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The Jennings Gang

the last of the Doolin gang to go
Dick West, dead at the hands of deputy U.S. Marshals.

You're a liar! Those fighting words, uttered during the course of a civil suit being tried in the county courthouse at Woodward were the seed from which sprouted the Jennings Gang. The matter in dispute concerned the nonpayment of rental on county-owned rangeland, a suit brought by Sheriff Jack Love, who also was collecting fees as corporation commissioner as the result of a rather obvious bit of political skulduggery which was bitterly resented by the Jennings clan, headed by ex-Judge J. F. D. Jennings, who wanted the sinecure for one of their own.

Judge Jennings had four sons: Ed, John and Al were lawyers; Frank, at the time, was in Denver, Colorado, where he was a court clerk. Al, next to the youngest, and only five feet-two, had been for a time Canadian County prosecutor at El Reno. He had come up for the trial, in which he had a personal interest, his brother Ed having been retained as counsel for the defendant. But that was only part of it. Love, in his dual role of sheriff and corporation commissioner, had engaged Temple Houston, the long-time foe of the Jennings clan to prosecute his case.

Temple Houston was the youngest son (not the grandson, as Rascoe has it) of General Sam Houston, father of the Texas Republic, and he never let anyone forget it. In 1886, then only twenty-four, he had been appointed state's attorney for the unorganized counties of the Texas Panhandle, with his headquarters at Old Mobeetie. It was there that he developed a perpetual scowl and certain eccentricities, often appearing in fringed buckskins, snakeskin hatbands, and allowing his hair to grow long. Too inexperienced to be considered a good trial lawyer, he nevertheless quickly became an impressive courtroom orator. He had a big voice and he used it to infuriate opposing counsel. When he roared and shook his long mane, the effect, coupled with his self-avowed prowess with his pistols, was that few men could stand up against him. When he appeared in Oklahoma Territory ten years later, he was a swaggering, often offensive, extrovert.

Ed Jennings had a belligerent nature. He and Houston clashed repeatedly as the trial proceeded. In a heated argument over a legal technicality, the latter became so enraged that he pounded the table with his fist and shouted, "Your Honor, opposing counsel is grossly ignorant of the law!"

Al always said it was he who gave Houston the lie; he was never modest about such things. His brother Ed and Houston squared off at each other, but they were separated before any blows were struck or shots fired. Onlookers did not expect the matter to end there.

That evening, Ed and John Jennings were playing cards in a saloon when Houston walked in. Ed immediately drew a revolver. Houston shot and killed him before he could get out of his chair. John Jennings leaped up, a pistol in his hand, but Houston's second shot struck him in the shoulder and Jennings' six-guns clattered to the floor. Temple Houston was tried for this shooting and, acting as his own lawyer, was acquitted on his plea of self-defense, witnesses swearing that Ed Jennings had been the first to draw.

Frank had come from Denver. He and Al attended the trial and were bitter over Houston's acquittal. Fortified with a few drinks, Al made some threats against Houston. Frank got him away before anything came of and they went to Tecumseh, where their father was then sitting as judge of the Pottawatomie County court. He had previously been a judge at Woodward.

Al (Alfonso) Jennings, born in 1862, was a Virginian by birth, as were his brothers. The Judge had fought under Lee in the Army of Virginia. He was a man of excellent character, and though ruined financially by the War between the States, he had given his sons more advantages than most. Ed was the leader. Al's grandiose dreams of the future political and economic importance of the family were woven around him. If Ed had lived, they might have been realized. With his death, they vanished.

The full measure of Al Jennings' hatred of Temple Houston can be appreciated only when viewed from that angle. In the two books attributed to him, he says he "hunted" Houston, determined to kill him. This is to be doubted. Houston went where he pleased, and if Al was looking for him it was in places, such as the wilds of the Sac and Fox country, where the man was least likely to be.

It has become the fashion to downgrade Al Jennings as an outlaw and to portray him as a fumbling comic figure, confused, boastful, hungry for public acclaim, who was deluded into believing that the tales of derring-do he invented about himself were true. It is an opinion advanced by those writers who know him only throngh the several books which he co-authored. It is justified in part; as a bandit, he had little to recommend him, for as Marshal Nix had once told me, "Al was never half as bad as he thought he was." Perhaps it was just as well that he was not, since any man with a rifle in his hands is dangerous. But whatever AI Jennings' faults were, he paid for his mistakes.

