Cherokee Bill was a member of the notorious Cook Gang that had been terrorizing the Indian Territory. He was apprehended near Newt, I. T. on January 29, 1895, and delivered to Judge Parker's Court in Fort Smith where he was found guilty of murdering Ernest Melton during the gang's robbery of the Shufeldt store in Lenapal I. T., on November 9. 1894. He was sentenced, by Parker, to hang on June 25, 1895. His lawyers appealed the case and won him a stay of execution.

While in jail Cherokee Bill and Henry Star were housed on the same floor of the jail, the lower floor of the jail known as "Murderer's Row". Henry was in jail awaiting a new trial for the murder of Deputy Marshal Floyd Wilson. He had been tried, found guilty and sentenced to hang by Parker. However, his lawyers were successful in winning an appeal to the U.S. Supreme Court, and he was granted a new trail. During their stay at the jail, the boys had met and become friends.

As days pasted by, Bill's mood grew uneasy. It was predicted by other prisoners that "something terrible" would happen. On July 10, where was a search of the entire prison. The guards found 9 45 cartridges and a 45 revolver was found in the bathroom of the lower floor. In the weeks that followed there was several rumors about Bill attempting a prison break. The guards remained alert and kept a close eye on Bill.

At 7 o'clock on July 26, Turnkey Campbell Eoff and Guard Lawrence Keating entered Murderers' Row to lock the prisoners in their individual cell. During the day the prisoners were granted use of the entire cell block area, and returned to their cell at night. Night guards Will Lawson, Bras Parker, and William McConnell had just came on duty and were outside the cell block.

As Eoff was locking the cells, at the cell next to Bill's Eoff had trouble inserting the key. The keyhole had been stuffed with paper. He called to Keating that something was wrong. At that moment Bill leaped from his cell with a pistol that had been smuggled him, and ordered them to throw up their hands.

Keating reached for his gun, and Bill shot him in the stomach. Eoff fled back up the corridor. Bill followed him and fired four shots at him. George Pearce, who was one of the ring-leaders of the plot, jumped from his cell and also chased after Eoff with a broken table leg he was using as a club. Meanwhile, Guard's Lawson, Parker, and McConnell opened fired on Bill and Pearce and drove them back down the corridor.

Lawson saw the dying Keating at the foot of the stairs. As he reached over to pick up the officers pistol, Keating called to him, "Kill the dog, Will, he has killed me," then he died.

Deputy Marshall Heck Bruner and Captain Berry, hearing the gunfire, raced to the jail and joined on the fight. By this time Bill was able to reach the safety of his cell, from there he could cover the corridor with little danger to himself. It was a virtual "stand-off", Bill couldn't leave his cell and the guards couldn't enter the cell block. A "sniping match" between Bill and the guards began. Every time that Bill would fire he would "gobble" like a turkey.

For Fifteen minutes the shooting continue. Bill even shot at two citizens that were trying to carry the body of Keating out of the cell block. Most of the prisoners had taken refuge under their bunks. Outside the cell block twenty or more armed men. Captain Berry tried to get Bill to surrender his gun, but Bill refused.

Outside a crowd had formed, and there were shouts of "Lynch him!" Bill yelled back: "I didn't want to kill Keating: I wanted my liberty. Damn a man that won't fight for his liberty! If I hadn't shot him, he would of shot me."

Star, who was watching the excitement from a cell on the west side of the cell block, told the marshals that: "If you promise not to kill Bill, I will go get his pistol."

It was an unheard of thing to do. The marshals with no other solution at hand to the situation, agreed. The order was given to the guards to hold their fire.

Star went to Bill's cell and talked with Bill. He told him it was useless, that he might get a few more guards, but that he was not going to get out. Bill took his advice and handed over his pistol to Star. Star walked to the end of the corridor and handed it over to the guards. The guards then entered and covered Bill with their guns while a thorough search of cell was conducted. He was then handcuffed, chained, and locked back in his cell.

At the autumn term of the court, Bill plead not guilty and his trial was set for August 8. The grand jury returned indictments against Star, Sherman Vann, George and John Pearce, Ed and John Shelley, and Ed's wife Lou, for participating in the breakout. They all plead not guilty.

Bill denied that any of these people had anything to do with it, that a trustee named Ben Howell brought him the revolver. His story was not believed. Vann had already admitted to bringing in the revolver that was found in the search. There was evidence that showed Mrs. Shelley had brought the second revolver in to her husband. And it was believed that Star was the one who threw the brake that would release the cells once the fight started, thus releasing Bill and Pearce.

Bill was convicted of Keating's murder, and sentenced to hang on September 10 by Judge Parker. His lawyer appealed, and a stay of execution was granted. On December 2, 1895 the Supreme Court affirmed the decision of the fort Smith court, and Cherokee Bill was sentenced to death. On St. Patrick's Day, March 17, 1896, Cherokee Bill was hanged on the gallows at Fort Smith, AK.