The Jennings Gang was a short-lived group of outlaws that operated only a few months in Oklahoma, making several failed train robbery attempts in 1897.
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 they were formed, 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 next 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 due to the legal efforts of his brother John, his sentence was reduced to five years. He was freed on technicalities in 1902 and received a presidential pardon in 1904 by President Theodore Roosevelt. Before he turned to a life of crime, Jennings, who was an attorney, ran for Oklahoma Governor in 1914 but was soundly defeated.