Going by various names, including the Cherokee Kid, John Williams; John Mayfield, Bill led the Cook Gang in terrorizing Indian Territory by robbing banks, trains, post offices, stores and individuals. In no time, the Cook Gang was pursued by dozens of lawmen who tracked them down one by one.

In June, 1894, Cherokee Bill, Jim, and Bill Cook were confronted at Fourteen Mile Creek near Tahlequah, Oklahoma  with a warrant for Jim’s arrest. In the inevitable shoot out that occurred, Cherokee Bill shot and killed lawman Sequoyah Houston. Jim Cook was also badly wounded and the other two took him to Fort Gibson. Forced to leave him, he was later captured by lawmen.

On July 14th, the gang held up a stagecoach and just two days later, they robbed a man named William Drew. On July 18th, they held up the Frisco train at Red Fork. However, due to the express messenger having had the foresight to hide the money behind some boxes, the gang escaped with very little.

On July 31, 1894, the gang stole $500 from the Lincoln County Bank in Chandler, Oklahoma, killing one person and wounding others. In the process, gang member, Elmer Luca, was shot and captured by authorities.

Hotly pursued, the Cook Gang was surrounded at the home of a friend some fourteen miles west of Sapulpa, Oklahoma on August 2, 1894. During the volley of gunshots, one of the lawmen was shot and severely wounded. Two of the gang members, Lon Gordon and Henry Munson were killed and Ad Berryhill was captured. The rest of the gang fled.

The gang then robbed the Kansas City and Missouri Express at Coretta, Oklahoma on  October 20^th, after which they robbed a number of stores and company offices, stealing large payrolls. When the gang robbed the Schufeldt and Son store in Lenapah, Cherokee Bill killed a man and the lawmen’s determined pursuit increased and all were eventually captured or killed.