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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. He was pardoned by President
Theodore Roosevelt in 1902.
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."
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Al
Jennings
Photo courtesy National Archives and Records Administration |
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 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' 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 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.
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
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.
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
trainstopping 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 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.
Trainrobbing 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.
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, 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.
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 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 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.
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 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, 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.
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. 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. |
