Al Jennings, a name synonymous with the Wild West’s most contradictory figures, embarked on a life path few could imagine, transitioning from a respected lawyer to a notorious train robber. The story of Al Jennings is a captivating tale of justice, vengeance, and a surprising redemption, etching his name into the annals of American history as an outlaw with an unexpected second act.
Early Life and Legal Ambition in Oklahoma
Born Alphonso J. Jennings in Virginia in 1863, Al’s early life offered no hint of the tumultuous path he would eventually tread. His family relocated to Oklahoma, settling in the burgeoning town of El Reno. Demonstrating intellectual prowess, Jennings pursued a legal education, successfully completing his studies. His legal career began auspiciously, serving as a prosecuting attorney for Canadian County from 1892 to 1894. This period marked him as a man of law and order, a stark contrast to his future exploits. Subsequently, he joined his brothers, Ed and John, establishing a joint law practice in Woodward, Oklahoma, in 1895, further solidifying his standing within the legal community.
A Tragic Turning Point: Vengeance and the Road to Outlawry
A tragic event in October 1895 irrevocably altered the course of Al Jennings’s life. His brothers, Ed and John, became embroiled in a violent shootout with Temple Lea Houston, a prominent rival attorney and the son of Texas legend Sam Houston. The confrontation resulted in the death of Ed and left John wounded. The following year, when Houston was acquitted of murder, a deep-seated sense of injustice and vengeance consumed Al. Feeling the legal system had failed his family, Jennings abandoned his legal career in Woodward. Along with his brother Frank, he sought a new life, initially working as cowboys. However, the allure of a different kind of justice, or perhaps simply a desperate turn, soon led them down a criminal path.
Formation of the Inept Jennings Gang
Driven by a desire for retribution and a growing disillusionment, Al and Frank Jennings decided to embrace a life outside the law. They quickly assembled a small crew, forming what became known as the Jennings Gang. Among their ranks was the infamous “Little Dick” West, a former member of the notorious Doolin Gang, whose experience in outlawry likely provided some guidance, albeit not always effective. The gang also included brothers Morris and Pat O’Malley. With this motley crew, they set their sights on the lucrative, though perilous, venture of train robbery, a common pursuit for desperadoes of the era.
A String of Fumbled Robberies and Quick Demise
The Jennings Gang embarked on their criminal spree with an audacious plan to rob a train on the night of August 16, 1897, near Edmond, Oklahoma. However, their inexperience quickly became apparent. After successfully stopping the train, they discovered they were utterly incapable of opening the safe, whether by shooting or blasting it. Their subsequent attempts were equally fumbled. Just nights later, they tried to flag down another train by standing directly on the tracks, a dangerous and ill-conceived strategy that resulted in the engineer roaring past, forcing Al Jennings to leap to safety at the last possible moment. Another attempt a few days later met the same fate. Their most ‘successful’ endeavor occurred on October 1, when they managed to blow up a baggage car on a train stopped for water eight miles south of Minco, Oklahoma. Yet, even this act yielded no money from the safe, forcing them to resort to robbing the bewildered passengers instead. Their string of failures continued with a store robbery in Cushing, Oklahoma, on October 29, 1897, which netted them a meager $15 before the frustrated and largely unsuccessful gang disbanded.
Capture, Conviction, and Presidential Pardon
The short-lived criminal career of Al Jennings and his brother Frank came to an end in December 1897 when they were captured by the formidable U.S. Deputy Marshal Bud Ledbetter. In 1899, Jennings was tried and convicted, receiving a life sentence for his involvement in the robberies. This seemed to be the definitive end for the former lawyer-turned-outlaw. However, fate, and the persistent legal efforts of his brother, intervened. His sentence was significantly reduced to five years. Remarkably, Al Jennings was freed on a technicality in 1902 and, in a truly extraordinary turn of events, received a presidential pardon in 1904 from none other than President Theodore Roosevelt. This act of clemency allowed him to re-enter society as a free man, a rare privilege for a convicted outlaw.
From Politics to Hollywood: A Reinvented Life
Following his release and pardon, Al Jennings channeled his considerable energy into legitimate pursuits, showcasing a remarkable capacity for reinvention. He became deeply active in politics, and in 1913, he published his autobiography, Beating Back, which recounted his tumultuous life, albeit with some dramatic embellishments. The following year, he made an ambitious bid for Governor of Oklahoma, openly campaigning on his past and using his experiences to connect with voters. Despite his compelling narrative, he was soundly defeated, demonstrating that while his story was captivating, it wasn’t enough to secure political office. Undeterred, Jennings eventually relocated to California, where he found a new calling in the burgeoning movie industry. Leveraging his outlaw past, he worked on Western films, often serving as a technical advisor and even acting in some productions. He became known for his exaggerated tales of his ribald outlaw days, further cementing his legendary status, even if much of it was self-created mythology. He spent his later years in California, passing away in Tarzana on December 26, 1961, at the ripe old age of 98.
Conclusion: The Enduring Legacy of a Contradictory Figure
The life of Al Jennings remains a fascinating study of transformation and the enduring appeal of the Wild West narrative. From a promising lawyer to an uncoordinated train robber, and then to a pardoned politician and Hollywood personality, Jennings’s journey was anything but ordinary. His story is a testament to the complex realities of the American frontier, where individuals could both fall from grace and achieve remarkable comebacks. Though his criminal exploits were often more comical than terrifying, his ability to adapt, survive, and ultimately thrive in vastly different worlds solidified his place as one of the most memorable figures of the era. His legacy is not just that of an outlaw, but of a man who continually reinvented himself against the backdrop of a changing nation, leaving behind a tale that continues to intrigue.
