Shepherd Brothers – Riding with the James-Younger Gang
The turbulent years of the American Civil War and its aftermath spawned a breed of men hardened by violence and disillusioned with the established order. Among these were George and Oliver Shepherd, two brothers who transitioned from Confederate guerrillas to members of the infamous James-Younger Gang. Their lives, though tragically short, are interwoven with some of the most daring and controversial episodes of the Wild West. This is the story of the Shepherd Brothers, their involvement with the James-Younger Gang, and the paths that led them to their respective fates.
George Washington Shepherd (1842-1917): A Life Marked by Conflict and Loss
Born in the state of Missouri in 1842, George Washington Shepherd’s life was immediately thrust into the chaos of a nation divided. In March 1861, he married Martha Sanders, a union that would later be strained by the hardships and violence of his chosen path. As the Civil War raged, George joined William Quantrill’s Raiders, a notorious guerrilla group known for its brutal tactics and unwavering loyalty to the Confederate cause. Quantrill’s men operated outside the conventional rules of warfare, engaging in raids, ambushes, and acts of terror against Union sympathizers. This experience undoubtedly shaped George Shepherd, instilling in him a capacity for violence and a disregard for the law.
Following the war’s conclusion, George, like many former Confederates, found himself struggling to reintegrate into a society that had branded him an enemy. Drawn to the allure of quick riches and the camaraderie of like-minded men, he cast his lot with the burgeoning James-Younger Gang. This group, led by the charismatic Jesse James and his brother Frank, along with the Younger brothers, Cole, Jim, John, and Bob, was rapidly gaining notoriety for its audacious bank robberies and stagecoach holdups. The Shepherd Brothers were now firmly entrenched in the world of outlawry.
George Shepherd’s association with the James-Younger Gang led him to participate in the robbery of the Southern Bank of Kentucky on March 21, 1868. The gang successfully absconded with approximately $14,000, a considerable sum at the time. However, their success was short-lived, as a posse quickly mobilized in pursuit. George was apprehended and sentenced to three years in prison for his role in the robbery. This period of incarceration proved to be a turning point in his life, though not for the better.
While George was serving his sentence, his wife, Martha, remarried without first obtaining a divorce. This betrayal, whether driven by desperation or a genuine change of heart, undoubtedly fueled George’s anger and resentment. Upon his release from prison, he sought retribution. George ended up in Texas, where he encountered James Anderson, the brother of the infamous William "Bloody Bill" Anderson, another notorious Confederate guerrilla leader. In a violent confrontation, George killed James Anderson, adding another layer of bloodshed to his already turbulent life. George Washington Shepherd died on February 23, 1917, leaving behind a legacy marked by violence, loss, and the long shadow of the Civil War. The life of George Shepherd is a stark reminder of the brutal realities of the Wild West, and the choices made by men caught in its unforgiving grip.
Oliver "Oll" Shepherd (1842-1868): A Short and Violent Trajectory
Oliver "Oll" Shepherd, George’s brother, was born on November 25, 1842. His life mirrored George’s in many ways, particularly in its early trajectory. On February 2, 1860, he married Mary Jane Vance, and together they had two children. Like his brother, Oliver answered the call to arms and joined Quantrill’s Raiders during the Civil War, participating in the same brutal campaigns and witnessing the same atrocities. The Shepherd Brothers, both molded by the crucible of war, were destined for a life outside the bounds of the law.
After the war, Oliver, too, joined the James-Younger Gang, drawn by the promise of wealth and adventure. He participated in what is considered the first daylight bank robbery in the nation, which took place in Liberty, Missouri, on February 13, 1866. The James-Younger gang successfully stole approximately $57,000. The robbery wasn’t without bloodshed. As the gang made their escape, a shooting erupted, and an innocent college student was tragically caught in the crossfire and killed. This incident further tarnished the gang’s reputation and solidified their image as ruthless outlaws. Oliver Shepherd was one of the participants in this deadly event.
Oliver Shepherd was also present during the robbery of the Southern Bank of Kentucky on March 21, 1868, the same robbery that led to his brother George’s capture. Unlike George, Oliver managed to evade capture and return to Missouri. However, his freedom was short-lived. A posse tracked him down in Jackson County, Missouri. When confronted, Oliver resisted arrest and attempted to shoot his way to freedom. In the ensuing gunfight, he was killed, riddled with an estimated 20 bullets. Oliver Shepherd’s life came to a violent end on April 4, 1868, at the young age of 25.
A Legacy of Outlawry and Violence
The story of the Shepherd Brothers is a microcosm of the larger narrative of the American West in the years following the Civil War. They were men shaped by violence, disillusioned with the status quo, and drawn to a life of outlawry. Their association with the James-Younger Gang placed them at the center of some of the most notorious events of the era. While their exploits may have contributed to the romanticized image of the Wild West, their lives were ultimately marked by tragedy and bloodshed.
The Shepherd Brothers, George and Oliver, represent the complex and often contradictory nature of the individuals who populated the American frontier. Were they simply products of their environment, victims of a society scarred by war and economic hardship? Or were they men driven by greed and a thirst for violence, who willingly chose a path of lawlessness? The answer, like the lives of the Shepherd Brothers themselves, is likely a complicated mix of both. Regardless, their story remains a compelling and cautionary tale of the Old West.
The lives of George and Oliver Shepherd, intertwined with the notorious James-Younger Gang, offer a glimpse into the brutal realities of the American West following the Civil War. Their participation in bank robberies, their encounters with violence, and their ultimate fates serve as a reminder of the turbulent times and the enduring legends that emerged from them. The Shepherd Brothers‘ story, though relatively brief, is a testament to the allure and the perils of a life lived outside the law.