After a few weeks in Tecumseh, he and Frank were broke. They fell in with two brothers, Morris and Pat O'Malley, who, if they could claim any occupation, were cowboys. They were between jobs and getting hungry enough to be reckless. Al has told two versions of who first broached the idea of filling their empty pockets by holding up a train. At one time, he said it was his suggestion; at another, that Morris O'Malley made it. Very likely it came from Al, for he had an ace up his sleeve in the person of Little Dick West, the lone survivor of the Doolin Gang, whom he was confident he could get to throw in with them. They recruited another member of their so-called gang in Sam Baker, a worthless character. Baker was to prove to be one of Al's greatest mistakes.

The five of them left Tecumseh and, somewhere in the Sac and Fox country, met Little Dick. Jennings never disclosed where and how he first made contact with the wizened little runt for whom Nix and his deputies had been hunting for months. He is equally vague about where he, the O'Malley brothers and Baker met the hairy little man. "In the Sac and Fox country," which would be north of Tecumseh, is as close as he comes to saying'

Little Dick had come up from Texas with a herd of horses for the H X Bar. More out of pity for the friendless range stray than because he needed him, Oscar Halsell had kept him on. The little man proved his worth, for he had a way with horses. But he was ignorant, dirty, smelling more like a wild thing than a human being. He refused to sleep under a roof. Summer and winter, he unrolled his blankets on the ground.

Doolin and his clique tolerated him. He was ambidextrous and could draw a pair of six-guns with catlike swiftness and was deadly accurate with both hands. That was something they could admire. Later on, both Bill Tilghman and Heck Thomas were to have occasion to comment on the lightning speed with which Little Dick could draw and fire. Both said they had never seen his equal. He was hard and tough, and there was something deadly about him, all of which recommended him to Doolin; and when the latter left the H X Bar after the Coffeyville fiasco and began putting his own gang together, he took Little Dick With him.

One of the foremost commentators on the horseback outlaw wonders what persuaded Little Dick West, an accomplished, veteran bandit, to join a band of raw, inexperienced amateurs-and why he permitted Al Jennings, rather than himself, to become its leader. The circumstances would seem to be explanation enough. For months he had lived a friendless, lone-wolf existence, hunted from pillar to post. Undoubtedly he would have associated himself with anyone who offered to take him in. Leadership was beyond him; he was not geared for it. Had it been offered, it well might have aroused his wolfish wariness and warned him of what he was letting himself in for.

If Al can be believed, there was no talk of organizing an outlaw gang at that time; he and Frank were interested only in sticking up a train, making a stake and getting out of the country. As he tells it, they had no money and soon ran out of food. To remedy that extremity, they rode up to a crossroads store, determined to beg, borrow or steal enough grub to tide them over for a few days. While the others waited outside, he and Little Dick entered the store. The proprietor was waiting for them with a shotgun. As he shoved it across the counter, Little Dick killed him. They robbed the till, took what food they could carry, and rode off. It was a shabby beginning, but there was no turning back now; the Jennings Gang was born; they were outlaws. They began by holding up a Santa Fe train near Edmond, about halfway between Guthrie and Oklahoma City. Two of them climbed into the cab of the locomotive as it was taking on water, and forcced the engineer to pull out of town a mile. There the other members of the gang were waiting. The express car was entered and the strongbox broken open. It held only a few hundred dollars. Apparently unnerved by their own boldness, they neglected to relieve the passengers of their valuables. But it was a beginning.

Ten days later they attempted to hold up a Katy train at Bond Switch, between Muskogee and Braggs, by piling ties on the track. This was good outlaw practice, successfully used by the James Youngers and the Daltons. There was nothing wrong with their technique, but the engineer saw the barricade in time, opened his throttle and the train plowed through, scattering ties right and left and leaving the discomfited bandits shaking their heads.

Shortly after this misadventure, Sam Baker left them and returned to Tecumseh. Though no longer a member of the gang, he kept in touch with them. He also kept in touch with the law, passing on information that enabled the marshals to keep one step ahead of the Jennings Gang who, in their inexperience, failed to suspect that Baker was betraying them.

