Jennings was a bad outlaw, not in the sense that he was dangerous
or feared but in the sense that he wasn't very good at outlawry.
Jennings was, however, a good storyteller, and good stories last
longer than bad outlaws unless, of course, a bad outlaw is telling
the story. That was the case when Al Jennings was the storyteller.
The Al Jennings stories include all manner of Old West characters,
from writer O. Henry to Sam
Houston's gunslinging, lawyering son Temple
Lea Houston to the Lone Ranger.
That's a lot of ground to cover, but we'll begin in 1895 in Woodward,
Oklahoma where Al and his brother John were lawyers. They had the
misfortune to try a case against the wildly popular and successful
Houston, son of Sam. The Jennings boys and Houston almost came
to blows during the trial, the disagreement stretching into the
evening and culminating with a gunfight that found John dead and
Sam Houston's son charged with murder.
dead, but Temple
Houston won his own freedom in court, same as he did for many
another alleged killer.
"The future, which seemed so bright to me as a young lawyer in a
new country, died with my brother," Al Jennings later wrote. "I
reverted to the primitive man that was within me."
The primitive man inside Al Jennings wasn't very smart. First, he
and his remaining brother, Frank, laid hands on some fake U.S. Marshall
badges and used them to charge gullible trail herders a fictional
toll for driving their cattle across the territory.
That was fun, but Jennings wanted more out of life. He wanted to
be a train robber so he recruited a few members of the Doolin gang
to help him reach his full potential. The gang included him and
Frank, Little Dick West, Dynamite Dick Clifton and the O'Malley
brothers, Morris and Pat. Together, they demonstrated the many ways
not to rob a train.
One sure way to not rob a train is to stand on the tracks waving
a lantern and firing your pistol in the air. Doesn't work. Engineer
can't stop the train in time even if he wants to, and he doesn't
want to if all he gets out of it is robbed. Al Jennings tried this
tactic, and succeeded only in jumping out of the way of the train
before it ended his primitive phase (and all future phases) right
then and there.
The gang also learned how hard it is to open a safe by banging on
it and shooting at it. The gang demonstrated the folly of this method
in another attempt. On the bright side, they rode away with a jug
of whiskey and some bananas. Things were looking up. They just had
a few details to work out.
Al did some thinking about it and decided it would be a lot to easier
to rob a train that was already stopped rather than stopping one
that was already rolling full speed. They put the new strategy to
work at a watering station near Minco, Oklahoma. This time they
took along plenty of dynamite to open that pesky safe. Al set down
the dynamite, lit the fuse and ran like hell. Seconds later, the
entire baggage car exploded into splinters.
The safe, and any money that might have been in it, vaporized. The
gang had to settle for robbing the passengers, none of whom turned
out to be rich. The gang then made a crucial and atypically wise
decision - they broke up.
A few weeks later U.S. Marshal Bud Ledbetter found the Jennings
brothers hiding under some blankets on a wagon and hauled them off
to jail. A jury convicted them and the judge sentenced Al Jennings
to life in prison. At Leavenworth prison, Al Jennings befriended
a bank teller from Austin
named William Sydney Porter, who was in the slammer for embezzlement.
Since Jennings liked to talk and Porter liked to listen, the two
became good friends. When Porter left prison and began writing under
the name O Henry, one of the first stories he published was called
"Holding Up a Train," which Jennings actually wrote.