Al Jennings, Outlaw or Out of His Mind?

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Tony Maples Photography


Al Jennings of Oklahoma, largely through masterful self-promotion, became for a time the best-known of the outlaws of the American West. He was a genuine bandit, he did go to a Federal penitentiary for attempted murder on a life sentence which was commuted to five years in 1900.

Al Jennings, Outlaw or Out of His Mind

Photo: ravepad.com

He was pardoned by President Theodore Roosevelt in 1902. He went to Hollywood in the early years of the movies and became a freelance technical adviser on Western movies and later on television Westerns. Five movies, including the 1927 silent epic Beating Back, were based on the life and career of Al Jennings–as recalled and told by Al.

In the days before heavy income taxes his percentages amounted to a tidy fortune. The lobby cards for Beating Back featured a copy of Al’s Teddy Roosevelt pardon, which, they implied, came because Teddy recalled the exploits of his ‘old Rough Rider buddy,’ Al, at San Juan Hill. Teddy refused to allow such a brave soldier to rot away in prison. The catch slogan for the movie was “He Robbed More Trains than Jesse James — He Killed More Men than Billy the Kid.”

If pressed–you didn’t have to press hard–Al would admit to ‘twenty or twenty-five’ face-to-face shootouts. He was, though vague about who-what-when-where “in case somebody might start digging that old trouble up and making something out of it again.”

Al Jennings, Outlaw or Out of His Mind

Photo: O. Henry from Wikipedia

While in prison Al made the acquaintance of a bookish young man who had been sentenced from Austin, Texas–a one-time newspaper man and bank teller who was doing time for using the depositors’ assets to back slow horses. The young man’s name was William Sydney Porter, and he would become, as O. Henry, the undisputed master of the only purely American literary form, the short story. Porter was apparently as good a listener as Al was a talker. Al filled the future short-story master’s ears with tales of a second career ‘on the border,’ which he insisted he pursued “while every lawman in Texas, Oklahoma, Kansas, Arkansas, and Missouri was out shaking the hills looking for me.”

If you have a good story, don’t tell it to a writer. We have no principles at all. We’ll steal it, file the serial numbers off, change it just enough that you can’t prove it’s yours, and sell it for money. Whether or not Porter believed Al’s yarns is moot, but he used them to create a character called The Cisco Kid (O. Henry’s original Cisco Kid was an Anglo, by the way) who still lives in Saturday-morning syndication all over the civilized world. If you consider Al the original Cisco Kid, he is without question the best-known outlaw who ever lived.

Al Jennings, Outlaw or Out of His Mind

Photo: Al Jennings arrest photos from Wikimedia Commons

Al Jennings’ entire outlaw career lasted a total of 108 days, from August 14, 1897, until December 6 of that year. In that time he successfully robbed one train, robbed a post office with semi-success, burgled one general store, and stole a wagon and mule from a couple of Cherokee teenagers. He got in one gunfight in which no one was killed and only one person was wounded. He surrendered without a fight. He was chased by only one lawman, a Territorial Deputy Sheriff named Bud Ledbetter.

The largest reward ever offered for him was $100, and it wasn’t ‘dead or alive.’ The only reason he got a life sentence was his insistence, on the witness stand at his trial, that he was, too, shooting to kill in his only gunfight–to the utter dismay of his attorney, who had a five-year sentence in the bag until the client shot off his mouth.

Al Jennings, Outlaw or Out of His Mind

Photo: www.truewestmagazine.com

Al and Frank Jennings were the sons of ‘the town Republican’ of Edmond, Oklahoma. Republicans controlled the White House–and all political patronage–from 1860 until 1912, with only two four-year breaks for Grover Cleveland’s non-consecutive terms. Every town in the South– and Oklahoma was full of ex-Confederates–had to have a nominal ‘town Republican’ to serve as post master, judge, or whatever.

