Two months later near Chickasha, Indian Territory, five men attempted to holdup the southbound Rock Island passenger train. Unable to force the safe in the express car, the train robbers escaped with an assortment of valuables taken from the passengers, a jug of whiskey, and a bunch of bananas.
The perpetrators of these audacious crimes were Oklahoma outlaws known as Little Dick West, the O’Malley brothers, and Frank and Al Jennings, or the Jennings gang. The Jennings gang “terrorized” Oklahomans from June until December 1897 when United States Marshal Bud Ledbetter, arrested Al Jennings outside Muskogee. In their tenure as outlaws, the Jennings’ gang described in newspaper accounts as penniless, hungry and wearing tattered clothing, unsuccessfully robbed three passenger trains, a number of local merchandise establishments, and a post office.
Early picture of Al Jennings
Regardless of the bumbling efforts of Al Jennings and his gang, Jennings was known as a western outlaw. He was hunted and tracked down by United States marshals who apprehended such notables as the Doolin and Starr gangs, Little Dick West, and Dynamite Dick. But, Jennings was more than as inept outlaw. He was a clever little man who turned his misfortune into profit and fame. Jennings was at the right place at the right time in regard to the American Public’s insatiable interest in the exploits of western frontier characters. Evidently aware of the readers’ interest in western melodrama, Jennings wrote a series of articles in 1913 for the Saturday Evening Post about his “life story.” The articles were then incorporated into his two novels Beating Back (1913) and Through the Shadows with O. Henry (1921). Both are fictitious renderings of Jennings’ outlaw days. Al Jennings’ literary efforts, however, did more than entertain the American reader. His self-proclaimed outlaw notoriety and his fabrication of outlaw exploits prompted western writers to employ Jennings’ fiction as evidence of the true character of a western outlaw.
Alphonso J. Jennings was born in Virginia in 1863. He was the son of Judge J.D.F. Jennings who, before settling in Oklahoma in 1889, was a Methodist minister, a physician, and a lawyer. Al Jennings was also a lawyer, receiving his law degree from West Virginia State University and Military Academy. Jennings established a law practice at El Reno, Oklahoma, in 1892, and was subsequently elected attorney of Canadian County. After being defeated for a second term, he moved his law practice to Woodward in 1894, where he practiced law with his brothers, Ed and John. It was in the cowtown of Woodward that Al Jennings made the decision to give up the practice of law for the life of an outlaw.
The transition took place on the evening of October 8, 1895, in Jack Garvey’s saloon, where Temple Houston, the son of General Sam Houston, and Ed and John Jennings, Lawyers all, exchanged gunfire. When the contest ended, Ed Jennings was dead; John Jennings was badly wounded, and Temple Houston was charged with murder. The dispute between Houston and the Jennings brothers started in a Woodward courtroom the preceding afternoon. The trouble was over a lawsuit in which Houston and the Jenningses were opposing counsel. Evidently unable to keep personalities from entering into the proceedings, Houston and the Jenningses argued in the courtroom to the point where bystanders had to keep them from ensuing a courtroom brawl. They continued the argument that evening when Ed and John Jennings encountered Houston in Garvey’s saloon.
Temple Houston, tall man in the middle
Al Jennings, on the night of the fateful killing, was at his father’s home evidently defusing his anger from the day’s courtroom proceedings. Ed Jennings’ death, and the subsequent acquittal of Temple Houston, embittered Al, and brother Frank from Colorado. Disillusioned by the legal system, they devoted the next couple of years of their lives to Oklahoma outlawry. According to Jennings, “The future, which seemed so bright to me as a young lawyer in a new country, died with my brother. I reverted to the primitive man that was within me.” It was not until June of 1897, however, almost two years later, that United States marshals pursued the notorious Jennings gang for various sundry crimes in Oklahoma.
After six months of their notorious exploits, on December 8, 1987, Marshal Ledbetter captured the four members of the Jennings’ gang outside of Okmulgee, Indian Territory. The capture of Al Jennings was just as enthralling as his adventure on the outlaw trail.
The gang took refuge at the Spike S. Ranch, a ranch often used by outlaws as a convenient place to gather between robberies. Marshal Ledbetter and his officers staked out the ranch on November 29, 1897. On November 30 an officer found one member of the gang hiding in a wagon. He was apprehended and tied up in the barn. Al Jennings opened fire from the house where he was hiding. After an exchange of 100 shts, and the wounding of several occupants in the house, the outlaws escaped. The fugitives were eventually captured after one of their own men turned them in to Marshal Ledbetter. Ledbetter found the outlaws hiding under straw and blankets in the back of a wagon that Frank Jennings was driving across the line into Arkansas.
