Al Jennings: The Most Inept Outlaw of the Old West

by Jay Robert Nash

One of the more comic characters of the American frontier, Al Jennings, born on November 25, 1863, was raised with his brothers Edward, Frank, and John at Kiowa Creek, Oklahoma, near the town of Woodward. The Jennings boys, sons of Judge J. D. F. Jennings, were a fun-loving lot who dreamed of becoming bandits. Al and Frank Jennings did, indeed, follow that criminal pursuit and, Al, the leader of a motley gang, proved to be the most incompetent outlaw of the Old West.

In the mid-1890s, while working as cowboys, Al and Frank Jennings decided to become outlaws. They started off by obtaining fake U.S. marshal's badges and using them to collect "tolls" from gullible trail herders moving their cattle through the Oklahoma Territory. They were later joined by several members of the Doolin Gang. Under Al's leadership, they planned to rob trains.

Their first outing was a disaster. On the night of August 16, 1897, Al and Frank Jennings, with Little Dick West and Morris and Pat O'Malley, stopped a southbound Santa Fe train at Edmond, but they were unable to shoot or blast the safe open. They rode off cursing their bad luck, which, as all their fumbling criminal acts would laughingly demonstrate, was really colossal stupidity.

Al Jennings, an Oklahoma bandit who botched his every attempt at robbe
Al Jennings, an Oklahoma bandit who botched his every attempt at robbery, later claiming he had been a great bandit. (image from the Jay Robert Nash Collection)

A few nights later, Al Jennings tried to flag down another train by standing directly in the center of the railroad tracks, holding a lantern and frantically waving a red flag. The engineer, however, kept his hand on the throttle and the train roared forward. Jennings, screaming for the engineer to halt, finally leaped out of the way at the last moment. The train raced on into the night as Jennings and the rest of the outlaws stood foolishly in the darkness.

Some days later, Jennings and his brother Frank rode alongside a fast-moving Santa Fe train, near Bond Switch, firing their six-guns in the air as a signal to the engineer to stop. The engineer leaned from the window of the locomotive's cabin, waved a friendly hello, and kept going. The Jennings brothers, their horses exhausted, fell behind and then came to a panting stop as they watched their prey chug from sight.

These miserable failures were capped by a disastrous raid on a southbound Rock Island passenger train at 11 a.m. on October 1, 1897. Al and Frank Jennings, Little Dick West and the O'Malley brothers found the train stopped at a water station eight miles south of Minco. They boarded the baggage car, but again could not open the safe.

"I've been waiting for that," Al Jennings said and he produced several sticks of bound dynamite. He inserted a long fuse into one stick, lit it, and placed the dynamite next to the safe. The baggage car clerk and the outlaws leaped from the train car and ran some distance from it, waiting.

"How much dynamite did you use, Al?" Frank asked his brother.

"You got to use a lot of dynamite to dent a big safe like that," Al Jennings answered knowingly.

A few seconds later, the entire car blew up, sending a shower of wooden and iron splinters in all directions. There was no safe, let alone money, to be found. The frustrated gang members then went through the passenger coaches and robbed everyone down to their last dollar. They even stole a new pair of boots from a traveling salesman.

The gang fled into the Indian nation where, on October 29, 1897, they robbed the till of the Crozier and Nutter Store in the town of Cushing in Payne County. The robbery netted the thieves a mere $15. This was the last straw for Little Dick West and the O'Malleys. They rode in one direction, the Jennings brothers in another.

Marshal James F. "Bud" Ledbetter of Muskogee, Oklahoma, one of the toughest lawmen in the West, then received a tip that the Jennings brothers would be hiding in a covered wagon moving through the Indian Nation. He tracked down the wagon and ordered Al and Frank Jennings to come out from under some blankets where they had been hiding. The boys meekly surrendered.

This was the end of the Al Jennings gang, an outlaw band that never really got started, and one that earned its members less than $200 each from all of their ridiculous exploits. Frank Jennings was given five-year terms in Leavenworth.

Al Jennings, the preposterous mastermind of the most absurd train robbery attempts on record, was sent to the federal prison at Columbus, Ohio, to serve a life term. Here, Jennings met the writer, William Sydney Porter (imprisoned for embezzlement), who wrote under the pseudonym of O. Henry. Jennings filled Porter's ears with mythical tales about himself, which the writer later used in some of his best stories.

Al Jennings was freed within five years, given a pardon by President Theodore Roosevelt (who had known Judge Jennings, Al's father). His brother Frank had been set free earlier and returned to the family homestead in Oklahoma.

Al, however, headed for California. He settled in Hollywood, where he became a fixture, an "adviser" on motion pictures about the West. He told wild tales of his outlaw years, all of his claims being complete fabrications. Sheriff Jim Herron of Oklahoma later stated: "Old Al Jennings was around California for years, stuffing dudes with nonsense and telling them wild yarns about himself in the early days."

Jennings convinced many a film producer that he was an expert on western banditry and he earned a considerable living as a consultant. He even wrote two books about his imagined life and his story was made into a motion picture, Al Jennings of Oklahoma, 1951, starring Dan Duryea as Al. Although none of his claims were true, Jennings came to believe he had been one of the great outlaws of the Old West, right up to the time of his death in Tarzana, California, on December 26, 1961.