The Jennings boys’ father was Edmond’s. The Jennings brothers’ bosom pals were the O’Malley boys, Patrick and Morris. Their father was the town grocer. All four were in their late teens, too old for school and too young for adults to take them seriously. They also had a problem. In a day when men rode tall in the saddle Frank, the tallest, stood five feet four. Al, the acknowledged leader, stood five-one. The O’Malleys stood five-three.

Al Jennings, Outlaw or Out of His Mind

Photo: Post-mortem Richard ‘Little Dick’ West from Jim Spencer

According to those who knew them all four–Al in particular–were addicted to Ned Buntline’s Wild West stories. Sometime in the spring of 1897–the exact date isn’t clear, nor are the circumstances–Al met a real, genuine outlaw. His name was Richard West, the same ‘Little Dick’ West who rode with Bill Doolin. He was a typical ‘cowboy gone bad.’

Harry Halsell, in his 1937 classic COWBOYS AND CATTLEMEN, had nothing but good to say about West when he worked with him on the Waggoner and Halsell ranches near Wichita Falls in the 1880s. West came by his nickname honestly. He stood five-six in his socks, which was little when standing next to Bill Doolin but must have been bordering on giantism to Al Jennings. Nobody knows for sure who talked who into a train robbery, but on the evening of August 14, 1897, Al Jennings’ outlaw career began. The beginning would have made a good sequence for the Three Stooges in “Train Robbers.”

To begin with, they tried it in Edmond, where everybody in town knew the Jennings and O’Malley brothers. When a Santa Fe passenger train pulled up for water, Morris O’Malley mounted the tender and in true Ned Buntline style threw down on the engineer and fireman from atop the coal. The rest of the gang–All, Frank, Pat, and Dick West–began pounding on the express-car door with their six-shooters.

The noise attracted the conductor, who had been with the road for years and had known the Jennings and O’Malley brothers since they were in diapers. He ambled up, appropriately clad in brass-buttoned black frock coat and pillbox cap, and carrying a bullseye lantern. He recognized Al and demanded “What do you think you’re doing, Al Jennings?” “It’s the Pinkertons!” Al screamed. The four would-be train robbers bolted for the woods. Morris, who was still on the tender holding a gun on the engine crew, saw his support legging it for the tall timber. He leaped off the tender screaming “Wait for me!” and hit the ground at a high lope, heading for the trees.

The attempted robbery was duly reported and–holding six-shooters on a train crew being downright illegal, not to mention annoying–the local law issued warrants for Al, Frank, Pat, Morris, and a John Doe. The Santa Fe Railroad issued a reward notice listing $100 apiece for the would-be robbers.

Al Jennings, Outlaw or Out of His Mind

Photo: www.examiner.com

On August 30, the gang tried again. This time they got completely out of their home territory, way over in Indian Territory near Muskogee. Al decided to rob the Katy between Muskogee and Oktaha and to stop the train by piling ties on the track, one of the sure-fire train-stopping tricks he learned from Ned Buntline. You can, of course, stop a train that way–but you have to know how to do it. It works when the train is already moving slowly and can’t increase speed, like on a very tight curve or a long, steep hill.

Al stacked his ties dead in the middle of about the longest and smoothest stretch of track in the entire eastern half of Oklahoma. He also picked a moonlit night. The engineer could see the pile of ties and the waiting horsemen a good two miles away. The Katy engineer opened the big Baldwin wide, hauled back on the whistle cord, and told the fireman to sit on the pop-off. He rammed the cowcatcher into the stack of ties at a solid sixty miles an hour. Pieces of broken tie rained all over Muskogee County–and Al went back to Ned Buntline to figure out what went wrong.

Train robbing was proving downright unprofitable, not to mention embarrassing. The boys decided to take on an express office. The American Railway Express Company’s office in Purcell, about 45 miles south of Edmond on the South Canadian, was the target. The boys surrounded the office and began to peek into the windows to see if the express agent was alone. The express agent, seeing faces with bandannas over them pop up at his windows and then disappear, got a little perturbed. He went to the telephone–this was 1897, and every town of any size had a telephone system by then–and called the law. The town marshal, accompanied by about a half-dozen shotgun-armed citizens showed up–sometimes having a party line can work to your advantage–and the boys departed without firing a shot or taking fire. The Purcell fiasco was on the September 8.