Unaware that the finger was on them, they rode south, crossed the Canadian River and set up to stop another Santa Fe train at Purcell, in the Chickasaw country. The night was black, and as they waited on the sidin', in the gloom of a boxcar for the southbound train to pull up at the water tank, they mistook a group of mounted men riding up the right-of-way for a posse. They did not linger to make certain, and it was just as well they did not, for Sam Baker had informed on them. Tilghman was riding in the cab with the engineer and fireman. In the express car another deputy marshal and several possemen were ready for the summons to "open up."

Not having had any luck stopping trains, Al led his men across country to Minco, a little town on the Rock Island, twenty-odd miles south of El Reno, to rob the bank. This was country he knew from his days as prosecuting attorney of Canadian County. They pulled up outside the town. Fearing he might be recognized in Minco, he sent Pat O'Malley in to reconnoiter the bank.

Pat was unknown there, which was fortunate for him. Minco was a one-street town, and as he rode past the bank, he noticed three or four armed men lounging in the doorways of buildings opposite. They seemed so alert that he was convinced they were watching the bank. He kept right on riding circled the town and rejoined the others. They were no longer interested in Minco, when they heard what he had to say. Cursing their luck, they struck off back east the way they had come. Nothing was going right for them and they could not understand it. They were playing with a loaded deck, of course. Sam Baker had heard them talking about Minco on one of his visits to their camp with food and had promptly notified the officers, who had been guarding the bank for several days.

Instead of returning to their old haunts, the gang headed south. Far down in the Chickasaw Nation, at a place named Berwyn, ten miles north of Ardmore, they had a try at another Santa Fe train; and this time, not having Sam Baker around to divulge their plans, they hit the jackpot. Jennings always claimed that they got $35,000. Discounting his usual propensity for exaggeration, one may estimate that it likely amounted to no more than $20,000. But it was a stake. They cut up the loot and scattered for a few months. Al and his brother Frank got passage on a tramp steamer at Galveston and landed in Honduras, from which there was no extradition.

In the cantinas of Puerto Barrios they fell in with a shabby, overweight and congenial refugee from Texas who had fled his native country to escape an indictment for embezzling funds from an Austin bank. With pseudo-histrionic dignity, he informed them that he was William Sydney Porter. They had money and he a nagging thirst. The three of them embarked on a drunken carouse, lasting for weeks, and ending only when they ran out of funds.

Penniless when they sobered up, Al says he suggested robbing the Puerto Barrios bank. Porter refused to have a hand in it. He was going back to Texas, he said, and face the embezzlement charge that he claimed had been brouoht against him to cover the peculations of the bank's officers. (A point which his numerous biographers have always made.) He was found guilty, however, and sentenced to five years in the Ohio State Penitentiary, where, under the pen name of O. Henry he began writing the short stories that were to make him world-famous.

In the fall of 1897, the Jennings brothers were back in the Territory. The gang soon gathered again. They greeted treacherous Sam Baker as an old friend. If he learned where their next strike was to occur, he was too late in getting the information to the officers for them to have time to frustrate it. But the gang supplied their own frustration. It was to be a daylight robbery this time, and they bungled it with disgraceful amateurishness.

At noon on October 1, a section gang working on the Rock Island track near Pocasset, eleven miles north of Chickasha, saw five masked men gallop down on them, brandishing their rifles. The foreman was ordered to flag the train that was soon due, and the gang hid out in the brush. The foreman's red flag stopped the train. Frank Jennings and Pat O'Malley covered the engine crew; Morris O'Malley stood guard beside the express car. Al and Little Dick climbed inside. They found two safes, a small one resting on top of a large one. They attacked them with an ax but without results. They were plentifully supplied with dynamite, however. They pried up the smaller safe, Little Dick inserted a stick of dynamite under it, lit the fuse and jumped out of the car with Al and the express messenger to await the explosion.

Little Dick West, for all of his proficiency with his six-guns, was a rank novice when it came to using dynamite. In his haste to leap out of the car, he had left three or four sticks of it lying on the floor close to the safe. When one stick exploded, the detonation set off the others. The roof of the car was blown off and the safes catapulted into a dich. But neither of them was broached by the blast.

