Al Jennings Out Of Prison Story of Educated Bad Man, Well Known Here Reads Like a Romance A college Man, Lawyer, Outlaw A Son of Ex-Probate Judge of This County Prosecuting Attorney of Canadian Co—Convicted Train Robber Organized and Led the Famous Jennings Gang Sought to Avenge the Killing of His Brother Interviewed in Kansas City Submitted by: Mollie Stehno

Everybody in Shawnee and Pottawatomie County remembers Al Jennings, formerly of this county, son of ex-Probate Judge Jennings, and leader of the famous Jennings gang. The Kansas City Journal of Saturday says of him, in part:

Al Jennings, college graduate, lawyer ex-prosecuting attorney, convicted train robber and leader o f the notorious Jennings gang, which operated throughout the Southwest from 1895 to 1897, is in Kansas City. In addition to his other claims to a place in the “hall of fame,” Jennings occupies the unique position of being the only man on record in Americana history who has server two separate sentences for the distinct crimes at one and the same time for while being confined in the penitentiary at Columbus, O., on a charge of train robbery, he was technically incarcerated in the military prison at Fort Leavenworth for felonious assault.

This man Jennings, the story of whose life would furnish plots for the most sanguine of blood and thunder novels or lurid melodramas, was discharged yesterday at noon from the military prison at Fort Leavenworth, where he had been doing time since last June on a charge of assault with intent to kill for shooting Deputy Marshal Ledbetter in the great fight at the “Spike S” ranch near Tulsa, I. T., in December 1897. Prior to being taken to Fort Leavenworth he had served a term in the penitentiary at Columbus, O., commuted from life to five years, for complicity in the holdup of a Rock Island train hear Chickasha, I. T., in October 1897. The events leading up to his arrest and imprisonment constitutes an interesting chapter in the annals of the southwest and the legal fight that resulted in his release under an order from the United States court is unique in American criminal jurisprudence. That Jennings was here last night is due to the fact that his fight for liberty was waged and won by two Kansas City lawyers, Judge S. C. Price and Frank P. Sebree, who took up the case after the best legal talent in several eastern cities, had declared it hopeless.

Al J. Jennings—his name was Alphonso—but he cut out the last two syllables when he went to Oklahoma to keep them from being shot off—is a Virginian by birth and was brought up in the tradition of the Old dominion where “one man is as good as another and a damned sight better suh.” He graduated from the law department of the University of West Virginia and later from the Virginia Military Institute. His father came to Missouri soon after the war and when al was through school he join the family in Oklahoma.

There were four of the Jennings boys, Ed, Frank, John and Al, all lawyers, and the entire family, father and sons, was active in territorial politics, in which they took the Democratic end.

J. D. Jennings, the father, was at various time probate judge at Woodward and Tecumseh, and it was before him during his incumbency in Pottawatomie County that application was made for a write of habeas corpus to prevent Alexander Jester, charged with the murder of the brother of John W. Gates, the trust magnate, being brought back to Missouri for trial. The application was granted, but the night before the hearing Jester was taken from the jail, spirited across the line and taken to Mexico, Mo.

Al Jennings was elected prosecuting attorney of Canadian County in 1890 and again in 1892, and, with his brothers, practiced law for several years at El Reno. Frank went to Denver, where he was made deputy clerk of the district court, and in 1894 Ed and Frank located at Woodward, then one of the wildest and woolliest cattle towns on the range. In the fall of 1895 Al visited hi brothers at Woodward, and it was an altercation between him and Temple Houston, during the trial of a case in which they were opposing counsel, that led to the killing of Ed Jennings and made his brothers man hunters and outlaws.

For two years they tracked Houston through Oklahoma, Texas and the Indian Territory and once followed him into Mexico. Only twice did they sight their man, and then, they say, they could have assassinated him, but he was with women and they spared his life.

“I didn’t want to murder the man,” said Al last night; “I wanted to meet him face to face. I fully intended to kill him, but I wanted him to see me first and know why and by whose hand he died.”

It is hard to determine just when the Jennings gang as an entity was organized. Al and Frank were known as desperate men, the business of whose life was to avenge the killing of their brother and gradually, possibly with justice, various crimes began to be laid at their door. Some time in 1896, Maurice and Pat O’Malley, two wild Irish boys, brothers, “who knew nothing but fight and didn’t care a d—n for anything else,” is the way al characterized them, were associated with them, and the doing of the Jennings gang began to break into print. Banks were looted in Texas, Arkansas and Oklahoma, stages were help up, trains robbed, mysterious murders committed, and the Jennings gang became as much of a bugbear in its way as the James gang of strenuous memory.

There was a particularly audacious train robbery in the Indian Territory on the Katy. Near Guthrie in August 1896, a Santa Fe train was held up and while the passengers were not molested it is said the robbers got $65,000 in transit to Galveston to help move the cotton crop. The climax was reached October 1 1897, when the rock Island express train was held up just north of Chickasha, I. T., by five men, who were said to be the Jennings brothers, the two O’Malleys and an unknown confederates. The express car was wrecked and $7,000 taken from the way safe, but the through safe, which had in it $90,000 “grass money” for the Indians on its way from Washington to Anadarko in charge of Captain Baldwin, while cracked, could not be opened. The robbers then lined up the 300 passengers, including seven deputy marshals who were supposed to guard the treasure, disarmed the whole crowd and sent through them. Only one man was hurt, an inquisitive individual from the East who struck his head out of the window too soon and had an ear shot off.

This robbery roused the authorities, and rewards, aggregating $9,000 was offered for the conviction of any one of the robbers, the Jennings gang being specifically mentioned. The Southwest was already getting too hot for the gang, and they had disbanded with the understanding that when possible they would meet at the “Spike S” ranch on Snake creek, in the Creek nation, about twenty miles south of Tulsa, and go from there to Pawhuska, where they were to give themselves up to Morris Roebucker, Deputy United States marshal and chief of Indian police for the Osage nation.

Their rendezvous was discovered, and during the night of the last day of November 1897, thirty deputy marshals and small farmers took strong positions in a log cabin, an old barn and a point of timber on three sides of them. The woman at the ranch, who had gone for water, discovered the deputies and she prepared to get away after warning the outlaws. Just as the woman left the house, a flimsy one-room box, the deputies began firing, and for thirty minutes there was a fierce battle in which 500 shots were exchanged. When the firing was over Al Jennings and Pat O’Malley were found to have been shot in the leg, Maurice O’Malley through the shoulder while Frank Jennings, although unhurt, had thirty-seven bullet holes in his clothing. Three marshals were also wounded. The outlaws escaped to the south and late the same evening captured an Indian with a wagon and forced him to haul them south for three day and nights. They were nearly starved, their wounds were not dressed, and when at the house of a friend they received a proposition to take them to Arkansas they accepted it.

At midnight on the fourth day they started, the three wounded men in the bottom of a wagon covered with a tarpaulin and Frank driving.

| The Shawnee Hearld Page |  | Mollie's Corner Page |  | Home |