Life and times of dangerous Al Jennings

Al Jennings was a bad outlaw but not bad in the sense that he was dangerous or feared but bad in the sense that he wasn’t very good at outlawry. Jennings was, however, a good storyteller and good stories outlast bad outlaws unless, of course, a bad outlaw is telling the story. 

The Al Jennings stories include all manner of Old West characters, from writer O. Henry to Temple Houston, to the Lone Ranger. We begin in 1895, in Woodward, Oklahoma, where Al and his brother John are lawyers with the misfortune to try a case against the wildly popular and successful Temple Houston, son of Sam and certified defense lawyer and gunfighter.  

The Jennings boys and Houston almost came to blows during the trial. The disagreement stretched into the evening and culminated with a gunfight that found John Jennings 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 miscreant. 

“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 made some serious and none-too-bright mistakes. First, he and his surviving 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 and reasonably profitable but what Al Jennings really wanted to do, more than anything else, was rob trains. He recruited his brother, along with Little Dick West, Dynamite Dick Clifton, and Morris and  Pat O’Malley—former employees of the Doolin Gang— to form the Jennings Gang. Together, they learned the do’s and don’ts of robbing trains, mostly the don’ts.

 For example:

* Don’t stand on the tracks waving a lantern and firing your pistol in the air and expect the train to stop. 

* Do jump out of the way when the train tries to run over you. 

* Don’t try to open a safe by banging on it with a pistol. 

* Don’t shoot a safe with a pistol at close range. 

* Don’t resort to robbing passengers lest you end up with nothing but a jug of whiskey and some bananas for your day’s work. 

* Definitely do use dynamite in moderation.  

Eventually, the gang became smart enough to break up but not enough to escape capture. Patient and persistent U.S. Marshal Bud Ledbetter found the Jennings boys hiding under some blankets on a wagon and hauled them off to jail. A judge sentenced Al Jennings to life in prison for failing to rob all those trains. 

At Leavenworth, Jennings befriended a bank teller from Austin named William Sydney Porter, who was in the slammer for embezzlement. 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 dictated to him. President Theodore Roosevelt, who knew Al’s father, pardoned Al in 1904. Jennings celebrated by getting married and running unsuccessfully for governor of Oklahoma. 

Newspaper and magazine writers loved Al Jennings 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 took his stories to California where he talked his way into the movies as a consultant and occasional actor on more than 100 westerns. He was 82 when he sued a California radio station for defamation of character because the popular “Lone Ranger” serial had, among other grievous inaccuracies, belittled his talents as a gunman. 

 “They made me mad,” Jennings told an 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 while chasing down an alleged chicken thief. Jennings and the actor Hugh O’Brien, who played Wyatt Earp on TV, attracted the police when they squared off in a showdown with blanks. While showing an old friend how well he could handle a six shooter, Jennings shot the old friend in the elbow.  

Neighbors, old friends, actors and roosters alike breathed a big sigh of relief in 1961 when Jennings died in California at the age of 97 because they knew better than most just how dangerous Al Jennings could be.