Alphonso J. “Al” Jennings – Lawyer to Train Robber
Alphonso J. "Al" Jennings, a figure whose life reads like a dime novel, embarked on a dramatic trajectory from respected legal professional to infamous outlaw. His story, steeped in the rough-and-tumble atmosphere of the American West, is one of ambition, tragedy, and ultimately, reinvention. This narrative explores the compelling journey of a man who traded the courtroom for a Colt revolver, forever etching his name into the annals of frontier lore.
Born in the Old Dominion state of Virginia in 1863, Alphonso J. Jennings’ early life provided little indication of the path he would eventually tread. As a young boy, his family migrated westward, seeking opportunity and a fresh start in the burgeoning territory of Oklahoma. They established their home near the town of El Reno, a location that would become central to the Jennings family history. Here, amidst the vast prairies and the promise of a new life, young Alphonso grew into adulthood, absorbing the spirit of independence and the allure of the untamed frontier.
Jennings initially pursued a path of respectability and civic duty. Displaying an aptitude for law, he attended law school and successfully passed the bar. His legal acumen quickly garnered recognition, leading to his appointment as a prosecuting attorney in Canadian County. From 1892 to 1894, he served the community, upholding the law and advocating for justice. This period marked a significant chapter in his life, establishing him as a pillar of the community and setting the stage for what many believed would be a long and distinguished career in law.
In 1895, Jennings joined his brothers, Ed and John, in establishing a law practice in Woodward, Oklahoma. The formation of this family firm seemed to solidify the Jennings’ commitment to a life of law and order. However, the tranquility of their professional lives was soon shattered by a tragic event that would irrevocably alter the course of their destinies, particularly that of Alphonso J. "Al" Jennings.
October of that year witnessed a violent confrontation that would forever haunt the Jennings family. Ed and John became embroiled in a shootout with a rival attorney named Temple Lea Houston. Houston was not just any lawyer, but the son of the legendary Sam Houston, a towering figure in Texas history. The altercation resulted in Ed’s death and John’s wounding. The subsequent trial acquitted Houston of murder, a verdict that deeply impacted Alphonso J. "Al" Jennings. Consumed by grief and perhaps a sense of injustice, Al left Woodward. Accompanied by another brother, Frank, he abandoned his legal career and embraced the life of a cowboy, working the land and seeking solace in the vastness of the open range. However, the allure of the law had faded, replaced by a restlessness and a growing disillusionment with the traditional path.
The transition from lawman to outlaw was not immediate, but the seeds of rebellion had been sown. It wasn’t long before Alphonso J. Jennings and his brother Frank decided to embark on a life of crime. They were joined by a motley crew of individuals, including "Little Dick" West, a former member of the notorious Doolin Gang, and brothers Morris and Pat O’Malley. Together, they formed the infamous "Jennings Gang," a group that would attempt to make its mark through daring train robberies. The story of Alphonso J. "Al" Jennings takes a sharp turn into the realm of outlawry.
The Jennings Gang’s initial foray into train robbery proved to be far from successful. Their first attempt on August 16, 1897, near Edmond, Oklahoma, was a complete failure. Despite stopping the train, they were unable to breach the safe, their efforts thwarted by its impenetrable construction. Undeterred, they attempted to flag down another train a few nights later, standing defiantly in the center of the tracks. However, the engineer refused to yield, speeding forward and forcing Jennings to leap out of the way at the last moment to avoid being run over. Another attempt met with similar results, highlighting the gang’s lack of experience and the inherent dangers of their chosen profession.
On October 1, the Jennings Gang made another desperate attempt, targeting a train stopped for water eight miles south of Minco, Oklahoma. This time, they resorted to explosives, detonating a charge in the baggage car. However, their efforts were once again in vain, as they found no money in the safe. Frustrated and desperate, they resorted to robbing the passengers, a move that further solidified their reputation as inept and opportunistic criminals. The life of Alphonso J. "Al" Jennings as an outlaw was proving to be more challenging than he had anticipated.
Their string of failures continued when the gang turned their attention to robbing a store in Cushing, Oklahoma, on October 29, 1897. This audacious attempt yielded a paltry sum of only $15, a meager reward that further underscored their incompetence. Disheartened and disillusioned, the failed gang members dispersed, each seeking their own path in the aftermath of their disastrous criminal endeavors.
In December 1897, Al and his brother Frank were apprehended by U.S. Deputy Marshal Bud Ledbetter, a lawman known for his tenacity and unwavering pursuit of justice. The capture marked a significant turning point in the lives of the Jennings brothers, bringing their brief but tumultuous criminal career to an abrupt end. In 1899, Al Jennings was sentenced to life in prison, a harsh penalty that seemed to signal the end of his story.
However, the legal battle was far from over. His brother, John, a skilled lawyer, tirelessly fought for Al’s release, leveraging legal technicalities and advocating for leniency. His efforts proved successful, and Al’s sentence was reduced to five years. He was eventually freed on technicalities in 1902, a testament to his brother’s unwavering dedication and legal expertise. Further solidifying his redemption, Jennings received a presidential pardon from President Theodore Roosevelt in 1904, officially erasing his criminal record and paving the way for a new chapter in his life.
Following his release, Alphonso J. "Al" Jennings embarked on a remarkable reinvention, returning to the public sphere with a renewed sense of purpose. He became actively involved in politics, leveraging his colorful past to gain attention and support. In 1913, he published his autobiography, Beating Back, a candid account of his life, from his legal career to his outlaw days and eventual redemption. The book became a sensation, further cementing his status as a captivating and controversial figure.
In 1914, Jennings ran for Governor of Oklahoma, campaigning openly and honestly about his past. While he garnered a significant number of votes, his checkered history ultimately proved to be an insurmountable obstacle, and he was soundly defeated. Despite the loss, his foray into politics demonstrated his resilience and his desire to contribute to society in a meaningful way.
Later in life, Jennings moved to California, where he found work in the burgeoning movie industry. He capitalized on his outlaw persona, appearing in Westerns and regaling audiences with exaggerated tales of his past exploits. He became a popular figure, his stories adding to the romanticized image of the Wild West.
Alphonso J. "Al" Jennings died in Tarzana, California, on December 26, 1961, at the age of 98. His life, a tapestry woven with threads of law, crime, and redemption, serves as a testament to the complexities of human nature and the enduring allure of the American West. He remains a fascinating figure, his story continuing to captivate and intrigue those interested in the legends of the frontier. The life of Alphonso J. "Al" Jennings is a quintessential Western tale.