David C. "Doc" Middleton, an alias for James Riley, was referred to as the "King of the Horse Thieves" and alleged leader of the gang called "The Pony Boys" who held rendezvous in the Sandhills area during the 1870s. Doc had many careers in his lifetime, including cowboy, saloon owner and deputy sheriff.
It is generally thought Middleton found his way into Nebraska in 1876 when he and a half-brother hired out as cowhands on a cattle drive over the famous Chisholm Trail after Doc had killed a man in a gunfight in Texas.
It was during a gambling spree at a Sidney saloon one night in 1877 that a soldier from Fort Sidney decided to beat up on the 5 foot, 10 inch Middleton. Doc, who had neglected to check his guns in at the door, drew his pistol, fired and killed the soldier. All reports indicated that Doc shot in self defense, but he left town with the law hot on his trail.
Doc organized a gang of some of the toughest men in the area, call The Pony Boys. They soon became known all over the Sandhills for their lawlessness. They stole or rustled horses and sold them in the Clack Hills of South Dakota, Iowa, and as far south as Texas. The gang operated in the Custer, Blaine and Loup County areas, as well as all territories north, west, and east as far as Holt County.
Doc claimed that he stole only from the Indians and the government and occasionally a rancher. But as his fame grew, every missing horse was blamed on the gang. Middleton was making such a name for himself that drovers coming up from the south were warned of the famous horse thief, and then told about the Indians, water holes, the violent storms and other perils that might beset their herds.
Doc Middleton has been described as "the unwickedest outlaw" who had scores of friends among the region's ranchers, merchants and homesteaders. Some referred to Middleton as Nebraska's Version of Robin Hood. A lot of these people apparently helped hide Doc when the law was near. And Doc was known to help many people who had fallen on hard times. Occasionally, he would even give away a good horse he had stolen if the need was apparent.
Doc himself maintained he was a "dealer in stock" and true enough he was ... in a somewhat less that legitimate capacity.
The law finally caught up with Doc and on September 18, 1879, he started to serve a five year prison term at the Nebraska State Penitentiary at Lincoln. His record gives his age as 28, his birthplace as Mississippi. After his release, Doc returned to the sandhill area where he worked at a variety of jobs, ranging from ranchhand, operator of shooting galleries and saloons and, in 1886, deputy sheriff of Sheridan County. He even worked for several months with Buffalo Bill's Wild West Show. In September of 1887, Doc established a saloon and gambling joint on the east side of main street in Brewster.
The Taylor Clarion, dated October 6, 1887, states: "The celebrated Doc Middleton has purchased the Brewster saloon from the Butcher Bros. and duly opened up as proprietor of the institution. He is chief dispenser of Jersey lightning and has notified the boys that he will keep an orderly establishment."
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