Al Jennings, Outlaw or Out of His Mind?

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Al Jennings of Oklahoma, largely through masterful self-promotion, became for a time the best-known of the outlaws of the American West. He was a genuine bandit, he did go to a Federal penitentiary for attempted murder on a life sentence which was commuted to five years in 1900.

Al Jennings, Outlaw or Out of His Mind

Photo: ravepad.com

He was pardoned by President Theodore Roosevelt in 1902. He went to Hollywood in the early years of the movies and became a freelance technical adviser on Western movies and later on television Westerns. Five movies, including the 1927 silent epic Beating Back, were based on the life and career of Al Jennings–as recalled and told by Al.

In the days before heavy income taxes his percentages amounted to a tidy fortune. The lobby cards for Beating Back featured a copy of Al’s Teddy Roosevelt pardon, which, they implied, came because Teddy recalled the exploits of his ‘old Rough Rider buddy,’ Al, at San Juan Hill. Teddy refused to allow such a brave soldier to rot away in prison. The catch slogan for the movie was “He Robbed More Trains than Jesse James — He Killed More Men than Billy the Kid.”

If pressed–you didn’t have to press hard–Al would admit to ‘twenty or twenty-five’ face-to-face shootouts. He was, though vague about who-what-when-where “in case somebody might start digging that old trouble up and making something out of it again.”

Al Jennings, Outlaw or Out of His Mind
Photo: O. Henry from Wikipedia

While in prison Al made the acquaintance of a bookish young man who had been sentenced from Austin, Texas–a one-time newspaper man and bank teller who was doing time for using the depositors’ assets to back slow horses. The young man’s name was William Sydney Porter, and he would become, as O. Henry, the undisputed master of the only purely American literary form, the short story. Porter was apparently as good a listener as Al was a talker. Al filled the future short-story master’s ears with tales of a second career ‘on the border,’ which he insisted he pursued “while every lawman in Texas, Oklahoma, Kansas, Arkansas, and Missouri was out shaking the hills looking for me.”

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