In May of 1898, The United States Court for the Northern District of Indian Territory convicted Al Jennings on a charge of assault with intent to kill. Jennings also was tried and convicted for robbery of the United States mails in 1899 and was given a life sentence at the Federal Penitentiary in Columbus, Ohio.
It was in the Federal prison that Al Jennings’ literary outlaw image began to take form. As luck would have it, incarcerated with Jennings was William Sydney Porter, later known to American readers as O. Henry, the short story writer.
O'Henry
Porter entered the Ohio Penitentiary as a down and out bank teller and an amateur political satirist (convicted of embezzlement). His life experiences and associations with fellow prisoners provided him with story material that enabled him within three years to become one of the country’s most famous literary artists.
In 1904, O. Henry published two short stories entitled, “Holding Up A Train,” and a shorter version of the story entitled, “The Roads We Take.” “Holding Up A Train” is the only short story in The Complete Works of O. Henry published by Doubleday in 1926 that has a note by O.Henry establishing the authenticity of the story. According to O. Henry, “The man who told me these things was for several years an outlaw in the Southwest and a follower of the pursuit he so frankly described…. I give the story in almost exactly his own words.” The man alluded to by O. Henry as the expert on robbing trains was Al Jennings. Correspondence between O. Henry and Jennings revealed that it was actually Jennings who wrote the story. O. Henry, in 1902, wrote a letter to Jennings indicating that he had interested the editor of Everybody’s in an article about the “art and humor of holding up a train” and explained to the editor that the article would be written by an “expert in the business.” O. Henry, however, turned the story into his own style of writing as explained in a letter to Jennings about the article being accepted for publication. “When you see your baby in print don’t blame me if you find strange ear marks and brands on it.” The story “Holding Up A Train” has some bases of truth but the actual exploits of the train robbers bears no resemblance to Jennings’ reign as an outlaw.
The story opens with the description of five down and out cowboys who drift into Oklahoma from Colorado to “transact a little business with the railroads.” The business was the holdup of the Santa Fe passenger train on an isolated track where the train stopped to take on water. Instead of hiding behind the tender as reported in the newspaper account of Jennings gang holdup of the Santa Fe in 1897, the narrator describes the event, “The engine had hardly stopped when I jumped on the running-board on one side, while Jim mounted he other. As soon as the engineer and fireman saw our guns they threw up their hands without being told, and begged us not to shoot, saying they would do anything we wanted them to.” The nerve and prowess of the outlaws versus the cowardness of the victims was related throughout the story. For example, the description of the male passengers, who were lined up and told to empty their pockets, was, “ The men who looked as frightened and tame as a lot of rabbits in a deep snow.” The narrator then offered a word of advice. “If you want to find out what cowards the majority of men are, all you have to do is rob a passenger train. Big, burly drummers and farmers and ex-soldiers and high collared dudes and sports that, a few moments before, were filling the car with noise and bragging, get so scared that their ears flop.” The train crew was also described in the manner of a docile animal. “As to train crews, had any more trouble with them than if they had been so many sheep.” In this version of the Jennings gang robbery of the Santa Fe, each gang member rode away with $1, 752.85. The narrator also bragged that the gang had continued financial success for the next eight years—netting as much as $48,000 in one train robbery.
Although “Holding Up A train” does not follow the events of the Jennings’ gang in regard to their holdup of the Santa Fe passenger train south of Edmond, Oklahoma in 1897, or any other of their train robbery exploits, the story does illustrate a general theme found in Jennings’ literary accomplishments—a theme that vindicates the perpetrators of crime. In the story, the reader is led to believe that the outlaw was a victim of the men of justice, the marshals and their deputies who were once “lawbreakers, horse thieves, rustlers and highwaymen and outlaws like himself, and that they gained their positions, and immunity by turning state’s evidence, by turning traitor and delivering up their comrades to imprisonment and death.” The final message is that if one is going to enter into the career of a train robber it would behoove oneself to carefully choose one’s traveling companion and that perhaps it would be wiser to choose a collateral occupation such as “politics or cornering the market.” Al Jennings did not try to corner the market but he did try to capture political prominence.
