“Doc” Middleton – King of the Horse Thieves

The annals of the American West are replete with figures who, for better or worse, etched their names into the collective memory of the nation. Among the cowboys, ranchers, lawmen, and outlaws, few stories are as compelling and contradictory as that of James M. Riley, more widely known as "Doc" Middleton. A man who walked a tightrope between lawlessness and respectability, Middleton’s life was a testament to the fluid morality and the ever-present allure of the frontier.

Born on February 9, 1851, in Mississippi, James M. Riley’s early life offered little indication of the notoriety that awaited him. As he matured, he migrated westward, finding work as a cowboy in the vast expanses of Texas. It was here, amidst the cattle drives and wide-open spaces, that the seeds of his outlaw persona began to sprout. A lifelong fascination with horses, combined with a disregard for conventional law, led him down a path that would ultimately define his legacy.

By the tender age of 14, "Doc" Middleton was already rumored to have stolen his first horse, an act that foreshadowed his future as a notorious horse thief. The allure of the animal, its power, and its value, proved irresistible. He became deeply involved in the dangerous and often lucrative trade of acquiring and redistributing horses, a practice that would both sustain him and constantly put him at odds with the law.

In 1870, Riley’s criminal activities took a more serious turn when he was convicted of murder in Texas. Details surrounding the crime remain murky, lost to the passage of time and the embellishments of legend. However, the conviction served as a catalyst for a dramatic transformation. Facing the prospect of imprisonment or worse, Riley made a daring escape, severing ties with his past and embarking on a new chapter under a different guise.

It was after this escape that James M. Riley likely adopted the alias David Charles Middleton. However, the moniker that truly stuck, and the one by which he is most commonly remembered, was simply "Doc." The origin of this nickname remains uncertain, with some speculating it was a nod to medical knowledge or perhaps just a common frontier appellation. Whatever the reason, "Doc" Middleton became synonymous with horse thievery, daring escapes, and a life lived outside the boundaries of the law.

Over the course of his outlaw "career," "Doc" Middleton adopted a variety of aliases, further blurring the lines of his identity. He was known as Jack Lyons, "Texas Jack," "Gold-Tooth Jack," and "Gold-Tooth Charley," among others. These ever-shifting identities allowed him to move through the West with relative ease, evading capture and maintaining a degree of anonymity. Each new name was a mask, concealing the man beneath and allowing him to operate with impunity.

In 1876, Middleton’s journey led him north on a cattle drive to Ogallala, Nebraska, a bustling hub of frontier activity. It was here, in the saloons and gambling dens of the town, that he encountered further trouble. In January 1877, he was involved in an altercation in a Sidney, Nebraska saloon that resulted in the death of a soldier named James Keefe.

Again, Middleton found himself on the wrong side of the law. He was arrested for the killing, but true to his nature, he managed to escape custody once more. This escape propelled him further north to Wyoming, where he began to solidify his reputation as a leader of outlaws. This move was to further cement the legends of "Doc" Middleton.

In Wyoming, "Doc" Middleton began organizing a gang of outlaws known as the Pony Boys. This group quickly gained notoriety for their primary activity: stealing horses. While they occasionally targeted government livestock or those belonging to ranchers, their preferred victims were the Native American tribes of the region.

Operating across a vast territory that included Nebraska, Iowa, the Dakotas, and even as far south as Texas, the Pony Boys stole thousands of horses. Their raids were audacious and relentless, leaving a trail of resentment and anger in their wake. The impact of their actions was felt throughout the region, exacerbating tensions between settlers and Native Americans.

The Native American tribes, already struggling with the encroachment of settlers and the loss of their traditional way of life, were particularly incensed by the theft of their horses. These animals were not merely possessions; they were vital to their survival, used for hunting, transportation, and warfare. In retaliation, the tribes began taking horses from ranchers, further escalating the conflict.

Before long, every stolen horse in the region was attributed to the Pony Boys, regardless of whether they were actually responsible. The public outcry grew, and a $1,000 reward was placed on Middleton’s head, making him a marked man. Law enforcement agencies and vigilante groups alike were determined to bring him to justice.

In 1878, after the gang stole 40 horses, the Wyoming Stock Grower’s Association, an organization dedicated to protecting the interests of ranchers, took action. They dispatched detective Billy Lykins, a seasoned lawman, to track down Middleton and his gang. Lykins gathered a posse and pursued the outlaws, eventually catching up with them near Julesburg, Colorado.

A fierce shootout ensued, during which Middleton was captured and the stolen horses were recovered. However, in a display of his uncanny ability to evade capture, Middleton managed to escape again that very night, leaving Lykins and his posse frustrated and determined to recapture him.

Lykins then joined forces with the Union Pacific Railroad and Department of Justice Special Agent William Llewellyn, pooling their resources and expertise to track Middleton down. Their combined efforts led them to the Niobrara Valley in Nebraska, where they finally cornered Middleton after another shootout, during which he was shot in the stomach.

This time, Middleton’s luck had run out. He was captured and taken first to Sidney, Nebraska, and then transferred to Cheyenne, Wyoming, to stand trial. Faced with overwhelming evidence, Middleton pleaded guilty to horse stealing and received a five-year sentence. He was incarcerated in a Nebraska prison on September 18, 1879, and released on June 18, 1883.

Upon his release, "Doc" Middleton found that the landscape of the West had changed. Many members of his old gang had been captured or killed, and the era of large-scale horse thievery was coming to an end. Middleton, ever the pragmatist, adapted to the changing times and sought legitimate employment.

He relocated to Gordon, Nebraska, where he spent several years working in a variety of occupations. He was a bartender, a gambler, a deputy sheriff, and even a performer in Buffalo Bill’s Wild West Show for a few months. This period of his life demonstrated his adaptability and his ability to blend into different social circles.

In the 1890s, Middleton moved to Edgemont, South Dakota, where he opened a saloon that he operated for several years. In 1893, he participated in the famed Chadron, Nebraska, to Chicago horse race at the Columbian Exposition in Chicago, Illinois. Though he completed the race, he did not win.

Later, he opened another saloon at Ardmore, Nebraska, and engaged in the illegal practice of bootlegging alcohol to the Sioux Indians on the Pine Ridge Reservation. After soldiers from Fort Robinson raided and wrecked his saloon, he moved again to Orin Junction, near Douglas, Wyoming, where he continued to operate an illegal saloon.

It was in this final saloon that Middleton’s life came to an end. During a knife fight, he was stabbed in the stomach. He was arrested and held in the county jail, but infection soon set in. He died on December 13, 1913, and was buried in the Douglas Cemetery in Douglas, Wyoming.

Despite his life of crime, "Doc" Middleton was described by those who knew him as a likable man, good-tempered, sober, and industrious. He was not known to drink or gamble, and he made friends across the frontier, including figures like Bill Cody, Jim Cook, Print Olive, and even some of the ranchers from whom he stole horses. The Cheyenne Daily Sun described him as a "golden-toothed lover of other folks’ cattle and horseflesh."

"Doc" Middleton remains a fascinating figure in the history of the American West. His life, filled with daring escapes, criminal enterprises, and unexpected turns, captures the spirit of a bygone era. Whether viewed as a villain or a folk hero, his story continues to captivate and intrigue, a reminder of the complex and often contradictory nature of the Wild West.