Al Jennings.
The Jennings Gang was a short-lived outlaw group that operated only for a few months in Oklahoma. In 1897, they attempted several train robberies but failed.
Comprised of brothers Frank and Al Jennings; former Doolin Gang member Little Dick” West; and brothers Morris and Pat O’Malley, the gang made several failed train robbery attempts in 1897. After blowing up a railroad car that held a safe and finding no “booty” for their efforts, they robbed the train passengers. A few weeks later, they robbed a store, making off with just $15. Then, less than a year after forming, they broke up.
The Jennings and O’Malley brothers were soon arrested and sent to jail. However, little Dick West remained on the “lamb” until the following year, when he was killed on April 8, 1898, by U.S. Marshal Chris Madsen.
In 1899, Jennings was sentenced to life in prison, but his brother John’s legal efforts reduced the sentence to five years. He was freed on technicalities in 1902 and received a presidential pardon in 1904 from President Theodore Roosevelt. Before he turned to a life of crime, Jennings, an attorney, ran for Oklahoma Governor in 1914 but was soundly defeated.
©Kathy Alexander/Legends of America, updated September 2026.
Train Robbery.
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