From the time the Cherokee Nation was conceived until Oklahoma became a state, because of legal confusion, crime and the number of criminals steadily increased. When the Nation was founded a significant number of white settlers and fur traders were already present and even then there were differences of opinion over what laws which group, Indians or white settlers, should obey. In 1828 the “Old Settlers” as the Western Cherokee were known, moved from Arkansas Territory and established a government with laws, but they only applied to the tribe. White settlers, many of whom arrived 20 years earlier, were exempt. Their laws, such as they were, were defined and enforced by the army representing the federal government. This confusion eventually became a recipe for disaster, a magnet for criminals of all descriptions to move to Indian Territory.

There were no “typical” criminals, some were vicious, some had citizen support, some were products of the media, others were simply incompetent and they came from all walks of life. The Encyclopedia of Western Gunfighters lists 107 different original occupations of criminals ranging from rogue lawmen to a school superintendent. Northeast Oklahoma had a variety and some were young hardened criminals. Eighteen year old Bob Rogers shot Vinita attorney Jesse Elliot, kicked and stomped the corpse, then placing Elliot’s hat on his head, sat on the body while he rifled through the dead man’s clothes. After a brief but violent career, he was killed just before his 22nd birthday. Crawford Goldsby aka Cherokee Bill also began breaking the law as a teen ager. He was a vicious killer and unrepentant to the end. When condemned to hang by Judge Isaac Parker, Goldsby was asked if he had any last words as he stood on the gallows, he replied, “I came here to die, not give a speech.”

Ordinary law abiding citizens also became criminals for a variety of reasons and often had the support of their neighbors. The Dalton brothers, Bob and Grat, were lawmen before they turned to crime, their brother Frank was killed in the line of duty as a Deputy Marshal attempting to apprehend a suspected murderer. The Dalton Gang’s career lasted only 1½ years ending with the disastrous attempt to rob two banks in Coffeyville that resulted in the deaths of four, including Bob and Grat, and the capture of their brother Emmett. But Evan Barnard, a farmer interviewed afterwards stated “These boys, like the average western man, were bighearted and generous in every way. They attended the dances in the country and were liked by all the settlers.” Bill Doolin who usually rode with the gang was not present or at least escaped. Soon after Coffeyville he organized his own gang known as The Wild Bunch. Doolin and his gang were idolized by some citizens who lauded his moral code, always treating women with respect. The gang members were polite, always removing their Stetsons in the presence of women. One local paper reported that “When robbing a train, the Doolin Gang refuses to take anything from a woman.” Their politeness paid dividends. According to reports there were many who would get up in the middle of the night if necessary to ride to Doolin and warn him of the approach of law officers.

Another category of Wild West criminals was created by the national media or dime novels. Bell Starr became nationally known after an eastern publisher distributed Belle Starr, the Bandit Queen, a paperback presenting a glamorous but fictitious life style, even Belle would not have recognized. For the most part a horse thief that slept around, some say she was waylaid and killed coming home from a dance by her latest husband, or a jealous lover, or her own son.

Al Jennings organized the “Jenning’s Gang” through whose ineptness the media entertained the nation. A lawyer living in western Oklahoma, Jennings turned to crime after his brother was killed in a saloon shoot out and formed a ragtag bunch that became a public laughing stock. Their foray into crime evolved into a series of bumbles exemplified by the report of an attempted train robbery on October 1, 1897. Several members boarded a passenger car with Jennings disguising himself wearing a mask, a piece of bearskin over his head to hide his identity. Other gang members entered a box car and affixed dynamite to a safe supposedly containing $93,000. They blew up the box car, but not the safe. Undeterred, they ordered everyone off the train. Told to line up, the 110 passengers were ordered to place their valuables in a feed sack. The “take” amounted to $400 and some jewelry. After a series of similar failed escapades the gang finally was captured and sentenced to prison. To compound the melodrama that was his life, when he was finally released, Jennings unsuccessfully ran for Oklahoma County Attorney, then Governor. His political aspirations as unsuccessful as his life of crime, Al Jennings moved to Hollywood and, finally finding his niche in life became a moderately successful actor. Killers and clowns both products of a broken legal system.

Bruce Howell is an author and retired educator. His work includes 1806, an exploration of the Cherokee Nation in Indian Territory. He resides on Grand Lake with his wife, Kay.