Holding Up a Train

O. Henry (1862–1910)
From O. Henry: 101 Stories

Interesting Links

Virtual tour: “The O. Henry Museum: More Than Just a One-Story House” (Katie Keckeisen, ArGIS Story Maps)

Alphonso J. Jennings (The Encyclopedia of Oklahoma History and Culture, Oklahoma Historical Society)

Previous Story of the Week selections
• “A Retrieved Reformation,” O. Henry
• “How I Escaped Being Killed in a Duel,” Mark Twain
• “The Story of an Hour,” Kate Chopin

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O. Henry: 101 Stories
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“You’ll excuse my taking a look at the contents.” Illustration by Canadian American artist Charles Henry White (1878–1918) for the McClure’s Magazine publication of “Holding Up a Train.”

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Shortly after moving to New York in 1902, William Sydney Porter, who had begun publishing under the name O. Henry, was digging around for short story ideas. He wrote to Al Jennings, who had become a friend while both men served their respective sentences in the Ohio Penitentiary: Jennings for train robbery and Porter for embezzlement. Porter suggested that the two men work together writing a story based on Jennings’s criminal adventures—“‘The Art and Humor of the Hold-up,’ something like that”—and they would split in half whatever payment O. Henry received for the selection.

Porter asked Jennings to write the first draft, and he would then revise, polish, and submit it for publication. “Begin abruptly, without any philosophizing, with your idea of the best times, places and conditions for the hold-up,” Porter advised. “Get as much meat in it as you can, and, by the way—stuff it full of western genuine slang—(not the eastern story paper kind). . . . Information is what we want, clothed in the peculiar western style of the character we want to present. The main idea is to be natural, direct, and concise.”

Jennings, who hailed from a family of lawyers (his father was a judge), had been a district attorney in Oklahoma Territory before setting up a private legal practice with his brothers Ed and John. In October 1895 Ed got into a shouting courtroom battle with Temple Lea Houston (son of Sam Houston) that turned into a drunken shootout in a saloon, during which Ed was killed and John wounded. “The future, which had seemed so bright to me as a young lawyer in a new country, died there with my brother when he drew his last breath,” Jennings wrote in an article published in the Kansas City Star in 1912. “I admit here and now that I reverted to the primitive man within me.”

Although the original goal was revenge against Temple Houston, Al Jennings and yet another brother, Frank, embarked instead on a series of crimes. Along the way, apparently on the lam, they made a six-month detour to Honduras, where they first met Porter, also a fugitive—a meeting previously detailed in our introduction to O. Henry’s “A Retrieved Reformation.” After the two Jennings brothers returned to Oklahoma, they fell in with a group of underemployed cattlemen turned bandits during the summer of 1897. “It was a wild, reckless country, filled with outlaws, but we were the wildest of them all.”

In truth, the Jennings Gang was notoriously bad at robbing trains and by the end of the year both brothers were in jail.

For a summary of Jennings’s train-robbing career, we turn to John J. Kinney’s well-documented (and immensely entertaining) book, Captain Jack and the Dalton Gang:

The Jennings Gang . . . planned to rob their first train near Edmund, Oklahoma, on August 16, 1897. But the train’s conductor, seeing them inspecting the express car door, sternly asked them their business, and they meekly slunk away. Three days later, Al attempted to stop a speeding train by standing on the tracks and frantically waving his arms. He was nearly run over. On August 23, the gang tried a new tactic, galloping their horses beside the train while firing pistols in the air. The engineer calmly advanced his throttle, waved goodbye, and left them behind.

Finally, on October 1, 1897, the gang managed to stop a Rock Island passenger train near Minco, Oklahoma. But they could not force open the express car door. Announcing that he had come prepared for just such an eventuality, Al pulled from his saddlebags a quantity of dynamite and proceeded to blow the entire car into splinters. No safe was found in the rubble. A search of the smoking wreckage yielded only, by one report, a miraculously unbroken two-gallon jug of whiskey and a bunch of—we would suppose—rather badly bruised bananas. Enraged, the gang robbed the passengers of practically everything they had, even stripping a pair of new boots from a traveling salesman.

Some historical accounts of Jennings’s career include a far more successful train robbery near Berwyn—a small town in Oklahoma now known as Gene Autry—where the gang netted between $25,000 and $30,000. Yet Jennings himself appears to be the primary source for the incident and his brief, vague account (including the amount of loot) seems suspiciously like the widely reported Berwyn train robbery of November 1889.

Readers will struggle to find the parallels between Jennings’s actual career and O. Henry’s “Holding Up a Train.” Their collaboration also includes a brief description of a hold-up conducted by the Dalton gang—a summary that is (according to Kinney) “perhaps the most inaccurate account of the Adair train robbery ever written.” Jennings sent his draft to Porter, who responded positively—as did, apparently, the editor at McClure’s Magazine, whose letter, forwarded to Jennings, seems to have hinted at provisional acceptance and a payment on the way. “When you see your baby in print,” Porter wrote to Jennings, “don’t blame me if you find strange ear marks and brands on it. I slashed it and cut it and added lots of stuff that never happened, but I followed your facts and ideas, and that is what made it valuable. . . . As soon as check mentioned in letter comes I’ll send you your ‘sheer’ of the boodle.”

The story appeared more than a year later in the April 1904 issue of McClure’s. While claiming at the outset to be based on actual events, the story is pure fiction—endearingly comic and utterly fanciful in a style very much like O. Henry’s other stories set in the Southwest.

Jennings was still in prison when he sent Porter his draft. He had originally been sentenced to life for the (failed) robbery of the U.S. mail car near Minco, but various appeals by his father and brother prompted President William McKinley in 1900 to commute the term to five years, with time off for good behavior, and he was released in November 1902. Remarkably, in February 1907 he somehow finagled a full pardon from President Theodore Roosevelt, who may well have been swayed by Jennings’s romanticized view of train robbery depicted in the O. Henry story. Jennings went on to a career as a silent movie director, writer, and actor and the author of two memoirs, including the wholly unreliable Through the Shadows with O. Henry.

Notes: Among the problems affecting employment prospects for cattlemen by end of the nineteenth century were the increase in nesters, or homesteaders, and the proliferation of barbed wire fences used by farmers to keep cattle out of their crops—both of which diminished the wide, empty ranges required to run cattle. Among O. Henry’s train references: The Santa Fé flyer was the fast passenger train on the Atchison, Topeka & Santa Fe Railway; M. K. & T. was the Missouri-Kansas-Texas Railway and Katy was a slang term for it (derived from its KT stock symbol). Prince Albert of Great Britain created a fashion trend for top hats when he began wearing them frequently in the 1850s. French harp is regional American slang for a harmonica. The Cimarron is a river that begins in northeastern New Mexico and cuts across Oklahoma to just west of Tulsa, where it empties into the Arkansas River; it was also a branch of the Santa Fe Trail near the western edge of the state's panhandle.

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