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Oklahoma’s Deadliest Outlaw Wasn’t Jesse James – It Was Cherokee Bill

Oklahoma’s Deadliest Outlaw Wasn’t Jesse James It Was Cherokee Bill
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The Wild West was a time of lawlessness, brutality, and larger-than-life figures. Among these notorious outlaws, many names stand out, with Jesse James often being the most famous. However, there’s one figure whose reign of terror in Oklahoma surpassed that of even Jesse James: Cherokee Bill. Born Crawford Goldsby, Cherokee Bill became one of the deadliest and most feared outlaws in the Indian Territory. His life story is marked by tragedy, violence, and the scars of a troubled upbringing, culminating in a series of crimes that made him infamous.

A Troubled Childhood and Early Life

A Troubled Childhood and Early Life
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Crawford Goldsby, later known as Cherokee Bill, was born on February 8, 1876, in Fort Concho, Texas. His mother, Ellen Beck Goldsby Lynch, had a diverse heritage that included Cherokee, African American, and white ancestry. As a Cherokee Nation citizen, Ellen played a significant role in Crawford’s early life. However, the young boy’s childhood was far from idyllic.

Crawford’s father, George Goldsby, was a former Buffalo Soldier who had served in the 10th Cavalry during the Civil War. He had a tumultuous past, escaping slavery and later facing racial tensions with local white cowboys and hunters. In the 1870s, following an altercation between black soldiers and white cowboys in San Angelo, Texas, George Goldsby fled to Indian Territory, where his family sought refuge.

A Harsh Reality

A Harsh Reality
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After George’s departure, Crawford’s mother moved the family to Fort Gibson in Indian Territory, but Crawford’s upbringing took another dark turn. At just seven years old, Crawford was sent to live with a woman named Auntie Amanda Foster and spent several years at Indian schools, where he was subjected to the harsh realities of education in the late 1800s. Despite these early struggles, he returned to Fort Gibson to find his mother had remarried, and his new stepfather was not someone Crawford got along with.

The Emergence of a Violent Young Man

The Emergence of a Violent Young Man
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By the time Crawford was 15, he had already developed a reputation for violence. He was known for getting drunk and challenging authority figures, often engaging in physical altercations. But his true path toward outlaw status began with a deadly fight at the age of 18. In 1893, he killed a man named Jake Lewis, who had previously humiliated him. This act of vengeance, carried out in a moment of anger over a personal affront, marked the beginning of Cherokee Bill’s violent criminal career.

Though Lewis survived the initial attack, Bill believed he had killed him. Fearing retribution under Cherokee law, which would have likely resulted in a brief jail sentence, Bill fled Fort Gibson, marking the start of his life on the run.

The Cook Gang and the Beginning of a Crime Wave

The Cook Gang and the Beginning of a Crime Wave
Image Credit: Wikipedia

In the summer of 1894, Bill formed an alliance with the Cook brothers, Jim and Bill Cook, both of whom shared his mixed Cherokee and African American heritage. Together, they created one of the most feared gangs in the Indian Territory. Bill’s newfound gang, known as The Cook Gang, quickly became notorious for their bank robberies, stagecoach hold-ups, and violent killings.

The gang’s criminal spree began with a small-time robbery in the town of Wonka, Oklahoma, on May 26, 1894. By the summer, their violence escalated, and they were committing more brazen crimes, including the robbery of banks, stagecoaches, and trains. On June 17th, the gang was involved in a deadly shootout with lawmen, which further solidified their reputation as one of the most dangerous groups in Oklahoma.

A Pattern of Brutality and Fear

A Pattern of Brutality and Fear
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As Cherokee Bill’s criminal career progressed, he became increasingly ruthless. In one of his most notorious acts, he shot and killed Samuel Collins, a railroad worker, in July 1894 after a confrontation with a drunken man. Bill’s cold-blooded actions set the tone for the rest of his gang’s criminal activities.

