Stories about American outlaws are some of the most captivating and beloved in American culture. It’s almost impossible to go to the theaters and not see at least one movie being promoted that isn’t Western related.
For years, people watched John Wayne, Clint Eastwood, and others dominate the box offices with their superb acting skills as they played the roles of both hero and outlaw.
Despite the theme and genre being popular, very little is actually known about the real American outlaws. The ones who do acheive fame, like Jesse James and Billy the Kid, are well documented. But there are a few names that deserve more recognition. Not for the great feats or accomplishments they had, but rather the amount of crime and villainy they got away with.
One of these men was Cherokee Bill.
Who Was Cherokee Bill?
Cherokee Bill, or Crawford Goldsby, was an outlaw who operated in Indian Territory, or modern Oklahoma. He was a gang leader who led robberies and murders in the late 1800s. He was born in Fort Concho, Texas in February 1876. He was the son of mixed racial parents, his father a sergeant from Alabama and his mother a Cherokee Freedmen with African, Native American, and Caucasiun ancestry.
By the time that Cherokee Bill was seven, his parents split up and he left with his mother to Indian Territory where he attended school in nearby Kansas. Over the next few years, he struggled with his mother remarrying, leaving to live with his sister, and becoming an outlaw when he turned 18.
Early Crimes of Cherokee Bill
At the age of 18, Cherokee Bill got himself into a gang after he thought he killed a man near his home. He ran away and ran into notorious outlaws Jim and Bill Cook near the Seminole nation.
It is unknown if Bill had intentions of being a gang leader at this point, or if he was just looking for security. Everything changed when Cherokee Bill found himself in a tough spot when law officers showed up to arrest Jim Cook.
A shootout ensued and Bill officially killed his first victim, Sequoyah Houston. From this point on, Bill was wanted by police and decided to live a life of crime.
Bill Cook and Cherokee Bill decided to team up and build a gang, consisting of mostly black men with Indian blood, to terrorize Oklahoma. At first, these crimes were horse theft and smaller crimes, but eventually it grew to bank robberies, stagecoach holdups, and shooting anyone who got in their way.
Only a few months after beginning a life of crime, the Cook Gang was being hotly pursued, with occasional shootouts resulting in gang members and law enforcers being killed. However, every time Cherokee Bill and most of the gang would escape.
Having gained more influence and power, Bill began to rob bigger banks and stores in Oklahoma, stealing a reported $60,000 in Okmulgee, Oklahoma. A few weeks later, they robbed the Missouri Pacific Railroad depot in Claremore, and then turned around and robbed a railroad agent in Chouteau.
Bill continued to rob railroads, causing crashes, and killing anyone who got in the way. His final crime was a solo railroad holdup in Nowata, Oklahoma.
Capture and Death
In January of 1895, some of Cherokee Bill’s acquaintances turned him in as part of a $1,500 reward in Fort Smith, Arkansas. Bill was tried for the death of a man he killed at a train station, Ernest Melton, and found guilty and ultimately sentenced to death on April 13th.
In July he attempted a jailbreak with a gun that had been smuggled into the jail by a trustee. A back and forth gun battle broke out and one of the guards was killed. Another outlaw, Henry Starr, then disarmed Bill in an act that he believed would help him gain his own freedom.
Despite appeals by attorneys fighting for Cherokee Bill, the outlaw was hung on March 17, 1896 in front of a few hundred bystanders.
In total, Cherokee Bill killed at least eight men, robbed at least $65,000 worth of money and goods, and had at least four train holdups. Even crazier, unlike some outlaws who lived a life of crime, all of Bill’s crimes were done in less than a two year period.