Al Jennings, Outlaw or Out of His Mind?

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The Jennings boys’ father was Edmond’s. The Jennings brothers’ bosom pals were the O’Malley boys, Patrick and Morris. Their father was the town grocer. All four were in their late teens, too old for school and too young for adults to take them seriously. They also had a problem. In a day when men rode tall in the saddle Frank, the tallest, stood five feet four. Al, the acknowledged leader, stood five-one. The O’Malleys stood five-three.

Al Jennings, Outlaw or Out of His Mind
Photo: Post-mortem Richard ‘Little Dick’ West from Jim Spencer

According to those who knew them all four–Al in particular–were addicted to Ned Buntline’s Wild West stories. Sometime in the spring of 1897–the exact date isn’t clear, nor are the circumstances–Al met a real, genuine outlaw. His name was Richard West, the same ‘Little Dick’ West who rode with Bill Doolin. He was a typical ‘cowboy gone bad.’

Harry Halsell, in his 1937 classic COWBOYS AND CATTLEMEN, had nothing but good to say about West when he worked with him on the Waggoner and Halsell ranches near Wichita Falls in the 1880s. West came by his nickname honestly. He stood five-six in his socks, which was little when standing next to Bill Doolin but must have been bordering on giantism to Al Jennings. Nobody knows for sure who talked who into a train robbery, but on the evening of August 14, 1897, Al Jennings’ outlaw career began. The beginning would have made a good sequence for the Three Stooges in “Train Robbers.”

To begin with, they tried it in Edmond, where everybody in town knew the Jennings and O’Malley brothers. When a Santa Fe passenger train pulled up for water, Morris O’Malley mounted the tender and in true Ned Buntline style threw down on the engineer and fireman from atop the coal. The rest of the gang–All, Frank, Pat, and Dick West–began pounding on the express-car door with their six-shooters.