Al Jennings, Outlaw or Out of His Mind

Image: Bank robbery taking place in the Wild West by Ron Embleton

Discouraged by a certain lack of success with trains and express offices, the gang decided to try a bank. Minco, about 30 miles southwest of Edmond, was chosen. When the boys showed up to rob the Minco bank early on the morning of September 20, it was pretty obvious something had gone wrong. The bank was surrounded by shotgun-armed locals. There had obviously been a leak somewhere. The most likely suspect was Al, who had a bad habit of shooting his mouth off. The Al Jennings Gang rode into Minco and out the other side without stopping.

On October 1, 1897, after having been a bandit for 46 days without a single success, Al Jennings, the Notorious Oklahoma Bank and Train Robber, the man who “Robbed More Trains than Jesse James and Killed More Men than Billy The Kid,” finally managed to steal something.

The gang pulled what the press described as a ‘daring daylight robbery’ of the Rock Island passenger train 8 miles north of Chickasha, at the water stop now known as Pocasset. Well, it was. It was straight out of Ned Buntline–up to a point, anyway. They piled the passengers out, lined them up alongside the cars, and went through their pockets in the best Beadle’s Dime Library approved fashion. The take from the passengers was some $300 in currency and assorted loose change, a silver pocketwatch worth about $15, a bunch of bananas, and a jug of busthead whiskey.

The train had an express car, the express car had a safe–two of them, in fact–and the safes had money in them. The boys wanted the money. They demanded the combinations from the messenger. He denied knowing them. That, of course, was a lie, but one the company insisted all messengers tell. All express-company messengers had the combinations to both the through and way safes, but they could be fired for admitting it to bandits. A good many messengers died rather than give up the combinations to the company safes.

Al Jennings, Outlaw or Out of His Mind

Photo: wonderopolis.org

Al, however, had read his Ned Buntline well. He came prepared. He had two one-pound sticks of dynamite, which was more than enough to open both safes if he’d known how to open a safe with dynamite. Unfortunately, Ned Buntline had always been sort of vague about exactly how one went about opening a safe with dynamite. Al found himself in the express car faced with two safes, two sticks of dynamite in his hands, and he didn’t know chocolate pie from cowflop about how to blow a safe.

Of course, he didn’t know any more than that about how to be an outlaw, either, but it hadn’t slowed him down so far. He decided to improvise. The through safe was the big one and Al couldn’t lift it. He put the two sticks of dynamite atop the through safe, set the way safe atop it, precariously balanced on the dynamite, lit the fuses, and ran.

Al Jennings, Outlaw or Out of His Mind

Photo: fiftieswesterns.wordpress.com

It would make a much better story, not to mention a great scene in a movie, had the dynamite blown the way safe out the top of the express car. Unfortunately, that’s not what happened. The way safe tilted. The force of the explosion went sideways. It blew the side out of the express car, tore up the mail, did the interior no good at all, and simply flipped the way safe back onto its wheels on the floor.

The boys fired a few shots into the air because that’s what Ned Buntline said you were supposed to do. Then they galloped away into the postoaks. They holed up not far from Chickasha, where they split the money and– according to the records–ate the bananas and drank all the whiskey. How they survived the combination is not part of the record. Dick West took his $60 and drifted. Nobody said who wound up with the watch.

What Al, Frank, Morris, and Pat did between October 1, the Rock Island stickup, and November 14, the next time they were heard from, nobody but Al ever said. His story about wine-women-song in St. Louis isn’t supported by the $60 he had in his pocket.

