Known by many aliases, the infamous Doc Middleton, born James M. Riley, carved a notorious path through the American West as a prolific horse thief and an elusive outlaw. His life story is a compelling blend of audacious criminal acts, thrilling escapes, and an unexpected posthumous reputation that paints a more nuanced picture of this frontier figure.
From the vast plains of Texas to the dusty trails of Wyoming, Doc Middleton consistently defied capture, becoming a legend in his own time. This article delves into the intriguing life of a man who managed to be both a feared criminal and, surprisingly, a likable personality among many on the frontier.
The Formative Years and Early Criminality of James M. Riley
Born James M. Riley on February 9, 1851, in Mississippi, his early life hinted at the path he would eventually take. By the age of 14, he had already committed his first reported act of horse theft, an activity that would define much of his infamous career. As he grew, Riley found work as a cowboy in Texas, a common profession that often blurred the lines between law-abiding life and opportunistic crime on the rugged frontier.
In 1870, Riley’s criminal exploits escalated when he was convicted of murder in Texas. However, the confines of a prison cell could not hold him, and he swiftly made his escape, a pattern that would become characteristic of his life. Following this brushes with the law, Riley adopted the alias David Charles Middleton, though he was more commonly and familiarly known as “Doc.” Over his years as a horse thief and outlaw, he would employ various other monikers, including Jack Lyons, “Texas Jack,” “Gold-Tooth Jack,” and “Gold-Tooth Charley,” each adding to his mystique and helping him evade identification.
The Rise of the Pony Boys Gang and Widespread Horse Theft
Doc Middleton’s journey took him north in 1876, arriving in Ogallala, Nebraska, after a cattle drive. His violent tendencies resurfaced in January 1877, when he killed a soldier named James Keefe in a Sidney, Nebraska, saloon. Arrested once more, Middleton again demonstrated his uncanny ability to escape, disappearing into the vast wilderness of Wyoming.
It was in Wyoming that Middleton began to consolidate his power, organizing a formidable gang of outlaws known as the Pony Boys. This notorious group quickly gained a reputation for stealing horses, primarily targeting Native Americans but also appropriating steeds from government entities. Their operations spanned an enormous territory, ranging from Nebraska and Iowa to the Dakotas and as far south as Texas, enabling them to steal thousands of horses and become a serious menace to the region.
The widespread horse theft incensed the Native American tribes, leading to retaliatory actions where they began taking mounts from ranchers. Soon, nearly every stolen horse in the territory was attributed to the Pony Boys. The escalating crime wave prompted authorities to place a substantial $1,000 reward on Middleton’s head, cementing his status as one of the most wanted men in the West.
The Relentless Pursuit and Eventual Capture
The brazen theft of 40 horses in 1878 galvanized the Wyoming Stock Grower’s Association. Detective Billy Lykins assembled a determined posse and set out in pursuit of the Pony Boys. He eventually caught up with the bandits near Julesburg, Colorado, leading to a fierce shootout where Middleton was finally captured and the stolen horses recovered. However, true to his reputation, Middleton once again escaped that very night, a testament to his resourcefulness and daring. Detective Lykins, undeterred, intensified his resolve.
Recognizing the formidable challenge Middleton presented, Lykins joined forces with the Union Pacific Railroad and Department of Justice Special Agent William Llewellyn. Their combined efforts led them to track Middleton to the Niobrara Valley in Nebraska. Here, a final, dramatic shootout ensued, during which Middleton sustained a stomach wound but was ultimately captured. He was initially taken to Sidney, Nebraska, before being transferred to Cheyenne, Wyoming, to face justice. At trial, Middleton pleaded guilty to horse stealing, receiving a five-year sentence. He was incarcerated in a Nebraska prison on September 18, 1879, and was eventually released on June 18, 1883.
Life After Prison: A New Chapter for Doc Middleton
Upon his release, Doc Middleton found that his old gang, the Pony Boys, had largely disintegrated, with many members either captured or killed. With his criminal career as a horse thief seemingly behind him, Middleton embarked on a new, surprisingly varied chapter of his life. He settled in Gordon, Nebraska, where he spent several years working in various legitimate, and not so legitimate, occupations.
His resume from this period is strikingly diverse: he worked as a bartender, tried his hand as a gambler, and even served a stint as a deputy sheriff, a remarkable turn for a former outlaw. Perhaps most surprisingly, he spent a few months performing in Buffalo Bill’s renowned Wild West Show, showcasing his skills or perhaps merely his notoriety to captivated audiences across the nation. This period highlights Middleton’s adaptability and willingness to integrate into society, despite his past.
Later Years, Final Days, and Enduring Legacy
In the 1890s, Middleton relocated to Edgemont, South Dakota, where he successfully operated a saloon for several years. Demonstrating an adventurous spirit, he even entered the famed Chadron, Nebraska, to Chicago horse race in 1893, coinciding with the Columbian Exposition in Chicago, Illinois. While he finished the grueling race, victory eluded him.
His entrepreneurial spirit continued, leading him to open another saloon in Ardmore, Nebraska. Here, he engaged in bootlegging, illegally selling alcohol to the Sioux Indians on the Pine Ridge Reservation. This venture, however, was abruptly ended when Fort Robinson soldiers wrecked his establishment. Undeterred, he moved once more, establishing another illegal saloon in Orin Junction, near Douglas, Wyoming.
It was in this final establishment that Doc Middleton’s life met its end. A knife fight broke out in the saloon, and Middleton was stabbed in the stomach. He was subsequently arrested and held in the county jail. Tragically, an infection developed from his wounds just days later, and he died on December 13, 1913. He was laid to rest in the Douglas Cemetery in Douglas, Wyoming, bringing a quiet close to a life filled with dramatic highs and lows.
Despite his undeniable history as a horse thief and outlaw, contemporary accounts often painted a complex picture of Doc Middleton. He was frequently described as a likable man, known for being good-tempered, sober, and surprisingly industrious. It was said he was never known to drink or gamble excessively, a stark contrast to many of his outlaw contemporaries. He forged friendships with prominent figures on the frontier, including the legendary Buffalo Bill Cody, Jim Cook, and Print Olive, and even some of the ranchers from whom he was known to steal horses. The Cheyenne Daily Sun famously described him as a “golden-toothed lover of other folks’ cattle and horseflesh,” capturing the ironic charm and criminal inclination that defined this unique figure of the Old West. Doc Middleton’s story remains a fascinating chapter in the annals of frontier history, a testament to the complex characters who shaped the American West.
