James M. Riley was born on February 9, 1851, in Texas.
He took the name David C. Middleton or "Doc" Middleton when he was in his mid-20s, but he was also known as "Texas Jack," "Jack Lyons," "Gold-Tooth Jack" and "Gold-Tooth Charley."
He stole his first horse at the age of 14 and his last at the age of 39. He stole horses from settlers and from Indians.
He served time in prison for horse theft and murder, escaped from jail twice, and finally ended up in the wild northern Nebraska Territory. The third time he was imprisoned he served four years.
He started fresh by marrying for a third time. His bride was almost 16. He was 33. They lived in the Nebraska Panhandle and he started a saloon in Gordon, Nebraska. For a brief time, he was deputy sheriff at Gordon. He also appeared with Buffalo Bills Wild West Show. When he couldnt make money on the lecture circuit, he traveled as a professional gambler and began bootlegging liquor up to the Pine Ridge Reservation.
Doc couldnt resist one last horse raid, especially when the pickings were so easy. He stole horses from the Sioux during the confusion after the Wounded Knee Massacre and drove them south, but was caught at the Snake River and the ponies were returned to the Sioux.
Doc moved to Chadron and participated in the Chadron to Chicago Horse Race in 1893. Ten years later, he moved to Ardmore, South Dakota and built a saloon. In 1913, after ten years at Ardmore, he moved on to Orin Junction, Wyoming, and ran a "blind pig" or illegal saloon in this unincorporated town.
Later that year, Doc died. He was buried in a donated space in Douglas Park Cemetery in Douglas, Wyoming, at the countys expense, on December 29, 1913, twenty-three years after the Wounded Knee Massacre. He lies in Section 3, Block 2, Lot 3, Grave 2.
Docs story reminds me of another story, told to my dad by the Sioux medicine man Chief Fools Crow. He said that we each have two dogs living inside of us-- one light colored dog, one dark colored dog. These dogs fight over a persons soul. When my dad asked Fools Crow which dog would win-- the light or the dark-- Fools Crow replied, "The dog that wins is the dog you feed the most." Doc Middleton kept his black dog well fed.