The stick-up did have one major effect. Before, the law had been only mildly annoyed with the Al Jennings gang. Now it was downright put out with them. The Rock Island was also more than a little perturbed. It posted a $100 apiece reward for the boys. Of course, everybody knew exactly who they were. Al made sure of that. He told everybody he robbed who he was.

Al Jennings, Outlaw or Out of His Mind

Photo: James Bud Ledbetter from eBay

Territorial Deputy Sheriff Bud Ledbetter of Muskogee County was an old-time law-dog. He’d served as town and county law in Missouri, Arkansas, and Texas before becoming a Deputy US Marshal out of Judge Isaac C. Parker’s court at Ft. Smith. With the closing of Parker’s jurisdiction and the opening of Oklahoma and Indian Territories to Anglo settlement, Bud moved to Muskogee. Now this seasoned professional got the job of running down the four most inept, amateur bandits the 19th Century ever produced.

It gets cold in Oklahoma come November. The boys hadn’t been home since mid-August. On the night of November 14 they broke into Nutter’s Store at Cushing about 25 miles southeast of Stillwater, just over the line in Indian Territory. At the time, what is now the State of Oklahoma was divided, the eastern half being known as Indian Territory, the western half as Oklahoma Territory. Al lived in OT and, with the exception of the abortive attempt to stop the Katy near Muskogee, all his ‘career’ had been in OT.

The burglary was not to Al’s liking. He pictured himself as a dashing bank and train robber, not a burglar. Still, he didn’t intend to lose credit for the crime. The boys stole warm clothes, blankets, canned food, cartridges, tobacco, and about $40 from the till. Al left a note claiming credit.

Al Jennings, Outlaw or Out of His Mind

Photo: pay.apps.ok.gov

A little less than a week later, on November 20, the gang burst into the US Post Office at Foyil, 11 miles northeast of present Claremore. In a classic stickup straight out of Ned Buntline’s best, they lined up the customers and employees, rifled the till, sacked up some $300, caroled their horses, fired a few shots in the air for effect, and galloped away in a cloud of dust. There was just one minor hitch. There were two sacks in the place. One was the one they’d put the money in. The other sack–identical to that one–contained the postmaster’s collection of cancelled stamps. The boys picked up the wrong sack.

The burglary at Cushing and the stick-up at Foyil told Bud Ledbetter the gang was headed for the Spike S ranch, which had been a notorious bandit haven in the early years of the territory and might still take in a man on the dodge. The lawman decided Al would try to talk the folks at the Spike S into letting him and the boys hole up until spring. Bud rode ahead and waited for them. He was right.

On October 29, Al and the boys rode into the Spike S. At that point, the prototype for every long-term gunfight Republic Pictures ever put into a 13-chapter serial began. “The Gunfight at The Spike S” lasted nearly 15 minutes, one of the longest shootouts on record. It was also one of the least lethal. Only Morris O’Malley was wounded, hit in the leg with a slug from Ledbetter’s Winchester. The wound wasn’t especially dangerous, but Morris thought he was dying. Bud did nothing to disabuse him of the notion.

The rest of the gang escaped, but Bud made sure the first thing he did was spook their horses. They lost their blankets, spare clothes, food, smokes, and extra ammo. Al covered the retreat, six-gun blazing in true Ned Buntline style– marred by the unfortunate fact that the gang was now afoot. Morris, who apparently thought he was making a deathbed statement, spilled everything. He detailed both successful stickups, the burglary, and the four fiascos, and identified the John Doe at Edmond, Purcess, Minco, and Chickasha as Dick West. He also told Bud that Al told him to break jail as quickly as he could and head for ‘the corners,’ where Texas, Oklahoma, and Arkansas meet. The gang, Al said, would meet him there.

Ledbetter was a Territorial officer. He had no jurisdiction in Arkansas or Texas. Though the gang had committed a Federal offense–sticking up a post office–the crime had been less than an unqualified success. Federal Deputy Marshals, who received only those expenses they could produce receipts for and any rewards offered for bandits in lieu of salary, could hardly be expected to go chasing off after a bunch of teenaged kids for a paltry $200 apiece.

