History

Al Jennings, Outlaw or Out of His Mind?

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If you have a good story, don’t tell it to a writer. We have no principles at all. We’ll steal it, file the serial numbers off, change it just enough that you can’t prove it’s yours, and sell it for money. Whether or not Porter believed Al’s yarns is moot, but he used them to create a character called The Cisco Kid (O. Henry’s original Cisco Kid was an Anglo, by the way) who still lives in Saturday-morning syndication all over the civilized world. If you consider Al the original Cisco Kid, he is without question the best-known outlaw who ever lived.

Al Jennings, Outlaw or Out of His Mind

Photo: Al Jennings arrest photos from Wikimedia Commons

Al Jennings’ entire outlaw career lasted a total of 108 days, from August 14, 1897, until December 6 of that year. In that time he successfully robbed one train, robbed a post office with semi-success, burgled one general store, and stole a wagon and mule from a couple of Cherokee teenagers. He got in one gunfight in which no one was killed and only one person was wounded. He surrendered without a fight. He was chased by only one lawman, a Territorial Deputy Sheriff named Bud Ledbetter.

The largest reward ever offered for him was $100, and it wasn’t ‘dead or alive.’ The only reason he got a life sentence was his insistence, on the witness stand at his trial, that he was, too, shooting to kill in his only gunfight–to the utter dismay of his attorney, who had a five-year sentence in the bag until the client shot off his mouth.

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

Al and Frank Jennings were the sons of ‘the town Republican’ of Edmond, Oklahoma. Republicans controlled the White House–and all political patronage–from 1860 until 1912, with only two four-year breaks for Grover Cleveland’s non-consecutive terms. Every town in the South– and Oklahoma was full of ex-Confederates–had to have a nominal ‘town Republican’ to serve as post master, judge, or whatever.