Determined to get at least something, the bandits went through the coaches and collected some watches, jewelry and few hundred dollars. It was a humiliating fiasco that set them to quareling among themselves, each blaming the other. Little Dick must have borne the brunt of it, for without saying a word, he saddled his horse one evening and rode off. It was the last they were to see of him.

The worst was yet to come. A number of passengers identified Al and the O'Malleys as they went through the coachs at Pocasset. The marshals were soon on their trail, and they had to run for it. After a week of being coninuously on the go, their horses gave out. In order to keep moving, they stole a wagon and a team of plodding farm animals. In a beeline they were nealy a hundred miles northeast of Pocasset when they drove through Cushing, below the Cimarron.

They were without food and in tatters. The town was asleep. Throwing caution aside, they robbed a store, took clothing, food and a few dollars from the till. They could no longer regard themselves as bandits; they were just thieves. But they were too desperate to care.

In some manner Sam Baker learned that the fugitives were hiding at the ranch of a man named Harkless, in the Creek Nation, northeast of Okmulgee. He passed the information on to Deputy Marshal Bud Ledbetter, who was leading one of the posses pursuing the Jennings Gang. A day later, Ledbetter had the Harkless place surrounded. He permtted Mrs. Harkless and her Indian hired girl to leave the house. When the gang refused to come out with their hands raised, what Al describes as the "battle" began. The posse did most of the shooting, but as evening came on, the four fugitives helped themseves to Harkless' horses and managed to escape - which fringes on the incredible. Neither in his books nor by word of mouth to me was Al able to explain it to my satisfaction.

And now it was to Sam Baker, of all men, that they turned for succor. AI had a slug in his right leg below the knee. Frank had been slightly scratched. Baker took them in and rode the five miles to Checotah for a doctor and to get word to Ledbetter, telling him how and where he planned to turn the four men over to him.

As soon as Al was able to travel, Baker put him, his brother Frank and Pat O'Malley in a covered wagon. Morris O'Malley and he, both mounted, followed behind. As the wagon neared Carr Creek, Baker moved up alongside and spoke to Al, who was doing the driving, and told him not to turn off to the north until he was a mile beyond the crossing. Al nodded that he understood. Baker then turned back, and Morris O'Malley turned back with him.

The trap was set and Ledbetter was waiting. A log had been placed across the narrow dirt road. The team stopped on reaching it. Ledbetter stepped out from the brush and called on the occupants of the wagon to surrender. There was no resistance. The Jennings brothers and Pat O'Malley climbed out, leaving their rifles behind them.

Bud Ledbetter had boasted that he could take them singlehanded. He had made good, but he was not taking any chances. He had a posse with him. Their presence was not disclosed, however, until after the shamefaced bandits had been taken into custody.

Morris O'Malley was picked up a few days later. All four served five-year sentences at Columbus, Ohio. Al had been sentenced to life imprisonment, but he came out with the others, freed on a presidential pardon. At Columbus, he was assigned to the dispensary, and there he met his friend from Honduras, William Sydney Porter, from which came many years later Through the Shadows with O. Henry, a shoddy attempt to capitalize on another man's misfortune and fame. Also into that little circle at Columbus came Bill Raidler.

They were a chastened crew when they came out. Al tried the lecture platform for a time, his theme "Crime Does Not Pay," and was moderately successful. He tried the law again, and in 1914 had the audacity to campaign for the Democratic nomination for governor of Oklahoma. He was soundly defeated. Whatever else he was, he was an excellent storyteller, and his tales were seldom about himself. It has been said that O. Henry got some of his short stories from him. I know that I did-many of them. One of his most amusing anecdotes concerned his campaign for governor. I'll try to tell it in his words:

I was going up to Guthrie to speak at a political rally. An elderly man in a faded green Prince Albert and a black hat got on the train at Seward. I knew right off that he was a minister. He looked around and then sat down beside me. To make conversation, I said: I suppose you're going up to Guthrie to hear the outlaw candidate speak. I am not! he snorted. Only the horse thieves will vote for that man. I hope you're right, I told him. If all the horse thieves in Oklahoma vote for him he'll be elected by an overwhelming majority.'

