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Texas | Columns | "Letters from Central Texas"

Dangerous Al Jennings

by Clay Coppedge

Al Jennings was a bad outlaw, not in the sense that he was dangerous or feared but in the sense that he wasn't very good at outlawry. Jennings was, however, a good storyteller, and good stories last longer than bad outlaws unless, of course, a bad outlaw is telling the story. That was the case when Al Jennings was the storyteller.

The Al Jennings stories include all manner of Old West characters, from writer O. Henry to Sam Houston's gunslinging, lawyering son Temple Lea Houston to the Lone Ranger.

That's a lot of ground to cover, but we'll begin in 1895 in Woodward, Oklahoma where Al and his brother John were lawyers. They had the misfortune to try a case against the wildly popular and successful Temple Houston, son of Sam. The Jennings boys and Houston almost came to blows during the trial, the disagreement stretching into the evening and culminating with a gunfight that found John dead and Sam Houston's son charged with murder.

John stayed dead, but Temple Houston won his own freedom in court, same as he did for many another alleged killer.

"The future, which seemed so bright to me as a young lawyer in a new country, died with my brother," Al Jennings later wrote. "I reverted to the primitive man that was within me."

The primitive man inside Al Jennings wasn't very smart. First, he and his remaining brother, Frank, laid hands on some fake U.S. Marshall badges and used them to charge gullible trail herders a fictional toll for driving their cattle across the territory.

That was fun, but Jennings wanted more out of life. He wanted to be a train robber so he recruited a few members of the Doolin gang to help him reach his full potential. The gang included him and Frank, Little Dick West, Dynamite Dick Clifton and the O'Malley brothers, Morris and Pat. Together, they demonstrated the many ways not to rob a train.

One sure way to not rob a train is to stand on the tracks waving a lantern and firing your pistol in the air. Doesn't work. Engineer can't stop the train in time even if he wants to, and he doesn't want to if all he gets out of it is robbed. Al Jennings tried this tactic, and succeeded only in jumping out of the way of the train before it ended his primitive phase (and all future phases) right then and there.

The gang also learned how hard it is to open a safe by banging on it and shooting at it. The gang demonstrated the folly of this method in another attempt. On the bright side, they rode away with a jug of whiskey and some bananas. Things were looking up. They just had a few details to work out.

Al did some thinking about it and decided it would be a lot to easier to rob a train that was already stopped rather than stopping one that was already rolling full speed. They put the new strategy to work at a watering station near Minco, Oklahoma. This time they took along plenty of dynamite to open that pesky safe. Al set down the dynamite, lit the fuse and ran like hell. Seconds later, the entire baggage car exploded into splinters.

The safe, and any money that might have been in it, vaporized. The gang had to settle for robbing the passengers, none of whom turned out to be rich. The gang then made a crucial and atypically wise decision - they broke up.

A few weeks later U.S. Marshal Bud Ledbetter found the Jennings brothers hiding under some blankets on a wagon and hauled them off to jail. A jury convicted them and the judge sentenced Al Jennings to life in prison. At Leavenworth prison, Al Jennings befriended a bank teller from Austin named William Sydney Porter, who was in the slammer for embezzlement. Since Jennings liked to talk and Porter liked to listen, the two became good friends. When Porter left prison and began writing under the name O Henry, one of the first stories he published was called "Holding Up a Train," which Jennings actually wrote.

Al Jennings 1902 mugshot
Al Jennings 1902 mugshot

Jennings was released from prison in 1904 when President Theodore Roosevelt, who knew Al's father, a judge, pardoned him. Jennings married, ran unsuccessfully for governor of Oklahoma and then made his way to California where he talked his way into the movies as a consultant and occasional actor on more than 100 westerns. He was popular on the lecture circuit a favorite subject for interviewers because of his remarkable stories, like the one about the time he beat Jesse James in a shooting match, a feat all the more remarkable when you consider that Jesse had been dead for many years when the alleged shooting match took place.

Jennings was 82 years old in 1945 when he sued a California radio station for defamation of character because the popular "Lone Ranger" serial had, among other grievous historical inaccuracies, belittled his talents as a gunman.

"They made me mad," Jennings told the amused jury. "They had this Lone Ranger shooting a gun out of my hand, and me an expert." The jurors ruled in favor of the radio station.

A few years later he accidentally killed one of his own roosters with his trusty six-shooter while chasing down an alleged chicken thief. Neighbors called the police on Jennings again when he and the actor Hugh O'Brien, who played Wyatt Earp on TV, squared off in a showdown with blanks. A couple of years later, while showing an old friend how well he could handle a six shooter, Jennings shot the old friend in the elbow.

Jennings died in California 1961 at the age of 97. Neighbors, old friends, actors and roosters alike probably breathed a big sigh of relief because they found out first-hand just how dangerous Al Jennings could be.

Clay Coppedge
"Letters from Central Texas" August 17, 2017 column

Related Stories:

  • Al Jennings by C. F. Eckhardt
  • Temple Lea Houston by C. F. Eckhardt
  • Temple Lee Houston, son of Sam by John Troesser
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