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. He was pardoned by President Theodore Roosevelt
in 1902. |
Photo courtesy National Archives and Records Administration
| He went
to Hollywood in the early years of the movies and became a free-lance 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.”
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 Sidney
Porter, and he would become, as O.
Henry, the undisputed master of the only purely American literary form, the
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.
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
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.
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. According to those who knew them all four—Al in
particular—were addicted to Ned Buntline’s Wild West stories.
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.”
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 sixshooters. 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 sixshooters 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 issued a reward notice
listing $100 apiece for the would-be robbers.
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 trainstopping tricks he learned from Ned Buntline.
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 popoff. 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.
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.
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.
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, 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 fuzes, and ran.
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.
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
stickup 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.
Territorial Deputy Sheriff Bud Ledbetter
of Muskogee County was an old-time lawdog. He’d served as town and county law
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.
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, carcoled 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 stickup 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, sixgun 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
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, 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 stickup. 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 sixshooter 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.
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?
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
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.
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. 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.