Outlaw Jennings Gang of Oklahoma – Legends of America
The late 19th century in the American West was a period rife with tales of daring outlaws, relentless lawmen, and the untamed spirit of a frontier constantly in flux. Among the many stories that emerged from this era, the saga of the Jennings Gang of Oklahoma, though short-lived, offers a glimpse into the motivations, misadventures, and ultimate fates of those who chose a life outside the law. This narrative explores the brief but eventful existence of the Jennings Gang, their ill-fated attempts at train robbery, and the subsequent paths of its members, particularly the transformation of its leader, Al Jennings, from outlaw to aspiring politician.
Genesis of an Outlaw Group
In the year 1897, against the backdrop of Oklahoma’s vast landscapes and burgeoning settlements, the Jennings Gang came into being. This group of outlaws, led by the brothers Frank and Al Jennings, sought to make their mark through a series of audacious heists. The gang’s ranks were further bolstered by the inclusion of Little Dick West, a former member of the notorious Doolin Gang, and the brothers Morris and Pat O’Malley. Together, these men embarked on a campaign of train robberies, hoping to strike it rich and secure a life of wealth and freedom.
A Comedy of Errors
The Jennings Gang’s exploits, however, were far from the stuff of legend. Their attempts at train robbery were marked by a series of comical failures and miscalculations. In one instance, the gang targeted a railroad car, believing it to contain a safe filled with valuable treasure. In a display of brute force, they detonated explosives to breach the car, only to discover that their efforts had been in vain. The car held no such treasure, leaving the gang empty-handed and frustrated.
Undeterred, the Jennings Gang resorted to robbing the train’s passengers, a move that underscored their desperation and lack of planning. A few weeks later, they targeted a store, hoping for a more lucrative haul. However, their efforts yielded a mere $15, a paltry sum that highlighted their ineptitude as outlaws.
The Demise of the Jennings Gang
The Jennings Gang’s reign of terror was short-lived. Less than a year after their formation, the gang disbanded, its members scattered and their dreams of wealth and infamy shattered. The Jennings and O’Malley brothers were soon apprehended and incarcerated, bringing an end to their brief foray into the world of crime.
Little Dick West, however, managed to evade capture for a time. He remained on the run until April 8, 1898, when he was killed by U.S. Marshal Chris Madsen, a formidable figure in the pursuit of outlaws in the American West. West’s demise marked the end of an era for the Jennings Gang, as its members were either behind bars or six feet under.
Al Jennings: From Outlaw to Politician
Among the members of the Jennings Gang, Al Jennings stands out as a figure of particular interest. Following his arrest, Jennings was sentenced to life in prison in 1899. However, his brother John, a skilled lawyer, tirelessly worked to secure his release. Through legal maneuvering and appeals, John managed to have Al’s sentence reduced to five years.
In 1902, Al Jennings was freed on technicalities, marking the end of his prison sentence. In a surprising turn of events, he received a presidential pardon from President Theodore Roosevelt in 1904, effectively erasing his criminal past.
Before his descent into a life of crime, Al Jennings had been an attorney. With his criminal past behind him, Jennings decided to re-enter the world of politics. In 1914, he ran for Oklahoma Governor, seeking to lead the state he had once terrorized. However, his past as an outlaw proved to be too much to overcome, and he was soundly defeated in the election.
Conclusion
The story of the Jennings Gang of Oklahoma is a cautionary tale of ambition, misadventure, and the consequences of choosing a life outside the law. While their exploits were far from legendary, their story offers a glimpse into the complexities of the American West and the lives of those who sought to make their mark, whether through legitimate means or otherwise. The transformation of Al Jennings from outlaw to aspiring politician is a testament to the enduring allure of redemption and the challenges of escaping one’s past.