Al Jennings, Oklahoma Bad Boy

Al Jennings

Oklahoma train robber Al Jennings has become the model for outlaw incompetence in the Old West. He did however, manage to provide some comic-relief to lawmen. His less-than sensational career has been called the shortest and funniest on record.

During his illustrious career Al Jennings was a cowboy, lawyer, train robber, jailbird, evangelist, politician, author and movie star.

On his first attempt to rob a train, Al stood on the tracks and aimed his pistol at the engine as it came racing towards him barely escaping by jumping out of the way at the last minute.

His take on the second one was a bunch of bananas and a jug of whiskey.

On December 6th, 1897, after just 109 days on the prod, Al and his brother were captured single-handed by U.S. Marshal, Bud Ledbetter.

He was sentenced to life in prison but managed to get a pardon from President Teddy Roosevelt after five years.

He went on the lecture circuit during which, he sold a highly embellished story of his life as a daring train robber to a national magazine. His “life story” was turned into a movie. Al went on to act and serve as technical advisor for several shoot-em-ups out in Hollywood. He told so many tall tales about being a great train robber that he eventually began to believe them himself.

Al stood only 5’1” with his boots on but the only thing tall about him were his tales. His wife Maude, whom insisted on calling “the little woman,” towered over him by several inches, something that made him look even shorter.

Al was at his best when yarnspinning. One time he referred to himself the “fastest gun on the range,” and claimed to have beaten Jesse James in a shooting match. Al’s math was as bad as his train robbing as Jesse was already dead at the time Al said the match took place.

He eventually went to California where he became an advisor for western movies. Al eventually bought himself a chicken ranch where he had his only gunfights. The first one he accidently shot a neighbor in the elbow while cleaning a loaded pistol. The other was when he shot at chicken thief, missed and killed his prize rooster.

In 1945 Al sued the producers of “The Lone Ranger” radio show for defamation of character after an episode had the masked man shoot a pistol out his hand. He maintained that even in the world of make believe, nobody was good enough to shoot the gun out the hand of the great gunslinger Al Jennings. The jury was amused but Al lost that one too.

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