History

Al Jennings, Outlaw or Out of His Mind?

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The noise attracted the conductor, who had been with the road for years and had known the Jennings and O’Malley brothers since they were in diapers. He ambled up, appropriately clad in brass-buttoned black frock coat and pillbox cap, and carrying a bullseye lantern. He recognized Al and demanded “What do you think you’re doing, Al Jennings?” “It’s the Pinkertons!” Al screamed. The four would-be train robbers bolted for the woods. Morris, who was still on the tender holding a gun on the engine crew, saw his support legging it for the tall timber. He leaped off the tender screaming “Wait for me!” and hit the ground at a high lope, heading for the trees.

The attempted robbery was duly reported and–holding six-shooters on a train crew being downright illegal, not to mention annoying–the local law issued warrants for Al, Frank, Pat, Morris, and a John Doe. The Santa Fe Railroad issued a reward notice listing $100 apiece for the would-be robbers.

Al Jennings, Outlaw or Out of His Mind
Photo: www.examiner.com

On August 30, the gang tried again. This time they got completely out of their home territory, way over in Indian Territory near Muskogee. Al decided to rob the Katy between Muskogee and Oktaha and to stop the train by piling ties on the track, one of the sure-fire train-stopping tricks he learned from Ned Buntline. You can, of course, stop a train that way–but you have to know how to do it. It works when the train is already moving slowly and can’t increase speed, like on a very tight curve or a long, steep hill.

Al stacked his ties dead in the middle of about the longest and smoothest stretch of track in the entire eastern half of Oklahoma. He also picked a moonlit night. The engineer could see the pile of ties and the waiting horsemen a good two miles away. The Katy engineer opened the big Baldwin wide, hauled back on the whistle cord, and told the fireman to sit on the pop-off. He rammed the cowcatcher into the stack of ties at a solid sixty miles an hour. Pieces of broken tie rained all over Muskogee County–and Al went back to Ned Buntline to figure out what went wrong.