The gang’s crime spree continued into the fall of 1894 with a robbery of the Lincoln County Bank in Chandler, Oklahoma. During the robbery, Bill killed a barber who tried to warn the town about the gang’s plans. This senseless murder sparked a manhunt, as authorities began offering bounties for the capture of the outlaws.

Betrayal and the End of the Cook Gang

Betrayal and the End of the Cook Gang
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Despite the efforts of lawmen and an increasing bounty on his head, Cherokee Bill managed to evade capture for several months. His gang slowly began to crumble as many of its members were either captured or killed in subsequent shootouts. However, Bill remained elusive. It wasn’t until January 31, 1895, that he was finally apprehended by two men, Ike Rogers and Clint Scales, who managed to track him down in Noada, Oklahoma.

Once captured, Bill was taken to Fort Smith, Arkansas, to await trial. His capture, though, was not the end of the story. Cherokee Bill’s attempt to escape from jail in July 1895 only served to highlight his defiance and desperation. With a gun smuggled into his cell, Bill tried to fight his way out but was stopped before he could escape.

The Trial and Sentencing

The Trial and Sentencing
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Cherokee Bill’s trial began in April 1895, and the charges against him were grave. The prosecution focused on his role in the murder of Ernest Melton, which had been one of his most infamous killings. The trial was short, lasting only three days, and Bill was quickly found guilty of murder.

On May 30, 1895, Judge Isaac C. Parker, known as “Hanging Judge Parker,” sentenced Bill to death. However, his execution was delayed by a last-ditch appeal to the U.S. Supreme Court. Unfortunately for Bill, the Supreme Court upheld the trial court’s ruling, and his execution was rescheduled for St. Patrick’s Day, 1896.

The Execution

The Execution
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In his final days, Cherokee Bill remained calm, even whistling and singing to those around him. On March 17, 1896, he was escorted to the gallows in Fort Smith, Arkansas. He reportedly told his mother not to attend his execution, but she insisted on being there. At 2:13 p.m., the trap door opened, and his neck was snapped instantly. Despite his defiant nature, Cherokee Bill’s violent life ended with the same finality as many of his victims: quickly and without mercy.

Legacy and Infamy

Legacy and Infamy
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Cherokee Bill’s life has become a legend in the annals of the Wild West. His name has been immortalized in tales of crime and retribution, and his violent streak has been a subject of both fascination and horror. As an outlaw, he exemplified the dangers of a lawless society, where violence was often met with even more violence.

What sets Cherokee Bill apart from other outlaws of his time is not just the brutality of his crimes but also the personal tragedy that shaped his character. A troubled childhood, compounded by family issues and systemic injustice, created a volatile individual who turned to violence as a means of asserting control over his life.

The Curse of the Number 13

The Curse of the Number 13
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One of the most intriguing aspects of Cherokee Bill’s legend is his association with the number 13. Superstitions about the number 13 seemed to follow him throughout his life. His trial lasted 13 hours, his jury deliberated for 13 minutes, and even his death was set for April 13th. The number 13 loomed large over his life, adding a layer of mystique and eeriness to his already terrifying legacy.

Reflection on a Life of Violence

Reflection on a Life of Violence
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Cherokee Bill’s story is one of tragedy, violence, and ultimately, death. While some might see him as a figure of rebellion, his actions were largely driven by personal grievances and an inability to reconcile with the world around him. His life is a stark reminder that the allure of lawlessness can quickly spiral into destruction, not just for the individual but for everyone around them.

In the end, Cherokee Bill was more than just an outlaw; he was a symbol of the chaotic and often tragic nature of the Old West. His reign of terror in Oklahoma left a deep scar in the history of the region, and though he met his end on the gallows, his legacy lives on as one of the deadliest figures of the Wild West.

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The article Oklahoma’s Deadliest Outlaw Wasn’t Jesse James – It Was Cherokee Bill first appeared on Survival World.

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