Following the Civil War, because white men were exempt from Indian laws, the Oklahoma of the latter part of the 19th century was a breeding ground as well as a magnet for law breakers from all parts of the country. That vacuum is understandable, bad men are attracted to a region where law enforcement is very difficult. What is unclear is why so many seemingly upright citizens, born and raised in the region, switched sides and became criminals. Some set aside their original occupations as law officers, cowboys, ranchers, saloon keepers, even as dentists and school teachers. They joined or formed gangs that were organized and efficient in stealing money from railroad and bank heists, then moving on until the inevitable showdown with the law. Was it the excitement? Was it the easy money? Eventually, most died as a result of their new found occupation, very few walked away and survived.

In Northeastern Oklahoma we have our own “home grown” example of honest men gone wrong, the four Dalton brothers, Bill, Bob, Grat and Emmett. For several years the boys and their family farmed in the Success community north of Ketchum. Unfortunately for the family name, within the annuals of the history of our region, Dalton is synonymous with the boys’ ill- fated decision to rob two banks at one time in Coffeyville, Kansas, during October of 1892. Their effort was the result of an ego trip by brother Bob who wanted the gang’s exploit to go down in history as the first (perhaps only) gang to rob two banks at the same time. Bob’s decision resulted not only in his death, but that of his brother Grat and two other gang members. Only his younger brother Emmett survived, shot 23 times, miraculously lived, was imprisoned for 14 years and upon his release, became a productive citizen again. There are several versions regarding Bob’s absence from the massacre but soon after he organized another gang, the Wild Bunch, and was killed in 1894

As a result of the Coffeyville fiasco the prevailing image of the family name is associated with crime and criminals, but in fact the four brothers, were only a small portion of what collectively was a family of 15 children, an infant twin died in 1878 and the couple’s first child died when he was seven. While it is true that Adelaide, the mother of this clan, was the daughter of Cole Younger, infamous leader of the Younger-James gang with Jesse James, there is no evidence that her background influenced the children. Nor did their father Ben. Ben Dalton, was born in Kentucky, farmed throughout his life and died two years before the Coffeyville episode. At the time, most of the family were farming and ranching in Kingfisher county.

The early childhood years of the Dalton children, ten boys and three girls, were typical of any farm family with chores and any kind of employment available. Interestingly, as the boys grew older, several turned to law enforcement. In 1884, Frank became a U.S. Deputy Marshal, served under Judge Isaac Parker and developed a reputation as being brave and efficient. Frank served for three years on many dangerous assignments, but was killed in 1887 attempting to arrest a horse thief. He was buried in the same Coffeyville cemetery his brothers Grat and Bob would occupy five years later.

Bob Dalton began assisting Frank before his death and afterward applied to be commissioned as a Deputy Marshal and was assigned to work for the Wichita, Kansas, Osage Court. Bob hired his younger brother Emmett as his deputy and both continued to work as law enforcement officers for the next three years. During April, 1890 Bob and Emmett were sent to Claremore in Indian Territory to arrest Alex Cochran who was accused of killing a U.S. deputy marshal. The brothers picked up Cochran’s trail and spotted a rider. After attempts to get him to stop, Bob shot the rider from a distance, only to discover it was not Cochran, it was his son. He continued to work for the Osage court until rumors began to spread accusing Bob and Emmett of illegally selling whiskey to Indians. The killing of Cochran’s innocent son combined with the rumors led to Bob’s termination. Apparently, it also led to Bob and Emmett’s change of attitude toward the law. In July of 1890 Bob, Emmett and their brother Grat, were accused of stealing horses near Claremore and selling them in Kansas. With rumors of a posse being formed to capture them, the three brothers fled to Turlock, California, to stay with their older brother Bill. Bill, only 24, apparently well regarded locally, had been elected representative to the California legislature from Stanislaus County, but for reasons unknown, was persuaded by his brothers to join them in robbing a train. He and Grat were soon captured but escaped, eventually reconnected with the other two and returned to Oklahoma. Their notoriety was about to begin, but the question “why’ they chose that path like so many others, still remains unanswered.

Note: Snapshots of Cherokee Country is available at and

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.