If Al actually reached ‘the corners’ there was a better than even chance the gang would get away free. There was, however, only one good trail going from the Spike S to where Al wanted to go. It crossed the Deep Fork of the Canadian at a place called Rock Creek Crossing. Bud Ledbetter went to the crossing and waited.

Al Jennings, Outlaw or Out of His Mind

Image: www.contemplator.com

Al, Frank, and Pat, meanwhile, were making their slow, painful way afoot through the icy brush. On the cold, wet evening of December 2, Al pulled his final stick-up. Along a farm trail not far north of Okmulgee he stepped in front of a rickety farm wagon driven by two Cherokee teenagers and pulled by a ragged mule. He leveled his six-shooter on them and croaked, through his laryngitis “Do you know who I am?” “No, sir,” they admitted. “I’m Al Jennings, the great train robber and bandit,” he announced. The boys looked blank. Jesse James they’d heard of, the Youngers, and the Daltons. They knew about Bill Doolin and Turkey Creek and Red Buck and Dick West, and of course Ned Christie and Cherokee Bill, but who was this Al Jennings? Al’s next remark was “Gimme that mule an’ wagon or I’ll blow your heads off.”

Maybe the boys had never heard of Al Jennings, but he did have a gun. They gave him the mule and wagon. The ragged, dirty, shivering man climbed onto the seat. Two more equally ragged, dirty men stumbled out of the brush and flopped down in the wagon bed. The wagon rattled away into the gathering night, leaving two very bewildered Cherokee boys alongside the trail.

Four days later, on the afternoon of December 6, 1897, Al drove the wagon into Rock Creek Crossing–and found himself looking into the muzzle of Bud Ledbetter’s Winchester. “Please, Mr. Ledbetter,” the disconsolate bandits begged, “take us someplace where it’s warm.”

In April, 1898, the Al Jennings gang went on trial. Frank and the O’Malleys drew five years each for train robbery. Al was convicted of assault with intent to kill an officer of the law–for reasons previously mentioned–and drew a life sentence. All were sent to the supposedly escape-proof Ohio State Pen, which took Federal prisoners at the time.

Al’s sentence was commuted to five years on June 23, 1900. Frank and the O’Malleys were pardoned in 1901. Al got his Teddy Roosevelt pardon in 1902, but it had nothing to do with Rough Rider service. Al spent the Spanish-American War in prison. After he got out of prison Al returned to Edmond, where he read law and was ultimately admitted to the Oklahoma bar. He practiced law for a while, but Al always had a serious case of the itch-foot–and he could never let go of his ‘outlaw career.’ He might have tried it again, but something else intervened.

Al Jennings, Outlaw or Out of His Mind

Photo: Al Jennings from www.dailymail.co.uk

Shortly after he got out of prison he saw ‘the wonder of the age’–a motion picture filmed in the wilds of New Jersey and along New York City’s Central Park bridle paths. It was called “The Great Train Robbery,” and it starred Gilbert N. Anderson, who became known to an entire generation of American kids as ‘Broncho Billy.’ Al thought about it for a while, and the longer he thought about it the better the idea looked. He’d show ‘em how it was really done. He’d go to wherever they made these movin’ pictures and he’d see to it they made ‘em right–told how to do it by the Great Oklahoma Bandit and Train Robber, the Oklahoma Robin Hood, Al Jennings himself. And that’s just what he did.

From the early days of the silents until the mid-1950s, Al Jennings, the self-styled Oklahoma Robin Hood, the Man Who Robbed More Trains Than Jesse James and Killed More Men Than Billy The Kid–only he didn’t–was the final arbiter of what went and what didn’t in the B Westerns turned out by Hollywood’s poverty row. Now you know why those movies–and early TV shows–were so phony. The guy who ‘told ‘em how we really done it, ‘cause I was there an’ did it for real’ was a total fake.