Born in Virginia in 1863, Jennings and his family moved to Oklahoma and settled at El Reno. When he grew up, he attended law school and served as a prosecuting attorney in Canadian County from 1892 to 1894. He then joined his brothers, Ed and John in a law practice at Woodward, Oklahoma in 1895.
In October of that year, his brothers Ed and John were involved in a shootout with a rival attorney named Temple Lea Houston. When the smoke cleared, Ed was dead and John was wounded. When Houston, who was the son of one of Texas‘ greatest hero’s Sam Houston, was acquitted for murder the next year, Al left Woodward, and along with another brother, Frank, the two went to work as cowboys. Before long, Al and Frank decided to turn to a life of crime.
Joined by former Doolin Gang member “Little Dick” West, his brother Frank, and brothers Morris and Pat O’Malley, the “Jennings Gang” planned their first train robbery on the night of August 16, 1897. However, after stopping the train at Edmond, they found it impossible to shoot or blast the safe open. A few nights later they tried to flag down another train by standing in the center of the tracks, but the engineer kept his hand on the throttle and roared forward, with Jennings leaping out of the way at the last moment. Another attempt a few days later had the same results. On October 1st, they tried again, blowing up a baggage car on a train stopped for water eight miles south of Minco, Oklahoma. When no money was found in the safe, they proceeded to rob the passengers.
Miserable failures at train robbery, the gang then turned to robbing a store in Cushing, Oklahoma on October 29, 1897. Netting only $15, the failed gang split up.
In December 1897, Al and his brother Frank were captured by U.S. Deputy Marshal Bud Ledbetter. In 1899 he was sentenced to life in prison, but due to the legal efforts of his brother, John, the sentence was reduced to five years. He was freed on technicalities in 1902 and received a presidential pardon in 1904 by President Theodore Roosevelt.
He then became active in politics and published his biography, Beating Back in 1913. The next year, he ran for Oklahoma Governor and won votes campaigning honestly about his past, but was soundly defeated.
By Kathy Weiser-Alexander, updated January 2020.