At age twelve, Goldsby shot and killed his first man. It was his brother-inlaw, who told him to feeds some hogs. Because of his age he was not prosecuted. As a teenager Goldsby took to petty thievery. He got into fights regular, and when he could not settle them with his fists he would go for his guns. By the age of fifteen he had became an expert shot.

In 1894 he shot and wounded Jake Lewis while attending a dance at Fort Gibson. The two men had got into a fight over a woman, and as Goldsby was getting the worst of the fight, he drew his six-gun and shot Luis. Goldsby didn't hang to answer to the law, he took to the brush. He was charge with assault with intent to kill.

At the age of eighteen, a wanted man on the run, Goldsby fell in with some of the worst outlaws in the Indian Nations, William and James Cook. Goldsby was given the nickname "Cherokee Bill" by Bill Cook. He was with the Cook brothers when a posse cornered the three desperadoes near Tahlequah, I. T., in June of 1894. Lawmen had a warrant for the arrest of Jim Cook on a charge of larceny, but when they moved forward to arrest Cook, all three youths went for their guns. The outlaws were able to drive the lawmen back and they quickly mounted their horses and made a run for it, but the posse was hot on their heels. As they were being chased Cherokee Bill turned in his saddle and fired a shot that killed Deputy Sequoyah Houston.

After the fight with marshals at Tallequah, Cherokee Bill used his sister's home, Maud Brown, to hide out from the law. Her husband, George Brown, a vicious drunkard, took a whip to Maud one day for not responding fast enough to his orders. While he was beating the woman, Cherokee Bill walked up behind him and shot him to death. He then rejoined the Cook brothers.

In the summer of 1894, Cherokee Bill robbed the railroad depot at Nowata, I. T. At the depot he shot and killed station agent Richard Richards as he went for his gun. Then he waited on the platform for the next train to arrive. When it did, he ordered the express car to open up. When conductor Sam Collins opened the door, he order Bill to leave, at which point Bill shot him in the face and killed him. Then the brake man came running down the platform, and Bill shot and wounded him. He then mounted his horse and rode away.

In July of 1894, Cherokee Bill and the Cook gang performed their only bank robbery by robbing the  Lincoln County Bank in Chandler, OT. During the robbery Bill shot and killed the town's barber who was trying to raise the alarm that the bank was being robbed.

That same year, Cherokee Bill and some of his confederates robbed every store in town of Talala, I. T. It is said they simply started at one end of town and robbed their way to the other end of town. They are reported to have repeated this same crime on another occasion.

Later that year of 1894, Cherokee Bill and the Cook Gang robbed the Shufeldt & Son store at Lenapal, I. T. During the robbery Cherokee Bill shot and killed Ernest Melton, an innocent by-stander. It was for this murder that Judge Isaac Parker placed a $1,300 reward on Cherokee Bill, payable dead or alive.

Deputy Marshal W. C. Smith learned that Bill was infatuated with Maggie Glass, a cousin of Isaac "Ike" Rogers, who had been a deputy for Smith on several occasions when posses were needed. Smith arranged for Roger's to lure Bill to Roger's home to meet the girl. Bill showed up at the Roger's the evening of Jan. 29, 1895, and after dinner as the night wore on he fell asleep. Rogers and a neighbor, Clifton Scales, jumped Bill as he laid asleep and tied him up and took him to Fort Smith.

On Feb. 26, 1895, Cherokee Bill was tried for the murder of Melton by jury before Judge Isaac Parker. He was found guilty. Judge Parker sentenced him to hang on June 25, 1895. Cherokee Bill seemed unconcerned about the sentence, and joked that no one would ever put a noose around his neck. His lawyer, J. Warren Reed, managed to file several appeals that delayed the execution date.

In the meantime, Bill was working on his "appeal". Sherman Vann, a trusty at the jail, had smuggled a six-gun into Bill, which he hid in a hole in the wall of his cell. On July 27, 1895, Bill attempted a jail break using the weapon. When the night guards came to lock the prisoners in their individual cells for the night, he jumped them. Guard Lawrence Keating reached for his gun and Bill shot him in the stomach. Keating wheeled and staggered down the corridor. Bill shot him again in the back. Other guards arrived and were able to keep Bill from escaping. In a spectacular gun battle that lasted several minutes, neither the guards were able to enter the jail nor was Bill able to leave his cell. Then another prisoner, Henry Starr, was able to convince the guard that he could enter the cell and bring out Bill if they promised not to shoot him. They reluctantly agreed, and Starr walked down the corridor and entered Bill's cell, then moments later reappeared with the disarmed killer. (for more details on the jail break)

Cherokee Bill was quickly tried for the murder of Keating. He was once again found guilty and sentenced to hang on Dec. 2, 1895. His lawyer once again filed several appeals, but the U.S. Supreme Court upheld the verdict in the Keating murder, and a execution date was set for March 17, 1896. On March 17, 1896, Cherokee Bill was led from his cell to the gallows. As he stood on the gallows with a noose around his neck, he was asked if he had any final words, he said, "No! I came here to die, not make a speech." A moment later he was dead. His mother took his body to Fort Gibson to bury it.