Floyd robbed banks in Henryetta and his home town of Sallisaw.
Since territorial days, Oklahoma lawmen had been fighting train robbers, banks robbers, bootleggers and just about every other type of outlaw. But in 1933, something new challenged the officers of the state. On the evening of July 22, Charles F. Urschel, a wealthy oilman, was kidnapped at gunpoint from his home in Oklahoma City by George "Machine Gun" Kelly. News of the sensational crime swept the nation. The federal government responded by sending agents from the Department of Justice's Bureau of Investigation, later called the FBI. After a ransom was paid, Urschel was released. "G-Men" were quick to track down "Machine Gun" Kelly, his wife and outlaw Harvey Bailey. All were convicted of kidnapping. Bailey escaped from the Dallas, Texas, county jail while awaiting transfer to Oklahoma City, but was captured later the same day by Ardmore, Oklahoma lawmen.
In 1934, Bonnie Parker and Clyde Barrow were killed in a shootout with lawmen in Louisiana, and "Pretty Boy" Floyd was killed by G-Men in Ohio. In 1935, Kate "Ma" Barker and her son Fred were killed in a shootout with G-men in Florida. The Barker clan is buried in a cemetery near Welch, Oklahoma and "Pretty Boy" Floyd is buried in the Akins cemetery near his home town of Sallisaw. The "outlaw era" was drawing to a close. Efforts were being made in police departments around the state to modernize. Challenges still faced Oklahoma lawmen in the years to come, but the days when only a handful of lawmen pursued notorious outlaws, and capturing badmen meant first winning a gunfight, began to pass into history.
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