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The Bungling Bandit, Al Jennings

Updated on August 28, 2015

It was said Al Jennings killed more men than Billy the Kid and robbed more trains than Jesse James. The only thing wrong with that statement is Jennings was describing himself. He often said he was "The fastest gun on the range,” but the truth was he could spin a tall tale faster than he could sling a gun. At the time Jennings said these events occurred, Jesse James was already in his grave.

He also claimed to have killed 18 men. "I always shot 'em in the throat so they couldn't talk back,” he would say. But no records exist he ever killed anybody. In fact, he was one the most inept outlaws ever to come out of the Old West.

Alfonso Jackson Jennings was born in Tazewell County, Virginia in 1863 and grew up reading the daring exploits of notorious Wild West outlaws in dime novels written by authors such as Ned Buntline. Apparently he took them as technical “How To” manuals and studied them religiously. In later years he would bungle practically every crime he and his gang would attempt. It’s said he ran away from home at 11 and worked as a ranch hand in Indian Territory where he learned the art of gun fighting and supposedly met such men as Bat Masterson and Wyatt Earp.

The son of a lawyer, he followed in his father’s footsteps and began practicing law in Oklahoma Territory in 1889. Although Al liked being a lawyer, he desperately wanted to make a name for himself, just like the characters he had read about as a youngster.

He got his chance when Al’s law-partner, his brother Ed Jennings, was shot in the back by three men angry over a trial victory. Jennings, standing only 5 feet and one inch in his boots, claimed he tracked the three down to a general store, where he “filled 'em full of lead.” Then he robbed the store. According to Jennings a $5000 bounty was offered for his capture. The truth was Jennings was chased by only one lawman. A Deputy Sheriff named Bud Ledbetter. The largest reward ever offered for him was $100, and it wasn’t “dead or alive.”

Now that he was a full-fledged, honest to goodness outlaw he and his brother Frank joined up with a few others and took to rustling cattle and horses. They soon graduated to robbing trains. By his own admission he robbed about 20 trains in Oklahoma, Kansas, Texas, and Arkansas. That is, if Jennings accounts can be believed. One story about Jennings has him trying to flag down a train, but the engineer ignored the attempt and nearly ran him over.

Their first mistake was committing crimes on their own stomping grounds where they had been raised and everyone knew them. The gang attempted to rob a Santa Fe train in 1897. They tried to get the guy in charge of the mail car to open it up. The man inside refused and the conductor ran them off.

They adopted another plan. On their next job they piled up railroad ties across the tracks. That always seemed to work in Buntline’s books. However, instead of stopping, the engineer set the locomotive at full throttle and simply plowed through the ties. Next they tried to rob an express office. By this time every town of any consequence had telephones. One phone call brought a posse of armed men heading for the office and the gang fled empty handed.

Then they tried a bank but Jennings had a big mouth and was always boasting of his exploits and daring schemes so of course, everybody knew exactly who they were. When they arrived, they were quickly surrounded and forced to flee, once again empty handed. They went back to robbing trains…or at least trying.

On their third attempt at robbing a train they flagged down a passenger train and tried to blow up a couple of safes on board with dynamite. The safes remained unscathed, but the box car was instantly transformed into a flat bed. They did manage to rob the passengers of $300. However, they were soon caught. The gang members were sentenced to 5 years in prison, except for Al, who got a life sentence for robbery with intent to kill.

While Al was in prison he continued his bragging to the delight of fellow inmates. One was a man named William Sidney Porter, better known as O. Henry, later to become a noted author of favorite American short stories. O. Henry found a fertile ground for his writings in Jennings, which did much to polish his image as a famed outlaw. Jennings was released from prison in 1902 after being pardoned by President Theodore Roosevelt.

Jennings returned to his law practice in Oklahoma. But, he still desired to be famous. How does a lawyer and bungling train robber accomplish that? With his prowess at stretching the truth a mite…okay, he lied a lot, he ran for public office. He threw his hat in the ring for the position of county attorney in 1912. Although he lost the election he did win the nomination. Still seeking fame and glory he ran for Governor in 1914, but he lost that bid also.

While in prison his old pal O. Henry had encouraged him to write so he went to Hollywood and ghost wrote several B class western movies, some supposedly based on his life and at least one starring himself. Of course, those portrayed him as being a dangerous, gun slinging desperado who was involved in over 20 gun fights. Perhaps, the only truth to any of his scripts was his name. Real outlaws like the Dalton Gang mocked Jennings as "the guy who held the horses" during bank robberies.

But, undaunted he stayed to work as a technical consultant, screenwriter and character actor in over 100 silent and early talkie westerns. Jennings eventually bought a ranch in the western end of the San Fernando Valley and raised chickens. He would sit on his front porch and reminisce about his “glory days.”

In 1945 he sued the producers of the "Lone Ranger" radio serial for defamation of character. He claimed the show had belittled his prowess as a gunman because in one episode the Lone Ranger had shot a gun out of his hand. Although the jury was amused he still lost the case. His autobiography, "Al Jennings of Oklahoma,” was filmed in 1951.

Jennings died at 98 years old in 1961 shortly after the passing of his beloved wife Maude.

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    • brianlokker profile image

      Brian Lokker 5 years ago from Washington DC metro area

      Whatever else he may or may not have been, Jennings certainly was a colorful character. The O. Henry connection is interesting ... and I'm curious about why Teddy Roosevelt pardoned him. Good hub, voted up and interesting.

    • profile image

      Lynn S. Murphy 5 years ago

      Interesting character in that he reinvented himself several times, and some not for good but all colorful.

    • JY3502 profile image
      Author

      John Young 5 years ago from Florence, South Carolina

      brianlokker, I think it had something to do with O. Henry's portrayal of him.

      Lynn S. Murphy, well that's a politician for you.

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