Worst Outlaw in the History of the American West Inspired Others


Al Jennings-Worst Outlaw in the West

Al Jennings-Worst Outlaw in the West

On This Date in History: Al Jennings was born in 1863 Virginia. His father was aTemple Houston-the one in the middle judge and Al began practicing law in the Oklahoma Territory in 1889. Al’s law-partner, brother Ed Jennings, was shot to death in October 1895 by another lawyer named Temple Houston, who was the son of famous Texan General Sam Houston. When Houston was acquitted, Al and another brother Frank vowed vengeance. They took off after Houston but never caught up to him. So, what does any good lawyer who fails at a vengeance killing do? Join a gang. He and Frank robbed a Santa Fe train with their new found friends in 1897. Well, they tried to rob a train. This may be where the scene in Butch Cassidy and the Sundance Kid comes from because these guys tried to get the guy in charge of the mail car to open it up but he refused, just like Woodcock did with Butch. But, instead of blowing up the rail car, these desperados got chased away by the conductor.

Temple Houston

Temple Houston

They tried again. This time they piled up railroad ties across the tracks. instead of stopping, the engineer opened up the locomotive at full throttle and simply plowed through the obstruction. They then tried to rob an express office but a simple phone call from the office brought the town sheriff and a bunch of armed men. The would be robbers fled with nothing. Then they tried a bank but someone must have blabbed because when they arrived, the bank was surrounded by numerous armed men. The bumbling robbers left empty handed. So, they gang decided to return to what they knew best…train robbing!

CabinetSaloon

Cabinet Saloon Where Temple Shot Ed

In another probable Butch Cassidy and the Sundance Kid inspiration, they tried a 3rd time when they flagged down a Rock Island passenger train and tried to blow up the two safes on board in a box car. The safes did not open but they did manage to blow up the box car. They did get $300 from the passengers though. But, they got no more chances. They were caught and sentenced to 5 years in prison…except for Al, who got a life sentence for robbery with intent to kill.

Jennings Mugshot 1902

Jennings Mugshot 1902

Al goes to prison and who does he share a cell with but a guy named William Sidney Porter. After spending time listening to the tales of Jennings, Porter was released and took up the profession of a scribe, taking the pen name, O. Henry. O. Henry is considered one of the finest American short story writers of his time. Through his short stories, Henry managed to rehabilitate the image of Jennings and, On This Date in 1902, Al Jennings was released from prison after his sentence was commuted to 5 years by none other than President William McKinley. Jennings returned to Oklahoma to practice law. So, what does a lawyer who was a terrible train robber do? Why run for office. Not just any office…why not county attorney! In 1912, he ran on the promise that “when was a train robber, I was a good train robber. And if you choose me, I will be a good prosecuting attorney.” Obviously, Al had developed a politicians ability to stretch the truth and it helped because he won the nomination but lost the election. He ran for Governor in 1914 but opposition by newspapers left his campaign in third place when the votes were counted. So, where does a failed train robber and failed politician go? Why to Hollywood!

Jennings with Fatty Arbuckle's Cousin Andrew In Hollywood

Jennings with Fatty Arbuckle's Cousin Andrew

O. Henry had encouraged him to write so he went out west and ghost wrote several movies, several of which were supposedly based on his life. The westerns portrayed him as being more treacherous than Billy the Kid, robbed more men than Jesse James and was a participant in nearly 25 face to face shootouts. I would say that there wasn’t much mystery in who the ghost was behind those scripts. Al continued this sort of thing the rest of his life as he was behind many of the B-movie westerns through the 1950′s with the lame scripts that were as phony as the image Jennings created for himself. To perhaps illustrate the level of Al’s position in Hollywood, the photo to the left is not of Al with star Fatty Arbuckle, but instead Fatty’s cousin, Andrew. Nevertheless, it was an interesting and certainly long life for Al, who did not pass away, for real, until 1961. He lived through Reconstruction, the Indian Wars, the closing of the frontier, two world wars and the dawn of the space age. So much to write about yet he chose to write about…himself…and most of that was not true, except his name, Al Jennings. Here is a biography, which is really funny.

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One Response

  1. Your post is really funny, too. I thought when I saw “worst” outlaw you mean, you know – worst. The most terrifying, the most vicious, the most cold-hearted. I didn’t even consider you might mean, “inept”.

    I’m going to have to read this a couple of extra times just to get the details down. Wonderful post.

    By the way – I once double-dated in the summer of 1963 with Warren Earp, who was some kind of descendent of Wyatt Earp. There’s my personal connection to the Wild West. ;-)

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