Most people today define the term “cowboy” as an animal herder who tends to horses and cattle, does a myriad of ranch related tasks, and perhaps has something to do with the modern day rodeo. But in reality, for a period of time, the term referred to a gangster who rustled cattle; robbed trains and stage coaches; smuggled alcohol and tobacco; and murdered anyone who got in their way. This description fits James M. Riley, better known as Doc Middleton, to a tee. Born in 1851, this bloodthirsty cutthroat stole his first horse at the tender age of 14, was later convicted of murder in 1870, and sentenced to life in prison in Huntsville, Texas. After serving four years of that sentence, Doc craftily escaped from his confinement and traveled north to Iowa where he was captured and convicted for stealing horses. After serving 18 months, like a good member of society, Middleton received parole and traveled west to Nebraska where he promptly gunned down a soldier in a bar fight at Fort Sidney. He narrowly escaped a lynch mob that was hot on his heels and made a break for Wyoming. In the late 1870s, Middleton had bounties placed on his head by two of the largest corporations in the entire country, the Wyoming Stock Growers Association and the Union Pacific Railroad. Army officer William H.H. Llewellyn, who was trying to protect pony herds on the Pine Ridge Reservation from the crazed outlaw, took an Army detachment and lured Middleton into a meeting in Cheyenne, Wyoming. Llewellyn told Doc he would receive a governor’s pardon if he showed. Doc, after arriving with members of his gang, realized it was an ambush and shot it out with the military officers. The gun battle ended with Doc in irons and two of his gang lying dead in pools of their own blood. After toiling just shy of four years in prison, Middleton received parole. Doc eventually settled in Orin Junction, Wyoming where he died at the age of 62 in 1913 from a bacterial infection. Middleton contracted the infection after being incarcerated in a filthy jail for his involvement in a knife fight and illegally selling liquor in a saloon he owned. Along with his outlaw enterprises and a rap sheet as long as his beard; Middleton also married three times, fathered at least two children, had six different aliases, worked as a deputy sheriff, and rode with Buffalo Bill’s Wild West show. Checkout history.denverlibrary.org for more information Doc Middleton and outlaws like him.