Tuesday, August 20, 2013

The Failed and Flawed Exploits of the Jennings Gang - by Tom Rizzo

On the night of August 16, 1897, three members of an outlaw gang, hidden behind the tender of a southbound Santa Fe locomotive, climbed into the cab and ordered the engineer to stop.

When the passenger train lumbered to a halt, a few miles outside Edmund in Oklahoma Territory, four other gang members who were hiding in the tall brush alongside the tracks rushed the express car to rob the Wells Fargo safe. All attempts at opening the safe however, failed. They even tried dynamiting it—twice. The train robbers gave up and rode away, empty-handed.

Mugshot: Al Jennings

The Jennings Gang, as it was called, included Frank and Al Jennings, Little Dick West, and the O'Malley brothers.

A couple of months later, they struck again—this time, the southbound Rock Island passenger train near Chickasha, Indian Territory. Again, they were unable to crack the safe and, instead, blew up the express car.
Rather than leave  empty-handed this time, they robbed passengers of about $300, and managed to get away with a jug of whiskey and bunch of bananas.

Third time's a charm, so the saying goes. But not with these guys. On the next attempt, they stacked railroad ties across the track, but the engineer merely coaxed more speed out of the locomotive, smashed through the barrier, and kept going.

US Marshal, Oklahoma TerritoryThe gang then turned its attention to an express office, then a bank, but found the places surrounded by authorities each time they showed up to rob them.

You only get so many chances to prove your skills at being a successful outlaw and the gang's comedic attempts to practice outlawry ended a few months later when US Marshal Bud Ledbetter took Al Jennings into custody outside Muskogee after a shootout at the Spike S Ranch, an occasional hideout for outlaws.

Newspapers described the gang as "penniless, hungry, and wearing tattered clothing."

Others dubbed Jennings the worst outlaw in the West. But, even though he lacked the skills to succeed as an outlaw, Jennings wasn't a total bumbling fool. He ended up being a shrewd self-promoter.

Jennings was born in 1863 in Virginia. He and his brothers followed in the career footsteps of their father - who served as a judge - got law degrees and began practicing in the Oklahoma Territory in 1889.

Attorney Temple HoustonSix years later, his brother Ed was shot to death by another lawyer—Temple Houston, son of famous Texas General Sam Houston. Temple was eventually acquitted. But Al and Frank Jennings, bitter about the verdict, vowed payback. They pursued Houston, but never caught him.

It was then the brothers made their decision to give up law and turn criminal.

Following his capture at Spike S Ranch, Jennings was convicted in May 1898 of assault with intent to kill, and given a life sentence at the federal penitentiary in Columbus, Ohio.
But his exploits didn't end there.

Serving time in the same facility was William Sidney Porter, later known to readers as short story writer, O. Henry, who was imprisoned for embezzlement.

O'HenryIn three years behind bars, Porter collected enough material from fellow prisoners to write stories that would rank him among the country's most famous literary personalities.

In 1904, Porter published a couple of stories based on fictionalized exploits of Al Jennings, who the writer alluded to as an expert in train robbery.

His association with Porter enabled Jennings to pump up his own image and credibility despite the lack of actual facts.

President William McKinley, in 1902, released Jennings, reducing his life sentence to five years with allowance for good behavior and, ultimately restored full citizenship. Jennings returned to Oklahoma and established a law practice in Lawton with his brother, John.

Ironically, crime paid off for Al Jennings.

Beating Back, the Film
He ran for public office, unsuccessfully, including a bid for the  Democratic gubernatorial nomination in Oklahoma in 1914.

The next year, his life story appeared in the Saturday Evening Post, followed by a motion picture, Beating Back, in which some scenes featured Jennings playing himself.

Jennings moved to Hollywood, California, and served as a consultant on films about the West. Although he regaled folks with tales of his wild outlaw years, most all of it amounted to complete fabrication.

"Old Al Jennings was around California for years," said Sheriff Jim Herron of Oklahoma, ". . . stuffing dudes with nonsense and telling them wild yarns about himself in the early days."
Jennings died December 21, 1961, at his home in Tarzana, California.


  1. Tom, this was fascinating stuff - and great to know the real background of Al Jennings. Thanks so much!

  2. Hi Courtney-Glad you enjoyed it. Interesting character.

  3. I guess persistence pays. Jennings might not have been a successful thief, but he did provide you with a heckuvan interesting story!

  4. Yes, Jacquie, I guess failure has its merits.

  5. Tom, I knew a bit about Al Jennings since I grew up here in Oklahoma, but never realized he was such a failure! LOL Awful to be remembered for that, I guess. What an interesting story. I think Temple Houston is fascinating, too. I always enjoy your posts so much!

  6. Hi Cheryl--I found Jennings a fascinating character, especially because of his connection with O.Henry. A Temple Houston, too, is a good study. Thanks for dropping by.

  7. Tom, this was hilarious, mostly because of the way you told the tale. If nothing else, I guess we can admire the Jennings Gang for their determination to "get back on the horse." (Personally, I think the horse had their number from the get-go. ;-) )

    Temple Houston -- now there's an interesting character. Maybe you'll write about him, too? :-)

  8. I didn't know anything about Al Jennings and thoroughly enjoyed this post, Tom. Thanks for writing it.

  9. Kathleen--Jennings, indeed played the class clown, so to speak. He was a study in laughable determination.
    And, I agree, Temple Houston is quite a character in his own right.

  10. Keith--So glad you enjoyed the post. It was fun writing about him.

  11. This guy sounds like some of the juveniles I used to deal with in lock-up. They just never quite got it right, but they kept trying. Unfortunately their stories did not end as well. Thank you so much for taking the time to did up the story and tell it so well. Doris

  12. You beat me to the punch, Tom. Al Jennings is (was) on my list of future posts. Another great example of the scoundrels who came out of the Indian Territory and Oklahoma, and such an incompetent one. You just can't make stuff up like his bumbling exploits. Great post!

  13. Oh my Lord, the gang should have been called the Bumbling Burgulars. Good thing Al got it together in prison and took another tact on his career.
    Great post, Tom, as always.

  14. I wonder if O. Henry's Ransom of Red Chief (with bumbling kidnappers) was inspired by ole Al Jennings. LOL