In 1902, Al Jennings was released from the Ohio Penitentiary. Because of the efforts of his brother John and a family friend, Judge Amos Ewing, President William McKinley reduced Jennings’ sentence from a life term to five years with allowance for good conduct. Jennings returned to Oklahoma, where he set up a law practice in Lawton with his brother John. In 1907, President Theodore Roosevelt restored Jennings’ full citizenship. In 1912, Jennings moved to Oklahoma City and announced his candidacy for Oklahoma County Attorney. In his campaign, Jennings appealed to the public with such rhetoric as “when I was a train robber and outlaw I was a good train robber and outlaw. If you choose me as prosecuting attorney, I will be a good prosecuting attorney.”
Jennings lost his bid for Oklahoma County Attorney, but all was no hopeless. The popularity of Jennings’ life story in the Saturday Evening Post in 1913 persuaded Thanhouser Film Company to back financially a motion picture based on the Saturday Evening Post story. Although not yet released, the movie Beating Back provided Jennings with enough publicity to encourage him to run for the Oklahoma gubernatorial Democratic nomination in 1914. In a close contest between J.B.A. Robertson, Judge Robert L. Williams, and Jennings, Williams received 35, 605 votes, Robertson received 33,504 and Jennings received 21, 732 votes.
Realizing that the life of an outlaw was not lucrative, and the life of a politician was difficult to obtain, Jennings turned his outlaw career around to his advantage with the release of Beating Back in 1913. The movie was not an accurate account of Jennings’ outlaw exploits. As similar to O. Henry’s story, “Holding Up A Train,” Jennings depicted the outlaws in the movie as gallant heroes who, for one reason or another, were forced to live outside the law. The author glamorized the deeds of the Jennings’ gang and depicted outlawry as profitable. Jennings also described the marshals in Beating Back as disgusting individuals who enjoyed killing, or as spineless cowards who could not stand up to the gallantry of the criminals.
The release of Beating Back with its fictitious accounts of Jennings’ outlaw successes angered the United States marshals who pursued and eventually arrested him. In retaliation, or in order to straighten the record, former Marshals E. D. Nix, William Tilghman, and Chris Madsen formed the Eagle Film Company. Their goal was to defend the image of the lawmen so degraded in Jennings’ movie. Entitled The Passing of the Oklahoma Outlaws, the movie depicted the history and destruction of the Doolin, Jennings, and Starr gangs. The main message was that crime does not pay and that the outlaw led a sordid unglamorous life. Although infuriated by Jennings’ rendition of outlawry in Oklahoma, the producers of The Passing of the Oklahoma Outlaw understood the box office attraction of featuring in their movie an outlaw with a “notorious” image. Scenes about the Jennings gang robbing a bank in Cache, Oklahoma, actually starred Al Jennings. Also, while the film crew was at Tilghman’s ranch filming the concluding scenes, marshals received word that the Henry Starr gang, Indians Territory outlaws, had just robbed two banks near Stroud, Oklahoma. The gang was captured and Tilghman’s film crew made it in time to film the gang under guard as they were escorted into jail.
The notoriety of Al Jennings’ outlaw career provided some western writers with evidence of the true nature of the outlaw on which to base historical fact. In Kalton C. Lahue’s Winners of the West: The Sagebrush Heroes of the Silent Screen, a chapter entitled, “Al Jennings the Bandit King of the Screen,” begins with, “If any man were qualified to appear on the western screen by virtue of an appropriate past career, that man would have to be Al Jennings of Oklahoma.” In Paul I. Wellman’s A Dynasty of Western Outlaws. Wellmann admits Jennings’ propensity to exaggeration but still distorts the facts. In referring to the attempts to rob Wells Fargo, Wellman accounts that “Nothing but fiascos had occurred thus far, but the gang struck luck. They blasted open a Wells Fargo chest at Berry, south of Ardmore, and got a wad of money. Al Jennings said it was $35,000. Allowing for his inclination to exaggerate, it might have been $10,000.”