Al was in his middle fifties when I became acquainted with him-a lean, wiry little man, with twinkling blue eyes in a grizzled face, and dyed red hair. He passed away in 1962, aged ninety-eight by his reckoning, projecting to the end the illusory image of himself that he had used for half a century and more to cancel out his frustrations.

Soon after he and the rest of his gang were captured, Sam Baker, who betrayed them, became involved in a violent argument with a neighbor named Torrence over the ownership of a wagon. It is a pleasure to report that Torrence killed him and was acquitted, a witness testifying that he had shot in self-defense.

For months after the breaking up of the Jennings Gang the marshals were at a loss to say what had become of Little Dick West. Tilghman, Heck Thomas and others, who had done their best to flush him out of hiding, expressed the opinion that he had left the Territory for Texas or Mexico. They were shocked when they discovered that for most of that time he had been no farther away from Guthrie than a dozen to fifteen miles. A woman's babbling led to his undoing.

If Little Dick had no friends, he at least had some acquaintances left from his cowboys days on the H X Bar. They knew that he was wanted and that they were going against the law in setting out food for him and his horse. But they did. Ironically enough, they were the ambitious, thrifty men whom Oscar Halsell had helped to set up as the owners of their own small spreads. Among them was Herman Arnett. He had bought a piece of range from Colonel Zack Mulhall, down Beaver Creek from the vast Mulhall holdings. Halsell had given him the nucleus of a herd on credit. Arnett did so well that in 1897 he took unto himself a wife, and it changed his life considerably, for he found he now had someone looking over his shoulder, telling him what not to do.

One of the things she objected to was her husband's insistence on taking in for a meal or two any range stray who appeared out of nowhere. She particularly objected to a hairy little man with an oversized mustache, who smelled to high heaven and had a pair of eyes that frightened her. He came at unpredictable intervals, but too often to be the cowboy down on his luck riding the grub line that Arnett said he was. When he came, he stabled his horse in the barn, and whatever the two men had to say to each other was said there. Mrs. Arnett expressed her fear of the little man to a neighbor woman, who passed it on to her friends. Eventually it reached the wife of the clerk of the U.S. District Court in Guthrie. He communicated at once with Marshal Nix.

Nix called in Bill Tilghman and Heck Thomas. Yes, they agreed, the description of Herman Arnett's visitor fitted Little Dick. But was it he, Marshal Nix ordered them to investigate and assigned deputies Frank Rinehart and William Fossett to accompany them.

It was incredible to Tilghman and Thomas that, after months of scouring the Territory for the little outlaw, they were to find him almost in their own backyard, so to speak. But until they knew to a certainty that Arnett's visitor was not Little Dick, they had to proceed in the firm conviction that he was. Being realists, they knew that death could be waiting for them at the end of this short ride. The chances that West, if it were he, lightning fast with his guns, could be taken alive were almost negligible. He would go down fighting, and it would be nothing short of a miracle if he did not take one or more of them along with him. Dawn was breaking when the marshals came up Beaver Creek on April 7, 1898. They left their horses in the willows that fringed the creek bottoms and proceeded cautiously on foot, coming up through the orchard in back of Arnett's barn.

There was a horse in the corral. A man came out of the barn and began grooming the animal with currycomb and brush. As the light strengthened, Tilghman and Thomas recognized him. It was Little Dick. They could have killed him without warning. But that was not their way. "Hands up!" Tilghman called out.

The little outlaw shook his hands free of brush and comb and as they went flying, drew his pistols. The marshals did not give him a second chance. Their guns cracked and Little Dick went down, his .45's clutched in his stiffening fingers. Tilghman retrieved the currycomb and brush. "They were the difference," he said later. "If Little Dick hadn't lost a fraction of a second getting rid of them, he'd have downed one or two of us."

With the killing of Little Dick West, horseback outlawry in Oklahoma Territory had almost run its course - but not quite. Henry Starr was still in the penitentiary; but he was not to remain their long. To him was to go the distinction of being the last of the noted horseback outlaws.

Harry Sinclair Drago. Outlaws on Horseback: The History of the Organized Bands of Bank and Train Robbers Who Terrorized the Prairie Towns of Missouri, Kansas, Indian Territory, and Oklahoma for Half a Century. Bramhall House, New York, 1964.


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