James “Butt” Riley claimed he had “the hardest head in all Christendom,” and proved it by battering down doors and people with his impervious dome.
Born in New York in 1848, Riley sailed to San Francisco in 1868 where he quickly established himself as the “King of the Hoodlums.” Although he wasn't part of any gang, “there wasn't a band of rowdies in the city that wouldn't flock to his support when he called upon it,” according to The Barbary Coast, Herbert Asbury's 1933 history of our city's seedy beginnings.
Riley was also reportedly so handsome that he sold nude photographs of himself to the city's prostitutes.
“The greatest pride of scores of San Francisco's most popular and prosperous courtesans was the signed photograph of the King of Hoodlums which hung above their beds,” Asbury wrote.
Riley even roamed the red light district with a black satchel filled with images of himself in the buff, selling them to ladies of the evening for 50 cents a pop.
[jump] And just because this all sounded like so much bull, Asbury added a footnote claiming, “At least a dozen old-time San Franciscans, whose names cannot be published for obvious reasons, told the present author that they remembered having seen Riley's photographs in the houses of prostitution.”
When he wasn't selling selfies to hookers, Riley often led raids on Chinatown whorehouses, a seemingly popular pastime for lofan lowlifes in the 1870s. During these sieges, Riley entertained his men by showing them how far he could head-butt Chinese immigrants, reportedly sending a 160-pound man flying 10 feet back.
Riley's career at the top of crime in San Francisco was a comparatively short one, however. In September 1871, Riley was ramming his noggin into the stomach of John Jordan, described by Asbury as a 22-year-old carriage painter. As Riley backed up to do deliver another blow, Jordan pulled out an “English self-cocking pistol” and shot Riley in the gut.
At the county hospital, when physicians mistook Riley for a dead man, he shocked a coroner by waking up with a rant.
“I ain't going to die,” Riley proclaimed. “There's a chance for me yet. I know lots of men who lived with bullets in their belly.”
While Riley survived, he was left diminished by the shot and years of crashing his skull through doors. Once a king, Riley was reduced to toiling in the lower levels of thuggery. In 1872, he was sentenced to 16 years in San Quentin for robbery and burglary. During his trial, witnesses recalled Riley repeatedly head-butting a man who wouldn't shake hands with him “until his wish was complied with” according to a Jan. 17, 1872 Daily Alta California article.
“Men and women in the neighborhood where he lived, on Sixth Street, were afraid of him, and dared not protest against his low actions and conduct,” the Daily Alta California reported.
Judge Davis Louderback waxed almost lyrically while sentencing Riley. “You are a bold and bad man,” the judge scolded. “You respect neither the laws of God nor man.”
On Feb. 28, 1876, Riley risked his life to help fight a deadly fire that broke out in San Quentin. Riley's hoodlum friends and a San Francisco attorney lobbied the governor to pardon Riley, and the State Prison Committee recommended commutation of his sentence in March 1876.
Riley was released from prison on Nov. 5, 1880 after serving half his sentence. What became of him afterwards is lost to history.