In 1886, they moved again to a place near Coffeyville, Kansas. In this rough and wild area, the Dalton brothers inherited a tradition of violence on the bloody ground of the Missouri -Kansas border, where Quantrill’s raiders and other guerilla bands operated during and after the Civil War.

When the Oklahoma Territory opened for settlement in 1889, the family headed south again. However, Lewis died along the way leaving Adaline to raise the younger children alone. Adaline continued on, placing a claim on the banks of Kingfisher Creek in Indian Territory, where initially she and the family lived in a dugout. By this time the older Dalton brothers were on their own.

For a short time the brothers served on the side of the law, working as U.S. Deputy Marshals. Their older brother, Frank Dalton, was commissioned a Deputy Marshal for the federal court in Fort Smith, Arkansas and Bob Dalton served on several of his posses. On November 27, 1887 in a gun battle with the Smith-Dixon Gang, Frank Dalton was shot and killed in the line of duty.

Grat Dalton followed in Frank's footsteps, first taking his place as a Deputy Marshal in Fort Smith, Arkansas and two years later as a Deputy Marshal for the Muskogee court in Indian Territory in 1889. That same year he received a bullet in his arm while attempting to arrest a suspect. Bob Dalton was also commissioned as a Deputy Marshal for the federal court in Wichita, Kansas, working in the Osage Nation, in 1889.

Bob Dalton, who would later become the leader of the Dalton Gang, was the wildest of the bunch. When he was just 19, he killed a man, claiming it was in the line of duty. Nevertheless, some suspected that the victim had tried to take away Bob's girl.

While Emmett Dalton worked as member of some of his brothers’ posses, he made his living working as a cowboy on the Bar X Bar Ranch near the Pawnee Agency. While working at the ranch, Emmett met two men who would later become members of the gang -- Bill Doolin and William St. Power, alias Bill Power. Power, also known as Tom Evans, had drifted into the area from Texas with a trail herd from the Pecos.