Al Jennings’ two books and subsequent movie also became historical evidence for the mysterious life of O. Henry in South America. In his book Through the Shadows with O. Henry, Jennings recounts his first encounters with William Sydney Porter. In the story, Jennings’ Honduras days began when he and his brother, dressed in full suits, silk hats, and white gloves, along with $32,000 of ill gotten gains, hitched a ride on a old ramp banana steamer for South America. Once in Trujillo, Jennings noticed a “dignified figure in immaculate white duck” sitting on the porch of the American consulate. After an exchange of dialogue, which reestablished that the two were fugitives, Jennings wrote “the merest flicker of a smile touched his lips, he got up, took my arm and together we helped each other down the street, that was narrow as a burrow path, to the nearest cantina…Together, we struck out on a long road that lost itself, for many years, in a dark tunnel. When the path broadened out again, it was the world’s highway. The man at my side was no longer Bill Porter, the fugitive, the ex-convict. He was O.Henry, the greatest of America’s short-story writers.”
Others picked up on Al Jennings’ assertions. In E. Hudson Long’s book, O. Henry The Man and His Work, Long states that “The only account of Porter’s life in Honduras comes from Al Jennings, a train robber who, with his brother Frank, was also a fugitive from justice.” Richard O’Connor in O.Henry The Legendary Life of William S. Porter remarks, “his [O. Henry’s] life as a fugitive in Honduras may be glimpsed in the colorful but impressive recollections of Al Jennings (Through the Shadows with O. Henry.)” Although O’Conner does qualifies that Jennings’ recollections may be imprecise, he continues to elaborate on Jennings’ outlawry. “Jennings and his brother Frank, who arrived on a tramp steamer shortly after Will Porter, were also fugitives and much more highly prized by the U.S. Government…The last gasp of the old West they were successors to the James and Dalton family enterprises of train and bank robbing. Recently they had relieved a Texas bank of $30,000.” The earliest of O. Henry biographers, Alphonso J. Smith, a personal friend of O. Henry’s, also bases his facts about O. Henry’s activities in Honduras on Jennings’ books.
There is sufficient evidence that O. Henry was indeed in Honduras during the period in which his biographers describe. Letters written by O. Henry to his wife testify to this fact. Al Jennings, however, was not in Honduras in 1897, the period when Jennings supposedly met O. Henry. According to Jennings he was in Honduras from March until August 1897. Marshal Ledbetter in Northern Indian Territory, however, pursued the Jennings gang, in June and July of 1897. Jennings, therefore, was not in Honduras and could not have met O. Henry at that time.
Al Jennings’ books and O. Henry’s story “Holding Up A Train” were also the basis of Upton Sinclair’s play, Bill Porter: A Drama of O. Henry in Prison published in 1925. In the foreword to the play, Sinclair informs the reader of the plays authenticity in regard to O. Henry’s life. According to Sinclair, “The writer of the play has had the advantage of much conversation with Al Jennings, who was Porter’s intimate both in prison and previously in Central America, where they went south for refuge from the law. Mr. Jennings, who appears as a character in the play, has been good enough to go over the manuscript, and the author here pays tribute to the kindness and general spirit of an ex-train bandit, ex-convict, ex-lawyer, ex-evangelist and almost successful candidate for governor of Oklahoma.” Sinclair’s characterization of the outlaw Jennings throughout the play is based on the exploits of the train robbers in O. Henry’s story “Holding Up A train.” Jennings’ real outlaw exploits would hardly make for adventurous dramatization.
One last attempt to depict the daring outlaw life of Al Jennings was in 1956 with the release of the movie Al Jennings of Oklahoma. In keeping with the image of the western outlaw, the movie reforms Jennings into the character of Jesse James. According to William K. Everson in his book A Pictorial History of the Western Film, “Jennings had been a minor and some what inept train robber, and physically was something of a runt. Al Jennings of Oklahoma almost doubled his size to that of Dan Duryea and gave his outlawry the crusading stature of Jesse James!”
Al Jennings
Al Jennings was the glorified ideal of a western outlaw because he could somewhat authenticate his outlawry. Although inept, Jennings was an outlaw from the last vestige of the frontier West-Oklahoma. His literary collaboration with O. Henry in the Ohio penitentiary helped to elevate his outlaw image and gave it further credibility. His association with O. Henry also enabled Jennings to incorporate in his books details about events in both of their lives that made adventurous reading but held little fact. Some western writers, looking for evidence of the true character of a western outlaw, found their man in Al Jennings. One writer however, who diligently researched his outlaws before testifying to their endeavors, fittingly footnoted the end of Jennings life. Glenn Shirley in West of Hell’s Fringe noted “Al Jennings died with his boots off in his tree-shaded white frame home at Tarzana [California] December 26, 1961.”
