The night of February 7, 1921 found Al Jennings, whose booking photo is shown below,  in a nostalgic mood as he wandered 25^th Street towards Park Avenue. “I had gone down there because I’d been thinking all evening of Bill, and my mind was filled with reveries about him, most of them sad. I was walking along almost feeling that Bill’s spirit would come out and speak to me…”

Jennings’ path to 25^th Street was a long one. He and his brothers opened a law practice in Woodward, Oklahoma, a cattle town filled with saloons, brothels, and gambling dens. Attorney Temple Lea Houston (Sam Houston’s son), ignored  the old joke that “a small town cannot afford one lawyer, but any size town can afford two,” and resented the imposition. Houston and the Jennings boys got in a shootout, which left Al’s brother Ed Jennings dead, and wounded John Jennings.

After the Woodward County Court freed Houston on a plea of self defense, Al Jennings fled to the Creek Indian Reservation, where he worked as a cattle hand, but he and his brother Frank quickly became suspected of a number of train robberies. Perception became reality when they joined a band of outlaws in the Arbuckle Mountains in South Central Oklahoma. Al maintained that they’d joined the band of outlaws simply for protection from the law but regardless, Al Jennings was a member of the “Long Riders” who stopped a Rock Island train between Minco and Chickahsa in October, 1897. Their target was $100,000 in U.S. Army payroll, but the nitroglycerine with which they’d intended to blow the safe failed to go off. Taking what they could from the passengers, they fled. A friend betrayed his hideout, and a posse captured him at the Spike S ranch. The court sentenced him to life imprisonment, which he served at the Ohio State Penitentiary.

Here he met Bill, the man he’d been thinking of on that winter’s evening in 1921. Bill was serving a five year sentence for embezzlement from an Austin, Texas bank, and the two became fast friends, always ready to share a laugh at the expense of the guard assigned to the hospital wing where they worked, Orrin Henry. Bill was released in 1901 for good behavior, and Al Jennings followed him in 1903, released on a technicality after strident legal efforts by his brother Ed. In 1907, Theodore Roosevelt himself issued Al a full pardon, wiping his slate clean.

Bill and Al met up in New York City, trading drinks at Pete’s Tavern in Gramercy Park, and generally having a good time. Perhaps they lived it up a bit too much. Bill was an alcoholic; his wife left him in 1909 after he failed to give up the bottle, and he died in 1910 of cirrhosis of the liver and an enlarged heart. Al went back to Oklahoma, served as an advisor on a silent film detailing robberies in the Old West, and unsuccessfully ran for sheriff and governor, and wrote his autobiography, and became pretty famous. In 1921, he returned to New York City to revisit some of his old haunts.

It was during this trip down Memory Lane and 25^th Street that Al was held up. “He was a big guy, kind of foreign-looking, with an accent of some sort” Al later unhelpfully described him to police. With a gun in his ribs, Al dutifully raised his arms and remonstrated, “Listen, pal,” Al said, “You don’t want to hold me up.”

“Shut yer trap and come across with what you’ve got.”

“But I’m Al Jennings.” The name meant nothing to the bandit.

“Yeh, I’m Bill Bryan.” The now duly introduced stick up man proceeded to loot Jennings of wallet, diamond stick pin, and $82.00.

“I felt positively afraid for my life, like a rabbit coming out of the mesquite. I was sure my lights were going to be put out, and I thought of my Airedale dog and the rest of the family out home. I even saw myself lying cold and stiff in the morgue.” He made one last attempt to reason with the bandit.

“Wait a minute old timer. All I’ve got left is a dime. You wouldn’t leave a pal stranded with only a dime, would you? I’ve got to have carfare home.” Playing on sympathy didn’t help.

“Aw, shut up. So’ve I, and this only gives me enough to get where I’m going. You can have the dime though.” The bandit took off, leaving Al with his dime and his thoughts. His opinion of New York’s criminal element was none too kindly “The man who robbed me was coarse and uncouth. When we used to rob out in Oklahoma we used to make ‘em feel comfortable, but this man made me feel ill at ease. He was not only rough, but insulting.”

“I’m not kicking about his taking my money – $82 and my pin, but I would like to have back the pardon which President Roosevelt gave me. You know, I think a lot of that. The old Colonel isn’t here anymore to sign his name. If that guy has the principle of a cootie he’ll send that back to me.”

Al knew at least one man would have gotten a laugh out of the great train robber being held up and left with a thin dime, his old friend Bill, full name William Preston. Bill had written short stories under a pen name, taken either from their guard at the hospital wing, Orrin Henry, or from the various letters of Ohio State Penitentiary.

“O. Henry would have thought this a good joke on me” Jennings chuckled when interviewed by the New York World, “Maybe it is, but I’m not going out nights alone after this.”