Al Jennings, Outlaw or Out of His Mind?

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Al, Frank, and Pat, meanwhile, were making their slow, painful way afoot through the icy brush. On the cold, wet evening of December 2, Al pulled his final stick-up. Along a farm trail not far north of Okmulgee he stepped in front of a rickety farm wagon driven by two Cherokee teenagers and pulled by a ragged mule. He leveled his six-shooter on them and croaked, through his laryngitis “Do you know who I am?” “No, sir,” they admitted. “I’m Al Jennings, the great train robber and bandit,” he announced. The boys looked blank. Jesse James they’d heard of, the Youngers, and the Daltons. They knew about Bill Doolin and Turkey Creek and Red Buck and Dick West, and of course Ned Christie and Cherokee Bill, but who was this Al Jennings? Al’s next remark was “Gimme that mule an’ wagon or I’ll blow your heads off.”

Maybe the boys had never heard of Al Jennings, but he did have a gun. They gave him the mule and wagon. The ragged, dirty, shivering man climbed onto the seat. Two more equally ragged, dirty men stumbled out of the brush and flopped down in the wagon bed. The wagon rattled away into the gathering night, leaving two very bewildered Cherokee boys alongside the trail.

Four days later, on the afternoon of December 6, 1897, Al drove the wagon into Rock Creek Crossing–and found himself looking into the muzzle of Bud Ledbetter’s Winchester. “Please, Mr. Ledbetter,” the disconsolate bandits begged, “take us someplace where it’s warm.”

In April, 1898, the Al Jennings gang went on trial. Frank and the O’Malleys drew five years each for train robbery. Al was convicted of assault with intent to kill an officer of the law–for reasons previously mentioned–and drew a life sentence. All were sent to the supposedly escape-proof Ohio State Pen, which took Federal prisoners at the time.